Modular synthesis of thiazoline and thiazole derivatives by using a cascade protocol

Alsharif, Zakeyah; Alam, Mohammad A.

doi:10.1039/c7ra05993k

Cited by 36 publications

(23 citation statements)

References 20 publications

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“…Intermediate 5-methyl-2-(pyridin-3-yl)-1,3-thiazole-4-carbohydrazide (1) was prepared as reported earlier [17,18] by the condensation of ethyl 5-methyl-2-(pyridin-3-yl)thiazole-4-carboxylate with hydrazine hydrate as outlined in Scheme 1. Furthermore, both 5-methyl-2-(pyridin-3-yl)-1,3thiazole-4-carbohydrazide (1) and 4-fluorobenzladehyde were taken in equal quantities and a catalytic amount of acetic acid was added and refluxed for 4 h. Following this, the synthesized compound was confirmed by elemental analysis, FT-IR, LCMS, 1 H-NMR, and 13 C-NMR.…”

Section: Resultsmentioning

confidence: 99%

(E)-N′-(4-Fluorobenzylidene)-5-methyl-2-(pyridin-3-yl)thiazole-4-carbohydrazide

Kamat

Santosh

Nayak

2019

Molbank

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5-methyl-2-(pyridin-3-yl)-1,3-thiazole-4-carbohydrazide (1) on treatment with 4-fluorobenzaldehyde in presence of catalytic amount of acetic acid, accessed the target compound (2) with the yield of 79%. The target compound was confirmed by 1 H-NMR, 13 C-NMR, FT-IR and LCMS. In vitro antibacterial activity against Staphylococcus aureus (S. Aureus), Bacillus subtilis (B. subtilis), Escherichia coli (E. coli), and Pseudomonas aeruginosa (P. aeruginosa) were carried out and compound 2 showed promising activity against B. subtilis. In addition, compound 2 was analyzed for DNA binding study. It revealed that compound 2 has a promising affinity towards DNA double helix.

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Section: Resultsmentioning

confidence: 99%

(E)-N′-(4-Fluorobenzylidene)-5-methyl-2-(pyridin-3-yl)thiazole-4-carbohydrazide

Kamat

Santosh

Nayak

2019

Molbank

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“…In our quest to synthesize bioactive molecules 35−37 and to develop new domino reactions to synthesize heterocycles, 38,39 we planned the synthesis of thiazolino-androstanedione derivatives by using our recently reported methodology, the synthesis of thiazoline derivatives ( 2 ) by reacting thioamides with γ-bromoenones ( 1 ). 40 Reaction of 6β-bromoandrostenedione ( 3 ) with thiourea derivatives formed aminothiazoloandrostenone derivative ( 4 ) by an unexpected mechanism. 41 Surprisingly, reaction of thioamide derivative ( 5 ) with the electrophile ( 3 ) did not form the product in refluxing ethanol, as we expected from our previous report (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Hexafluoroisopropanol-Mediated Domino Reaction for the Synthesis of Thiazolo-androstenones: Potent Anticancer Agents

et al. 2018

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A cascade reaction of thioamides with 6β-bromoandrostenedione in hexafluoroisopropanol formed substituted thiazolo-androstenones. This is a simple and mild protocol to synthesize novel molecules by using readily available reagents and substrates. Feasibility of the reaction has been rationalized by density functional theory calculations. Moreover, these compounds are potent growth inhibitors of colon, central nervous system, melanoma, ovarian, and renal cancer cell lines with 50% growth inhibition values as low as 1.04 μM.

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“…Several methods for the synthesis of thiazoles and their derivatives were developed by various catalysts, conditions, and strategies [12][13][14][15][16][17][18][19][20][21]. From these methods, we were interested in the synthesis of thiazoles by condensation of α-halo ketones with thioamides [22][23][24][25][26][27][28]. Beyzaei et al reported the one-pot synthesis of thiazol-2(3H)-imines through nucleophilic substitution of chloride in 3chloroacetylacetone with thiocyanate group followed by cyclo condensation with various hydrazine or hydrazide derivatives.…”

Section: Introductionmentioning

confidence: 99%