Design and synthesis of imidazo[2,1-b]thiazole linked triazole conjugates: Microtubule-destabilizing agents

Shaik, Siddiq Pasha; Nayak, V. Lakshma; Sultana, Faria; Rao, A. V. Subba; Shaik, Anver Basha; Babu, K. Suresh; Kamal, Ähmed

doi:10.1016/j.ejmech.2016.09.060

Cited by 51 publications

(19 citation statements)

References 48 publications

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“…Compounds 442c and 442l demonstrated an anti‐proliferative effect with GI 50 = 0.06 ± 0.001 μM, 0.26 ± 0.02 μM, 0.13 ± 0.01 μM and 0.18 ± 0.03 and 0.04 ± 0.001 μM, 0.079 ± 0.001 μM, 0.091 ± 0.002 μM and 0.052 ± 0.001 μM which was found to be comparable and superior to that of combretastatin A‐4. Shaik et al synthesised imidazo[2,1‐b]thiazole‐linked triazole conjugates (Scheme ) and assayed them against HeLa, DU‐145, A549, MCF‐7 and HepG2 cell lines. Compound 445h was the most potent derivative with IC 50 values of 2.690, 3.090, 0.788, 1.013 and 5.821 μM against doxorubicin as the standard drug and caused cell cycle arrest at G2/M phase (Table ).…”

Section: Pharmacological and Synthetic Profiles Of Benzimidazole Derimentioning

confidence: 99%

Benzimidazole Scaffold as Anticancer Agent: Synthetic Approaches and Structure–Activity Relationship

Shrivastava

Naim

Alam

et al. 2017

Archiv der Pharmazie

129

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Cancer, also known as malignant neoplasm, is a dreadful disease which involves abnormal cell growth having the potential to invade or spread to other parts of the body. Benzimidazole is an organic compound that is heterocyclic and aromatic in nature. It is a bicyclic compound formed by the fusion of the benzene and imidazole ring systems. It is an important pharmacophore and a privileged structure in medicinal chemistry. According to the World Health Organisation (2015 survey), one in six deaths is due to cancer around the globe, accounting for 8.8 million deaths of which 70% of the cases were from low- and middle-income countries. In the efforts to develop suitable anticancer drugs, medicinal chemists have focussed on benzimidazole derivatives. This review article covers the current development of benzimidazole-based anticancer agents along with the synthetic approaches and structure-activity relationships (SAR).

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Section: Pharmacological and Synthetic Profiles Of Benzimidazole Derimentioning

confidence: 99%

Benzimidazole Scaffold as Anticancer Agent: Synthetic Approaches and Structure–Activity Relationship

Shrivastava

Naim

Alam

et al. 2017

Archiv der Pharmazie

129

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“…Remaining aromatic protons resonated at 7.64 ppm as a singlet and in the range of δ 7.80–7.82 ppm as a doublet of doublet with coupling constants 1.5 Hz and 7.5 Hz. Furthermore, –NH proton appeared at δ 8.95 ppm as a broad signal which in turn confirmed the formation of the target molecule [23]. The structure of new Schiff base 5e was also confirmed by 13 C NMR spectrum.…”

Section: Resultsmentioning

confidence: 60%

“…Aromatic protons appeared in the range of δ 6.78–8.01 ppm. A broad singlet at δ 8.99 ppm evidences the presence of the N– H group [23]. Similarly, 13 C NMR also justified product formation by giving the expected peaks.…”

Section: Resultsmentioning

confidence: 68%

Synthesis of novel Schiff bases containing arylpyrimidines as promising antibacterial agents

Nayak

Poojary

2019

Heliyon

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Pursuing our recent interest regarding the antimicrobial activity of Schiff bases derivatives, we have synthesized a series of 6-(substitutedphenyl)- N' -(( E )-(substitutedphenyl)methylidene)-2-methylpyridine-3-carbohydrazides ( 5a-n ) and evaluated their antibacterial activity. Structures of these compounds were confirmed by standard studies of FTIR, 1 H NMR, 13 C NMR, MS and elemental analysis. Antibacterial activity of synthesized molecules was tested against Gram-positive ( S. aureus and E. faecalis ) and Gram-negative ( E. coli and P. aeruginosa ) bacterial strains. Synthesized compounds showed good antibacterial activity at a lower concentration than standard. Most of the compounds ( 5a , 5c , 5i , 5j and 5n ) are potent against all the tested bacterial strains with MIC values ranging from 1.56-12.5 μg/mL.

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“…The designed imidazo[2,1-b]thiazole-sulfonyl piperazine conjugates (9aa-ee) were prepared according to pathways outlined in Scheme 1. Ethyl-2-aminothiazole-4-carboxylate (3) was synthesized by the condensation of ethyl bromopyruvate (2) and thiourea (1) in ethanol under reflux for 4 h. Cyclization of intermediate (3) with various phenacyl bromides (4a-e) in ethanol at reflux temperature resulted in the formation of intermediates (5a-e), which upon ester hydrolysis in the presence of lithium hydroxide monohydrate (LiOH•H2O) produced carboxylic acids (6a-e) [18]. Aryl sulfonyl piperazine intermediates (8a-e) were synthesized based on previous reported procedures Based on the literature, sulfonamides were the most investigated class of CA inhibitors [11,12].…”

Section: Chemistrymentioning

confidence: 99%

“…General Synthetic Procedure for the Preparation of Compound 3 Compound 3 was synthesized according to the procedures described in the literature [18].4.1.2. General Synthetic Procedure for the Preparation of Compound 5a-eCompound 5a-e was synthesized based on previous synthetic procedures[18].4.1.3. General Synthetic Procedure for the Preparation of Compound 6a-eCompound 6a-e was synthesized based on previous synthetic procedures[18].…”

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confidence: 99%

Synthesis and Biological Evaluation of Imidazo[2,1-b]Thiazole based Sulfonyl Piperazines as Novel Carbonic Anhydrase II Inhibitors

et al. 2020

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A novel series of imidazo[2,1-b]thiazole-sulfonyl piperazine conjugates (9aa-ee) has been synthesized and evaluated for carbonic anhydrase (CA, EC 4.2.1.1) inhibitory potency against four isoforms: The cytosolic isozyme hCA I, II and trans-membrane tumor-associated isoform hCA IX and hCA XII, taking acetazolamide (AAZ) as standard drug, using a stopped flow CO2 hydrase assay. The results revealed that most of the compounds showed selective activity against hCA II whereas none of them were active against hCA I, IX, XII (Ki > 100 µM). The physiologically dominant cytosolic isoform hCA II was inhibited by these molecules with inhibition constants in the range of 57.7–98.2 µM. This new derivative, thus, selectively inhibits hCA II over the hCA I, IX, XII isoforms, which may be used for further understanding the physiological roles of some of these isoforms in various pathologies.

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Design and synthesis of imidazo[2,1-b]thiazole linked triazole conjugates: Microtubule-destabilizing agents

Cited by 51 publications

References 48 publications

Benzimidazole Scaffold as Anticancer Agent: Synthetic Approaches and Structure–Activity Relationship

Benzimidazole Scaffold as Anticancer Agent: Synthetic Approaches and Structure–Activity Relationship

Synthesis of novel Schiff bases containing arylpyrimidines as promising antibacterial agents

Synthesis and Biological Evaluation of Imidazo[2,1-b]Thiazole based Sulfonyl Piperazines as Novel Carbonic Anhydrase II Inhibitors

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