Synthesis and biological evaluation of new sydnone based derivatives

Patel, Yogesh M.; Patel, Keshav C.

doi:10.1016/j.jscs.2012.02.005

Cited by 8 publications

(4 citation statements)

References 18 publications

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“…As described by Patel and his colleage [8], the prepared esters 6-10 (0.02 mol) and sodium hydroxide (0.04 mol) were heated at 80-85°C in a mixture of water and ethanol (36:8 mL) for 1 h. After cooling to ambient room temperature, the reaction mixture was acidified by fuming hydrochloric acid in a dropwise manner to precipitate the corresponding amino acids 13-17 ( Fig. 2) which were collected via filtration and used for the next step without further purification.…”

Section: Synthesis Of N-arylglycine 13-17mentioning

confidence: 96%

“…2, a mixture of the corresponding para substituted aniline 1-5 (0.1 mol), ethyl chloroacetate (0.2 mol) and anhydrous sodium acetate (0.2 mol) were refluxed for 12 h in 100 mL absolute ethanol. The mixture was kept in the fridge overnight after adding 100 mL hot water [8]. The precipitated solid was vacuumfiltered and then recrystallised from 95% ethanol to produce N-arylglycine esters 6-10.…”

Section: Synthesis Of Ethyl N-arylglycinate Esters 6-10mentioning

confidence: 99%

“…Stirring at ambient room temperature continued for 0.5-4 h until a clear liquor solution was achieved. The concentrated hydrochloric acid was then added slowly, and the precipitated nitroso derivatives were vacuum-filtered [8]. The products 27-36 were used for the following steps without further purification.…”

Section: Synthesis Of N-nitroso-n-arylglycine 27-36mentioning

confidence: 99%

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Discovery of Bis-sydnone styryl ketone as a selective cyclooxygenase-2 inhibitor

et al. 2021

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Background Various literature sources have documented a wide spectrum of therapeutic properties of sydnones including anti-inflammatory, anticancer, antimicrobial activities. Phenyl styryl ketones and their derivatives as members of the chalcone family have also been reported as significant bioactive molecules. The current study was initiated to evaluate the anti-inflammatory activity of sydnone-based compounds including some novel bis-sydnone styryl ketone hybrids. Results Twenty-five sydnone-containing compounds were successfully synthesized. Compounds 46-48 and 56-58 were reported as new sydnone derivatives. Whereas, compounds 61-63 were synthesized as novel molecules containing two sydnone rings linked via α,β-unsaturated ketone. The structures of the synthesized compounds were confirmed by FTIR, 1H NMR, 13C NMR and ToF-MS analyses. The in vitro COX inhibition assay showed varied activity. Compounds 47, 51, 58 and 63 showed the most potent COX inhibitory effects at a concentration of 200 μM. The selectivity index revealed that 63 was the best selective COX-2 inhibitor. Acetylation of the sydnone ring at C-4 was fruitful for the COX inhibitory effects. Docking analysis showed that COX-2 selectivity was due to a favourable positive charged interaction occurring between the sydnone ring of 63 and Arg513 of COX-2. Compound 51 was hydrogen bonded to Arg513. On the other hand, the low inhibitory effect of 63 against COX-1 was due to an unfavourable polar interaction with His513 in the binding pocket of COX-1. Conclusions The compounds were successfully synthesized and characterized. Compound 63 had a common architecture and pharmacophoric features with known selective COX-2 inhibitors (the coxib family) which make it a suitable candidate for the designing of selective and safe NSAID.

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Section: Synthesis Of N-arylglycine 13-17mentioning

confidence: 96%

Section: Synthesis Of Ethyl N-arylglycinate Esters 6-10mentioning

confidence: 99%

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Discovery of Bis-sydnone styryl ketone as a selective cyclooxygenase-2 inhibitor

et al. 2021

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“…The cyclocondensation of thiocarbohydrazide (1) with different carboxylic acids (formic, acetic, propionic and butyric acids) under reflux condition afforded 5-substituted-4-amino-3-mercapto-1,2,4-triazoles (2) [25,26]. The required substituted anilinoacetic acids (4) were synthesized by hydrolyzing their corresponding esters (3) in aqueous NaOH [27]. The latter compounds (3) were prepared by refluxing various anilines, sodium acetate and ethyl chloroacetate in ethanol solvent [28].…”

Section: Chemistrymentioning

confidence: 99%

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2018

AOICS

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The 1,2,4-triazole nucleus constitutes an integral component in drug discovery. It has been incorporated into both non-bridged drugs such as anastrozole (anticancer) [1,2], ribavirin (antiviral) [1,3], fluconazole, voriconazole (antifungal agents) [4] and in biologically active N-bridged drugs like triazolam (sedative agent) [1,5], estazolam and alprazolam (anxiolytic agents) [1,6,7]. The 1,3,4-thiadiazoles have attracted more interest to the researchers due to their prominent biological properties including anticonvulsant, anti-tubercular, anti-inflammatory, antileishmanial, antioxidant [8], antimicrobial and antidepressant activities [8,9]. There are also many drugs containing the 1,3,4-thiadiazole moiety such as acetazolamide, megazol and methazolamide [10]. Interestingly, some current reports showed that the fusion of the biolabile 1,2,4-triazole with 1,3,4-thiadiazole rings affords fused bicyclic compounds with improved biological activities than their corresponding non-bridged precursors. These include some ibuprofen-based 1,2,4-triazolo[3,4-b]-1,3,4thiadiazoles with enhanced anti-inflammatory and analgesic properties than precursor ibuprofen [11-13], and some naproxen-based 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles with enhanced analgesic, ulcerogenic, anti-inflammatory, and lipid peroxidation activities than starting naproxen [14]. Furthermore, N-(heteroarylmethyl) aniline derivatives with varied potent activities such as antimicrobial [15,16], antifungal, anticancer [17,18], herbicidal [19] and analgesic [20] were also reported. Prompted by these observations and in continuation of our research for new bioactive fused heterocycles [21,22], we herein describe the synthesis of a new series of 6-arylaminomethyl-3substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles as promising antioxidant agents. Materials and Methods ChemistryThe Innovative DTC-967A apparatus was used to determine the melting points of the newly synthesized compounds and the results are uncorrected. The IR-spectra were recorded on Shimadzu FT-IR Prestige-21 spectrophotometer in KBr pellets and are expressed in cm -1 . The mass spectra were recorded on a Shimadzu LC-MS-8030 mass spectrometer operating at 70 eV. The 1 H-NMR spectra were recorded on a Bruker Avance II 400 MHz instrument in DMSO-d 6 solvent and TMS as an internal standard. All chemical shift values were reported as δ (ppm), downfield from TMS. The Systronics spectrophotometer 106 was used to record the absorbance of DPPH radical scavenging antioxidant assay. The C, H, N analysis was carried out on Vario EL III Elemental Analyzer. The completion of the reaction and the purity of the compounds were monitored by

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