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Journal articles on the topic 'Morpholino Chemistry'

Author: Grafiati

Published: 7 September 2023

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1

Huber, Gerald, Annette Schier, and Hubert Schmidbaur. "The Stereochemistry of Chloro-bis(N-morpholino)phenylsilane." Zeitschrift für Naturforschung B 54, no. 1 (January 1, 1999): 18–20. http://dx.doi.org/10.1515/znb-1999-0106.

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Treatment of phenyltrichlorosilane with an excess of morpholine and N-lithium-morpholide in pentane/toluene affords only the disubstitution product Cl(Ph)Si(Mor)2 with Mor = O(CH2CH2)2N-. The third halogen atom is not replaced owing to sterical hindrance. The title compound crystallizes with two independent molecules in the unit cell. These two molecules can be classified as enantiomers, because a disrotatory twist of the two morpholino ligands away from the potential mirror plane induces a chiral conformation. In benzene solution there is racemization owing to completely free rotation, chair/boat interconversion, and nitrogen inversion of the morpholino groups on the NMR time scale, but all CH2 protons remain anisochronous (diastereotopic).

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2

Paul, Sibasish, and Marvin H. Caruthers. "Synthesis of Backbone-Modified Morpholino Oligonucleotides Using Phosphoramidite Chemistry." Molecules 28, no. 14 (July 13, 2023): 5380. http://dx.doi.org/10.3390/molecules28145380.

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Phosphorodiamidate morpholinos (PMOs) are known as premier gene knockdown tools in developmental biology. PMOs are usually 25 nucleo-base-long morpholino subunits with a neutral phosphorodiamidate linkage. PMOs work via a steric blocking mechanism and are stable towards nucleases’ inside cells. PMOs are usually synthesized using phosphoramidate P(V) chemistry. In this review, we will discuss the synthesis of PMOs, phosphoroamidate morpholinos (MO), and thiophosphoramidate morpholinos (TMO).

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3

Hao, Xue-chen, Jiu-fu Lu, Ye Chen, Yang Wang, Shi Ding, and Ju Liu. "Synthesis, Crystal Structure and Antitumour Activity of 3-Amino-N-(5-Fluoro-2-Methylphenyl)-4-Morpholino-1H-Indazole-1-Carboxamide." Journal of Chemical Research 41, no. 11 (November 2017): 624–26. http://dx.doi.org/10.3184/174751917x15065183733178.

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Compound 3-amino- N-(5-fluoro-2-methylphenyl)-4-morpholino-1 H-indazole-1-carboxamide has been synthesised by condensation of 4-fluoro-2-isocyanato-1-methylbenzene with 4-morpholino-1 H-indazol-3-amine, which was prepared from 2,6-difluorobenzonitrile by amination with morpholine and then cyclisation with hydrazine hydrate. The crystal structure of the title compound was determined. In addition, the compound inhibits proliferation of some cancer cell lines.

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4

Tang, Zhi-hua, and Wei-Jun Fu. "Synthesis, Crystal Structure and Antitumour Activity of 3-Amino-4-Morpholino-1H-Indazol-1-yl(3-Fluorophenyl)Methanone." Journal of Chemical Research 42, no. 11 (November 2018): 552–55. http://dx.doi.org/10.3184/174751918x15402939385990.

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3-Amino-4-morpholino-1H-indazol-1-yl(3-fluorophenyl)methanone was synthesised by condensation of 3-fluorobenzoic acid with 4-morpholino-1H-indazol-3-amine, which was prepared from 2,6-difluorobenzonitrile by amination with morpholine and then cyclisation with hydrazine hydrate. The molecular structure was tested by single crystal X-ray diffraction. Preliminary biological tests showed that the compound possesses distinct inhibition on the proliferation of A549, BGC-823 and HepG-2 cancer cell lines.

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5

Lu, Jiu-fu, Ling-xia Jin, Hong-guang Ge, Juan Song, Cai-bin Zhao, Xiao-hua Guo, Si-yu Yue, and Li Li. "Synthesis, Crystal Structure and Antitumour Activity of 4-(3-Amino-4-Morpholino-1H-Indazole-1-Carbonyl)Benzonitrile." Journal of Chemical Research 42, no. 6 (June 2018): 309–12. http://dx.doi.org/10.3184/174751918x15287920661730.

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The title compound, 4-(3-amino-4-morpholino-1 H-indazole-1-carbonyl)benzonitrile was synthesised by condensation of 4-cyanobenzoic acid with 4-morpholino-1 H-indazol-3-amine, which was prepared from 2,6-difluorobenzonitrile by amination with morpholine and then cyclisation with hydrazine hydrate. The crystal structure of the title compound was determined and the crystals belong to the monoclinic system, space group P21/ c. In addition, the compound showed some inhibition of the proliferation of some cancer cell lines.

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6

Ji, Xiao-hui, Ling-xia Jin, Cai-bin Zhao, Nan Zheng, Juan Song, Hong-guang Ge, Quan Liu, and Jiu-fu Lu. "Synthesis, Crystal Structure and Antitumour Activity of 3-Amino-N-[4-chloro-3-(Trifluoromethyl)Phenyl]-4-Morpholino-1H-Indazole-1-Carboxamide." Journal of Chemical Research 42, no. 10 (October 2018): 504–7. http://dx.doi.org/10.3184/174751918x15380423621264.

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Compound 3-amino-N-[4-chloro-3-(trifluoromethyl)phenyl]-4-morpholino-1H-indazole-1-carboxamide has been synthesised by condensation of 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene with 4-morpholino-1H-indazol-3-amine, which was prepared from 2,6-difluorobenzonitrile by amination with morpholine and then cyclisation with hydrazine hydrate. The crystal structure of the title compound was determined. In addition, the compound possesses a distinct inhibitory capacity against proliferation of the A549 and BGC-823 cancer cell lines.

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7

Lu, Jiu-fu, Xing-long Zhou, Yu-hang Xu, Si-yu Yue, Xiao-hui Ji, Nan Zheng, and Ling-xia Jin. "Synthesis, Crystal Structure, and Biological Activity of 3-Amino-4-Morpholino-N-[2-(Trifluoromethoxy)Phenyl]-1H-Indazole-1-Carboxamide." Journal of Chemical Research 41, no. 9 (September 2017): 526–28. http://dx.doi.org/10.3184/174751917x15033157981988.

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The title compound, 3-amino-4-morpholino- N-[2-(trifuoromethoxy)phenyl]-1 H-indazole-1-carboxamide has been synthesised by condensation of 1-isocyanato-2-(trifluoromethoxy)benzene with 4-morpholino-1 H-indazol-3-amine, which was prepared from 2,6-difluorobenzonitrile by amination with morpholine and then cyclisation with hydrazine hydrate. The crystal of the title compound belongs to the monoclinic system, space group P21/n with a = 11.0292(7) Å, b = 11.4332(8) Å, c = 15.6690(8) Å, α = 90°, β = 102.481(6)°, γ = 90°. In addition, the compound possesses distinct effective inhibition on the proliferation of cancer cell lines.

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8

Rádl, Stanislav, and Pavel Hradil. "Synthesis of some 1-alkyl-1,4-dihydro-4-oxo-1,7-naphthyridine-3-carboxylic acids." Collection of Czechoslovak Chemical Communications 56, no. 11 (1991): 2420–29. http://dx.doi.org/10.1135/cccc19912420.

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Reaction of substituted 2-aminopyridines IIIa, IIIb, IIIe, and IIIf with ethyl ethoxymethylene malonate provided corresponding pyridylaminomethylenemalonates Va-Vd, respectively. Thermal cyclization of Va, Vc, and Vd yielded substituted ethyl 4-hydroxy-1,7-naphthyridine-3-carboxylates VIa, VIc, and VId. Compounds VIc and VId treated with morpholine gave 8-morpholino derivatives VIe and VIf. These compounds were ethylated to mixtures of N-ethylated (VIIa, VIIb) and O-ethylated products (VIIIa, VIIIb). Compound VIIIb was also prepared from ethyl 4-chloro-6-fluoro-8-morpholino-1,7-naphthyridine-3-carboxylate VIIIc and sodium ethanolate. Esters VIIa and VIIb were hydrolyzed under acidic conditions to the respective acids VIIc and VIId.

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9

Tiravia, Martina, Federica Sabuzi, Francesca Valentini, Valeria Conte, and Pierluca Galloni. "3-Morpholino-7-[N-methyl-N-(4′-carboxyphenyl)amino]phenothiazinium Chloride." Molbank 2022, no. 4 (November 14, 2022): M1493. http://dx.doi.org/10.3390/m1493.

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The synthesis of 3-morpholino-7-[N-methyl-N-(4′-carboxyphenyl)amino]phenothiazinium chloride is reported here. Interestingly, non-symmetric phenothiazinium salt is functionalized with a carboxylic acid group that allows the easy and stable anchoring on metal oxides. In addition, the morpholine unit reduces the dye aggregation tendency; thus, improving its potential applications in the biomedical and photo-electrocatalytic field.

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10

Basha, S. Farook, and M. Syed Ali Padusha. "Ultrasonic Studies on the Nature of Molecular Interaction of Synthesized Mannich Bases in DMSO at Different Temperatures." Asian Journal of Chemistry 31, no. 4 (February 27, 2019): 960–64. http://dx.doi.org/10.14233/ajchem.2019.21893.

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This work deals with the ultrasonic studies of the Mannich bases (morpholin-4-yl)(pyridin-3- yl)methyl]hydrazine carboxamide (MPH) and (morpholino)(thiophen-2-yl)methyl)nicotine hydrazide (MTN) by the measurements of parameters such as ultrasonic velocity (U), density (ρ), viscosity (η), adiabatic compressibility (κ), intermolecular free length (Lf), molar volume (Vm), relaxation time (τ), specific acoustic impedance (Z), lenard jones potential (LJP), internal pressure (πi), free volume (Vf) and molecular cohesive energy (MCE), available volume (Va), Gibbs free energy (ΔG) and absorption coefficient (α/f2). These results are inferred that the strong interaction exists between the solvent (DMSO) and solute (MPH and MTN).

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11

Aung-Htut, May T., Craig S. McIntosh, Kristin A. West, Sue Fletcher, and Steve D. Wilton. "In Vitro Validation of Phosphorodiamidate Morpholino Oligomers." Molecules 24, no. 16 (August 12, 2019): 2922. http://dx.doi.org/10.3390/molecules24162922.

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One of the crucial aspects of screening antisense oligonucleotides destined for therapeutic application is confidence that the antisense oligomer is delivered efficiently into cultured cells. Efficient delivery is particularly vital for antisense phosphorodiamidate morpholino oligomers, which have a neutral backbone, and are known to show poor gymnotic uptake. Here, we report several methods to deliver these oligomers into cultured cells. Although 4D-Nucleofector™ or Neon™ electroporation systems provide efficient delivery and use lower amounts of phosphorodiamidate morpholino oligomer, both systems are costly. We show that some readily available transfection reagents can be used to deliver phosphorodiamidate morpholino oligomers as efficiently as the electroporation systems. Among the transfection reagents tested, we recommend Lipofectamine 3000™ for delivering phosphorodiamidate morpholino oligomers into fibroblasts and Lipofectamine 3000™ or Lipofectamine 2000™ for myoblasts/myotubes. We also provide optimal programs for nucleofection into various cell lines using the P3 Primary Cell 4D-Nucleofector™ X Kit (Lonza), as well as antisense oligomers that redirect expression of ubiquitously expressed genes that may be used as positive treatments for human and murine cell transfections.

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12

Min, So Jeong, Na Young Kim, Hyun Young Chae, and Keun Ho Chun. "Diastereoselective Synthesis of Phosphorodiamidate Morpholino Dimers." Bulletin of the Korean Chemical Society 41, no. 3 (February 11, 2020): 252–53. http://dx.doi.org/10.1002/bkcs.11958.

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13

Dostál, Jiří, Milan Potáček, and Miloslav Nechvátal. "Reactions of 5-Methylphenanthridinium Iodide with Nucleophiles and Reaction Products Conversion." Collection of Czechoslovak Chemical Communications 58, no. 2 (1993): 395–403. http://dx.doi.org/10.1135/cccc19930395.

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Reactions of 5-methylphenanthridinium iodide (I) with oxygen, nitrogen, and carbon nucleophiles, respectively, were studied. 5-Methylphenanthridinium iodide (I) yielded in the basic aqueous medium 5-methyl-6-phenanthridone (II) and 5,6-dihydro-5-methylphenanthridine (III). By NMR spectroscopy in the D2O-CD3CN solution 5,6-dihydro-6-deuteroxy-5-methylphenanthridine (IVb) (pseudobase) was observed as an immediate unstable product. 5-Methylphenanthridinium iodide (I) gave the corresponding adducts with methoxide and ethoxide anions, morpholine, piperidine, pyrrolidine, cyanide anion and acetone. Their structure was determined by IR, 1H and 13C NMR spectroscopy. Reactions of 5,6-dihydro-5-methyl-6-morpholinophenanthridine (VII) were followed by NMR spectroscopy. Morpholino adduct VII gave in the CD3CN-D2O solution pseudobase (IVb) and its products of disproportionation: oxophenanthridine II and dihydrophenanthridine III. Treatment of 5,6-dihydro-5-methyl-6-morpholinophenanthridine (VII) with H2O/D2O in (CH3)2CO/(CD3)2CO led to CH3COCH2-/CD3COCD2- adduct XIa/XIb formation, respectively.

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14

Leventić, Marijana, Teuta Opačak-Bernardi, Vesna Rastija, Josipa Matić, Dijana Pavlović Saftić, Željka Ban, Biserka Žinić, and Ljubica Glavaš-Obrovac. "The Mechanism of Anti-Tumor Activity of 6-Morpholino- and 6-Amino-9-Sulfonylpurine Derivatives on Human Leukemia Cells." Molecules 28, no. 16 (August 19, 2023): 6136. http://dx.doi.org/10.3390/molecules28166136.

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The aim of this study was to explore the mechanism of antitumor effect of (E)-6-morpholino-9-(styrylsulfonyl)-9H-purine (6-Morpholino-SPD) and (E)-6-amino-9-(styrylsulfonyl)-9H-purine (6-Amino-SPD). The effects on apoptosis induction, mitochondrial potential, and accumulation of ROS in treated K562 cells were determined by flow cytometry. The RT-PCR method was used to measure the expression of Akt, CA IX, caspase 3, and cytochrome c genes, as well as selected miRNAs. Western blot analysis was used to determine the expression of Akt, cytochrome c, and caspase 3. The results demonstrate the potential of the tested derivatives as effective antitumor agents with apoptotic-inducing properties. In leukemic cells treated with 6-Amino-SPD, increased expression of caspase 3 and cytochrome c genes was observed, indicating involvement of the intrinsic mitochondrial pathway in the induction of apoptosis. Conversely, leukemic cells treated with 6-Morpholino-SPD showed reduced expression of these genes. The observed downregulation of miR-21 by 6-Morpholino-SPD may contribute to the induction of apoptosis and disruption of mitochondrial function. In addition, both derivatives exhibited increased expression of Akt and CA IX genes, suggesting activation of the Akt/HIF pathway. However, the exact mechanism and its relations to the observed overexpression of miR-210 need further investigation. The acceptable absorption and distribution properties predicted by ADMET analysis suggest favorable pharmacokinetic properties for these derivatives.

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15

Bonacorso, Helio G., Melissa B. Rodrigues, Bernardo A. Iglesias, Carolina H. da Silveira, Sarah C. Feitosa, Wilian C. Rosa, Marcos A. P. Martins, Clarissa P. Frizzo, and Nilo Zanatta. "New 2-(aryl/heteroaryl)-6-(morpholin-4-yl/pyrrolidin-1-yl)-(4-trifluoromethyl)quinolines: synthesis via Buchwald–Hartwig amination, photophysics, and biomolecular binding properties." New Journal of Chemistry 42, no. 12 (2018): 10024–35. http://dx.doi.org/10.1039/c8nj01120f.

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16

McIntosh, Craig S., May Thandar Aung-Htut, Sue Fletcher, and Steve D. Wilton. "Removal of the Polyglutamine Repeat of Ataxin-3 by Redirecting pre-mRNA Processing." International Journal of Molecular Sciences 20, no. 21 (October 31, 2019): 5434. http://dx.doi.org/10.3390/ijms20215434.

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Spinocerebellar ataxia type 3 (SCA3) is a devastating neurodegenerative disease for which there is currently no cure, nor effective treatment strategy. One of nine polyglutamine disorders known to date, SCA3 is clinically heterogeneous and the main feature is progressive ataxia, which in turn affects speech, balance and gait of the affected individual. SCA3 is caused by an expanded polyglutamine tract in the ataxin-3 protein, resulting in conformational changes that lead to toxic gain of function. The expanded glutamine tract is located at the 5′ end of the penultimate exon (exon 10) of ATXN3 gene transcript. Other studies reported removal of the expanded glutamine tract using splice switching antisense oligonucleotides. Here, we describe improved efficiency in the removal of the toxic polyglutamine tract of ataxin-3 in vitro using phosphorodiamidate morpholino oligomers, when compared to antisense oligonucleotides composed of 2′-O-methyl modified bases on a phosphorothioate backbone. Significant downregulation of both the expanded and non-expanded protein was induced by the morpholino antisense oligomer, with a greater proportion of ataxin-3 protein missing the polyglutamine tract. With growing concerns over toxicity associated with long-term administration of phosphorothioate oligonucleotides, the use of a phosphorodiamidate morpholino oligomer may be preferable for clinical application. These results suggest that morpholino oligomers may provide greater therapeutic benefit for the treatment of spinocerebellar ataxia type 3, without toxic effects.

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17

Islas-Jácome, Perla, Cecilia García-Falcón, Sandra L. Castañón-Alonso, Ernesto Calderón-Jaimes, Daniel Canseco-González, Alejandro Islas-Jácome, and Eduardo González-Zamora. "2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one." Molbank 2023, no. 3 (July 10, 2023): M1693. http://dx.doi.org/10.3390/m1693.

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The new polyheterocyclic compound, 2-benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, was synthesized by a sequential combination of 4-chlorobenzaldehyde, (1-phenyl-1H-1,2,3-triazol-4-yl)methanamine, 2-isocyano-1-morpholino-3-phenylpropan-1-one, and maleic anhydride under a microwave-assisted one-pot process [Ugi-Zhu/aza Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration] with a 28% overall yield. The synthesized compound was fully characterized by 1D (1H, 13C) and 2D (COSY, HSQC, and HMBC) NMR, FT-IR, and HRMS.

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18

Bucci, Raffaella, Alessandro Contini, Francesca Clerici, Sara Pellegrino, and Maria Luisa Gelmi. "From glucose to enantiopure morpholino β-amino acid: a new tool for stabilizing γ-turns in peptides." Organic Chemistry Frontiers 6, no. 7 (2019): 972–82. http://dx.doi.org/10.1039/c8qo01116h.

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19

Paul, Sibasish, and Marvin H. Caruthers. "Synthesis of Phosphorodiamidate Morpholino Oligonucleotides and Their Chimeras Using Phosphoramidite Chemistry." Journal of the American Chemical Society 138, no. 48 (November 14, 2016): 15663–72. http://dx.doi.org/10.1021/jacs.6b08854.

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20

Bös, Markus, Marcus Herbig, Uwe Böhme, and Edwin Kroke. "Syntheses and molecular structures of some di(amidino)monosilanes." Main Group Metal Chemistry 44, no. 1 (January 1, 2021): 228–38. http://dx.doi.org/10.1515/mgmc-2021-0024.

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Abstract The syntheses of three different amidinosilanes of the type Me2Si[N=C(Ph)R]2 with R = pyrrolidino, morpholino, and diethylamino and one derivative with the composition R2Si[N=C(Ph)R]2 with R = morpholino are reported. These compounds were prepared in one-pot syntheses including three consecutive steps. All products are analysed by single crystal X-ray diffraction, NMR, and Raman spectroscopy. The Si–N=C–N units of these compounds show characteristic structural features and cause a significant high field shift of the 29Si NMR signals.

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21

Sadikov, K. D., A. S. Smirnov, S. V. Makarenko, and V. M. Berestovitskaya. "Synthesis of 2-morpholino(piperidino)-3-nitroacrylates." Russian Journal of Organic Chemistry 40, no. 10 (October 2004): 1544–45. http://dx.doi.org/10.1007/s11178-005-0061-x.

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22

Lai, Chin-Hung, Chia-Chin Chang, Yi-Lin Weng, and Ta-Hsien Chuang. "Synthesis, Experimental and Density Functional Theory (DFT) Studies on Solubility of Camptothecin Derivatives." Molecules 23, no. 12 (December 1, 2018): 3170. http://dx.doi.org/10.3390/molecules23123170.

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Two camptothecin derivatives, 10-cyclohexyl-7-methyl-20(S)-camptothecin and 7-methyl-10-morpholino-20(S)-camptothecin, were synthesized and their differences in solubility were investigated using four chosen solvent systems. Based on our results, 10-cyclohexyl-7-methyl-20(S)-camptothecin exhibited higher solubilities than 7-methyl-10-morpholino-20(S)-camptothecin in polar aprotic solvents. However, these two camptothecin derivatives did not exhibit apparent differences in solubility between 5% dimethyl sulfoxide (DMSO)/95% normal saline co-solvent system and 5% dimethylacetamide (DMAC)/95% normal saline co-solvent system. To rationalize their differences in solubility, we also tried to perform a DFT-B3LYP study to investigate their interaction with one water molecule.

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23

Palframan, Matthew J., Rima D. Alharthy, Paulina K. Powalowska, and Christopher J. Hayes. "Synthesis of triazole-linked morpholino oligonucleotides via CuI catalysed cycloaddition." Organic & Biomolecular Chemistry 14, no. 11 (2016): 3112–19. http://dx.doi.org/10.1039/c6ob00007j.

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24

Gong, Ping, Kang Wang, Yatao Liu, Kenneth Shepard, and Rastislav Levicky. "Molecular Mechanisms in Morpholino−DNA Surface Hybridization." Journal of the American Chemical Society 132, no. 28 (July 21, 2010): 9663–71. http://dx.doi.org/10.1021/ja100881a.

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25

Liu, Yatao, Damion Irving, Wanqiong Qiao, Dongbiao Ge, and Rastislav Levicky. "Kinetic Mechanisms in Morpholino–DNA Surface Hybridization." Journal of the American Chemical Society 133, no. 30 (August 3, 2011): 11588–96. http://dx.doi.org/10.1021/ja202631b.

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26

Ratemi, Elaref S., Nivedita Namdev, and Martin S. Gibson. "Pyridine and pyrimidine ring syntheses from 4-(4-morpholino)-3-pentenone and from ethyl 3-(4-morpholino)-2-butenoate." Journal of Heterocyclic Chemistry 30, no. 6 (December 1993): 1513–16. http://dx.doi.org/10.1002/jhet.5570300609.

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27

Naumczuk, B., R. Kawęcki, J. Sitkowski, W. Bocian, E. Bednarek, and L. Kozerski. "Spontaneous 2′-deoxyguanosine alkylation by a new generation of topoisomerase I inhibitors of the camptothecin family." New Journal of Chemistry 40, no. 4 (2016): 3010–13. http://dx.doi.org/10.1039/c5nj03497c.

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7-Ethyl-9-(N-morpholino)methyl-10-hydroxycamptothecin spontaneously binds covalently to 2′-deoxyguanosine under near-physiological conditions. This phenomenon may be important in the application of this type of camptothecin derivative in cancer chemotherapy.

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28

Maas, Gerhard, and Theo Mayer. "The Organocopper Route from (2-Propynylidene)morpholinium Triflates to Morpholinoallenes, 1-Morpholino-1,3-butadienes, and 2-Morpholino-1,3-butadienes." Synthesis 1991, no. 12 (1991): 1209–15. http://dx.doi.org/10.1055/s-1991-28421.

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29

Weber, Gunther, Jürgen Hartung, and Lothar Beyer. "Umsetzungen von N-(Morpholino-thocarbonyl)-benzimidchlorid mit Dinucleophilen." Zeitschrift für Chemie 26, no. 2 (August 31, 2010): 70–71. http://dx.doi.org/10.1002/zfch.19860260213.

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30

Zhang, Nan, Chunyan Tan, Puqin Cai, Yuyang Jiang, Peizhuo Zhang, and Yufen Zhao. "Synthesis and properties of morpholino chimeric oligonucleotides." Tetrahedron Letters 49, no. 22 (May 2008): 3570–73. http://dx.doi.org/10.1016/j.tetlet.2008.04.035.

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31

Anderluh, Marko. "An improved synthesis of morpholino-glycoamino acids." Tetrahedron Letters 47, no. 52 (December 2006): 9203–6. http://dx.doi.org/10.1016/j.tetlet.2006.10.133.

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32

Kamsani, Supriya, Sumathi Vodnala, A. K. D. Bhavani, and Nagamani Rayala. "Design and Synthesis of Novel Bis-Morpholinotriazine Analogs and their Antibacterial, Antifungal and Antioxidant Studies." Asian Journal of Chemistry 34, no. 3 (2022): 720–26. http://dx.doi.org/10.14233/ajchem.2022.23656.

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A series of novel analogues of bis-morpholino-1,3,5-triazine derivatives are synthesized from cyanuric chloride as starting precursor. The products are characterized by spectral data and their biological evaluation against microbials are reported. Antioxidant properties of these compounds are also studied.

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33

Chen, Jianbin, Jikui Wu, and Yunhan Hong. "The morpholino molecular beacon for specific RNA visualization in vivo." Chemical Communications 52, no. 15 (2016): 3191–94. http://dx.doi.org/10.1039/c5cc07124k.

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34

Paul, Sibasish, and Marvin H. Caruthers. "Retraction of “Synthesis of Phosphorodiamidate Morpholino Oligonucleotides and Their Chimeras Using Phosphoramidite Chemistry”." Journal of the American Chemical Society 141, no. 23 (May 30, 2019): 9430. http://dx.doi.org/10.1021/jacs.7b04308.

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35

Liao, Tangbin, Xiaorui Li, Qian Tong, Kai Zou, Hang Zhang, Lina Tang, Zhongyue Sun, and Guo-Jun Zhang. "Ultrasensitive Detection of MicroRNAs with Morpholino-Functionalized Nanochannel Biosensor." Analytical Chemistry 89, no. 10 (April 28, 2017): 5511–18. http://dx.doi.org/10.1021/acs.analchem.7b00487.

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Borowiecki, Paweł. "Chemoenzymatic Synthesis of Optically Active Ethereal Analog of iso-Moramide—A Novel Potentially Powerful Analgesic †." International Journal of Molecular Sciences 23, no. 19 (October 5, 2022): 11803. http://dx.doi.org/10.3390/ijms231911803.

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To develop potent and safer analgesics, we designed and synthesized a novel enantiomerically enriched ethereal analog of (R)-iso-moramide, namely 2-[(2R)-2-(morpholin-4-yl)propoxy]-2,2-diphenyl-1-(pyrrolidin-1-yl)ethan-1-one. The titled active agent can potentially serve as a powerful synthetic opiate with an improved affinity and selectivity toward opioid receptors (ORs). This hypothesis was postulated based on docking studies regarding the respective complexes between the designed ligand and µ-OR, δ-OR, and κ-OR. The key step of the elaborated asymmetric synthesis of novel analog involves lipase-catalyzed kinetic resolution of racemic 1-(morpholin-4-yl)propan-2-ol, which was accomplished on a 10 g scale via an enantioselective transesterification employing vinyl acetate as an irreversible acyl donor in tert-butyl methyl ether (MTBE) as the co-solvent. Next, the obtained homochiral (S)-(+)-morpholino-alcohol (>99% ee) was functionalized into corresponding chloro-derivative using thionyl chloride (SOCl2) or the Appel reaction conditions. Further transformation with N-diphenylacetyl-1-pyrrolidine under phase-transfer catalysis (PTC) conditions using O2-saturated DMSO/NaOH mixture as an oxidant furnished the desired levorotatory isomer of the title product isolated in 26% total yield after three steps, and with 89% ee. The absolute configuration of the key-intermediate of (R)-(–)-iso-moramide was determined using a modified form of Mosher’s methodology. The preparation of the optically active dextrorotatory isomer of the titled product (87% ee) was carried out essentially by the same route, utilizing (R)-(–)-1-(morpholin-4-yl)propan-2-ol (98% ee) as a key intermediate. The spectroscopic characterization of the ethereal analog of iso-moramide and the enantioselective retention relationship of its enantiomers using HPLC on the cellulose-based chiral stationary phase were performed. Moreover, as a proof-of-principle, single-crystal X-ray diffraction (XRD) analysis of the synthesized 2-[(2R)-2-(morpholin-4-yl)propoxy]-2,2-diphenyl-1-(pyrrolidin-1-yl)ethan-1-one is reported.

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GRAY, C., and K. PHILP. "Hydrodynamic and other properties of poly(morpholino)alginamide (PMA)." Carbohydrate Polymers 25, no. 1 (1994): 39–44. http://dx.doi.org/10.1016/0144-8617(94)90160-0.

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Langner, Heera K., Katarzyna Jastrzebska, and Marvin H. Caruthers. "Synthesis and Characterization of Thiophosphoramidate Morpholino Oligonucleotides and Chimeras." Journal of the American Chemical Society 142, no. 38 (August 31, 2020): 16240–53. http://dx.doi.org/10.1021/jacs.0c04335.

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Wieczorek, Micha? W., Wies?aw R. Majzner, Renata Kaczmarek, Janina Baraniak, and Wojciech J. Stec. "Crystal and molecular structures of isomeric 2-morpholino-2-thiono-4-methyl-1,3,2-dioxaphosphinane and 2-morpholino-2-oxo-4-methyl-1,3,2-dioxaphosphinane." Heteroatom Chemistry 9, no. 2 (1998): 271–79. http://dx.doi.org/10.1002/(sici)1098-1071(1998)9:2<271::aid-hc24>3.0.co;2-n.

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40

Hauck, Laura, Dan Mourich, and Patrick Iversen. "Analysis of phosphorodiamidate morpholino oligomer chemisrty CpG effects in murine and human cells (158.12)." Journal of Immunology 186, no. 1_Supplement (April 1, 2011): 158.12. http://dx.doi.org/10.4049/jimmunol.186.supp.158.12.

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Abstract Many RNA-based therapeutic oligomer backbone chemistries will elicit undesirable immunological response through a number of pathways. Additionally, it has been shown that certain sequences can also elicit cellular pro-inflammatory responses in the form cytokine and chemokines production. For example, non-methylated CpG DNA motifs are considered pathogen-associated molecular patterns (PAMPS) due to their abundance in microbial genomes and their recognition by TLR-9 receptors. Some synthetic oligonucleotides, containing modified backbone or other synthetic nucleotide motifs, will still retain potent immunostimulatory activity which may be inappropriate within the desired therapeutic effect. The purpose of this study was to look in vitro for immune activation resulting from exposure to optimized CpG sequences incorporated into the phosphorodiamidate morpholino oligomer (PMO) chemistry. Human and murine dendritic cells (DCs) were treated with varying concentration of PMO and culture media was assayed by multiplex cytokine and chemokine detection platform for simultaneous detection of multiple analytes. There was no evidence for a sequence- or chemistry-specific activation of the DCs indicating that PMO do not provide an innate stimulus to the immune system.

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Janaswamy, Srinivas, G. Sreenivasa Murthy, T. Mohan, and M. N. Sudheendra Rao. "Crystal structure analysis of (Morpholino)(Phenyl)(Dicyclohexylamino) phosphiniminocyclotrithiazene." Crystallography Reports 48, no. 1 (January 2003): 68–72. http://dx.doi.org/10.1134/1.1541746.

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Ukhin, L. Yu, L. V. Belousova, Zh I. Orlova, O. Ya Borbulevych, and O. V. Shishkin. "Reactions of 4-morpholino-1,2-naphthoquinone with enamines ando-phenylenediamine." Russian Chemical Bulletin 49, no. 4 (April 2000): 732–35. http://dx.doi.org/10.1007/bf02495492.

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Bell, Neil M, Raymond Wong, and Jason Micklefield. "A Non-Enzymatic, DNA Template-Directed Morpholino Primer Extension Approach." Chemistry - A European Journal 16, no. 7 (February 15, 2010): 2026–30. http://dx.doi.org/10.1002/chem.200902237.

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TAYYAB, SAAD, TUAN NOR NAZIAN TUAN MAT, and ADYANI AZIZAH ABD HALIM. "DIFFERENTIAL STABILIZING EFFECTS OF BUFFERS ON STRUCTURAL STABILITY OF BOVINE SERUM ALBUMIN AGAINST UREA DENATURATION." Latin American Applied Research - An international journal 52, no. 1 (January 1, 2022): 7–13. http://dx.doi.org/10.52292/j.laar.2022.738.

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The conformational stability of bovine serum albumin (BSA) against urea denaturation was investigated in aqueous solutions both in the absence and presence of buffers. Various buffers differing in polar and nonpolar characters such as sodium phosphate, Tris-HCl, (4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid) HEPES and [3-(N-morpholino)propanesulfonic acid] MOPS buffers were used in this study. Urea-induced structural changes were analyzed using different probes, i.e., intrinsic fluorescence, ANS fluorescence and UV-difference spectral signal. Presence of different buffers in the incubation medium offered different degrees of resistance to the protein against urea-induced structural changes compared to those obtained in water (in the absence of buffers). A similar trend of buffer-induced structural resistance was noticed with three different probes. The stabilizing effect of these buffers followed the order: MOPS > HEPES > sodium phosphate > Tris-HCl > water. As found in MOPS and HEPES buffers, the highest stability of BSA can be attributed to the presence of morpholine and piperazine rings, respectively, in their structures. These groups might have produced a hydrophobic environment around the protein surface, thus stabilizing protein conformation against urea denaturation.

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Sedlárová, Eva, Jozef Čižmárik, Dana Novosedlíková, Katarína Podhorová, Lucia Šranková, and Andrej Šrank. "Dependence of log k Obtained by HPLC on log P'exp in the Series Piperidino and Morpholinoethyl Esters of o-, m- and p-Alkoxy Substituted Phenylcarbamic Acids." Collection of Czechoslovak Chemical Communications 58, no. 2 (1993): 310–14. http://dx.doi.org/10.1135/cccc19930310.

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Dependence of log k obtained by the HPLC method on log P'exp obtained by the classical method was investigated in two series of basic ethyl phenylcarbamic acids. The linear dependence was found with o-substituted series and p-substituted morpholino derivatives. The relation with p-derivatives of the piperidino series is close to linearity, while that of m-derivatives of both series is not linear.

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Sherstyuk, Yuliya V., Nikita V. Ivanisenko, Alexandra L. Zakharenko, Maria V. Sukhanova, Roman Y. Peshkov, Ilia V. Eltsov, Mikhail M. Kutuzov, et al. "Design, Synthesis and Molecular Modeling Study of Conjugates of ADP and Morpholino Nucleosides as A Novel Class of Inhibitors of PARP-1, PARP-2 and PARP-3." International Journal of Molecular Sciences 21, no. 1 (December 27, 2019): 214. http://dx.doi.org/10.3390/ijms21010214.

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We report on the design, synthesis and molecular modeling study of conjugates of adenosine diphosphate (ADP) and morpholino nucleosides as potential selective inhibitors of poly(ADP-ribose)polymerases-1, 2 and 3. Sixteen dinucleoside pyrophosphates containing natural heterocyclic bases as well as 5-haloganeted pyrimidines, and mimicking a main substrate of these enzymes, nicotinamide adenine dinucleotide (NAD+)-molecule, have been synthesized in a high yield. Morpholino nucleosides have been tethered to the β-phosphate of ADP via a phosphoester or phosphoramide bond. Screening of the inhibiting properties of these derivatives on the autopoly(ADP-ribosyl)ation of PARP-1 and PARP-2 has shown that the effect depends upon the type of nucleobase as well as on the linkage between ADP and morpholino nucleoside. The 5-iodination of uracil and the introduction of the P–N bond in NAD+-mimetics have shown to increase inhibition properties. Structural modeling suggested that the P–N bond can stabilize the pyrophosphate group in active conformation due to the formation of an intramolecular hydrogen bond. The most active NAD+ analog against PARP-1 contained 5-iodouracil 2ʹ-aminomethylmorpholino nucleoside with IC50 126 ± 6 μM, while in the case of PARP-2 it was adenine 2ʹ-aminomethylmorpholino nucleoside (IC50 63 ± 10 μM). In silico analysis revealed that thymine and uracil-based NAD+ analogs were recognized as the NAD+-analog that targets the nicotinamide binding site. On the contrary, the adenine 2ʹ-aminomethylmorpholino nucleoside-based NAD+ analogs were predicted to identify as PAR-analogs that target the acceptor binding site of PARP-2, representing a novel molecular mechanism for selective PARP inhibition. This discovery opens a new avenue for the rational design of PARP-1/2 specific inhibitors.

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Lemeer, Simone, Chris Jopling, Joost Gouw, Shabaz Mohammed, Albert J. R. Heck, Monique Slijper, and Jeroen den Hertog. "Comparative Phosphoproteomics of Zebrafish Fyn/Yes Morpholino Knockdown Embryos." Molecular & Cellular Proteomics 7, no. 11 (June 11, 2008): 2176–87. http://dx.doi.org/10.1074/mcp.m800081-mcp200.

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Hermecz, István, Andrea Sánta-Csutor, Csaba Gönczi, Gergely Héja, Éva Csikós, Kálmán Simon, Ágota Smelkó-Esek, and Benjámin Podányi. "Chemical development of the vasopressin receptor 2 antagonist SR-121463." Pure and Applied Chemistry 73, no. 9 (September 1, 2001): 1401–9. http://dx.doi.org/10.1351/pac200173091401.

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A facile convergent total synthesis of the selective, potent, and orally active V2 non-peptide antagonist, SR-121463, was developed by modification of the discovery route. One of the late intermediates, the sulfonyl chloride 1, was synthesized from 3-hydroxybenzoic acid (19) by regioselective sulfonation, O-methylation and amidation in four steps. Another late intermediate, indolin-2-one 2, was prepared from p-phenetidine (8) through the indolin-2-one 16, where the cyclohexanone moiety of 27 was introduced into the active 3-methylene group of 16 by sequential transformation using methyl acrylate and KOtBu. After formation of the cyclic ketal moiety of 13, its ring-opening was achieved by using NaBH4 in the presence of CCl3COOH. The morpholino group in 2 was introduced in accordance with the discovery approach, starting from the 2-hydroxyethoxy derivative 14 through the tosyloxy derivative 15 with morpholine in a one-pot reaction. In this way, the indolin-2-one 2 was synthesized from 8 in six steps. Finally, acylation of the indolin-2-one 2 was achieved with the sulfonyl chloride 1 in the presence of KOtBu in dimethyl sulfoxide (DMSO) at room temperature. This synthetic route proved to be applicable for the large-scale synthesis of SR-121463.

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Bhat, Balkrishen, and A. P. Bhaduri. "Grignard Reaction of 2-Substituted-3-Cyanoquinolines." Zeitschrift für Naturforschung B 40, no. 7 (July 1, 1985): 990–95. http://dx.doi.org/10.1515/znb-1985-0724.

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Abstract Grignard reactions of 2-morpholino and 2-methylthio-3-cyanoquinoline, 2-chloro-3-cyanoquinoline, 2-chloro-3-cyano-6-methoxyquinoline and 2-chloro-3-cyano-7-methylquinoline with alkyl or aryl magnesium halides have been studied. It was found that 2-morpholino and 2-methylthio- 3-cyanoquinolines gave 1,4-addition products followed by rapid aromatisation. 2-Chloro-3- cyanoquinoline with alkyl magnesium halides furnished 1,4-addition products but with aryl magnesium halides 1,4- and 1,2-addition products were obtained. The cyano group of 4-aryl-2-chloro- 3-cyano-1,4-dihydroquinolines was found to participate in the Grignard reaction to yield 1,2- addition products. 2-Chloro-3-cyano-6-m ethoxyquinoline with alkyl and phenyl magnesium halides yielded exclusively 1,4-addition products. Similarly with p-m ethoxyphenyl magnesium bromide, 1,4-addition products were isolated which participated in the Grignard reaction to yield the expected adducts. Unlike the other chloroquinoline derivatives, 2-chloro-3-cyano-7-methylquinoline with alkyl magnesium halide formed 1 ,2-addition products but with aryl magnesium halides, 1,4-addition products were isolated. The 4-alkyl-2-chloro-3-cyano-l,4-dihydroquinolines were unstable as compared to their 4-aryl analogs. A couple of the Grignard reaction products were found to be unstable on activated surface.

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Slepukhin, P. A., L. N. Bazhenova, E. B. Letova, and V. I. Filyakova. "X-ray crystallographic study of 2-morpholino-5-trifluoromethyl-1,3,4-thiadiazole." Journal of Structural Chemistry 56, no. 7 (December 2015): 1415–16. http://dx.doi.org/10.1134/s0022476615070252.

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