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Journal articles on the topic '5-methylTHF'

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Author: Grafiati

Published: 11 March 2023

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1

Palmer, Ashley M., Elena Kamynina, Martha S. Field, and Patrick J. Stover. "Folate rescues vitamin B12 depletion-induced inhibition of nuclear thymidylate biosynthesis and genome instability." Proceedings of the National Academy of Sciences 114, no. 20 (May 1, 2017): E4095—E4102. http://dx.doi.org/10.1073/pnas.1619582114.

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Clinical vitamin B12 deficiency can result in megaloblastic anemia, which results from the inhibition of DNA synthesis by trapping folate cofactors in the form of 5-methyltetrahydrofolate (5-methylTHF) and subsequent inhibition of de novo thymidylate (dTMP) biosynthesis. In the cytosol, vitamin B12 functions in the remethylation of homocysteine to methionine, which regenerates THF from 5-methylTHF. In the nucleus, THF is required for de novo dTMP biosynthesis, but it is not understood how 5-methylTHF accumulation in the cytosol impairs nuclear dTMP biosynthesis. The impact of vitamin B12 depletion on nuclear de novo dTMP biosynthesis was investigated in methionine synthase-null human fibroblast and nitrous oxide-treated HeLa cell models. The nucleus was the most sensitive cellular compartment to 5-methylTHF accumulation, with levels increasing greater than fourfold. Vitamin B12 depletion decreased de novo dTMP biosynthesis capacity by 5–35%, whereas de novo purine synthesis, which occurs in the cytosol, was not affected. Phosphorylated histone H2AX (γH2AX), a marker of DNA double-strand breaks, was increased in vitamin B12 depletion, and this effect was exacerbated by folate depletion. These studies also revealed that 5-formylTHF, a slow, tight-binding inhibitor of serine hydroxymethyltransferase (SHMT), was enriched in nuclei, accounting for 35% of folate cofactors, explaining previous observations that nuclear SHMT is not a robust source of one-carbons for de novo dTMP biosynthesis. These findings indicate that a nuclear 5-methylTHF trap occurs in vitamin B12 depletion, which suppresses de novo dTMP biosynthesis and causes DNA damage, accounting for the pathophysiology of megaloblastic anemia observed in vitamin B12 and folate deficiency.

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2

Pfeiffer, Christine M., Maya R. Sternberg, Zia Fazili, David A. Lacher, Mindy Zhang, Clifford L. Johnson, Heather C. Hamner, et al. "Folate status and concentrations of serum folate forms in the US population: National Health and Nutrition Examination Survey 2011–2." British Journal of Nutrition 113, no. 12 (April 28, 2015): 1965–77. http://dx.doi.org/10.1017/s0007114515001142.

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Serum and erythrocyte (RBC) total folate are indicators of folate status. No nationally representative population data exist for folate forms. We measured the serum folate forms (5-methyltetrahydrofolate (5-methylTHF), unmetabolised folic acid (UMFA), non-methyl folate (sum of tetrahydrofolate (THF), 5-formyltetrahydrofolate (5-formylTHF), 5,10-methenyltetrahydrofolate (5,10-methenylTHF)) and MeFox (5-methylTHF oxidation product)) by HPLC–MS/MS and RBC total folate by microbiologic assay in US population ≥ 1 year (n approximately 7500) participating in the National Health and Nutrition Examination Survey 2011–2. Data analysis for serum total folate was conducted including and excluding MeFox. Concentrations (geometric mean; detection rate) of 5-methylTHF (37·5 nmol/l; 100 %), UMFA (1·21 nmol/l; 99·9 %), MeFox (1·53 nmol/l; 98·8 %), and THF (1·01 nmol/l; 85·2 %) were mostly detectable. 5-FormylTHF (3·6 %) and 5,10-methenylTHF (4·4 %) were rarely detected. The biggest contributor to serum total folate was 5-methylTHF (86·7 %); UMFA (4·0 %), non-methyl folate (4·7 %) and MeFox (4·5 %) contributed smaller amounts. Age was positively related to MeFox, but showed a U-shaped pattern for other folates. We generally noted sex and race/ethnic biomarker differences and weak (Spearman's r< 0·4) but significant (P< 0·05) correlations with physiological and lifestyle variables. Fasting, kidney function, smoking and alcohol intake showed negative associations. BMI and body surface area showed positive associations with MeFox but negative associations with other folates. All biomarkers showed significantly higher concentrations with recent folic acid-containing dietary supplement use. These first-time population data for serum folate forms generally show similar associations with demographic, physiological and lifestyle variables as serum total folate. Patterns observed for MeFox may suggest altered folate metabolism dependent on biological characteristics.

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3

Taflin, Helena, Yvonne Wettergren, Elisabeth Odin, Göran Carlsson, and Kristoffer Derwinger. "Folate Levels and Polymorphisms in the Genes MTHFR, MTR, and TS in Colorectal Cancer." Clinical Medicine Insights: Oncology 8 (January 2014): CMO.S12701. http://dx.doi.org/10.4137/cmo.s12701.

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Aim The aim of the study was to explore and describe the effect of polymorphisms in folate-associated genes regarding the levels of different folate forms and their distribution in tumors and mucosa in patients with colorectal cancer. Materials and Methods Tumor and mucosa tissues from 53 patients with colorectal cancer were analyzed. The concentrations of tetrahydrofolate (THF), 5-methylTHF, and 5,10-methyleneTHF were measured by liquid chromatography—mass spectrometry. Genotyping of polymorphisms in the folate-associated genes methylenetetrahydrofolate reductase ( MTHFR, C677T), methionine synthase ( MTR, A2756G), and thymidylate synthase ( TS, 5'-TSER 28 bp tandem repeat and 3'-TSUTR 6 bp deletion/insertion), were done by real-time polymerase chain reaction. Folate levels and distributions were determined in the total patient cohort and after subgrouping by genotypes. Results The total folate level, as well as the THF and 5,10-methyleneTHF levels, were significantly higher in the tumor compared with mucosa tissue ( P = 0.030, 0.031, and 0.015, respectively). The individual variation in folate levels in both tumor and mucosa were larger than the variation found when the patients were subgrouped by the gene polymorphisms. No significant differences in the mean concentration of any folate in the mucosa or tumor tissue were found in relation to the analyzed polymorphisms. The percentage level of 5,10-methyleneTHF in tumors was highest in patients with the MTHFR 677 CC genotype, and lowest in patients with the TT genotype ( P = 0.033). A significantly lower percentage level of the 5,10-methyleneTHF level was found in tumors of patients with the 5'-TSER 3R/3R genotype ( P = 0.0031). Conclusion A significant difference was found between the percentage level of 5,10-methyleneTHF in tumor tissues in relation to the MTHFR C677T and 5'-TSER 28 bp repeat polymorphisms. However, no differences were found in the actual tissue folate levels, or in their distribution, in relation to the polymorphisms in the MTHFR, MTR, or TS genes. These findings could be of importance for further research in the field by explaining some of the difficulties of obtaining reproducible and uniform results when using a few selected polymorphisms as predictive markers.

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4

Dattilo, Maurizio, Carolina Fontanarosa, Michele Spinelli, Vittorio Bini, and Angela Amoresano. "Modulation of Human Hydrogen Sulfide Metabolism by Micronutrients, Preliminary Data." Nutrition and Metabolic Insights 15 (January 2022): 117863882110653. http://dx.doi.org/10.1177/11786388211065372.

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Background: Hydrogen sulfide (H2S) is a pivotal gasotransmitter networking with nitric oxide (NO) and carbon monoxide (CO) to regulate basic homeostatic functions. It is released by the alternative pathways of transulfuration by the enzymes Cystathionine Beta Synthase (CBS) and Cystathionine Gamma Lyase (CSE), and by Cysteine AminoTransferase (CAT)/ 3-Mercaptopyruvate Sulfur Transferase (3MPST). A non-enzymatic, intravascular release is also in place. We retrospectively investigated the possibility to modulate the endogenous H2S release and signaling in humans by a dietary manipulation with supplemented micronutrients (L-cystine, Taurine and pyridoxal 5-phopsphate/P5P). Methods: Patients referring for antiaging purposes underwent a 10-day supplementation. Blood was collected at baseline and after treatment and the metabolome was investigated by mass spectrometry to monitor the changes in the metabolites reporting on H2S metabolism and related pathways. Results: Data were available from 6 middle aged subjects (2 women). Micronutrients increased 3-mercaptopyruvate ( P = .03), reporting on the activity of CAT that provides the substrate for H2S release within mitochondria by 3MPST, decreased lanthionine ( P = .024), reporting the release of H2S from CBS, and had no significant effect of H2S release from CSE. This is compatible with a homeostatic balancing. We also recorded a strong increase of reporters of H2S-induced pathways including 5-MethylTHF ( P = .001) and SAME ( P = .022), reporting on methylation capacity, and of BH4 ( P = .021) and BH2 ( P = .028) reporting on nitric oxide metabolism. These activations may be explained by the concomitant induction of non-enzymatic release of H2S. Conclusions: Although the current evidences are weak and will need to be confirmed, the effect of micronutrients was compatible with an increase of the H2S endogenous release and signaling within the control of homeostatic mechanisms, further endorsing the role of feeding in health and disease. These effects might result in a H2S boosting effect in case of defective activity of pathologic origin, which should be checked in duly designed clinical trials.

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5

Mosnier, Hannah, Erin Kelly, Kamaya Lawrence, Sarah Cruickshank, Sarah Stacey, Adelina McCall, Sunny Dhatt, Erland Arning, Teodoro Bottiglieri, and Nafisa Jadavji. "The Role of One-Carbon Metabolism After Ischemic Stroke in an Aged Mouse Model." Current Developments in Nutrition 4, Supplement_2 (May 29, 2020): 1226. http://dx.doi.org/10.1093/cdn/nzaa057_042.

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Abstract Objectives Nutrition is a modifiable risk factor for stroke, which is one of the leading causes of death and disability world-wide. In humans deficiencies in one-carbon metabolism, including the methyltetrahydrofolate reductase (MTHFR) polymorphism, have been linked to increased risk of stroke. The Mthfr+/− mice mouse model mimics the phenotype of the MTHFR677C – >T polymorphism. In our work using in vitro and in vivo models of ischemic stroke we have observed decreased recovery after stroke through reduced neuronal and astrocyte viability and increased apoptosis in MTHFR-deficient mice. In addition, we have previously shown dietary supplementation of one-carbon metabolites increases neuroplasticity and reduced oxidative stress after ischemic stroke. Using the MTHFR-deficient mouse model, the aim of this study was to investigate the impact of dietary supplementation with one-carbon metabolites on stroke outcome. Methods Male Mthfr+/− and wildtype littermate control mice were aged to 1.5-year-old and were placed on control diet (CD) 4-weeks prior to sensorimotor cortex damage using photothrombosis (PT), a model for ischemic stroke. Post-operatively, one group of Mthfr+/− and wildtype littermate mice were fed a supplemented diet (SD) containing 5-methylTHF, vitamin B12, and choline. Four weeks after PT damage and SD motor function was assessed and brain tissue was processed to assess lesion volume and investigate biochemical and molecular changes. Results Mthfr +/− mice fed a SD after PT did not have an impaired neuroscore compared to CD Mthfr+/− mice. When compared to CD, SD Mthfr+/− mice were able to stay on the accelerating rotarod longer and travelled further, they also used their impaired forepaw more. Total homocysteine levels in plasma and lesion volume were reduced in SD Mthfr+/+ and Mthfr+/− mice. In the brain, within the damage site, there were reduced levels of apoptotic cell death and an increased neuroprotective cellular response in SD treated Mthfr+/− mice. Conclusions This study reveals a critical role for one-carbon supplementation in supporting improvement of function after ischemic stroke. Our data suggests that in stroke affected patients, nutritional supplementation maybe an important component to post-operative care, in addition to pharmacological and rehabilitation therapies. Funding Sources NSERC.

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6

Sufrin, Janice R., Arthur J. Spiess, Debora L. Kramer, Paul R. Libby, John T. Miller, Ralph J. Bernacki, Younha Lee, Ronald T. Borchardt, and Carl W. Porter. "Targeting 5'-deoxy-5'-(methylthio)adenosine phosphorylase by 5'-haloalkyl analogs of 5'-deoxy-5'-(methylthio)adenosine." Journal of Medicinal Chemistry 34, no. 8 (August 1991): 2600–2606. http://dx.doi.org/10.1021/jm00112a039.

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7

SUFRIN, J. R., A. J. SPIESS, D. L. KRAMER, P. R. LIBBY, J. T. MILLER, R. J. BERNACKI, Y. LEE, R. T. BORCHARDT, and C. W. PORTER. "ChemInform Abstract: Targeting 5′-Epoxy-5′-(methylthio)adenosine Phosphorylase by 5′-Haloalkyl Analogues of 5′-Deoxy-5′-(methylthio)adenosine." ChemInform 23, no. 2 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199202319.

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8

Alam, L. V., R. V. Kharbash, and G. I. Koldobskii. "2-Substituted 5-methylthio- and 5-methylsulfonyltetrazoles." Russian Journal of Electrochemistry 36, no. 6 (June 2000): 916–18. http://dx.doi.org/10.1007/bf02757456.

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9

Yu-Xiu, Liu, Cui Ming-Bo, Zhao Qi-Qi, Wang Qing-Min, Liu Ying, and Huang Run-Qiu. "Reduction of Pyrimidine Derivatives by LiAlH4." Journal of Chemical Research 2007, no. 8 (August 2007): 490–93. http://dx.doi.org/10.3184/030823407x240872.

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The reduction of ethyl 2-methylthio-(or 2-ethoxy)pyrimidine-5-carboxylate by LiAlH4 afforded ethyl 2-methylthio-(or 2-ethoxy)-1,6-dihydropyrimidine-5-carboxylate as the main product. Similarly, the reduction of 2-methylthio-(or 2-methoxy)pyrimidine-5-carboxamide by LiAlH4 gave 2-methylthio-(or 2-methoxy)-1,6-dihydropyrimidine-5-carbonitrile as main product.

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10

Singh, Okram Mukherjee, H. Junjappa, and H. Ila. "A Facile Synthesis of 3-Cyclopropyl- and 5-Cyclopropyl-isoxazoles." Journal of Chemical Research 23, no. 6 (June 1999): 398–99. http://dx.doi.org/10.1177/174751989902300627.

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11

Lynch, Daniel E., and Ian McClenaghan. "4,6-Dichloro-2-methylthio-5-phenylpyrimidine." Acta Crystallographica Section E Structure Reports Online 57, no. 3 (February 28, 2001): o264—o265. http://dx.doi.org/10.1107/s1600536801003154.

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12

Alam, L. V., R. V. Kharbash, and G. I. Koldobskii. "ChemInform Abstract: 2-Substituted 5-Methylthio- and 5-Methylsulfonyltetrazoles." ChemInform 32, no. 16 (April 17, 2001): no. http://dx.doi.org/10.1002/chin.200116140.

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13

Kumar, N., A. Vats, V. S. Parmar, and W. Errington. "[3-(4-Chlorophenyl)-5-methylthio-4,5-dihydro-5-isoxazolyl]acetonitrile." Acta Crystallographica Section C Crystal Structure Communications 52, no. 5 (May 15, 1996): 1239–41. http://dx.doi.org/10.1107/s0108270195016076.

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14

Näslund, M., I. Klášterská, A. Kolman, and L. Ehrenberg. "Mutagenic and comutagenic action of 5′-deoxy-5′-(methylthio) adenosine." Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis 161, no. 1 (June 1986): 1–7. http://dx.doi.org/10.1016/0027-5107(86)90094-1.

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15

Angulwar, Jaman A., Gopinath S. Khansole, and Vijay N. Bhosale. "Novel Synthesis and Antimicrobial Activity of 7-Substituted Derivatives of 7-(methylthio)-5-oxo-2-phenyl-5H-[1,3,4]thiadiazolo[3,2-b]- pyrimidine-6-carbonitrile." Asian Journal of Organic & Medicinal Chemistry 4, no. 1 (March 30, 2019): 40–45. http://dx.doi.org/10.14233/ajomc.2019.ajomc-p171.

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2-Amino-5-phenyl-1,3,4-thiadiazole on reaction with ethyl-2-cyano-3,3-bis(methylthio)acrylate in the presence of N,N′-dimethyl formamide and catalytic amount of anhydrous potassium carbonate afforded 7-(methylthio)-5-oxo-2-phenyl-5H-[1,3,4]thiadiazolo[3,2-b]pyrimidine- 6-carbonitrile under similar experimental condition, compounds 7-(methylthio)-5-oxo-2-phenyl-5H-[1,3,4]thiadiazolo[3,2-b]pyrimidine-6-carbonitrile on treatment independently with aryl amines/ heteryl amines/phenols containing active methylene group yielded correspon-ding 7-substituted derivatives. All these newly synthesized compounds were screened for antimicrobial activity.

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16

Kalogirou, Andreas S., and Panayiotis A. Koutentis. "Synthesis of 2-Cyanopyrimidines." Molbank 2019, no. 4 (October 22, 2019): M1086. http://dx.doi.org/10.3390/m1086.

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4,6-Dichloro-2-(methylthio)pyrimidine (7) was converted to 4-chloro-6-methoxy-2-(methylthio)pyrimidine (15) and 4,6-dimethoxy-2-(methylthio)pyrimidine (14). Chlorination of the latter with N-chlorosuccinimide (NCS) affords 5-chloro-4,6-dimethoxy-2-(methylthio)pyrimidine (16) in 56% yield. Both methylthiopyrimidines 15 and 14 were converted in two steps to 4-chloro-6-methoxypyrimidine-2-carbonitrile (13) and 4,6-dimethoxypyrimidine-2-carbonitrile (12), respectively, after oxidation to sulfones and displacement of the sulfinate group with KCN. 4,6-Dimethoxypyrimidine-2-carbonitrile (12) was chlorinated with NCS to give 5-chloro-4,6-dimethoxypyrimidine-2-carbonitrile (10) in 53% yield. All new compounds were fully characterized.

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Sufrin, Janice R., Arthur J. Spiess, Canio J. Marasco, Donna Rattendi, and Cyrus J. Bacchi. "Novel Trypanocidal Analogs of 5′-(Methylthio)-Adenosine." Antimicrobial Agents and Chemotherapy 52, no. 1 (October 22, 2007): 211–19. http://dx.doi.org/10.1128/aac.00480-07.

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ABSTRACT The purine nucleoside 5′-deoxy-5′-(hydroxyethylthio)-adenosine (HETA) is an analog of the polyamine pathway metabolite 5′-deoxy-5′-(methylthio)-adenosine (MTA). HETA is a lead structure for the ongoing development of selectively targeted trypanocidal agents. Thirteen novel HETA analogs were synthesized and examined for their in vitro trypanocidal activities against bloodstream forms of Trypanosoma brucei brucei LAB 110 EATRO and at least one drug-resistant Trypanosoma brucei rhodesiense clinical isolate. New compounds were also assessed in a cell-free assay for their activities as substrates of trypanosome MTA phosphorylase. The most potent analog in this group was 5′-deoxy-5′-(hydroxyethylthio)-tubercidin, whose in vitro cytotoxicity (50% inhibitory concentration [IC50], 10 nM) is 45 times greater than that of HETA (IC50, 450 nM) against pentamidine-resistant clinical isolate KETRI 269. Structure-activity analyses indicate that the enzymatic cleavage of HETA analogs by trypanosome MTA phosphorylase is not an absolute requirement for trypanocidal activity. This suggests that additional biochemical mechanisms are associated with the trypanocidal effects of HETA and its analogs.

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18

Olszak, T. A., O. M. Peeters, N. M. Blaton, and C. J. De Ranter. "1-Methyl-2-methylthio-5-nitroimidazole, C5H7N3O2S." Acta Crystallographica Section C Crystal Structure Communications 50, no. 6 (June 15, 1994): 919–21. http://dx.doi.org/10.1107/s0108270193012521.

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19

Jeckelmann, Jean-Marc, Therese Lüthi Nyffeler, Michael Altmann, Hans-Beat Bürgi, Philippe Renaud, and Jürg Hauser. "1,2,3-Tri-O-acetyl-5-deoxy-5-methylthio-β-D-ribofuranose." Acta Crystallographica Section E Structure Reports Online 61, no. 8 (July 23, 2005): o2689—o2690. http://dx.doi.org/10.1107/s1600536805022683.

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20

Abuelizz, Hatem A., Saied M. Soliman, Hazem A. Ghabbour, Mohamed Marzouk, Mohamed M. Abdellatif, and Rashad Al-Salahi. "DFT Calculation, Hirshfeld Analysis and X-Ray Crystal Structure of Some Synthesized N-alkylated(S-alkylated)-[1,2,4]triazolo[1,5-a]quinazolines." Crystals 11, no. 10 (September 30, 2021): 1195. http://dx.doi.org/10.3390/cryst11101195.

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The present work aimed to synthesize 2-methylthio-triazoloquinazoline derivatives and study their X-ray, NMR, DFT and Hirshfeld characteristics. The cyclocondensation of dimethyl-N-cyanodithiocarbonate with 2-hydrazinobenzoic acid hydrochloride resulted in an intermediate, 2-methylthio-[1,2,4]triazolo[1,5-a]quinazolin-5-one (A), which upon treatment with phosphorus pentasulfide, transformed into the 2-methylthio-[1,2,4]triazolo[1,5-a]quinazolin-5-thione (B). Reaction of 2-methylthio-triazoloquinazolines (A&B) with alkyl halides (allyl bromide and ethyl iodide) in basic medium afforded 4-allyl-2-methylthio-[1,2,4]triazolo[1,5-a]quinazolin-5-one (1; N-alkylated) and 5-ethylthio-2-methylthio-[1,2,4]triazolo[1,5-a]quinazoline (2; S-alkylated), respectively. Their molecular and supramolecular structures were presented. Unambiguously, the molecular structures of 1 and 2 were confirmed via NMR and single-crystal X-ray diffraction. The resulting findings confirmed the structures of 1 and 2 and determined their crystalized system (monoclinic system; P21/n space group). Hirshfeld analysis of 1 revealed the importance of the significantly short O···H (6.7%), S···S (1.2%) and C···C (2.8%); however, the short H···H (42.6%), S···H (16.3%) and C···C (4.3%) were showed in 2 by intermolecular interactions in the molecular packing. The 1,2,4-triazoloquinzolines (1&2) were anticipated to be relatively polar compounds with net dipole moments of 2.9284 and 4.2127 Debye, respectively. The molecular electrostatic potential, atomic charge distribution maps and reactivity descriptors for 1 and 2 were also determined. The calculated nuclear magnetic resonance spectra of the targets 1 and 2 were well correlated with the experimental data.

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Pachuta-Stec, Anna, Urszula Kosikowska, Anna Chodkowska, Monika Pitucha, Anna Malm, and Ewa Jagiełło-Wójtowicz. "Biological Activity of Novel N-Substituted Amides of endo-3- (3-Methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene-2- carboxylic Acid and N-Substituted Amides of 1-(5-Methylthio- 1,2,4-triazol-3-yl)cyclohexane-2-carboxylic Acids." Zeitschrift für Naturforschung C 67, no. 3-4 (April 1, 2012): 123–28. http://dx.doi.org/10.1515/znc-2012-3-403.

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N-Substituted amides of endo-3-(3-methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene- 2-carboxylic acid and 1-(5-methylthio-1,2,4-triazol-3-yl)cyclohexane-2-carboxylic acid were prepared by the condensation reaction of endo-S-methyl-N1-(bicyclo[2.2.1]hept-5-ene-2,3- dicarbonyl)isothiosemicarbazide and S-methyl-N1-(cyclohexane-2,3-dicarbonyl)isothiosemicarbazide with primary amines. The synthesized compounds were screened for their microbiological and pharmacological activities

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22

Al-Sheikh, Ahmad, Kamal Sweidan, Bassam Sweileh, Manfred Steimann, Hartmut Schubert, and Norbert Kuhn. "Synthesis and Crystal Structure of Triethylammonium 5-[(2,2-Dimethyl- 4,6-dioxo-1,3-dioxan-5-ylidene)(methylthio) methyl]-1,3-dimethylpyrimidine- 2,4,6-trionate." Zeitschrift für Naturforschung B 63, no. 8 (August 1, 2008): 1020–22. http://dx.doi.org/10.1515/znb-2008-0817.

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Triethylammonium 5-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan- 5-ylidene)(methylthio)methyl]-1,3-dimethylpyrimidine- 2,4,6-trionate (6) is obtained as red-orange stable crystals by reaction of 5-[bis(methylthio)methylene]-2,2-dimethyl- 1,3-dioxane-4,6-dione (5) with 1,3-dimethylbarbituric acid (2) in the presence of triethylamine in excellent yield. The crystal structure of 6 confirms the negative charge to be localized at the barbituric-acid ring in its enolate form.

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23

Puranik, V. G., S. S. Tavale, T. N. Guru Row, P. Umapathy, and A. P. Budhkar. "Structure of 5-methylthio-1,3,4-thiadiazole-2-thione." Acta Crystallographica Section C Crystal Structure Communications 42, no. 5 (May 15, 1986): 593–95. http://dx.doi.org/10.1107/s0108270186095276.

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24

Pomés Hernández, R., J. Duque Rodríguez, M. I. García Trimiño, H. Novoa de Armas, and R. A. Toscano. "6-Methylamino-4-methylthio-5-nitro-2-phenylpyrimidine." Acta Crystallographica Section C Crystal Structure Communications 51, no. 7 (July 15, 1995): 1392–94. http://dx.doi.org/10.1107/s0108270194013831.

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25

Sun, Yi, Wenfei Huang, Zhiqiang Li, Tao Wang, and Jin Luo. "Design, synthesis, and herbicidal activity of novel 2-(arylamino)-5-methyl-4-methylene-7-(methylthio)-4H-pyrido[4,3-d][1,3]oxazine-8-carbonitrile derivatives." Journal of Chemical Research 43, no. 3-4 (March 2019): 119–23. http://dx.doi.org/10.1177/1747519819845771.

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A series of 5-methyl-4-methylene-7-methylthio-2-arylmino-4 H-pyrido[4,3- d][1,3]oxazine-8-carbonitrile derivatives were synthesized via tandem aza-Wittig and annulation reactions with { N-[3-acetyl-5-cyano-2-methyl-6-(methylthio)pyridin-4-yl]imino}triphenylphosphorane and aryl isocyanate in dry dichloromethane. Their structures were clearly confirmed by infrared, 1H NMR, 13C NMR, high-resolution mass spectrometry, and X-ray single-crystal diffraction. All newly synthesized compounds were screened for herbicidal activities against monocotyledonous and dicotyledonous plants. The results indicated that the target compound 2-[(4-methoxyphenyl)amino]-5-methyl-4-methylene-7-(methylthio)-4 H-pyrido[4,3- d][1,3]oxazine-8-carbonitrile showed 100% inhibition rate to grain sorghum (monocotyledonous) at the concentration of 100 mg L−1.

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Dölling, Wolfgang, Kerstin Friedemann, Frank Heinemann, and Helmut Hartung. "Synthese von 5-Methylthio-2-thioxo-1,3-dithiol-4-carbonsäureamiden und -thiolestern, 3-Alkyl-5-bis(alkylthio)methylen-2-thioxo-1,3-thiazol-4(5 H)-onen sowie Röntgenkristallstrukturanalyse des 5-Methylthio-2-thioxo-1,3-dithiol-4-carbonsäure-(N-methyl-anilids) / Synthesis of 5-Methylthio-2-thioxo-1,3-dithiole-4-carboxamides and -thiolesters, 3-Alkyl-5-bis(alkylthio)methylene-2-thioxo-1,3-thiazole-4(5 H)-ones, and X-ray Analysis of 5-Methylthio-2-thioxo-1,3-dithiole-4-carboxyl N-methyl-anilide." Zeitschrift für Naturforschung B 46, no. 9 (September 1, 1991): 1251–57. http://dx.doi.org/10.1515/znb-1991-0919.

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5-Methylthio-2-thioxo-1,3-dithiole-4-carboxamides (2a–e), the methyl 5-methylthio-2-thioxo-1,3-dithiole-4-carboxythiolate (9), and 3-alkyl-5-bis(alkylthio)methylene-2-thioxo-1,3-thiazole-4(5 H)-ones (4a–f) are obtained by reaction of the corresponding N-substituted ethylxanthogen-acetamides (1, 3, 6) with carbon disulfide under basic conditions followed by alkylation.5-Methylthio-2-thioxo-1,3-dithiole-4-carboxyl N-methyl-anilide (2d) was characterized by an X-ray crystal structure determination (space group P 1̄, a = 877.3(1), b = 1111.1(2), c = 837.6(1) pm, α = 104.22(2), β = 110.41(1), γ = 69.64(2)°, Ζ = 2, R = 0.039 for 1746 observed unique reflections).The α-oxoketene dithioacetal moiety of the molecule exhibits a noticeable derivation from planarity by a twist of the carbonyl group out of the ethylene plane and shows a short intramolecular S ··· O contact of 277.1 (3) pm.

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27

Kalogirou, Andreas S., and Panayiotis A. Koutentis. "(Z)-2-{[(4-Chloro-5H-1,2,3-dithiazol-5-ylidene)amino](methylthio)methylene}malononitrile." Molbank 2022, no. 1 (March 13, 2022): M1354. http://dx.doi.org/10.3390/m1354.

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Reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with 2-[amino(methylthio)methylene])malononitrile (1 equiv) in the presence of pyridine (2 equiv) gave (Z)-2-{[(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino](methylthio)methylene}malononitrile in 20% yield. The compound was fully characterized.

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28

Jacobsen, NW, and SE Rose. "1,2,4-Triazines. 1. The Use of C-13 Nuclear-Magnetic-Resonance Spectroscopy to Determine the Methylation Products of 3-Methylthio-1,2,4-Triazin-5(2h)-One." Australian Journal of Chemistry 38, no. 12 (1985): 1809. http://dx.doi.org/10.1071/ch9851809.

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Carbon-13 nuclear magnetic resonance spectroscopy utilizing both proton coupled and decoupled spectra has been found to be a useful method to determine unequivocally the sites of methylation in the 1,2,4-triazine series. Specifically, the method identified the methylation products of 3-methylthio-1,2,4-triazin-5(2H)-one as the new zwitterion 1-methyl-3- methylthio-1,2,4-triazinium-5-olate and the previously reported N2, N4- and O-methyl isomers.

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29

Grześkiewicz, Anita M., Tomasz Stefański, Zbigniew Dutkiewicz, and Maciej Kubicki. "Weak intermolecular interactions in a series of biologically active 4′-methylthio-trans-stilbenes." Acta Crystallographica Section C Structural Chemistry 78, no. 2 (January 25, 2022): 107–15. http://dx.doi.org/10.1107/s2053229622000420.

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The crystal structures of nine methoxy-substituted 4′-methylthiostilbenes, which are potential inhibitors of human recombinant cytochrome P450 enzymes, were determined. These compounds included two mono-methoxy-substituted derivatives: 2-methoxy-4′-methylthio-trans-stilbene {systematic name: 1-[(E)-2-(2-methoxyphenyl)ethenyl]-4-(methylsulfanyl)benzene} (1) and 3-methoxy-4′-methylthio-trans-stilbene (2), both C16H16OS; four dimethoxy derivatives: 2,3-dimethoxy-4′-methylthio-trans-stilbene (3), 2,5-dimethoxy-4′-methylthio-trans-stilbene (4), 3,5-dimethoxy-4′-methylthio-trans-stilbene (5) and 2,4-dimethoxy-4′-methylthio-trans-stilbene (6), all C17H18O2S; and three trimethoxy compounds: 2,4,5-trimethoxy-4′-methylthio-trans-stilbene (7), 3,4,5-trimethoxy-4′-methylthio-trans-stilbene (8) and 2,4,6-trimethoxy-4′-methylthio-trans-stilbene (9), all C18H20O3S. The geometries of the compounds in the crystal structures were compared with those found during docking studies at the active site of the receptor, and some relevant differences were identified. Intermolecular interactions were analyzed using three different methods. First, the (3,−1) critical points of the gradient field of the electron density were identified, and then the appropriate contacts were analyzed using their geometrical characteristics and interaction energy calculations. The results confirmed the importance of weak delocalized interactions in the construction of the crystal structures, and the results of different methods (PIXEL and DFT) were comparable in the absence of strong well-defined intermolecular interactions.

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30

Sufrin, Janice R., Arthur J. Spiess, Debora L. Kramer, Paul R. Libby, and Carl W. Porter. "Synthesis and antiproliferative effects of novel 5'-fluorinated analogs of 5'-deoxy-5'-(methylthio)adenosine." Journal of Medicinal Chemistry 32, no. 5 (May 1989): 997–1001. http://dx.doi.org/10.1021/jm00125a012.

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31

North, Justin A., Anthony R. Miller, John A. Wildenthal, Sarah J. Young, and F. Robert Tabita. "Microbial pathway for anaerobic 5′-methylthioadenosine metabolism coupled to ethylene formation." Proceedings of the National Academy of Sciences 114, no. 48 (November 13, 2017): E10455—E10464. http://dx.doi.org/10.1073/pnas.1711625114.

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Numerous cellular processes involvingS-adenosyl-l-methionine result in the formation of the toxic by-product, 5′-methylthioadenosine (MTA). To prevent inhibitory MTA accumulation and retain biologically available sulfur, most organisms possess the “universal” methionine salvage pathway (MSP). However, the universal MSP is inherently aerobic due to a requirement of molecular oxygen for one of the key enzymes. Here, we report the presence of an exclusively anaerobic MSP that couples MTA metabolism to ethylene formation in the phototrophic bacteriaRhodospirillum rubrumandRhodopseudomonas palustris. In vivo metabolite analysis of gene deletion strains demonstrated that this anaerobic MSP functions via sequential action of MTA phosphorylase (MtnP), 5-(methylthio)ribose-1-phosphate isomerase (MtnA), and an annotated class II aldolase-like protein (Ald2) to form 2-(methylthio)acetaldehyde as an intermediate. 2-(Methylthio)acetaldehyde is reduced to 2-(methylthio)ethanol, which is further metabolized as a usable organic sulfur source, generating stoichiometric amounts of ethylene in the process. Ethylene induction experiments using 2-(methylthio)ethanol versus sulfate as sulfur sources further indicate anaerobic ethylene production from 2-(methylthio)ethanol requires protein synthesis and that this process is regulated. Finally, phylogenetic analysis reveals that the genes corresponding to these enzymes, and presumably the pathway, are widespread among anaerobic and facultatively anaerobic bacteria from soil and freshwater environments. These results not only establish the existence of a functional, exclusively anaerobic MSP, but they also suggest a possible route by which ethylene is produced by microbes in anoxic environments.

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32

Jenny, Christjohannes, Roland Prewo, Jost H. Bieri, and Heinz Heimgartner. "Synthese von (Methylthio)penam-Derivaten durch Keten-Addition an 4,5-Dihydro-5-(methylthio)-1,3-thiazole." Helvetica Chimica Acta 69, no. 6 (September 10, 1986): 1424–34. http://dx.doi.org/10.1002/hlca.19860690615.

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33

Chanda, Kaushik, Milan Dutta, Kaushal Kishore, and J. Vishwakarma. "Bis-(1-phenyl-5-nitro-6-methylthio-1,2,3,4-tetrahydropyrimidinyl)ethane and Bis-(1-phenyl-5-nitro-6-methylthio-1,2,3,4-tetrahydropyrimidinyl)butane." Molbank 2004, no. 1 (February 24, 2004): M367. http://dx.doi.org/10.3390/m367.

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34

Dutta, Milan, Kaushik Chanda, Kaushal Kishore, and J. N. Vishwakarma. "Bis-(1-phenyl-5-nitro-6-methylthio-1,2,3,4-tetrahydropyrimidinyl)benzene and Bis-(1-phenyl-5-nitro-6-methylthio-1,2,3,4-tetrahydropyrimidinyl)diphenyl." Molbank 2005, no. 3 (August 1, 2005): M428. http://dx.doi.org/10.3390/m428.

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35

Yates, Peter, Azza Seif-El-Nasr, Jennifer Stanton, and Jiri J. Krepinsky. "Reactions of δ-valerolactone with lithio trithio-orthoformates." Canadian Journal of Chemistry 69, no. 3 (March 1, 1991): 415–22. http://dx.doi.org/10.1139/v91-063.

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δ-Valerolactone (3), on treatment with tris(methylthio)methyllithium (7) followed by weakly acidic aqueous work-up, gave a tautomeric mixture of 1, 1-bis(methylthio)-6-hydroxy-2-hexanone (8a) and tetrahydro-2-bis(methylthio)methyl-2-pyranol (8b). Under analogous conditions 3 reacted with tris(phenylthio)methyllithium (10) to form tetrahydro-3-(phenylthiocarbonyl)-2-pyranone (11). With 2-(methylthio)-1,3-dithian-2-yllithium (16) it gave a tautomeric mixture of 2-(5-hydroxy-1-oxopentyl)-2-(methylthio)-1,3-dithiane (17a) and 2-(tetrahydro-2-hydroxy-2-pyranyl)-2-(methylthio)-1,3-dithiane (17b). Treatment of 17 with methanol in the presence of acidic ion-exchange resin gave a mixture of 2-(5,6-dihydro-3-(methylthio)-2(4H)-pyranyl)-1,3-dithiane (20), 2-(tetrahydro-2-methoxy-2-pyranyl)-1,3-dithiane (21), and 2-(tetrahydro-2-methoxy-4-(methylthio)-2-pyranyl)-1,3-dithiane (22). Similar treatment of 20 gave a mixture of 20, 21, and 22. Compound 21 was synthesized independently by similar treatment of 2-(tetrahydro-2-hydroxy-2-pyranyl)-1,3-dithiane (23). The origins of the anomalous products are discussed briefly. It is concluded that because of these anomalies the preparation of tetrahydro-2-hydroxypyran-2-carboxylic acid acetals and related glycosides via trithio-orthoformate derivatives can encounter difficulties, although dithioacetals may serve this purpose. Key words: 1,3-dithianes, α-hydroxy acids,δ-lactones, trithio-orthoformates.

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36

Chovatia, P. T., J. D. Akabari, P. K. Kachhadia, P. D. Zalavadia, and H. S. Joshi. "Synthesis and selective antitubercular and antimicrobial inhibitory activity of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazole derivatives." Journal of the Serbian Chemical Society 71, no. 7 (2006): 713–20. http://dx.doi.org/10.2298/jsc0607713c.

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The new compounds 1-aryl-3-{1-phenyl-3-[p (methylthio)phenyl]pyrazol-4-yl}-2-propen-1-ones 2a?l were prepared by the condensation of 1-phenyl-3-[p (methylthio)phenyl]-4-formylpyrazole 1 with different aryl ketones. Compounds 2a?l in reaction with hydrazine hydrate yielded 3-aryl-5-{1-phenyl-3-[p-(methylthio)phenyl]pyrazol-4 yl}-4,5-dihydro-(1H)-pyrazoles 3a?l and in the presence of hydrazine hydrate in glacial acetic acid gave 1-acetyl-3-aryl 5-{1-phenyl-3-[p-(methylthio)phenyl]pyrazol-4-yl}-4,5 dihydro-(1H)-pyrazoles 4a?l. These compounds were tested in vitro for their antitubercular and antimicrobial activities. The in vitro antimycobacterial activity of the newly synthesized compounds was investigated against Mycobacterium tuberculosis H37RV (ATCC 27294) in BACTEC 12B medium using the ALAMAR radiometric system. The antimicrobial in vitro activity was tested against Bacillus coccous, Bacillus subtilis Escherichia coli, Proteus vulgaris and antifungal activity against Aspergillus niger. The structures of the synthesized compounds were assigned on the basis of elemental analysis IR, 1H NMR and mass spectral data.

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37

Harnden, MR, and DT Hurst. "The Synthesis and Chlorination of Some Pyrimidin-4-ols Having 5-Nitrogen Functionality." Australian Journal of Chemistry 43, no. 1 (1990): 47. http://dx.doi.org/10.1071/ch9900047.

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Syntheses of a number of pyrimidin-4-ols having 5-nitrogen functionality are described. Phosphorus oxychloride/diethylaniline chlorination of 6-amino-2-methylthio-5-nitropyrimidin-4-ol gave the corresponding 6-chloro derivative. However, 2-amino-6-methylthio-5-nitropyrimidin-4-ol failed to yield a 4-chloro derivative under the same conditions. Similar chlorination of 2,5-diaminopyrimidine-4,6-diol gave a poor yield of the 4,6-dichloro product but under these conditions 2-amino-5-benzoylaminopyrimidine-4,6-diol* gave 7-chloro-2-phenyloxazolo[5,4-d]pyrimidin-5-amine. 5-Acetylamino-2-methylthiopyrimidine-4,6-diol yielded 7-chloro-2- methyl-5-methylthiooxazolo[5,4-d] pyrimidine as the major product together with some 5-acetylamino-4,6-dichloro-2-methylthiopyrimidine under the same chlorination conditions.

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38

Li, Yuhao, Shixiong Deng, Pengfei Cai, Chenyun Wang, Han Wang, and Yongjia Shen. "Synthesis, electropolymerization, and electrochromic performances of two novel tetrathiafulvalene–thiophene assemblies." e-Polymers 20, no. 1 (July 20, 2020): 382–92. http://dx.doi.org/10.1515/epoly-2020-0044.

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Abstract6,7-Bis(hexylthio)-2-[(2-hydroxyethyl)thio]-3-methylthio-tetrathiafulvalene (TTF-2) is coupled with thiophene-3-carboxylic acid and thiophene-3,4-dicarboxylic acid by Steglich esterification, respectively, to afford 2-((4′,5′-bis(hexylthio)-5-(methylthio)-[2,2′-bi(1,3-dithiolylidene)]-4-yl)thio)ethyl thiophene-3-carboxylate (TTF-Th) and bis(2-((4′,5′-bis(hexylthio)-5-(methylthio)-[2,2′-bi(1,3-dithiolylidene)]-4-yl)thio)ethyl)thiophene-3,4-di-carboxylate (DTTF-Th). Their structures were characterized by ESI-MS, 1H NMR, and elemental analysis. Electropolymerization of TTF-Th and DTTF-Th was conducted with 0.1 M n-Bu4NPF6. The results indicated that both assemblies could rapidly form polymers via electrochemical deposition. In addition, their electrochromic performances illustrated that the color of P(TTF-Th) could switch from orange-yellow to dark blue, while P(DTTF-Th) changed its color from orange in the neutral state to dark blue in the oxidation state. Moreover, the electrochromic performances of P(DTTF-Th) were better than P(TTF-Th) due to the introduction of one extra TTF unit.

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39

Zanatta, Nilo, Adriano F. Camargo, Mário A. Marangoni, Paulo A. de Moraes, Pablo A. Nogara, Blessing A. Afolabi, Carlos E. Bencke, João B. T. Rocha, Helio G. Bonacorso, and Marcos A. P. Martins. "Regioselective Synthesis of Pyrazolyl-pyrimidine Hybrids of Pharmacological Interest." Synthesis 52, no. 16 (May 12, 2020): 2347–56. http://dx.doi.org/10.1055/s-0040-1707948.

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The regioselective synthesis of twenty novel [3-substituted 5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl][6-aryl-(2-methylthio)pyrimidin-4-yl]methanones from the cyclocondensation reactions of new 6-aryl-2-(methylthio)pyrimidine-4-carbohydrazides with 4-substituted 1,1,1-trifluorobut-3-en-2-ones is reported. Human acetylcholinesterase (HsAChE) and butyrylcholinesterase (HsBChE) inhibition tests were performed on selected products in order to explore the possible pharmacological applications of these compounds. Two compounds showed significant and selective inhibitory activity for BChE.

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40

Jamison, Matthew T., Christopher N. Boddy, and Tadeusz F. Molinski. "Salvadenosine, a 5′-Deoxy-5′-(methylthio) Nucleoside from the Bahamian Tunicate Didemnum sp." Journal of Organic Chemistry 79, no. 21 (October 20, 2014): 9992–97. http://dx.doi.org/10.1021/jo501486p.

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41

Heffner, Robert J., and Madeleine M. Joullié. "Synthetic Routes to Ninhydrins. Preparation of Ninhydrin, 5-Methoxyninhydrin, and 5-(Methylthio)Ninhydrin." Synthetic Communications 21, no. 21 (November 1991): 2231–56. http://dx.doi.org/10.1080/00397919108055457.

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42

Abass, Mohamed, Mostafa Ismail, Wafaa Abdel-Monem, and Aisha Mayas. "Substituted pyridopyrimidinones, Part IV: 2-chloro-4h-pyrido[1,2-a]pyrimidin-4-one as a synthone of some new heterotricycles." Journal of the Serbian Chemical Society 75, no. 1 (2010): 11–17. http://dx.doi.org/10.2298/jsc1001011a.

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2-Chloro-4H-pyrido[1,2-a]pyrimidin-4-one (1) was utilized as a synthone precursor to prepare novel heterotricyclic systems. 2-Azido and 2-hydrazino derivatives (2 and 3) were obtained by nucleophilic replacement evolving compound 1. The hydrazine derivative 3 was transformed into the azido derivative 2 by nitrosation. Treatment of compound 3 with [bis(methylthio)methylene] malononitrile afforded 2-pyrazolylpyridopyrimidine 4. When compound 1 was reacted with 5-amino-3-(methylthio)-1H-pyrazole-4-carbonitrile, the same compound 4 was obtained with no evidence for the production of (pyrazolylamino) pyridopyrimidine 5 or pyrazolodipyridopyrimidine 6. Poly-functionalized dipyridopyrimidine 8 was obtained by reaction of compound 1 with 2-[(methylthio)-( phenylamino)methylene]propanedinitrile. Cyanoguanidine was reacted with compound 1 to afford N-pyridopyrimidinylguanidine 9, which was subjected to cyclization reaction, in presence of piperidinium acetate, to give pyridopyrimidopyrimidine 10.

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43

Lynch, Doreen C., James R. Miller, and Terence D. Spawn. "A Convenient Synthesis Of 2-Methyl-5-(Methylthio)Benzothiazole." Synthetic Communications 27, no. 5 (March 1997): 897–905. http://dx.doi.org/10.1080/00397919708004210.

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44

Choi, Hong Dae, Dek Hyun Geum, Yong Sil Kowak, and Byeng Wha Son. "Synthesis of 7-[p-(methylthio)benzoyl]-5-benzofuranacetic acid." Archives of Pharmacal Research 16, no. 4 (December 1993): 343–46. http://dx.doi.org/10.1007/bf02977529.

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45

SINGH, O. M., H. JUNJAPPA, and H. ILA. "ChemInform Abstract: Synthesis of Novel 3-Cyano-4-methylthio-6-(arylcyclopropyl)-3-(1H)-pyridones and 5(3)-Methylthio-3(5)-(arylcyclopropyl)pyrazoles." ChemInform 29, no. 25 (June 22, 2010): no. http://dx.doi.org/10.1002/chin.199825168.

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46

Morabia, Anil R., and Yogesh T. Naliapara. "Simple and Efficient Three Component One-Pot Synthesis of Pyrazolo[1,5,a]Pyrimidines." International Letters of Chemistry, Physics and Astronomy 41 (November 2014): 73–81. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.41.73.

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A series of novel 5-(2-bromophenyl)-N-cyclohexyl-2-(methylthio)-6-nitro-7-phenyl-4,7-dihydropyrazolo [1,5-a] pyrimidine-3-carboxamides were synthesized by a one-pot reaction of 5-amino-N-cyclohexyl-3-(methylthio)-1H-pyrazole-4-carboxamide, 1-(2-bromophenyl)-2-nitroethanone and aryl aldehydes in the presence of boric acid in water at refluxing temperature. Structures of compounds were demonstrated by Fourier transform infrared, 1H NMR, 13C NMR and elemental analysis. The advantages of this method are mild reaction condition, good yields, and operational simplicity.

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47

Morabia, Anil R., and Yogesh T. Naliapara. "Simple and Efficient Three Component One-Pot Synthesis of Pyrazolo[1,5,<i>a</i>]Pyrimidines." International Letters of Chemistry, Physics and Astronomy 41 (November 4, 2014): 73–81. http://dx.doi.org/10.56431/p-9odl83.

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A series of novel 5-(2-bromophenyl)-N-cyclohexyl-2-(methylthio)-6-nitro-7-phenyl-4,7-dihydropyrazolo [1,5-a] pyrimidine-3-carboxamides were synthesized by a one-pot reaction of 5-amino-N-cyclohexyl-3-(methylthio)-1H-pyrazole-4-carboxamide, 1-(2-bromophenyl)-2-nitroethanone and aryl aldehydes in the presence of boric acid in water at refluxing temperature. Structures of compounds were demonstrated by Fourier transform infrared, 1H NMR, 13C NMR and elemental analysis. The advantages of this method are mild reaction condition, good yields, and operational simplicity.

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48

Al-Sheikh, Ahmed, Masuma Begum, Bian Zhang, Richard A. Lewis, Nicholas E. E. Allenby, Paul G. Waddell, and Bernard T. Golding. "Molecular Diversity via Tetrasubstituted Alkenes Containing a Barbiturate Motif: Synthesis and Biological Activity." Molecules 25, no. 24 (December 11, 2020): 5868. http://dx.doi.org/10.3390/molecules25245868.

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The synthesis of a molecularly diverse library of tetrasubstituted alkenes containing a barbiturate motif is described. Base-induced condensation of N1-substituted pyrimidine-2,4,6(1H,3H,5H)-triones with 5-(bis(methylthio)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione gave 3-substituted 5-(methylthio)-2H-pyrano[2,3-d]pyrimidine-2,4,7(1H,3H)-triones (‘pyranopyrimidinones’), regioselectively. A sequence of reactions involving ring-opening of the pyran moiety, displacement of the methylthio group with an amine, re-formation of the pyran ring, and after its final cleavage with an amine, gave tetrasubstituted alkenes (3-amino-3-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)propanamides) with a diversity of substituents. Cleavage of the pyranopyrimidinones with an aniline was facilitated in 2,2,2-trifluoroethanol under microwave irradiation. Compounds were tested against Escherichia coli, Staphylococcus aureus, the yeast Schizosaccharomyces pombe, and the pathogenic fungus Candida albicans. No compounds exhibited activity against E. coli, whilst one compound was weakly active against S. aureus. Three compounds were strongly active against S. pombe, but none was active against C. albicans.

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49

El-Gokha, Ahmed, Francesco Ansideri, Stanislav Andreev, Dieter Schollmeyer, Stefan Laufer, and Pierre Koch. "N1-{4-[2-(Methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine." Molbank 2019, no. 1 (February 20, 2019): M1048. http://dx.doi.org/10.3390/m1048.

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The title compound N1-{4-[2-(methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine (2) was synthesized via nucleophilic aromatic substitution of 2-chloro-4-[2-(methylthio)-1H-imidazol-5-yl]pyridine (3) and p-phenylenediamine under acidic conditions. The synthesized compound 2 was characterized by 1H-NMR, 13C-NMR, MS HPLC, IR and UV-VIS. Additionally, the structure of 2 was confirmed by single crystal X-ray diffraction. Pyridinylimidazole 2 displays moderate affinity towards the c-Jun N-terminal kinase 3 and shows selectivity versus the closely related p38α mitogen-activated protein kinase.

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50

Al-Sheikh, Ahmad, Kamal Sweidan, Norbert Kuhn, Cäcilia Maichle-Mößmer, and Manfred Steimann. "Elimination of a Thiomethyl Substituent from an Anionic 5-Methylenebarbituric Acid Derivative by Oxidation and Substitution." Zeitschrift für Naturforschung B 64, no. 3 (March 1, 2009): 307–12. http://dx.doi.org/10.1515/znb-2009-0309.

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Triethylammonium 5-[(1,3-dimethyl-2,4,6-trioxo-tetrahydropyrimidin-5(6H)-ylidene)-(methylthio) methyl]-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate (5), obtained from 5-[bis (methylthio)methylene]-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione (2) and 1,3-dimethylbarbituric acid in the presence of triethylamine, is protonated by methanesulfonic acid to give 5,5ʹ-(methylthiomethanediylidene)bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) (6) in good yield. Compound 6 is oxidized in two steps by m-chloroperbenzoic acid to give 5,5ʹ- (methylsulfinylmethanediylidene)bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) (7) and 5-[(1,3-dimethyl-2,4,6-trioxo-tetrahydropyrimidin-5(6H)-ylidene)(methylsulfinyl)methyl]-5-hydroxy- 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (8), respectively. Excess pyridine eliminates methanesulfinic acid from 8 to give the zwitterionic 5-[(1,3-dimethyl-2,4,6-trioxo-tetrahydropyrimidin- 5(6H)-ylidene(pyridinium-1-yl)methyl]-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin- 4-olate (9). The crystal structures of compounds 6, 8, and 9 are reported.

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