Design and Synthesis of Some Oxadiazolyl, Thiadiazolyl, Thiazolidinyl, and Thiazolyl Derivatives of 1H-Pyrazole as Anti-inflammatory Antimicrobial Agents

Abstract

Four series of 1H‐pyrazole derivatives have been synthesized. The first series was prepared by cyclization of the intermediate 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐1H‐pyrazole‐4‐carbaldehyde aroylhydrazone 4a—c with acetic anhydride to afford the corresponding oxadiazoline derivatives 5a—c. The other series were prepared by the cyclization of the intermediate 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐4‐substituted thiocarbamoylhydrazonomethyl‐1H‐pyrazole 6a—c with acetic anhydride, ethyl bromoacetate or phenacyl bromide giving rise to 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐4‐[3‐acetyl‐5‐(N‐substituted acetamido)‐2,3‐dihydro‐1,3,4‐thiadiazol‐2‐yl]‐1H‐pyrazoles 7a—c, 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐4‐(3‐substituted‐4‐oxothiazolidin‐2‐ylidenehydrazonomethyl)‐1H‐pyrazoles 8a—c, or 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐4‐(3‐substituted‐4‐phenyl‐2,3‐dihydrothiazol‐2‐ylidenehydrazonomethyl)‐1H‐pyra zoles 9a—c respectively. Some of these compounds showed antiinflammatory, antibacterial or antifungal activities comparable to that of Proquazone, Ampicillin, or Clotrimazole respectively.

Design, synthesis, and pharmacological evaluation of fluorinated azoles as anti‐tubercular agents

“…Moreover, 1,3,4‐oxadiazole derivatives exhibit diverse biological profile such as anti‐HIV, antimalarial, analgesic, antiinflammatory, anticonvulsant, and as lipid peroxidase inhibitors . Interestingly, the constrained analogue of isopropyl phenyl ether such as 2,2‐dimethyl‐2,3‐dihydrobenzofuran has been found in zatosetron ( F ) as 5‐HT3 antagonist and derivative G as serotonin 2C agonist (Figure ).…”

Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

“…The 1,3,4-oxadiazoles have been found to exhibit diverse biological activities such as antimicrobial [29][30][31][32][33], antitubercular [34], antioxidant [35], antimalarial [36], analgesic [37], anti-inflammatory [38,39], anticonvulsant [40], hypoglycemic [41] activities, as well as other biological properties such as genotoxic [42] and lipid peroxidation inhibitory activities [43]. Two examples of compounds containing the 1,3,4-oxadiazole ring used in clinical medicine are raltegravir, an antiretroviral drug [44] and zibotentan, an anticancer agent [45] (Figure 2).…”

Synthesis and in-vitro antibacterial activity of some alkoxy based N-substituted-5-(furan-2-yl)-phenyl-bis-pyrazolines

“…The effective treatment for gastrointestinal is metronidazole; however, lengthy treatment or high doses often cause side effects such as headache, nausea, vomiting, dry mouth, metallic taste, dizziness, and neurological complications [5][6][7]. The chemistry of cyclised heterocyclic systems especially containing pyrazole moiety has been largely investigated due to their effective use in pharmacological areas [8][9][10][11][12][13][14][15][16]. Chalconoids group are the chalcone compounds which are the open chain molecule having two aromatic ring liked by the carbon fragment, exhibit a wide spectrum of beneficial biological activity anti-inflammatory, anti-invasive and optical properties [17].…”