4-Thiazolidinone – A biologically active scaffold

Isatin is an endogenous compound identified in humans that possesses a wide range of biological activities. Isatin has anxiogenic, sedative, anticonvulsant activities and acts as a potent antagonist on atrial natriuretic peptide receptors in vitro. A series of p-substituted isatin semicarbazones have shown anticonvulsant activity in MES, scPTZ and scSTY tests. Various isatin-N-Mannich bases of isatin-3-thiosemicarbazones have shown antiviral and tuberculostatic activity. Methisazone is an effective compound against variola and vaccinia viruses. The N-dimethyl and morpholino derivative of 5-methyl isatin and trimethoprim exhibited an EC50 of more than 4.3 and 17.7 mg mL(-1), respectively. Isatin (3-o-nitrophenyl) hydrazone has shown activity against Walker carcinoma-256. Various substituted indolinones showed antitubercular activity against M. tuberculosis H37Rv with MIC ranging from 10-20 microg mL(-1). Isatin derivatives of Mannich bases had fibrinolytic, muscle relaxant, antiallergic, immunosuppressant, and antithrombotic activity. Isatin showed cardioinhibitory effect on frog heart, and hypotensive, respiratory depression and antidiuretic effects.

/pdf/biological-activities-of-isatin-and-its-derivatives-2n13cxnlnf.pdf

Biological activities of isatin and its derivatives.

Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives.

Schiff bases of N-methyl and N-acetyl isatin derivatives with different aryl amines have been synthesized and screened for anticonvulsant activities against maximal electroshock (MES) and subcutaneous metrazole (ScMet). N-methyl-5-bromo-3-(p-chlorophenylimino) isatin (2) exhibited anticonvulsant activity in MES and ScMet with LD50 > 600 mg kg(-1), showing better activity than the standard drugs phenytoin, carbamazepine and valproic acid. Thus, compound 2 may be chosen as a prototype for development of new anticonvulsants.

/pdf/anticonvulsant-activity-of-schiff-bases-of-isatin-3z7p1lnq72.pdf

Frank D. Popp

Papers

Potential Anticonvulsants VI: Condensation of Isatins with Cyclohexanone and other Cyclic Ketones

Synthesis of potential anticonvulsants: Condensation of isatins with acetone and related ketones

Potential anticonvulsants. IX. Some isatin hydrazones and related compounds

Synthesis and antileukemic activity of spiro[indoline‐3,2′‐thiazolidine]‐2,4′‐diones

Synthesis of 3-hydroxy-3-phenacyloxindole analogs.