Antimicrobial Assessment of Some Heterocyclic Compounds Utilizing Ethyl 1-Aminotetrazole-5-carboxylate

Abstract

ABSTRACT. Ethyl 1-aminotetrazole-5-carboxylate (1) reacted with hydrazine hydrate to give the corresponding aminohydrazide 2. Cyclization of 2 by carbon disulfide yielded 1,3,4-oxadiazole-5-thiol structure 3. Reaction of 3 with either chloroacetone or ethyl chloroacetate furnished S-acyl 1,3,4-oxadiazole derivatives 4 and 5, respectively. Also compound 3 reacted with hydrazine hydrate afforded 4-amino-1,2,4-triazole-5-thiol derivative 6. 6-Methyl-1,3,4-triazolo[3,4-b]-1,3,4-thiadiazole structure 7 was synthesized by reaction of aminothiol 6 with glacial acetic acid. Diazotization of 1 with sodium nitrite in presence of hydrochloric acid yielding the diazonium salt which on treating with hippuric acid, oxazolone derivative 8 was obtained. Furthermore, tetrazolo[5,1-f]-1,2,4-triazine 9 was constructed via cyclization of aminoester 1 with formamide. Compound 9 reacted with carbon disulfide to furnish 8-thione derivative 10 which reacting with chloroacetone, ethyl chloroacetate, and hydrazine hydrate, the corresponding chemical structures 11, 12, and 13 were synthesized. 1,2,4-Triazolo [4,3-d]tetrazolo[5,1-f]-1,2,4-triazines 14 and 15 were resulted by treating of compound 13 with triethyl orthoformate, and glacial acetic acid, respectively. The structures of the newly synthesized products were elucidated according to elemental analyses and spectroscopic evidences. Some of the representative members of the prepared compounds were screened for antimicrobial activity.

Naphthalen-2-yl 1-(benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate

“…The development of click chemistry, which allows 1,2,3-triazoles to be obtained in a simple and efficient way, has flooded the literature in recent years with their ability to affect the reactivity of biological targets and to influence metabolism and pharmacokinetics [22]. Thus, their hybridization with other pharmacophores such as indole, quinoline, flavone, and other aminoesters have made it possible to evaluate anticancer activity [22,23]. For example, Nazariy et al synthesized a series of triazole molecules, derived from heterocyclic aminoesters [24], showing acceptable efficacy against cancer cells (lung, breast, and prostate cancer).…”

A new direct synthetic access to 4-amino-2-N-(glycosyl/propyl)-1,2,4-triazole-3-thiones via hydrazinolysis of 3-N-((acylated glycosyl)/allyl)-1,3,4-oxadiazole-2-thiones

“…They show antimicrobial, [1][2][3][4][5][6][7] antiproliferative, 8 antituberculosis, [9][10][11] anticonvulsant, 12 analgesic, 13 anti-inflammatory, 14 antitumor 15 and antidepressant 16 activities in addition to their inhibitory activity of trans-cinnamate 4-hydroxylase 17 and urease 18 enzymes. On this basis, searching for the synthesis of new 4-amino-1,2,4-triazole-thione derivatives is justified.…”

“…It is well known that reaction of hydrazine hydrate with 1,3,4-oxadiazolethione IV in ethanol gives 4-amino-1,2,4-triazole-thione I. [1][2][3][4][5][6][7][8][9][10][11][12][13] We wondered what would happen in its reaction with S-alkylated 1,3,4-oxadiazoles V and N-alkylated 1,3,4-oxadiazole-thiones VI. We doubted the report 19 that reaction of V with hydrazine hydrate leads to replacement of S-alkyl with a hydrazino group without breakdown of the oxadiazole moiety.…”