Synthesis of Some New 2‐(6‐Methoxy‐2‐Naphthyl)‐ 5‐Aryl‐1,3,4‐Oxadiazoles as Possible Non‐steroidal Anti‐inflammatory and Analgesic Agents

Abstract

The synthesis of some new 2-(6-methoxy-2-naphthyl)-5-aryl-1,3,4-oxadiazoles (4a-k) has been described. Ethyl-6-methoxy-2-naphthoate (1) yielded on treatment with hydrazine hydrate to 6-methoxy-2-naphthoic acid hydrazide (2). Compound 2 reacted with substituted aromatic carboxylic acids (3a-k) in phosphorus oxychloride yielded 2-(6-methoxy-2-naphthyl)-5-aryl-1,3,4-oxadiazoles (4a-k). Newly synthesized compounds were characterized by IR, (1)H-NMR and mass spectral data. All the compounds were screened for their anti-inflammatory and analgesic activity. Compound 4j exhibited promising anti-inflammatory and analgesic activities.

Synthesis, Antimicrobial and Cytotoxic Activities of Sulfonamidomethane Linked Heterocycles

“…The olefin moiety present in 3 and 4 was used to develop five membered heterocycles, pyrazoles and pyrroles. The 1,3-dipolar cycloaddition of diazomethane to 3 and 4 in the presence of Et 3 N in ether at −20°C for 40-48 h resulted in 2-(arylsulfonylaminomethyl)-5-(4-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-1,3,4-oxadiazoles (5) and 2-(arylsulfonylaminomethyl)-5-(4-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-1,3,4-thiadiazoles (6 chloranil in xylene to afford the aromatized compounds, 2-(arylsulfonylaminomethyl)-5-(4-phenyl-1H-pyrazol-3-yl)-1,3,4-oxadiazoles (7) and 2-(arylsulfonylaminomethyl)-5-(4-phenyl-1H-pyrazol-3-yl)-1,3,4-thiadiazoles (8). The absence of AMX splitting pattern due to pyrazoline ring protons in 7 and 8 indicated that aromatization took place.…”

“…5,6) 1,3,4-Oxadiazole scaffold can also act as hydrogen bond acceptors, which makes it possible to be used as an isosteric substituent for amide or ester groups. 7) Literature survey reveals that 2,5-disubstituted 1,3,4-oxadiazoles have been synthesized either by thermal/acid catalysed cyclization of 1,2-diacylhydrazines 8) or by oxidative cyclization of semicarbazone/hydrazone in the presence of an oxidant 9) or by microwave irradiation of hydrazide and carboxylic acid mixture.…”

Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents

“…Depending on numerous studies, it is regarded that the free carboxylic acid group situated in these molecules composes critical interactions with Arg120, Glu524 and Tyr355 in the COX active site [8][9][10] . The carboxylic acid structure, hence, is considered as an essential pharmacophoric core for COX activity 11 . According to studies, esterification or amidation of the free carboxylic acid group cause reduced COX inhibition activity 12 .…”

Synthesis and antimicrobial evaluation of some new quinazolin-4(3H)-one derivatives

“…The synthesis of novel quinazolin derivatives and investigation of their chemical and antimicrobial behavior has gained more importance in recent decades for biological, medicinal and agricultural reasons [5][6][7][8][9]. Quinazolinone nucleus has been gaining prominence due to the fact that its derivatives have been found to possess wide spectrum of pharmacological properties.…”