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Journal articles on the topic 'Synthesis of thioamide'

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Published: 18 May 2024

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1

Dong, Zhi-Bing, Meng-Tian Zeng, Min Wang, Han-Ying Peng, and Yu Cheng. "Copper-Catalyzed Synthesis of Aryl Thioamides from Aryl Aldehydes and Tetramethylthiuram Disulfide." Synthesis 50, no. 03 (October 12, 2017): 644–50. http://dx.doi.org/10.1055/s-0036-1590936.

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A novel and convenient method for the synthesis of aryl thioamides from aryl aldehydes and tetramethylthiuram disulfide (TMTD) without the use of sulfurating reagent was explored. In the presence of CuI and di-tert-butyl peroxide (DTBP), various aryl thioamides were prepared with good to excellent yields, tetramethylthiuram disulfide as thioamide source is essential for this transformation. The protocol features broad substrate scope, nice yields, operability and commercially available and inexpensive raw materials, showing its practical synthetic value in organic synthesis.

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2

Sauvé, Gilles, Vanga S. Rao, Gilles Lajoie, and Bernard Belleau. "Backbone-modified oligopeptidic bioregulators. The synthesis and configuration of thioamide, amidoxime, cyanoamidine, and amidrazone analogs of the chemotactic peptide N-formyl-methionyl-leucyl-phenylalanine (f-Met-Leu-Phe-OR)." Canadian Journal of Chemistry 63, no. 11 (November 1, 1985): 3089–101. http://dx.doi.org/10.1139/v85-511.

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Reaction conditions for the synthesis of thioamide, amidoxime, and N-substituted amidine analogs of the peptide bond are described. Several new amidine analogs of the chemotactic peptide f-Met-Leu-Phe-OR were synthesized using the thioamides as precursors. The assignment of the E/Z configuration was accomplished by nuclear magnetic resonance. The biological activity of these analogs is briefly described.

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3

Fong, Mei, Wit K. Janowski, Rolf H. Prager, and Max R. Taylor. "A Convenient Synthesis of 2-Substituted Thiazole-5-carboxylates." Australian Journal of Chemistry 57, no. 6 (2004): 599. http://dx.doi.org/10.1071/ch03252.

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The photolysis of ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxylate in acetonitrile containing 0.5% tri- fluoroacetic acid in the presence of thioamides gives moderate (40–60%) yields of thiazole-5-carboxylate esters. In the absence of trifluoroacetic acid, the intermediate vinyl thioesters can be isolated. That addition of the thioamide to the first formed carbene was, through sulfur, confirmed by X-ray crystal structures of 2-methylthiazole-5-carboxylic acid and a byproduct.

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4

Szantai-Kis, D., Christopher Walters, Taylor Barrett, Eileen Hoang, and E. Petersson. "Thieme Chemistry Journals Awardees – Where Are They Now? Improved Fmoc Deprotection Methods for the Synthesis of Thioamide-Containing Peptides and Proteins." Synlett 28, no. 14 (May 19, 2017): 1789–94. http://dx.doi.org/10.1055/s-0036-1589027.

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Site-selective incorporation of thioamides into peptides and proteins provides a useful tool for a wide range of applications. Current incorporation methods suffer from low yields as well as epimerization. Here, we describe how the use of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) rather than piperidine in fluorenylmethyloxycarbonyl (Fmoc) deprotection reduces epimerization and increases yields of thioamide-containing peptides. Furthermore, we demonstrate that the use of DBU avoids byproduct formation when synthesizing peptides containing side-chain thioamides.

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5

Zhang, Qiang, Laurent Soulère, and Yves Queneau. "Towards More Practical Methods for the Chemical Synthesis of Thioamides Using Sulfuration Agents: A Decade Update." Molecules 28, no. 8 (April 17, 2023): 3527. http://dx.doi.org/10.3390/molecules28083527.

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Compounds possessing a thioamide function play a crucial role in organic synthesis, serving as key building blocks. They are also important in the pharmaceutical chemistry and drug design, owing to their ability to mimic the amide function in biomolecules while retaining or developing biological activity. From the synthetic viewpoint, several methods have been developed for preparing thioamides using sulfuration agents. The purpose of this review is to give an update of the last decade of contributions focusing on the formation of thioamides employing different sulfur sources. When appropriate, the cleanness and practicality of the new methods are highlighted.

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6

Pham Xuan Thao. "Study on the synthesis of thioamides from aldehyde N-tert-butylsulfinyl amide and sulfur in aqueous media." Journal of Military Science and Technology, no. 76 (December 12, 2021): 54–60. http://dx.doi.org/10.54939/1859-1043.j.mst.76.2021.54-60.

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Thioamides have been widely used in the fields of medicine and organic chemistry, some of which are essential bioactive compounds, plant protection agents, and drugs. It could also be used as a vulcanizing agent, an additive to lubricants and greases, and a ligand in organic synthesis. Usually, thioamide is synthesized at high temperatures or in the microwave using an expensive noble metal complex as catalysts. This paper presented a straightforward method for synthesizing thioamides by using N-tert-butylsulfinyl amide, aldehyde, and sulfur. The reaction was carried out in water, which is an environmentally friendly solvent. The reaction selectivity and yield were up to 89%.

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7

Hammam, A. S., and B. E. Bayoumy. "Reaction of thioamides with 2,3-dichloro-1,4-naphthoquinone. A novel synthesis of naphtho[2,3-d]thiazole-4,9-diones." Collection of Czechoslovak Chemical Communications 50, no. 1 (1985): 71–79. http://dx.doi.org/10.1135/cccc19850071.

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The reaction of thioamide II with 2,3-dichloro-1,4-naphthoquinone (I) in ethanol gave naptho[2,3-d]thiazole-4,9-diones (IV). The intermediates, 2-thioamido-3-chloro-1,4-naphthoquinones III were also isolated from the reaction medium and could be separately transformed to IV by further boiling in aqueous ethanol containing bicarbonate. The reaction of thiosemicarbazide with I under similar conditions gave naphtho[2,3-e]-2-amino-4H-1,3,4-thiadiazine-5,10-dione (VII).

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8

Sharma, Shubham, Dharmender Singh, Sunit Kumar, Vaishali, Rahul Jamra, Naveen Banyal, Deepika, Chandi C. Malakar, and Virender Singh. "An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides." Beilstein Journal of Organic Chemistry 19 (March 2, 2023): 231–44. http://dx.doi.org/10.3762/bjoc.19.22.

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An operationally simple and metal-free approach is described for the synthesis of pyrazole-tethered thioamide and amide conjugates. The thioamides were generated by employing a three-component reaction of diverse pyrazole C-3/4/5 carbaldehydes, secondary amines, and elemental sulfur in a single synthetic operation. The advantages of this developed protocol refer to the broad substrate scope, metal-free and easy to perform reaction conditions. Moreover, the pyrazole C-3/5-linked amide conjugates were also synthesized via an oxidative amination of pyrazole carbaldehydes and 2-aminopyridines using hydrogen peroxide as an oxidant.

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9

Yeo, Chien, and Edward Tiekink. "O-Methyl m-Tolylcarbamothioate." Molbank 2018, no. 3 (September 15, 2018): M1020. http://dx.doi.org/10.3390/m1020.

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The synthesis, spectroscopic, and crystallographic characterisation of the title compound, O-methyl m-tolylcarbamothioate, MeOC(=S)N(H)(m-tolyl) (1), are described. The crystallographic study confirms the structure determined by spectroscopy and shows the presence of the thioamide tautomer, a syn-disposition of the thione-S and thioamide-N-H atoms and, in the crystal, thioamide-N-H…S(thione) hydrogen bonding leading to an eight-membered {…HNCS}2 synthon.

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10

Cakmak, M., I. I. Ozturk, C. N. Banti, M. Manoli, E. Moushi, A. J. Tasiopoulos, A. M. Grześkiewicz, M. Kubicki, and S. K. Hadjikakou. "Bismuth(III) bromide-thioamide complexes: synthesis, characterization and cytotoxic properties." Main Group Metal Chemistry 41, no. 5-6 (November 27, 2018): 143–54. http://dx.doi.org/10.1515/mgmc-2018-0035.

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Abstract New bismuth(III) bromine compounds of the heterocyclic thioamides were prepared and structurally characterized. The reaction of heterocyclic thioamides with bismuth(III) bromide resulted in the formation of the {[BiBr2(μ2-Br)(MMI)2]2·CH3COCH3·H2O} (1), {[BiBr2(MBZIM)4]·Br·2H2O} (2), {[BiBr2(μ2-Br)(tHPMT)2]2·CH3CN} (3), {[BiBr2(μ2-Br)(PYT)2]2·CH3CN} (4) and {[BiBr2(μ2-Br)(MBZT)2]2 2CH3OH} (5) complexes (MMI: 2-mercapto-1-methylimidazole, MBZIM: 2-mercaptobenzimidazole, tHPMT: 2-mercapto-3,4,5,6-tetrahydro-pyrimidine, PYT: 2-mercaptopyridine and MBZT: 2-mercaptobenzothiazole). The complexes 1–5 were characterized by melting point (m.p.), elemental analysis (e.a.), molar conductivity, Fourier-transform infrared (FT-IR), Fourier-transform Raman (FT-Raman), nuclear magnetic resonance (1H and 13CNMR) spectroscopy, UV-Vis spectroscopy and thermogravimetric-differential thermal analysis (TG-DTA). The molecular structures of 1–5 were determined by single-crystal X-ray diffraction. Complex 2 is a first ionic monomuclear octahedral bismuth(III) bromide, while the complexes 1, 3–5 are the first examples of dinuclear bismuth(III) bromide derivatives. Complexes 1–5 were evaluated in terms of their in vitro cytotoxic activity against human adenocarcinoma breast (MCF-7) and cervix (HeLa) cells. The toxicity on normal human fetal lung fibroblast cells (MRC-5) was also evaluated. Moreover, the complexes 1–5 and free heterocyclic thioamide ligands were studied upon the catalytic peroxidation of the linoleic acid by the enzyme lipoxygenase (LOX).

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11

Kumagai, Naoya, Masakatsu Shibasaki, Yuya Ota, and Zhao Li. "Catalytic Asymmetric Synthesis of syn Aldols with Methyl Ketone Functionality and anti Aldols with a Thioamide Group." Synlett 30, no. 05 (February 13, 2019): 620–24. http://dx.doi.org/10.1055/s-0037-1610690.

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Catalytic asymmetric syntheses of syn aldols with a methyl ketone functionality were studied to confirm the generality of the methodology. In addition, catalytic asymmetric synthesis of anti aldols with a thioamide group was carefully examined, giving the desired products, albeit with moderate diastereoselectivity.

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12

Valdez-Rojas, José Ernesto, Hulme Ríos-Guerra, Alma Leticia Ramírez-Sánchez, Guadalupe García-González, Cecilio Álvarez-Toledano, José Guadalupe López-Cortés, Rubén A. Toscano, and José Guillermo Penieres-Carrillo. "A study of the Willgerodt–Kindler reaction to obtain thioamides and α-ketothioamides under solvent-less conditions." Canadian Journal of Chemistry 90, no. 7 (July 2012): 567–73. http://dx.doi.org/10.1139/v2012-030.

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In this paper, the results obtained in the synthesis of thioamides and α-ketothioamides by a modification of the Willgerodt–Kindler reaction, under solvent-free and noncatalyst conditions using IR energy as a source of activation, are presented. The use of IR energy in these reactions has been shown to lead to a mixture of thioamide and α-ketothioamide as the main products in most cases, with the latter predominating. The yields of α-ketothioamides from most of these reactions are better than those reported previously. To the best of our knowledge, this is the first time that IR energy has been applied to promote the Willgerodt–Kindler reaction.

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13

Ranskiy, Anatoliy, and Natalia Didenko. "Direct Synthesis of Cuprum(II) Complex Compounds Based on Thioamide Ligands." Chemistry & Chemical Technology 8, no. 4 (December 5, 2014): 371–78. http://dx.doi.org/10.23939/chcht08.04.371.

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14

Wang, Yanxin J., D. Miklos Szantai-Kis, and E. James Petersson. "Semi-synthesis of thioamide containing proteins." Organic & Biomolecular Chemistry 13, no. 18 (2015): 5074–81. http://dx.doi.org/10.1039/c5ob00224a.

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To make thioamide protein folding experiments applicable to full-sized proteins, our laboratory has used a combination of native chemical ligation of thiopeptide fragments, unnatural amino acid mutagenesis to install fluorophore partners in expressed protein fragments, and chemoenzymatic protein modification to render these expressed protein ligations traceless.

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15

Mirjafary, Zohreh, Leila Ahmadi, Masomeh Moradi, and Hamid Saeidian. "A copper(ii)–thioamide combination as a robust heterogeneous catalytic system for green synthesis of 1,4-disubstituted-1,2,3-triazoles under click conditions." RSC Advances 5, no. 95 (2015): 78038–46. http://dx.doi.org/10.1039/c5ra16581d.

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16

Yamazaki, Takao, and Hiroki Takahata. "Synthesis of Heterocycles Using Thioamide Groups." HETEROCYCLES 27, no. 8 (1988): 1953. http://dx.doi.org/10.3987/rev-88-387.

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17

TAKAHATA, Hiroki, and Takao YAMAZAKI. "Synthesis of heterocycles using thioamide groups." Journal of Synthetic Organic Chemistry, Japan 45, no. 7 (1987): 682–90. http://dx.doi.org/10.5059/yukigoseikyokaishi.45.682.

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18

Vankar, Jigarkumar K., Ankush Gupta, Jaydeepbhai P. Jadav, Shankara H. Nanjegowda, and Guddeangadi N. Gururaja. "The thioamidation of gem-dibromoalkenes in an aqueous medium." Organic & Biomolecular Chemistry 19, no. 11 (2021): 2473–80. http://dx.doi.org/10.1039/d0ob02319a.

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19

De Zotti, Marta, Barbara Biondi, Cristina Peggion, Matteo De Poli, Haleh Fathi, Simona Oancea, Claudio Toniolo, and Fernando Formaggio. "Partial thioamide scan on the lipopeptaibiotic trichogin GA IV. Effects on folding and bioactivity." Beilstein Journal of Organic Chemistry 8 (July 24, 2012): 1161–71. http://dx.doi.org/10.3762/bjoc.8.129.

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Backbone modification is a common chemical tool to control the conformation of linear peptides and to explore potentially useful effects on their biochemical and biophysical properties. The thioamide, ψ[CS-NH], group is a nearly isosteric structural mimic of the amide (peptide) functionality. In this paper, we describe the solution synthesis, chemical characterization, preferred conformation, and membrane and biological activities of three, carefully selected, peptide analogues of the lipopeptaibiotic [Leu11-OMe] trichogin GA IV. In each analogue, a single thioamide replacement was incorporated. Sequence positions near the N-terminus, at the center, and near the C-terminus were investigated. Our results indicate that (i) a thioamide linkage is well tolerated in the overall helical conformation of the [Leu11-OMe] lipopeptide analogue and (ii) this backbone modification is compatible with the preservation of its typical membrane leakage and antibiotic properties, although somewhat attenuated.

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20

Liu, Yinbo, Xiaofeng Mo, Irfan Majeed, Mei Zhang, Hui Wang, and Zhuo Zeng. "An efficient and straightforward approach for accessing thionoesters via palladium-catalyzed C–N cleavage of thioamides." Organic & Biomolecular Chemistry 20, no. 7 (2022): 1532–37. http://dx.doi.org/10.1039/d1ob02349g.

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21

Wang, Xi-Cun, Zheng-Jun Quan, Bin Xu, and Xue Zhong. "An Aluminum(III)-Catalyzed Thioamide–Aldehyde–Styrene Condensation: Direct Synthesis of Allylic Thioamide Derivatives." Synlett 27, no. 15 (June 27, 2016): 2237–40. http://dx.doi.org/10.1055/s-0035-1562507.

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22

Szostak, Michal, and Jeffrey Aubé. "Synthesis and rearrangement of a bridged thioamide." Chemical Communications, no. 46 (2009): 7122. http://dx.doi.org/10.1039/b917508c.

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23

Dixon, Sally, and Richard J. Whitby. "Efficient synthesis of thioamide terminated molecular wires." Tetrahedron Letters 47, no. 46 (November 2006): 8147–50. http://dx.doi.org/10.1016/j.tetlet.2006.09.032.

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24

Shabani, Sadegh, and Craig A. Hutton. "Depsipeptide synthesis using a late-stage Ag(i)-promoted macrolactonisation of peptide thioamides." Chemical Communications 57, no. 16 (2021): 2081–84. http://dx.doi.org/10.1039/d0cc07747j.

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Ag(i)-Triggered activation of the thioamide and attack by the C-terminal carboxylate generates an isoimide intermediate that undergoes an intramolecular acyl transfer to furnish the cyclic depsipeptide.

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25

Beyzaei, Hamid, Reza Aryan, and Zahra Keshtegar. "Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives." Advances in Chemistry 2014 (July 14, 2014): 1–4. http://dx.doi.org/10.1155/2014/834641.

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Synthesis of new imidazolidine and tetrahydropyrimidine derivatives 3a, b and 4a–c as cyclic 1,3-diamines under two reaction conditions (A and B) is described. Under reaction conditions-A, a suspension of (E)-2-cyano-2-(oxazolidin-2-ylidene)ethanethioamide 1 (1 eq.) and diaminoalkanes 2a–e (2 eq.) in absolute ethanol is heated under reflux for 16–22 h to afford 3a, b and 4a–c. Alternatively, under reaction conditions-B, a solution of thioamide 1 (1 eq.) in diaminoalkanes 2a–e (3 eq.) is stirred under solvent-free conditions at room temperature for 3 days to give desired products. Reaction conditions-A for having higher yields, shorter reaction times, and required less diamines is more effective than reaction conditions-B. Oxazolidine ring opening is observed by reacting compound 1 with all of the diamines 2a–e, but the thioamide group only reacts with nonbulky diamines 2a, b. The chemical structures of novel compounds were confirmed by 1H NMR, 13C NMR, elemental analysis, and FT-IR spectrometry.

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26

Maini, Rumit, Hiroyuki Kimura, Ryo Takatsuji, Takayuki Katoh, Yuki Goto, and Hiroaki Suga. "Ribosomal Formation of Thioamide Bonds in Polypeptide Synthesis." Journal of the American Chemical Society 141, no. 51 (December 9, 2019): 20004–8. http://dx.doi.org/10.1021/jacs.9b11097.

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27

Poupaert, Jacques H., Sandro Duarte, Evelina Colacino, Patrick Depreux, Christopher R. McCurdy, and Didier L. Lambert. "WILLGERODT-KINDLER'S MICROWAVE-ENHANCED SYNTHESIS OF THIOAMIDE DERIVATIVES." Phosphorus, Sulfur, and Silicon and the Related Elements 179, no. 10 (October 1, 2004): 1959–73. http://dx.doi.org/10.1080/10426500490466995.

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28

Brain, Christopher T., Allan Hallett, and Soo Y. Ko. "Thioamide Synthesis: Thioacyl-N-phthalimides as Thioacylating Agents." Journal of Organic Chemistry 62, no. 12 (June 1997): 3808–9. http://dx.doi.org/10.1021/jo970528v.

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29

Wang, Yanxin J., D. Miklos Szantai-Kis, and E. James Petersson. "ChemInform Abstract: Semi-Synthesis of Thioamide Containing Proteins." ChemInform 46, no. 27 (June 18, 2015): no. http://dx.doi.org/10.1002/chin.201527307.

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30

Jang, Youngchan, and Richard A. Bartsch. "Synthesis of dibenzocrown ethers with pendant thioamide groups." Journal of Heterocyclic Chemistry 32, no. 5 (September 1995): 1441–44. http://dx.doi.org/10.1002/jhet.5570320505.

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31

Schwehm, Carolin, William Lewis, Alexander J. Blake, Barrie Kellam, and Michael J. Stocks. "Preparation and structural analysis of (±)-cis-ethyl 2-sulfanylidenedecahydro-1,6-naphthyridine-6-carboxylate and (±)-trans-ethyl 2-oxooctahydro-1H-pyrrolo[3,2-c]pyridine-5-carboxylate." Acta Crystallographica Section C Structural Chemistry 70, no. 12 (November 19, 2014): 1161–68. http://dx.doi.org/10.1107/s205322961402436x.

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Bicycle ring closure on a mixture of (4aS,8aR)- and (4aR,8aS)-ethyl 2-oxodecahydro-1,6-naphthyridine-6-carboxylate, followed by conversion of the separatedcisandtransisomers to the corresponding thioamide derivatives, gave (4aSR,8aRS)-ethyl 2-sulfanylidenedecahydro-1,6-naphthyridine-6-carboxylate, C11H18N2O2S. Structural analysis of this thioamide revealed a structure with two crystallographically independent conformers per asymmetric unit (Z′ = 2). The reciprocal bicycle ring closure on (3aRS,7aRS)-ethyl 2-oxooctahydro-1H-pyrrolo[3,2-c]pyridine-5-carboxylate, C10H16N2O3, was also accomplished in good overall yield. Here the five-membered ring is disordered over two positions, so that both enantiomers are represented in the asymmetric unit. The compounds act as key intermediates towards the synthesis of potential new polycyclic medicinal chemical structures.

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32

Kumar, Ramasamy Raj, Rengan Ramesh, and Jan Grzegorz Małecki. "Versatile coordination ability of thioamide ligand in Ru(ii) complexes: synthesis, computational studies, in vitro anticancer activity and apoptosis induction." New Journal of Chemistry 41, no. 17 (2017): 9130–41. http://dx.doi.org/10.1039/c7nj01828b.

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Two structurally different ruthenium(ii) complexesviadiverse coordination of thioamide ligand have been synthesised and characterized. The complexes exhibit significant cytotoxicity and induce apoptosis in cancer cells.

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33

Szesni, Normen, Matthias Drexler, Bernhard Weibert, and Helmut Fischer. "Ethynylthioamide Complexes: Synthesis, Reactivity and an Unusual Coupling Reaction with Diethylaminopropyne." Zeitschrift für Naturforschung B 62, no. 3 (March 1, 2007): 346–56. http://dx.doi.org/10.1515/znb-2007-0307.

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The reaction of [(CO)5Cr(THF)] with propynethioic acid amides, R-C≡C-C(=S)NMe2 (R = H, SiMe3), yields the thioamide complexes [(CO)5Cr-S=C(NMe2)C≡C-H] (1a) and [(CO)5Cr- S=C(NMe2)C≡C-SiMe3] (1b). Treatment of solutions of 1a or 1b with methyllithium generates, via deprotonation or desilylation, the lithium salt Li[(CO)5Cr-S=C(NMe2)C≡C] (2). On filtration over silica, 2 is readily reprotonated. Complex 1a is inert towards methanol, however, adds diethylamine across the C≡C bond to give the thioacrylamide complex [(CO)5Cr-S=C(NMe2)C(H)=C(H)NMe2] (3). Thiourea displaces the thioamide ligand to give [(CO)5Cr-S=C(NH2)2] (4). Complex 1a reacts with half an equivalent of diethylaminopropyne in a three-component coupling to form the homobinuclear complex [(CO)5Cr-S=C(NEt2)-C(CH3)=C(H)-C(H)=C(NMe2)-C≡C-C(NMe2)=S- Cr(CO)5] (5) in high yield. The solid state structures of complexes 1a and 5 were established by X-ray structural analyses.

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34

Lhoták, Pavel, and Antonín Kurfürst. "Synthesis of Luminophores Based on Thiazole Derivatives of PBD." Collection of Czechoslovak Chemical Communications 58, no. 8 (1993): 1898–904. http://dx.doi.org/10.1135/cccc19931898.

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Organic luminophore 2-(biphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole (PBD, III) was converted by series of reaction into thioamide VIII which cyclized with substituted bromoacetylarenes X to give the bifluorophore system XI. The thiazole analog XIII was obtained by analogous reaction of bromoacetyl derivative V with thiobenzamide. All the thus-prepared compounds exhibit pronounced fluorescence in solution as well as in the crystalline state.

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35

Ferla, Salvatore, Carmine Varricchio, William Knight, Pui Kei Ho, Fabiana Saporito, Beatrice Tropea, Giulio Fagan, et al. "Structure–Activity Relationship Studies on Novel Antiviral Agents for Norovirus Infections." Microorganisms 9, no. 9 (August 24, 2021): 1795. http://dx.doi.org/10.3390/microorganisms9091795.

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Human norovirus is the leading cause of acute gastroenteritis worldwide, affecting every year 685 million people. Norovirus outbreaks are associated with very significant economic losses, with an estimated societal cost of 60 billion USD per year. Despite this, no therapeutic options or vaccines are currently available to treat or prevent this infection. An antiviral therapy that can be used as treatment and as a prophylactic measure in the case of outbreaks is urgently needed. We previously described the computer-aided design and synthesis of novel small-molecule agents able to inhibit the replication of human norovirus in cell-based systems. These compounds are non-nucleoside inhibitors of the viral polymerase and are characterized by a terminal para-substituted phenyl group connected to a central phenyl ring by an amide-thioamide linker, and a terminal thiophene ring. Here we describe new modifications of these scaffolds focused on exploring the role of the substituent at the para position of the terminal phenyl ring and on removing the thioamide portion of the amide-thioamide linker, to further explore structure-activity relationships (SARs) and improve antiviral properties. According to three to four-step synthetic routes, we prepared thirty novel compounds, which were then evaluated against the replication of both murine (MNV) and human (HuNoV) norovirus in cells. Derivatives in which the terminal phenyl group has been replaced by an unsubstituted benzoxazole or indole, and the thioamide component of the amide-thioamide linker has been removed, showed promising results in inhibiting HuNoV replication at low micromolar concentrations. Particularly, compound 28 was found to have an EC50 against HuNoV of 0.9 µM. Although the most active novel derivatives were also associated with an increased cytotoxicity in the human cell line, these compounds represent a very promising starting point for the development of new analogues with reduced cytotoxicity and improved selectivity indexes. In addition, the experimental biological data have been used to create an initial 3D quantitative structure-activity relationship model, which could be used to guide the future design of novel potential anti-norovirus agents.

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36

Sośnicki, Jacek, Tadeusz Jagodziński, and Miroslawa Królikowska. "Thioamide derivatives of cannabinoids. A study of the influence of the thioamide function on regiochemistry in the synthesis of thioamide cannabinoids from 2,4-dihydroxybenzothioamides." Journal of Heterocyclic Chemistry 36, no. 4 (July 1999): 1033–41. http://dx.doi.org/10.1002/jhet.5570360434.

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37

Wang, Lu, and Phanstiel. "Synthesis ofN-(Hydroxy)amide- andN-(Hydroxy)thioamide-Containing Peptides." Journal of Organic Chemistry 65, no. 5 (March 2000): 1442–47. http://dx.doi.org/10.1021/jo991589r.

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38

Gao, Xiang, Jiao Liu, Xin Zuo, Xinyue Feng, and Ying Gao. "Recent Advances in Synthesis of Benzothiazole Compounds Related to Green Chemistry." Molecules 25, no. 7 (April 5, 2020): 1675. http://dx.doi.org/10.3390/molecules25071675.

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Benzothiazoles have played an important role in the field of biochemistry and medicinal chemistry due to their highly pharmaceutical and biological activity. The development of synthetic processes is undoubtedly one of the most significant problems facing researchers. In this review paper, we provided recent advances in the synthesis of benzothiazole compounds related to green chemistry from condensation of 2-aminobenzenethiol with aldehydes/ketones/acids/acyl chlorides and the cyclization of thioamide or carbon dioxide (CO2) as raw materials, and the future development trend and prospect of the synthesis of benzothiazoles were anticipated.

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39

Sosnicki, Jacek, Tadeusz Jagodzinski, and Miroslawa Krolikowska. "ChemInform Abstract: Thioamide Derivatives of Cannabinoids. A Study of the Influence of the Thioamide Function on Regiochemistry in the Synthesis of Thioamide Cannabinoids from 2,4-Dihydroxybenzothioamides." ChemInform 31, no. 5 (June 11, 2010): no. http://dx.doi.org/10.1002/chin.200005198.

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40

Doležal, Martin, Jiří Hartl, Antonín Lyčka, Vladimír Buchta, and Želmíra Odlerová. "Synthesis and Antituberculotic Properties of Some Substituted Pyrazinecarbothioamides." Collection of Czechoslovak Chemical Communications 61, no. 7 (1996): 1102–8. http://dx.doi.org/10.1135/cccc19961102.

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A series of N-substituted 3-amino-5-thiocarbamoyl-2-pyrazinecarboxamides was prepared. The structure of compounds was confirmed by elemental analysis, IR and 1H NMR spectra. The results of in vitro antifugal and antimycobacterial susceptibility testing shown no activity against pathogenic fungi and some effect on mycobacteria. The highest antituberculotic activity (MIC within 25-50 mg ml-1) against Mycobacterium tuberculosis and other mycobacterial strains in this series was shown by 3-(3-hydroxyphenylamino)-5-thiocarbamoyl-2-pyrazinecarboxamide. The antituberculotic activity of these compounds is mostly influenced by the presence of the thioamide moiety.

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41

Yeo, Chien, and Edward Tiekink. "N-(4-Bromophenyl)methoxycarbothioamide." Molbank 2018, no. 3 (August 17, 2018): M1012. http://dx.doi.org/10.3390/m1012.

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The synthesis, spectroscopic and crystallographic characterisation of the title compound, O-methyl-N-4-bromophenyl thiocarbamate, MeOC(=S)N(H)PhBr-4 (1), are described. Spectroscopy confirmed the formation of the compound and the molecular structure was determined crystallographically. Two independent but chemically similar molecules comprise the asymmetric unit of 1. The C‒S and C‒N bond lengths confirm the presence of the thioamide tautomer. The thione-S and amide-N‒H atoms are syn, enabling the formation of amide-N‒H…S(thione) hydrogen bonds between the two independent molecules that generates a two-molecule aggregate via an eight-membered {…HNCS}2 synthon. The aggregates are connected into a three-dimensional architecture via weak intermolecular interactions, including Br…π(4-bromophenyl), S…π(4-bromophenyl), and weak Br…S halogen bonding contacts. The overall molecular conformation, thioamide tautomer, and the presence of amide-N‒H…S(thione) hydrogen bonding in the crystal conform with expectation for this class of compound.

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42

EL-Hashash, M. A., Yaser Abdel-moemen El-badry, and J. M. Morsy. "4-(3,4-Dichlorophenyl)-6-(Furan-2-yl)Pyrimidine-2-Thiol as Building Block in Heterocyclic Synthesis." JOURNAL OF ADVANCES IN CHEMISTRY 5, no. 2 (September 17, 2009): 669–77. http://dx.doi.org/10.24297/jac.v5i2.2656.

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Pyrimidine-2-thiol (1) has been synthesized via one-pot, three component synthesis. Its behavior towards nitrogen nucleophiles like hydrazine hydrate, ethylamine, piperidine, and 2-aminobenzoic acid has been studied. A speculation to explain the activities of the thioamide-iminothiol equilibrium based on their thermodynamic and kinetic control under the experimental conditions were investigated. The hydrazinopyrimidine 2 and aminocarbamoyl derivative 8 were used as key starting materials for synthesis of some interesting nitrogen bridgehead compounds 10-13, hydrazones 14-16, and some mixed and non-mixed heterocyclic systems 17-19 respectively.

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43

Yang, Jiyoung, Brandon J. Johnson, Allan A. Letourneau, Christopher M. Vogels, Andreas Decken, Felix J. Baerlocher, and Stephen A. Westcott. "Synthesis, Characterisation, and Antifungal Activities of Novel Benzodiazaborines." Australian Journal of Chemistry 68, no. 3 (2015): 366. http://dx.doi.org/10.1071/ch14534.

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Eight new fluoro- and methoxy-substituted benzodiazaborines have been prepared by a simple condensation reaction in high-to-excellent yields. All new compounds have been characterised by several physical methods, including X-ray diffraction studies on three examples. All new compounds were examined for antifungal activities against five species of potentially pathogenic fungi (Aspergillus niger, Aspergillus fumigatus, Rhizoctonia solani, Verticillium albo-atrum, and Verticillium dahliae). While substitution of the aromatic group derived from the 2-formylphenylboronic acid group had an effect on bioactivities, substitution on the parent thioamide C(=S)NH2 group of the starting thiosemicarbazide greatly reduced activities.

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44

Wei, Jianpeng, Yiming Li, and Xuefeng Jiang. "Aqueous Compatible Protocol to Both Alkyl and Aryl Thioamide Synthesis." Organic Letters 18, no. 2 (January 6, 2016): 340–43. http://dx.doi.org/10.1021/acs.orglett.5b03541.

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45

JANG, Y., and R. A. BARTSCH. "ChemInform Abstract: Synthesis of Dibenzocrown Ethers with Pendant Thioamide Groups." ChemInform 27, no. 13 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199613185.

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46

BRAIN, C. T., A. HALLETT, and S. Y. KO. "ChemInform Abstract: Thioamide Synthesis: Thioacyl-N-phthalimides as Thioacylating Agents." ChemInform 28, no. 43 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199743216.

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47

Manzor, Kim, and Fintan Kelleher. "Synthesis of orthogonally protected thioamide dipeptides for use in solid-phase peptide synthesis." Tetrahedron Letters 57, no. 47 (November 2016): 5237–39. http://dx.doi.org/10.1016/j.tetlet.2016.10.036.

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48

Basyouni, Wahid Mohamed, and Khairy Abdel-Hamid Mohsen El-Bayouki. "Synthesis of Novel 1,3-thiazole-, 1,2,4-triazole- thione and Triazepine Derivatives." Journal of Chemical Research 2005, no. 6 (June 2005): 356–60. http://dx.doi.org/10.3184/0308234054506730.

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Reaction of the cyanoacetic hydrazide derivatives 1a–e with isothiocyanates gave the hydrazinocarboxamide and thioamide derivatives 2a–g and 1,2,4-triazole-3-thiones 3. Upon reacting 1b–d with ethyl bromoacetate followed by isothiocyanates; the 1,3-thiazole-5-carbohydrazides 5 were afforded. Cyclisation of products 1b–e with triethylorthoformate furnished the unexpected ethyl cyanoacetylhydrazonoformate 6; rather than the expected triazolethiones of type 7. A mechanism for the formation of product 6 was suggested and discussed. Upon heating product 6 with some arylamines in acetonitrile, the 5-aminotriazepin-7-ones 9 were afforded.

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49

Michel, Andre G., Chakib Ameziane-Hassani, Gaston Boulay, and Gilles Lajoie. "Étude structurale de la liaison thioamide: Synthèse et conformation de dérivés de la thioalanine et de la thioglycine." Canadian Journal of Chemistry 67, no. 8 (August 1, 1989): 1312–18. http://dx.doi.org/10.1139/v89-202.

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The present study reports the synthesis, crystal structure determinations, and the conformational analysis of N-tertiobutyloxycarbonyl N′-methylthioalanine (Boc-AlaS-NHCH3, C9H18N2O2S) and of N-tertiobutyloxycarbonyl N′-methylthioglycine (Boc-GlyS-NHCH3, C8H16N2O2S). The particular feature of these compounds is the replacement of the classical oxopeptide linkage by a thioamide bond. Crystals of Boc-AlaS-NHCH3 are tetragonal, space group P43212. Those of Boc-GlyS-NHCH3 are monoclinic, space group P21/c. Both structures were solved by direct methods and refined by full-matrix least-squares methods to Rw = 0.045 and 0.035 for 827 and 1335 reflections respectively, with intensities greater than 2.5σ(I). The conformations of both compounds correspond to conformational energy minima, calculated for classical amino acids. The C=S bond lengths of 1.665(9) and 1.650(3) Å constitute the major difference compared to oxopeptides; the crystal structures reveal that the presence of the sulfur atom does not change the electronic properties of the peptide bond. Using a classical method for the study of peptides (ECEPP/2), conformational energy maps were computed for derivatives of dithioalanine and dithioglycine and are compared to the oxo residues. We conclude that the synthesis and conformational analysis of thionated amino acids allow us to introduce the thioamide linkage into more complex peptide structures and to predict the conformational behaviour. Keywords: molecular conformations, peptidic structure, crystallography.

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50

Slouka, Jan, and Vojtěch Bekárek. "Synthesis and cyclization of some N-oxides of 2-pyridylhydrazones of mesoxalic acid derivatives." Collection of Czechoslovak Chemical Communications 53, no. 3 (1988): 626–32. http://dx.doi.org/10.1135/cccc19880626.

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Coupling of diazotized 2-aminopyridine-1-oxide with ethyl cyanoacetylcarbamate, cyanoacetamide, malononitrile, and 2-benzimidazolylacetonitrile in an acid medium afforded N-oxides of the corresponding 2-pyridylhydrazones Ia-Id, which also exist in the N-hydroxyazine tautomeric forms IIa-IId as confirmed by IR spectroscopy. Hydrazone Ia was thermally cyclized to give 2-(pyridine-1-oxide-2-yl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile (IIIa) which was converted into the corresponding thioamide IIIb, acid IIIc, and amidoxime IIId.

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