Synthesis of Novel 4-Thiazolidinone and Bis-Thiazalidin-4-One Derivatives Derived from 4-Amino-Antipyrine and Evaluated as Inhibition of Purine Metabolism Enzymes by Bacteria

Abstract

Novel 4-thiazolidione and 1,4-bis-thiazolidinone derivatives bearing antipyrine moiety have been obtained from condensation of 4-aminoantipyrine 1 with aromatic/heteroaldehydes followed by cycloaddition with mercaptoacetic acid in nonpolar solvents. Structure of the products has been deduced upon their elemental analysis and spectral measurements. Most of the targets evaluated as enzymatic effect towards some bacteria (E. coli) in compare with Xanthine oxidase (from buttermilk) where the role of compounds is an inhibition of purine metabolism enzymes caused by E. coli.

Synthesis and antitumor activity of new isolated and fused heterobicyclic nitrogen systems containing 1,3,4-thiadiazole moiety derived from N1,N2-diaryl hydrazine compound

“…M.p: 154-156° C. FT-IR (ATR, ῡ, cm -1 ): 3500-3200 (b, OH, NH), 3120 (NH), 1610 (C=N), 3050 (ArH), 700 (C-Cl). 1…”

“…M.p: 168-170° C. FT-IR (ATR, ῡ, cm -1 ): 3430-3380 (b, 2OH), 3060 (ArH), 2980, 2880 (aliphatic CH), 1700-1680 (C=O), 1610 (C=N), 1470, 1440 (deformation CH 2 ), 1090 (C-S-C), 710 (C-Cl). 1 2-(4-Chlorophenyl)-7-(2-hydroxyphenyl)-2,3-dihydro-4H-[1,3, 4]thiadiazolo[2,3-c][1,2,4]triazin-4-one (7) A mixture of compound 2 (2 g, 6.28 mmol) and monochloroacetic acid (0.593 g, 6.28 mmol) in DMF (50 ml) was refluxed for 2 h and then cooled. It was then poured onto ice.…”

“…In addition, one of the important aims of the present work is to combine two different heterocyclic nuclei as one system with the hope to enhance their biological effects. Thus, refluxing compound 2 with monochloroacetic acid in DMF yielded 2-(4chlorophenyl)-7-(2-hydroxyphenyl)-2,3-dihydro-4H- [1,3,4]thiadiazolo [2,3-c] [1,2,4]triazin-4-one (7), while refluxing with diethyl oxalate in THF, produced 2-(4-chlorophenyl)-7-(2hydroxyphenyl)-2H- [1,3,4] The former structure of the new products 2-10 was established with their corrected analysis and spectral data (FT-IR, 1 H/ 13 C NMR, Mass study). The FT-IR spectrum of compound 2 recorded ῡ at 3500-3200, 3120 cm -1 for OH, NH, NH and 1610, 700 cm -1 for C=N and C-Cl.…”

“…The design and synthesis of heterocyclic molecules from different small groups of heterocycles with influence on biological, pharmaceutical and therapeutic area, have been reported to control the high resistance of microbes towards the used antibiotics [1][2][3][4][5]. Cancer chemotherapy is complex, expensive and often rather inefficient because of toxicity levels and non-specificity of drugs and the emergence of drug resistance and multi-drug-resistant (MDR) strains [6][7][8].…”

“…It is interesting to note that substituted pyrazoles exhibited a wide range of biological, pharmacological, and medicinal activities [15][16][17][18][19][20]. Recently, functionally 1,2,4-triazine derivatives showed an important biological activity such as anti-HIV, and anticancer [21], antioxidant [22], anti-inflammatory [23], antifungal [24], herbicidal [25] and antibacterial [26,27] agents. Also, 1,3,4thiadiazoles containingsmall heterocyclic nitrogen nucleus exhibited a greatspectrum biological activity as anti-inflammatory [28], anticancer [29,30], antimicrobial [31,32], anti-HIV, and antitumor [33], and antimycotic [34] agents.…”