One-pot synthesis of new 2,4,5-trisubstituted 1,3-thiazoles and 1,3-selenazoles

Thomae, David; Perspicace, Enrico; Xu, Zhanjie; Henryon, Dorothée; Schneider, Serge; Hesse, S.; Kirsch, Gilbert; Seck, Pierre

doi:10.1016/j.tet.2009.01.104

Cited by 47 publications

(19 citation statements)

References 38 publications

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“…This latter derivative was obtained by a one-pot three-step sequential procedure, starting from the condensation of dimethyl cyanodithioimidocarbonate 4 and sodium sulfide, followed by the addition of 1-(3′,4′,5′-trimethoxyphenyl)-2-bromoethanone and cyclization with potassium carbonate (Scheme 1) [8]. Compounds 3d – o were prepared by one-pot four step procedure from 4 , which was condensed successively with the appropriate secondary amine, sodium sulfide, the corresponding α-bromoacetophenone and finally cyclized with potassium carbonate.…”

Section: Chemistrymentioning

confidence: 99%

One-pot synthesis and biological evaluation of 2-pyrrolidinyl-4-amino-5-(3′,4′,5′-trimethoxybenzoyl)thiazole: A unique, highly active antimicrotubule agent

Romagnoli¹,

Baraldi²,

Cara³

et al. 2011

European Journal of Medicinal Chemistry

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A wide variety of small molecules with diverse molecular scaffolds inhibit microtubule formation. In this article we report a one-pot procedure for the preparation of a novel 2-(N-pyrrolidinyl)-4-amino-5-(3′,4′,5′-trimethoxybenzoyl)thiazole in which the size of the substituent at the C-2 position of the thiazole ring plays an essential role in compound activity. The most active agent (3f) inhibited at sub-micromolar concentrations the growth of tumor cell lines. It also inhibited tubulin polymerization with an activity quantitatively similar to that of CA-4, and treatment of HeLa cells resulted in their arrest at the G2-M phase of the cell cycle. Furthermore, 3f was effective against multidrug resistant cancer cells and inhibited the growth of the HT-29 xenograft in a nude mouse model. This indicated that 3f is a promising new antimitotic agent with encouraging preclinical potential.

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Section: Chemistrymentioning

confidence: 99%

One-pot synthesis and biological evaluation of 2-pyrrolidinyl-4-amino-5-(3′,4′,5′-trimethoxybenzoyl)thiazole: A unique, highly active antimicrotubule agent

Romagnoli¹,

Baraldi²,

Cara³

et al. 2011

European Journal of Medicinal Chemistry

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“…Several methods for the synthesis of tri -substituted thiazoles have been reported [26][27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological activity of 1,3-Thiazolylidenehydrazinylidene ethylpyridiniumbromide monohydrate, 1,3-Thiazolylidenehydraziniumbromide and 1,3-Thiazolylidenehydrazine derivatives

Hassan

Mohamed

et al. 2015

JAC

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ABSTRACT1,3-Thiazolylidenehydrazinylidene ethylpyridinium bromide monohydrate, 1,3 -thiazolylidenehydrazinium bromide and 1,3-thiazolylidenehydrazine derivatives were synthesized by heterocyclization of 2-(1-substituted ethylidene)hydrazinecarbothioamides, characterized and screened for their anti-bacterial activities. 3h showed the highest inhibitory effect against all types of bacterial compared to Moxiflo xacin. The structures of synthesized compounds were established by spectroscopic (IR, 1 H,13 C-N MR, Mass) and X-ray analyses.

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“…Many natural and synthetic molecules containing the thiazole moiety play a significant role in the pharmaceutical industry due to their anti-inflammatory [3,4], anti-HIV [5], anti-bacterial [6], anti-cancer [7] properties. Today, there are many methods for the preparation of the thiazole moiety [8][9][10][11][12]. One of the most excellent and efficient method is the Hantzsch thiazole synthesis [13,14] that employs the reaction of -haloketones or -tosyloxyketones with thioamides.…”

Section: Introductionmentioning

confidence: 99%

Preparation of α-Bromoketones and Thiazoles from Ketones with NBS and Thioamides in Ionic Liquids

Izumisawa¹,

Togo²

2011

GSC

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Ketones smoothly reacted with NBS in the presence of a catalytic amount of p-toluenesulfonic acid to give α-bromoketones in good yields in typical ionic liquids, such as [bmim]PF 6 and [bmpy]Tf 2 N, and the ionic liquids could be repeatedly used for the same reaction after the extraction of the α-bromoketones. Then, the one-pot conversion of ketones into thiazoles by the treatment with NBS, and subsequently with thioamides could be also carried out in [bmim]PF 6 and [bmpy]Tf 2 N, respectively Thus, [bmim]PF 6 and [bmpy]Tf 2 N could be used as recyclable reaction media for the preparation α-bromoketones and thiazoles from ketones.

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One-pot synthesis of new 2,4,5-trisubstituted 1,3-thiazoles and 1,3-selenazoles

Cited by 47 publications

References 38 publications

One-pot synthesis and biological evaluation of 2-pyrrolidinyl-4-amino-5-(3′,4′,5′-trimethoxybenzoyl)thiazole: A unique, highly active antimicrotubule agent

One-pot synthesis and biological evaluation of 2-pyrrolidinyl-4-amino-5-(3′,4′,5′-trimethoxybenzoyl)thiazole: A unique, highly active antimicrotubule agent

Synthesis and Biological activity of 1,3-Thiazolylidenehydrazinylidene ethylpyridiniumbromide monohydrate, 1,3-Thiazolylidenehydraziniumbromide and 1,3-Thiazolylidenehydrazine derivatives

Preparation of α-Bromoketones and Thiazoles from Ketones with NBS and Thioamides in Ionic Liquids

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