- N-(4-FLUOROPHENYL)-5-PHENYL-[1,2,4] TRIAZOLO [1,5-A] PYRIDINE-2-CARBOXAMIDE DERIVATIVES AND THEIR SYNTHESIS THEREOF
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The present invention relates to the development of novel N-(4-fluorophenyl)-5-phenyl- [1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives for their different pharmacological activities. It particularly relates to the development of N-(4-fluorophenyl)-5-phenyl- [1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives as antiviral, anticancer, antifungal, hypoglycemic, anti-tubercular, sedative, anti-type 2 diabetes activity. It specifically relates to the N-(4-fluorophenyl)-5-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives for treatment of H37Rv and multidrug-resistant (MDR) strains of Mycobacterium tuberculosis (MTB). The present invention also relates to the process for synthesis of N-(4-fluorophenyl)- 5-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives. The invention further relates to method for treatment of method for treatment of diseases such as tuberculosis, type 2 diabetes, bacterial, viral and fungal infections. Invention addresses the challenges in working with chemical processes and products by inventing novel reaction methodology that can maximize the desired products and minimize by-products, designing new synthetic schemes that can simplify operations in chemical productions and seeking nontoxic reagent that are inherently environmentally and ecologically benign. Synthesis of novel N-(4- fluorophenyl)-5-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives is being employed to develop a novel synthetic methodology and their pharmacological applications. Novel series of N-(4-fluorophenyl)-5-phenyl-[1,2,4]triazolo[l,5-a]pyridine-2-carboxamide derivatives were designed synthesized evaluated for their in vitro anti-mycobacterial activity against H37Rv and multi-drug-resistant (MDR) strains of mycobacterium tuberculosis (MTB). All the synthesized compounds were characterized by spectroscopic methods like Mass, NMR and elemental analysis.
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Page/Page column 9; 15
(2021/08/20)
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- Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
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A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
- Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
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- Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur
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We have studied the mechanism of solvolysis of arenesulfonyl chlorides by propan-1-ol and propan-2-ol at 303-323 K. Kinetic profiles were appropriately fit by first-order kinetics. Reactivity increases with electron-donating substituents. Ortho-alkyl substituted derivatives of arenesulfonyl chlorides show increased reactivity, but the origin of this “positive” ortho-effect remains unclear. Likely, ortho-methyl groups restrict rotation around the C-S bond, facilitating the attack of the nucleophile. No relevant reactivity changes have been found with propan-1-ol and propan-2-ol in terms of nucleophile steric effect. The existence of isokinetic relationships for all substrates suggests a single mechanism for the series. Solvolysis reactions of all substrates in both alcohols show isokinetic temperatures (Tiso) close to the working temperature range, which is an evidence of the process being influenced by secondary reactivity factors, likely of steric nature in the TS. Solvation plays a relevant role in this reaction, modulating the reactivity. In some cases, the presence of t-Bu instead of Me in para- position leads to changes in the first solvation shell, increasing the energy of the reaction (ca. 1?kJ·mol?1). The obtained results suggest the same kinetic mechanism of solvolysis of arenesulfonyl chlorides for propan-1-ol and propan-2-ol, as in MeOH and EtOH, where bimolecular nucleophilic substitution (SN2) takes place with nucleophilic solvent assistance of one alcohol molecule and the participation of the solvent network involving solvent molecules of the first solvation shell.
- Iazykov, Mykyta,Canle, Moisés,Santaballa, J. Arturo,Rublova, Ludmila
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supporting information
(2017/09/08)
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- Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate
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A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with amines. Less electron-rich aryl- and heteroarylzinc reagents reacted with TCPC to afford sulfonyl chlorides that were converted in situ to sulfonamides.
- Colombe, James R.,Debergh, J. Robb,Buchwald, Stephen L.
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supporting information
p. 3170 - 3173
(2015/06/30)
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- Substituted Disulfonamide Compounds
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Substituted disulfonamide compounds corresponding to formula I: In which R1, R2, R3, R4a, R4b, R5a, R5b, R8, R9a, R9b, R10, R11, a, b, s, t and A have defined meanings, pharmaceutical compositions containing one or more such compounds, processes for preparing such compounds, and a method of using such compounds for the treatment or inhibition of pain and/or other conditions mediated by the bradykinin receptor 1 (BR1).
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Page/Page column 37
(2010/06/22)
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- A new, mild preparation of sulfonyl chlorides
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A new method was developed for the preparation of sulfonyl chlorides from sulfonic acids under neutral conditions using 2,4,6-trichloro-1,3,5-triazine as chlorinating agent.
- Blotny, Grzegorz
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p. 1499 - 1501
(2007/10/03)
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- Bispiperidines as antithrombotic agents
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Novel compounds which are inhibitors of the binding of fibrinogen to the Gp IIb/IIIa platelet receptors, and which can be used therepeutically as antithrombotic agents
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- Catalytic kinetic resolution of 5-alkoxy-2(5H)-furanones
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The kinetic resolution of racemic 5-alkoxy-2(5H)-furanones, using a chiral aminoalcohol catalyzed 1,4-addition of arylthiols, was examined. Using various butenolides it was shown that a γ-alkoxy substituent appears to be essential to reach high enantioselectivities whereas electron-donating substituents in the arylthiols also increase the selectivity. Cinchona alkaloids are the preferred catalysts for the kinetic resolution, with quinine and quinidine leading to the most efficient and selective thiol additions. A remarkable dilution effect and a strong dependency on the mode of addition of reactants were observed. Optimization studies are presented of the kinetic resolution of 5-methoxy-2(5H)-furanone 2 resulting in (R)-2 or (S)-2 with enantiomeric excesses exceeding 90%. A mechanism for the quinine (quinidine) catalyzed kinetic resolution is given.
- Faber, Wijnand S.,Kok, Johan,De Lange, Ben,Feringa, Ben L.
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p. 4775 - 4794
(2007/10/02)
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- CATALYTIC SULFONYLATION OF PHENOL BY STERICALLY HINDERED SULFONYL CHLORIDES
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The sulfonylation of phenol by substituted arenesulfonyl chlorides XArSO2Cl in the presence of triethylamine in benzene was studied by potentiometric titration.A linear relation was obtained between the logaritmhs of the catalytic rate constants and the steric constants Eso of the substituents in the sulfonyl chloride.The contribution from the induction and steric effects of the substituents at position2 to the kinetics of the process was assessed.It was concluded that the steric effect plays a predominant role over the induction and resonance effects.
- Vizgert, R.V.,Maksimenko, N.N.,Rubleva, L.I.
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p. 2144 - 2146
(2007/10/02)
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