Synthesis of New Rhodacyanines Analogous to MKT‐077 under Microwave Irradiation

Kasmi‐Mir, Souad; Djafri, Ayada; Hamelin, J.; Paquin, Ludovic; Bazureau, Jean Pierre; Rahmouni, Mustapha

doi:10.1080/00397910701575400

Cited by 10 publications

(3 citation statements)

References 12 publications

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“…The increasing diversity of azolidinone heterocyclica, particularly thiazolidin-4 one derivatives [1,2,3,4,5] has been widely investigated for a range of pharmacological activities [6], such antiviral, anticonvulsant [6], antibacterial [7], hypolipidaemic and anti-inflammatory effects, and potential anticancer drug candidates [8,9,10]. In recent years, the push-pull effects of thiazolidinone derivatives have been receiving special attention of physicists and chemists for their nonlinear optical properties [11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Determination of Novel 5-Arylidene-3-N(2-alkyloxyaryl)-2-thioxothiazolidin-4-ones

et al. 2012

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As part of our project devoted to the synthesis of heterocycles including thiazole rings, some new 5-arylidene-2-thioxo-3-N-arylthiazolidin-4-ones were synthesized by Knoevenagel condensation. An interesting feature of these compounds is that their chirality is induced by that of their 3-N-(2-alkyloxyaryl)-2-thioxothiazolidin-4-one precursors, which in turn is due to the presence of a C2 axis of chirality. These new compounds were characterized by spectroscopic methods (IR, 1 H-NMR, 13 C-NMR). The structure of compound (Z)-(2g) was further determined by X-ray diffraction.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Determination of Novel 5-Arylidene-3-N(2-alkyloxyaryl)-2-thioxothiazolidin-4-ones

et al. 2012

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“…However, Takasu and coworkers developed a facile, one-pot, three-step combinatorial synthesis of MKT-077 derivatives by sequential condensation of the methylthioninium, rhodanine, and iminium [152]. Kasmi-Mir et al refined the synthesis by employing microwave irradiation [153], greatly improving the reaction time and yields (60% in most cases). Taking advantage of these advances, our group assembled MKT-077 analogs and tested their binding to Hsp70 and their antiproliferative activity against breast cancer cells.…”

Section: Mkt-077mentioning

confidence: 99%

Allosteric Inhibitors of Hsp70: Drugging the Second Chaperone of Tumorigenesis

Srinivasan

Shao

et al. 2015

Topics in Medicinal Chemistry

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Cancer cells survive in the presence of stresses that would normally cause cell death. To accomplish this feat, they express elevated levels of the molecular chaperones: heat shock protein 70 (Hsp70) and heat shock protein 90 (Hsp90). Knockdown of these chaperones is selectively toxic to cancer cells, suggesting that they might be promising nodes for anticancer therapy. However, while inhibitors of Hsp90 are well known, progress in the development of Hsp70 inhibitors has proven more difficult. Hsp70 binds tightly to ATP through a highly conserved domain of the actin/hexokinase superfamily, making it challenging to identify selective, competitive inhibitors. Despite this obstacle, progress has been made and first-generation molecules are being deployed. To supplement these efforts, compounds that target important allosteric sites on the chaperone have also been discovered. In some of these cases, the molecules have been shown to control key protein-protein interactions between Hsp70 and its co-chaperones. In other cases, allosteric sites have been used to gain unexpected selectivity for members of the Hsp70 family. Here, we review recent progress in the development of Hsp70 inhibitors.

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“…2 Many researchers have demonstrated that heterocyclic chromophores containing thiazole ring exhibit higher hyperpolarizabilities (μβ) than their aryl analogues. 3 In our previous work 5 , we have studied the synthesis of several dyes rhodacyanines from a building block molecule, such as Δ-4-thiazolinethione 1. This compound has been easily prepared in reasonable amounts, ready for further applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Thiazolinethione-5-Carbaldehydes by Vilsmeier-Haack formylation and transformation into Imines Chromophores

2018

IJCTR

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A new series of Shiff bases chromophores 6 containing thiazole, rhodanine and dicyano moiety have been synthesized in four steps by functionalization of the corresponding Δ-4-thiazolinethione 1a-b via Vilsmeier-Haack reaction. The formylation of 1a has afforded to two aldehydes 3a and 3c. The orientation of this electrophilic substitution has been discussed. The structures of these newly compounds have been established on the basis of their analytical and spectral data

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Synthesis of New Rhodacyanines Analogous to MKT‐077 under Microwave Irradiation

Cited by 10 publications

References 12 publications

Synthesis and Structural Determination of Novel 5-Arylidene-3-N(2-alkyloxyaryl)-2-thioxothiazolidin-4-ones

Synthesis and Structural Determination of Novel 5-Arylidene-3-N(2-alkyloxyaryl)-2-thioxothiazolidin-4-ones

Allosteric Inhibitors of Hsp70: Drugging the Second Chaperone of Tumorigenesis

Synthesis of Thiazolinethione-5-Carbaldehydes by Vilsmeier-Haack formylation and transformation into Imines Chromophores

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