Synthesis of biginelli products of thiobarbituric acids and their antimicrobial activity

Abstract

A simple and efficient method has been developed for the synthesis of 2,4,7-tri(substituted) phenyl-2,4,8,10-tetraza-3,9-dithioxo-5-oxobicyclo-[4.4.0]dec-1(6)-ene (4) and 2,4,7-tri(substituted)phenyl-2,4,8,10-tetraza-3-thioxo-5,9-dioxobicyclo[4.4.0]dec-1(6)-ene (5), by a one-pot, three-component cyclocondensation reaction of a 1,3 dicarbonyl compound (thiobarbituric acid), an aromatic aldehyde, and urea/thiourea using catalytic a amount of concentrated HCl in refluxing ethanol. Representative samples were screened for their anti-microbial activity against the Gram-negative bacteria, Escherichia coli and Proteus aeruginosa, and the Gram-positive bacteria, Staphyllococcus aureus and Corynebacterium diphtheriae using the disc diffusion method. The structures of the products were confirmed by IR, 1 H-and 13 C-NMR spectroscopy, as well as by elemental analysis.

Design and synthesis of new barbituric- and thiobarbituric acid derivatives as potent urease inhibitors: Structure activity relationship and molecular modeling studies

“…Similarly thiobarbiturates behave as HIV integrase inhibitors [40], anticonvulsant and anesthetic [33], antibacterial [41,42], antifungal [43], antiviral [44] antitumor activities [45], tyrosinase inhibitors [46,47] and anticancer with anti-inflammatory activities [48].…”

Synthesis of New Deoxycholic Acid bis Thiocarbazones under Solvent-Free Conditions using Microwave Irradiation

“…Compound 3 was prepared by a known procedure. 19 Preparation of substituted benzaldehyde thiocarbohydrazones 2a-j 20 The aromatic aldehyde (10 mmol) in ethanol (40 mL) was added dropwise to the solution of thiocarbohydrazide (15 mmol) in H 2 O…”

Exploiting the Thiobarbituric Acid Scaffold for Antibacterial Activity

“…In addition, BA and TBA exhibit a wide range of biological activities, including antiepileptic, anticancer, antioxidant, anticonvulsant, immunomodulatory, gelatinase‐inhibiting, HIV integrase‐inhibiting, antifungal, antiviral, tyrosinase‐inhibiting, anti‐inflammatory, and antidiabetic effects. BA and TBA derivatives have also been evaluated for antimicrobial activity . 5‐Benzylidene BA and TBA show antibacterial activity, as well as an inhibitory effect against mushroom tyrosinase .…”