Syntheses of new 3-thiazolyl coumarin derivatives, in vitro α -glucosidase inhibitory activity, and molecular modeling studies

Salar, Uzma; Taha, Muhammad; Khan, Khalid Mohammed; Ismail, Nor Hadiani; Imran, Syahrul; Perveen, Shahnaz; Gul, Sahib; Wadood, Abdul

doi:10.1016/j.ejmech.2016.06.037

Cited by 83 publications

(36 citation statements)

References 52 publications

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“…Also, it is used in the treatment of urinary tract infections . Likewise, the thizole derivatives are useful for treatment of many of diseases such as hypertension, allergies, schizophrenia, microbial, inflammation and HIV infections . Many of drugs containing thiazole moiety in their structure used in wide rang in the pharmaceutical market such as fanetinole, combendazole, niridazole, tiazofuren, bleomycine and sulfathiazole (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis, Structural Activity Relationship, Molecular Modeling and In Vitro Biological Evaluation of New Urea Derivatives with Incorporated Isoxazole and Thiazole Moieties as Anticancer Agents

2019

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A new series of isoxazolyl and thiazolyl urea derivatives was synthesized, fully characterized and evaluated in vitro as anticancer agents. The chemistry involves a facile protocol for the preparation of urea derivatives 12–22 through the reaction of isocyanates (p‐tolylsulfonyl isocyanate, p‐tolyl isocyanate, benzoyl isocyanate and ethylisocyanate) 8–11 with the corresponding aminoisoxazoles and aminothiazoles 2, 3, 6 and 7. The cytotoxicity of the synthesized compounds 12–22 were evaluated using human lung adenocarcinoma cell line (A549), cervical cancer cell line (HeLa), and breast cancer cell line (MCF7). All novel compounds (except compounds 12, 17, and 18) were potential cytotoxic against lung cancer as it displayed IC50s less than the reference drug (5‐Fluro uracil (5FU)). All tested compounds (except 15 and 19) showed strong inhibition of breast cancer cell line even much better than the 5FU. The tested compounds were less cytotoxic against cervical cancer except compounds 16, 19, 20, and 21. The molecular docking studies of the synthesized compounds against the three different proteins Janus kinase 2 (JAK2), cyclin dependent kinase‐2 (CDK2), and B‐cell lymphoma‐2 (BCL2) that are major proteins involved in pathogenesis of cancer were discussed. The molecular‐docking analyses revealed that compounds 13, 14 and 20 were the best docked ligand compared to reference docked ligands against the tested targeted proteins. In conclusion, the urea derivatives 13 and 14 were the most promising compounds with lowest IC50s against the tested cancer cell lines, and they displayed the lowest binding energies, critical hydrogen bonds and hydrophobic interactions with the molecular targets compared to other tested compounds.

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Section: Introductionmentioning

confidence: 99%

Facile Synthesis, Structural Activity Relationship, Molecular Modeling and In Vitro Biological Evaluation of New Urea Derivatives with Incorporated Isoxazole and Thiazole Moieties as Anticancer Agents

2019

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“…On the other hand, thiazole derivatives are considered as another important class of heterocyclic compounds, which displayed a wide range of pharmacological activities such as anti-inflammatory [ 20 ], anticancer [ 21 ], anticonvulsant [ 22 ], and antibacterial [ 23 ]. It is interesting that numerous studies pointed out thiazole could be used as a useful moiety in the design of potent α-glucosidase inhibitors [ 24 , 25 , 26 , 27 , 28 ]. For example, compound series V [ 25 ], VI [ 28 ], and VII [ 26 ] displayed potent α-glucosidase inhibitory activity ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel Isatin-Thiazole Derivatives as α-Glucosidase Inhibitors

Xie

Wang

et al. 2017

Molecules

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A series of novel isatin-thiazole derivatives were synthesized and screened for their in vitro α-glucosidase inhibitory activity. These compounds displayed a varying degree of α-glucosidase inhibitory activity with IC50 ranging from 5.36 ± 0.13 to 35.76 ± 0.31 μm as compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μm). Among the series, compound 6p bearing a hydroxyl group at the 4-position of the right phenyl and 2-fluorobenzyl substituent at the N1-positions of the 5-methylisatin displayed the highest inhibitory activity with an IC50 value of 5.36 ± 0.13 μm. Molecular docking studies revealed the existence of hydrophobic interaction, CH-π interaction, arene-anion interaction, arene-cation interaction, and hydrogen bond between these compounds and α-glucosidase enzyme.

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“…The pharmaceutical agents, namely, inthomycin C, oxaprozin, pemoline, and bengazole A, contain oxazole motif. In addition, thiazoles are useful in the treatment of allergies , hypertension , inflammation , schizophrenia , microbial , and HIV infections . Sulfathiazole, bleomycin, and tiazofurin are some of the drugs having thiazole moiety.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antioxidant Activity of a New Class of Amido linked Azolyl Thiophenes

Thatha

Ummadi

Padmavathi

et al. 2018

Journal of Heterocyclic Chem

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A new class of amido linked azolyl thiophenes was prepared from the synthetic intermediates azolyl amines and 5‐chlorothiophene‐2‐carbonyl chloride adopting conventional and ultrasonication methodologies. It was observed that the reaction took place in shorter reaction times with higher yields under ultrasonication. The structures of the synthesized compounds were characterized by spectral parameters and also tested for antioxidant activity. Among all the tested compounds, methoxy substituted oxazolyl thiophene carboxamide (8c) displayed promising antioxidant activity. Besides, the electron donating groups on the phenyl ring enhanced the antioxidant activity when compared with the electron withdrawing groups.

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Syntheses of new 3-thiazolyl coumarin derivatives, in vitro α -glucosidase inhibitory activity, and molecular modeling studies

Cited by 83 publications

References 52 publications

Facile Synthesis, Structural Activity Relationship, Molecular Modeling and In Vitro Biological Evaluation of New Urea Derivatives with Incorporated Isoxazole and Thiazole Moieties as Anticancer Agents

Facile Synthesis, Structural Activity Relationship, Molecular Modeling and In Vitro Biological Evaluation of New Urea Derivatives with Incorporated Isoxazole and Thiazole Moieties as Anticancer Agents

Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel Isatin-Thiazole Derivatives as α-Glucosidase Inhibitors

Synthesis, Characterization, and Antioxidant Activity of a New Class of Amido linked Azolyl Thiophenes

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