Synthesis and Pharmacological Activities of Novel Bicyclic Thiazoline Derivatives as Hepatoprotective Agents. II. (7-Alkoxycarbonyl-2,3,5,6-tetrahydropyrrolo(2,1-b)thiazol-3-ylidene)acetamide Derivatives.

Abstract

A series of exomethylenic bicyclic thiazoline derivatives (3a--i) was synthesized and evaluated for hepatoprotective activity against galactosamine-induced and monoclonal antibody-induced acute liver injuries in rats. The structure-activity relationships were investigated. Among the compounds synthesized, N-methyl-(7-isopropoxy-carbonyl-6,6-dimethyl-2,3,5,6- tetrahydropyrrolo[2,1-b]thiazol-3-ylidene)acetamide (3i) exhibited the most potent hepatoprotective activity. This compound suppressed galactosamine-induced hepatic injury at 100 mg/kg by oral administration and further prevented monoclonal antibody-induced hepatic injury at 30 mg/kg by intraperitoneal injection, as judged from the changes in serum transaminase activities.

Catalyst-free Tandem 1,3-Dipolar Cycloaddition/Aldol Condensation: Diastereoselective Construction of the Azatetraquinane Skeleton

“…This approach is based on the noncatalytic tandem of 1,3-DC and aldol condensation between enediones 7 and ninhydrin-(thia)­proline azomethine ylide. Benzo­[4,5]­pentaleno­[1,6 a - b ]­(thia)­pyrrolizidine-6,12-diones 8 contain biologically active indane-fused cyclopentalene and pyrrolizidine or thiazolidine moieties and are of interest from the point of view of medicinal chemistry.…”

An expeditious and environmentally benign synthesis of dispiro-3-phenylpyrrolothiazoles in ACI/EG eutectic mixture and its antioxidant and antimicrobial activities against urinary tract pathogens

“…Having medicinal values, thiazolidine ring systems play an important role in organic synthesis particularly antimicrobial substances such as penicillins, cephalosporins, narcodicins, thienamicyn and other compounds that have physiological activities have been prepared from thiazolidine [8]. It is noted that spiropyrrolothiazole analogues are interesting because of their wide range of biological activities such as anti-cancer [9], anti-diabetic [10], antibiotic [11], anti-inflammatory [12], hepatoprotective [13], anti-convulsant [14], anti-leukemic agents [15], Alzheimer disease [16], and also good in anti-mycobacterial [17]. Spiro indolin-2-one nucleus was reported to treat diabetic patients, HIV-1 protease inhibitors, potent gastrain/CCK-B receptor antagonist and for growth hormone secretagogue receptor agonists [18].…”

A Regioselective Synthesis of Carbazole‐Appended Dispiropyrrolothiazoles/Pyrrolidines: Synthesis, Computational Studies and In Vitro Anticancer Activity

“…The spiro heterocycles containing pyrrolidine/pyrrolothiazole rings are of interest in organic synthesis due to their pronounced biological activities . In particular, spiropyrrolothiazoles are seen to be promising candidates for drug discovery as they display a wide range of biological activities, including anticancer, hepatoprotective, antimicrobial, antidiabetic, anticonvulsant and acetylcholinesterase inhibitory properties . Batracyclin is a potent antitumor alkaloid bearing indeno[1,2‐ b ]quinoxaline system.…”