Novel one-pot expeditious synthesis of 2,4-disubstituted thiazoles through a three-component reaction under solvent free conditions

Sujatha, Kodam; Vedula, Rajeswar Rao

doi:10.1080/00397911.2017.1399422

Cited by 24 publications

(13 citation statements)

References 34 publications

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“…[11] Recently, They also reported as one of the interesting antitumor inhibitors due to the induction of oxidative stress and ROS-mediated cell injury. [12,13] Thiazole are scaffolds of many natural and synthetic drugs with numerous exciting and significant pharmacological activities [14,18] (Figure 1 adapted from Sujatha and Vedula, 2019 [14]). Thiazole derivatives showed significant anticancer activity with a mechanism of action related to inhibition of matrix metalloproteinases kinases and anti-apoptotic BCL2 family proteins.…”

Section: Introductionmentioning

confidence: 99%

A Simple Synthesis, of Some Novel Bi-Thiazoles as Anti-Tumor Agents

Al‐Hussain

2020

Egypt. J. Chem.

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A series of novel bi-thiazoles was synthesized by reaction of 2-(1-(2-(2-(1-(4-fluorophenyl)ethylidene)hydrazinyl)-4-methylthiazol-5-yl)ethylidene) hydrazine-1-carbothioamide 3 with a variety of hydrazonoyl chloride derivatives 4a-d, and 7 a-d affording 6a-d and 9a-d respectively in dioxane in the presence of triethyl amine as a base. Also, hydrazine-1-carbothioamide 3 reacts with substituted phenacyl bromide derivatives 10 a-d yielding 12a-d in appropriate reaction conditions. The mechanisms of the titled reactions were discussed. Structural assignments were based on spectroscopic methods (NMR, FTIR, MS). The new compounds were tested in vitro for their were subjected to in vitro anticancer screening against human hepatocellular carcinoma (HCT-116), (HepG-2) and the results showed that compounds 6a, 6d, 9a, 9c and 12a have promising activities compared with cisplatin reference drug.

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Section: Introductionmentioning

confidence: 99%

A Simple Synthesis, of Some Novel Bi-Thiazoles as Anti-Tumor Agents

Al‐Hussain

2020

Egypt. J. Chem.

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“…In a similar way, acetylthiazole 1 reacted with thiosemicarbazide 2 and the appropriate hydrazonoyl chlorides 7a-d 34 in a one-pot three-component reaction in refluxing dioxane/TEA to afford the respective arylhydrazothiazolones 8a-d (Scheme 2). The structures of compounds 8a-d were confirmed by 1 H-NMR, 13 C-NMR, IR and MS. For example, the IR spectra of product 7a showed the exhibited presence of stretching bands for 3NH and C=O groups at the normal wave number v. The mass spectra of the products 8a-d revealed in each case a molecular ion peak m/z at the expected molecular weight calculated for each compound (see Experimental).…”

Section: Results and Discussion Chemistrymentioning

confidence: 88%

“…11,12 Thiazole heterocycles, derivatives of thiosemicarbazone, are scaffolds of many natural, synthetic and semi-synthetic drugs which exhibit numerous remarkable pharmacological activities including antiparasitic, antiinflammatory and antineoplastic activities. [13][14][15][16][17] Thiazole derivatives are also known to have potential anticancer activity with a mechanism of action related to inhibition of matrix metallo-proteinases, kinases and anti-apoptotic BCL2 family proteins. [18][19][20][21] Multicomponent reactions (MCR) are one-pot processes which always occupy great importance in the repertoire of sustainable synthetic tools because of their high efficiency and atom economy.…”

Section: Introductionmentioning

confidence: 99%

<p>One-Pot Synthesis of Novel Thiazoles as Potential Anti-Cancer Agents</p>

Sayed¹,

Gomha²,

Taher³

et al. 2020

DDDT

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Background: Thiazole and thiosemicarbazone derivatives are known to have potential anticancer activity with a mechanism of action related to inhibition of matrix metalloproteinases, kinases and anti-apoptotic BCL2 family proteins. Materials and Methods: A novel three series of 5-(1-(2-(thiazol-2-yl)hydrazono)ethyl) thiazole derivatives were prepared in a one-pot three-component reaction using 2-(2-benzylidene hydrazinyl)-4-methylthiazole as a starting precursor. MS, IR, 1 H-NMR and 13 C-NMR were used to elucidate the structures of the synthesized compounds. Most of the synthesized products were evaluated for their in vitro anticancer screening against HCT-116, HT-29 and HepG2 using the MTT colorimetric assay. Results: The results indicated that compounds 4c, 4d and 8c showed growth inhibition activity against HCT-116 with IC 50 values of 3.80 ± 0.80, 3.65 ± 0.90 and 3.16 ± 0.90 μM, respectively, compared to harmine (IC 50 = 2.40 ± 0.12 μM) and cisplatin (IC 50 = 5.18 ± 0.94 μM) reference drugs. Also, compounds 8c, 4d and 4c showed promising IC 50 values of 3.47 ± 0.79, 4.13 ± 0.51 and 7.24 ± 0.62 μM, respectively, against the more resistant human colorectal cancer (HT-29) cell line compared with harmine (IC 50 = 4.59 ± 0.67 μM) and cisplatin (IC 50 = 11.68 ± 1.54 μM). On the other hand, compounds 4d, 4c, 8c and 11c were the most active (IC 50 values of 2.31± 0.43, 2.94 ± 0.62, 4.57 ± 0.85 and 9.86 ± 0.78 μM, respectively) against the hepatocellular carcinoma (HepG2) cell line compared with harmine (IC 50 = 2.54 ± 0.82 μM) and cisplatin (IC 50 = 41 ± 0.63 μM). The study also suggested that the mechanism of the anticancer action exerted by the most active compounds (4c, 4d and 8c) inside HCT-116 cells was apoptosis through the Bcl-2 family. Conclusion: Thiazole scaffolds 4c, 4d and 8c showed anticancer activities in the micromolar range and are appropriate as a candidate for cancer treatment.

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“…Sujatha and Vedula [82] developed a single-step synthesis of substituted thiazoles (210) through a three-component approach by modified Hantzsch thiazole method (Scheme 70). A multicomponent single-step reaction was also studied.…”

Section: Thiosemicarbazidesmentioning

confidence: 99%

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

et al. 2020

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Thiazole frame work represents a vital pharmacophore in several areas of chemistry. Consequently, several synthetic protocols to construct and functionalize this core, in an attempt to generate diverse thiazole containing architectures have been developed by various researchers across the globe. These wide range of methodologies developed will allow the access to fully decorated thiazole containing new chemical entities that can find various application in the field of medicinal chemistry, agrochemicals and material science. This review will provide an insight in to the various synthons used in construction and diversification of this core. Diversely functionalized thiazole analogs are considered as a vital azole framework present in many natural products. This prominent heterocycle also constitutes an important pharmacophore in medicinal chemistry, in agrochemicals and in molecules for material science applications. All these above‐mentioned features of thiazole necessitates the continuous development of efficient methods to access this heterocycle. Accordingly, various researchers across the globe have come up with efficient synthetic protocols in an attempt functionalize different positions of this important scaffold. This review aims at highlighting some of the latest synthetic approaches to di/tri‐substituted thiazole analogs which are known to possess a wide spectrum of biological activities.

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Novel one-pot expeditious synthesis of 2,4-disubstituted thiazoles through a three-component reaction under solvent free conditions

Cited by 24 publications

References 34 publications

A Simple Synthesis, of Some Novel Bi-Thiazoles as Anti-Tumor Agents

A Simple Synthesis, of Some Novel Bi-Thiazoles as Anti-Tumor Agents

<p>One-Pot Synthesis of Novel Thiazoles as Potential Anti-Cancer Agents</p>

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

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