ChemInform Abstract: Synthesis and Antimicrobial Activity of Some Bridgehead Nitrogen Heterocycles.

Dhiman, A M; Wadodkar, K. N.; Patil, S. D.

doi:10.1002/chin.200141058

Cited by 3 publications

(3 citation statements)

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“…The reaction of isonicotinic acid hydrazide 1 with various aryl isothiocyanates afforded the corresponding hydrazinecarbothioamide derivatives 30,31) 2a-d. Oxidative cyclization of the latter compounds in 4 N NaOH using a mixture of I 2 / KI (5%) furnished the corresponding 5-(pyridin-4-yl)-N-substituted-1,3,4-oxadiazol-2-amines 32,33) (3a-d) via elimination of H 2 S. On the other hand, 5-(pyridin-4-yl)-N-substituted-1,3,4-thiadiazol-2-amines 32,34) (4a-d) were obtained by cyclization of 2a-d upon reaction with cold conc. H 2 SO 4 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles, 1,2,4-Triazoles and Mannich Bases

Abdo

Kamel

2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of 5-(pyridin-4-yl)-N-substituted-1,3,4-oxadiazol-2-amines (3a-d), 5-(pyridin-4-yl)-N-substituted-1,3,4-thiadiazol-2-amines (4a-d) and 5-(pyridin-4-yl)-4-substituted-1,2,4-triazole-3-thiones (5a-d) were obtained by the cyclization of hydrazinecarbothioamide derivatives 2a-d derived from isonicotinic acid hydrazide. Aminoalkylation of compounds 5a-d with formaldehyde and various secondary amines furnished the Mannich bases 6a-p. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data and elemental analyses. All the compounds were screened for their in vitro anticancer activity against six human cancer cell lines and normal fibroblast cells. Sixteen of the tested compounds exhibited significant cytotoxicity against most cell lines. Among these derivatives, the Mannich bases 6j, 6m and 6p were found to exhibit the most potent activity. The Mannich base 6m showed more potent cytotoxic activity against gastric cancer NUGC (IC50=0.021 µM) than the standard CHS 828 (IC50=0.025 µM). Normal fibroblast cells WI38 were affected to a much lesser extent (IC50>10 µM).

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Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles, 1,2,4-Triazoles and Mannich Bases

Abdo

Kamel

2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The same two compounds were formed in the reaction between 2-chloro-1, 3, 4-thiadiazole and benzylamine 64,65 .…”

Section: Rearrangements and Ring Opening Reactionmentioning

confidence: 83%

Chemistry, synthesis and progress report on biological activities of thiadiazole compounds - a review

Asif¹

2016

Mediterr.J.Chem.,

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Thiadiazoles are an important class of heterocyclic compounds that exhibit diverse applications in organic synthesis, pharmaceutical and biological applications. They are also useful as oxidation inhibitors, cyanine dyes, metal chelating agents, anti-corrosion agents. Researchers across the globe are working on this moiety due to their broad spectrum of applications of thiadiazole chemistry. This article provides information about developments, exploration, synthetic strategies, techniques for the synthesis of thiadiazoles and their diverse biological activities, structure-activity relationship of the compounds and physical properties. This article is an important tool for organic and medicinal chemists to develop newer thiadiazole compounds that could be better agents in terms of efficacy and safety.

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“…15–19 Alkylations with the appropriate α-halo ketone and microwave-assisted cyclodehydrations afforded the original hits 1a and 2b (Scheme 1). …”

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confidence: 99%

Optimization of pyrazole-containing 1,2,4-triazolo-[3,4-b]thiadiazines, a new class of STAT3 pathway inhibitors

LaPorte

Wang

Colombo

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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Structure-activity relationship studies of a 1,2,4-triazolo-[3,4-b]thiadiazine scaffold, identified in an HTS campaign for selective STAT3 pathway inhibitors, determined that a pyrazole group and specific aryl substitution on the thiadiazine were necessary for activity. Improvements in potency and metabolic stability were accomplished by the introduction of an α-methyl group on the thiadiazine. Optimized compounds exhibited anti-proliferative activity, reduction of phosphorylated STAT3 levels and effects on STAT3 target genes. These compounds represent a starting point for further drug discovery efforts targeting the STAT3 pathway.

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ChemInform Abstract: Synthesis and Antimicrobial Activity of Some Bridgehead Nitrogen Heterocycles.

Cited by 3 publications

References 0 publications

Synthesis and Anticancer Evaluation of 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles, 1,2,4-Triazoles and Mannich Bases

Synthesis and Anticancer Evaluation of 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles, 1,2,4-Triazoles and Mannich Bases

Chemistry, synthesis and progress report on biological activities of thiadiazole compounds - a review

Optimization of pyrazole-containing 1,2,4-triazolo-[3,4-b]thiadiazines, a new class of STAT3 pathway inhibitors

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