Synthesis and Antimicrobial Activity of 2-Bromo-7-methyl-5-oxo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidine

Salimov, T. M.; Kukaniev, M. A.; Sattorov, I. T.; Osimov, D. M.

doi:10.1007/s11094-005-0141-9

Cited by 10 publications

(3 citation statements)

References 2 publications

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“…For our investigation, we chose chloro‐functionalized benzothiazolo[3,2‐ a ]pyrimidin‐4‐one 1 as a readily available starting material . Compound 1 was synthesized by condensation of commercially available 2 ‐ amino ‐ 6 ‐ chlorobenzothiazole with ethyl acetoacetate (Scheme ) …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Benzothiazolo[3,2‐a]pyridimidin‐4‐ones with Potential Cytotoxic and Pro‐Apoptotic Potential

et al. 2018

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The combination of cyclocondensation with palladium catalysed cross‐coupling reactions, afforded a variety of 8‐functionalized benzothiazolo[3,2‐a]pyridimidin‐4‐ones in good to excellent yields. The anti‐proliferative potential of the synthetic compounds was evaluated in human cervical adenocarcinoma cells (HeLa) and hamster normal fibroblasts (BHK‐21). Three of the test derivatives exhibited the strongest cytotoxicity in HeLa cells with the median inhibitory concentration (IC50) of 0.93, 1.55 and 1.84 μM, respectively. Moreover, their anti‐proliferative effect was three times less strong in normal fibroblasts, asserting their possible anti‐cancer potential.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Benzothiazolo[3,2‐a]pyridimidin‐4‐ones with Potential Cytotoxic and Pro‐Apoptotic Potential

et al. 2018

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“…For example, 1,3,4-thiadiazolo(3,2-α)pyrimidine-7-sulfonamide derivatives were synthesized from 5-aminol-3,4-thiadiazole-2-sulfonamide via a two steps approach [24]. Salimov et al [25] prepared 2-bromo-7-methyl-5-oxo-5H-1,3,4-thiadiazolo(3,2-α)pyrimidine by two steps involving the addition of 2-aminothiadiazole derivatives to ethyl acetoacetate, tandem hydrolysis of the ester to the acid, and cyclization to give the ring-fused thiadiazolo(3,2-α)pyrimidines in PPA. Most of these are multistep protocols, which suffer from generation of by-products, low yields, and use of metal-containing reagents.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound Mediated One-Pot, Three Component Synthesis, Docking and ADME Prediction of Novel 5-Amino-2-(4-chlorophenyl)-7-Substituted Phenyl-8,8a-dihydro-7H-(1,3,4)thiadiazolo(3,2-α)pyrimidine-6-carbonitrile Derivatives as Anticancer Agents

Tiwari¹,

Seijas

Vázquez-Tato

et al. 2016

Molecules

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Herein, we report an environmentally friendly, rapid, and convenient one-pot ultrasoundpromoted synthesis of 5-amino-2-(4-chlorophenyl)-7-substituted phenyl-8,8a-dihydro-7H-(1,3,4) thiadiazolo(3,2-α)pyrimidine-6-carbonitrile derivatives. The in-vitro anticancer activities of these compounds were evaluated against four human tumor cell lines. Among all the synthesized derivatives, compound 4i, which has substituent 3-hydroxy-4-methoxyphenyl is found to have the highest GI 50 value of 32.7 µM, 55.3 µM, 34.3 µM, 28.9 µM for MCF-7, K562, HeLa and PC-3 cancer cell lines respectively. A docking study of the newly synthesized compounds were performed, and the results showed good binding mode in the active site of thymidylate synthase enzyme. ADME properties of synthesized compounds were also studied and showed good drug like properties.

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“…Although research on 1,3,4‐thiadiazolo[3,2‐ a ]pyrimidines is not a new one—the first article devoted to this problem was published 50 years ago [ 1], new articles devoted to the chemistry and biological activity of these compounds have been recently published [ 2–13]. In 2004, a monograph on chemistry and biological activity of 1,3,4‐thiadiazolo[3,2‐ a ]pyrimidines was published in Russian, but the book could not cover all the aspects of the aforementioned field [ 14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and conversion of 6‐fluoro derivatives of 1,3,4‐thiadiazolo‐[3,2‐a]pyrimidine

Kukaniev

Párkányi

2011

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).2-Alkyl-, 2-aryl-, and 2-halo-substituted derivatives of 7-methyl-6-fluoro-1,3,4-thiadiazolo[3,2-a]pyrimidin-6-one (3) were prepared by reaction of 2-substituted 5-amino-1,3,4-thiadiazoles (1) and ethyl 2-fluoroacetoacetate (2) in polyphosphoric acid. A convenient procedure was developed for the synthesis of new 2-amino derivatives of 2-R-7-methyl-6-fluoro-1,3,4-thiadiazolo[3,2-a]pyrimidin-6-one (5).

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Synthesis and Antimicrobial Activity of 2-Bromo-7-methyl-5-oxo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidine

Abstract: The synthesis of 2-bromo-7-methyl-5-oxo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidine is described. This compound exhibits a broad spectrum of antimicrobial action and can be useful in the search for new antimicrobial drugs.

Cited by 10 publications

References 2 publications

Synthesis of Novel Benzothiazolo[3,2‐a]pyridimidin‐4‐ones with Potential Cytotoxic and Pro‐Apoptotic Potential

Synthesis of Novel Benzothiazolo[3,2‐a]pyridimidin‐4‐ones with Potential Cytotoxic and Pro‐Apoptotic Potential

Ultrasound Mediated One-Pot, Three Component Synthesis, Docking and ADME Prediction of Novel 5-Amino-2-(4-chlorophenyl)-7-Substituted Phenyl-8,8a-dihydro-7H-(1,3,4)thiadiazolo(3,2-α)pyrimidine-6-carbonitrile Derivatives as Anticancer Agents

Synthesis and conversion of 6‐fluoro derivatives of 1,3,4‐thiadiazolo‐[3,2‐a]pyrimidine

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