Synthesis, Metal Ions Coordination, Antimicrobial Activity of Some L-Tartaric Acid Derivatives

Abstract

Abstract:The bis-1,3,4-oxadiazole-thione and bis-4-amino-1,2,4-triazole-thiol derivatives from L-tartaric acid were synthesized. The synthetic intermediates, ester, hydrazide and oxadiazole derivatives have shown a significant tendency to form complexes with Fe(III), Ni(II) and Cu(II) ions. The formation of complexes with metals was detected by UV-Vis and IR spectroscopy. A novel complex nucleoside from bis-4-amino-1,2,4-triazole-thiol derivative with l-arabinose was also synthesized. The antimicrobial activity for final and synthetic intermediates in vitro against the microorganisms: Escherichia coli, Pseudomonas aeruginosa, Yersinia pseudotuberculosis, Enterococcus faecalis, Staphylococcus aureus and Candida albicans were examined and some products showed noticeable activity against the tested microorganisms.

Synthesis and Antimicrobial Activity of 1,3,4-Oxadiazoline, 1,3-Thiazolidine, and 1,2,4-Triazoline Double-Tailed Acyclo C-Nucleosides

“…In this context, it seems interesting to investigate whether acetylation of the cyclic tautomer, namely, terephthaloyl bis-(β-D-glucosylhydrazide) (10) with hot acetic anhydride behaved similarly to acyclic tautomer 9 to give 3-acetyl-1,3,4-oxadiazoline structure or behaved differently to afford the proposed Nacetyl-D-glucohydrazide (Scheme 1). Corroboration of the obtained product assigned the structure of 1,3,4-oxadiazoline acyclo C-nucleoside 17 was made on the basis of its microanalytical data agreeing with the molecular formula C 44 H 54 N 4 O 24 .…”

“…On the other hand, in the recent 2 decades, significant growth in scientific publications dealing with the synthesis of numerous acyclo C-nucleosides analogues, especially after many the members showed diverse biological activities. Furthermore, several modifications have been made at the molecular structural level of acyclo C-nucleosides including a number of nucleobase − (head) and alditolyl chains , (tail). Among the structurally modified acyclo C-nucleosides, there are double-tailed acyclo C-nucleosides and a unique structural feature is the presence of two carbon-linked alditolyl chains of one or two of identical nucleobases or more of different nucleobase.…”

“…In order to utilize new double tailed acyclo C-nucleoside synthones, heating of the hydrazones 9−15 with an excess amount of thioglycolic in the presence of pyridine afforded the corresponding N,N-bis(2-alditol-1-yl-4-oxo-1,3-thiazolidin-3yl)terphthalamides 23−29. Also the reaction of hydrazone(9), glucosylhydrazide(10), or their tautomeric mixtures (11a ⇌ 11b), (14a ⇌ 14b ⇌ 14c) with hydrazine hydrate afforded 1,4-bis(3-alditol-1-yl-4-amino-1,2,4-triazolin-5-yl)benzenes 30−33. The preliminary antimicrobial activities of the new 1,3,4-oxadiazoline, 1,3-thiazolidine, and 1,2,4-triazoline double-tailed acyclo C-nucleosides showed promising results5.…”