Synthesis and evaluation of antitubercular activity of imidazo[2,1-b][1,3,4]thiadiazole derivatives

Kolavi, Gundurao; Hegde, Vinayak; Khazi, Imtiyaz Ahmed M.; Gadad, Pramod C.

doi:10.1016/j.bmc.2005.12.020

Cited by 136 publications

(132 citation statements)

References 15 publications

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“…Compounds having thiadiazole nucleus are reported to have a number of biological activities like antituberculosis, [6][7][8] antiproliferative, 9,10 antibacterial, 11,12 anticancer, [13][14][15] antifungal, 16,17 antihyperlipidemic, 18 and anti-inflammatory. 19 5-(1H-indol-5-yl)-1,3,4-thiadiazol-2-amines were also reported as potent PIM inhibitors showing excellent potency against all three PIM isoforms.…”

Section: Introductionmentioning

confidence: 99%

3D QSAR Studies on Some 5-(1H-Indol-5-yl)-1, 3, 4-Thiadiazol-2 Amines as Potential PIM-1 Inhibitors

Kumar¹,

Ghode²,

Kumar³

2017

JYP

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Objective: Proviral integration site for moloney murine leukemia virus (PIM) kinases are among the contemporary targets for cancer chemotherapy as they play a pivotal role in inhibition of apoptosis and oncogenic signaling. Owing to their structural and functional dissimilarity to other kinases, they can be specifically targeted. The present study is an attempt to establish three dimensional quantitative structure activity relationship (3D QSAR) between some 5-(1H-Indol-5-yl)-1,3,4-thiadiazol-2-amines for their inhibitory activity against PIM by partial least squares regression (PLSR) analysis. Method: PLSR coupled with different variable selection methods such as stepwise (forward-backward) (SW), genetic algorithm (GA) and simulated annealing (SA) was performed to derive QSAR models and these models were validated for statistical significance internally and externally and robustness. Results: Two most significant models were generated through GA with optimum values of validation parameters. Among these model 1 exhibited q 2 and pred_r 2 values of 0.7523 and 0.8714 and model 2 evinced 0.6577 and 0.7675 respectively. The steric field point in model 1 suggests the need of more bulky group at this position and the positive coefficients of electrostatic field points at positions E_999, E_1162 respectively indicate the need of electronegative groups for favorable biological activity. Model 2 suggests the requirement of a positive hydrophobic group at H_564 and less electronegative and more electronegative group at E_157 and E_630 respectively for more potent biological activity. Conclusion: More bulky and/or hydrophobic R groups apart from the electrostatic contribution may be favorable for better PIM-1 inhibition of 5-(1H-indol-5-yl)-1,3,4-thiadiazol-2 amines. Key words: 1,3,4-Thiadiazole-2-amine, PIM, QSAR, Anticancer, PLSR. Key MessageThe quantitative structure activity relationship analysis on 5-(1H-indol-5-yl)-1,3,4-thiadiazol-2 amines was carried out for PIM-1 inhibitory activity. The present study suggested the requirement of steric bulk and/or hydrophobic group at third position of indole ring for better activity.

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Section: Introductionmentioning

confidence: 99%

3D QSAR Studies on Some 5-(1H-Indol-5-yl)-1, 3, 4-Thiadiazol-2 Amines as Potential PIM-1 Inhibitors

Kumar¹,

Ghode²,

Kumar³

2017

JYP

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“…By virtue of the presence of N=C-S-group in thiadiazole molecule, it exhibits diverse biological properties such as antifungal, 15 anticancer, 15 antioxidant, 15 anti-inflammatory, 15 anticonvulsants, 15 antimicrobial, 15 antidepressant, 15 cytotoxic, 16 antitubercular, 17 and anxiolytic. 18 An important and most familiar thiadiazole is acetazolamide, a carbonic anhydrase inhibitor, used in prevention and cure of acute altitude illness, 15 glaucoma, 15 idiopathic intracranial hypertension, 19 congenital myasthenic syndromes 20 and cystinuria.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and characterization of [1,3,4]thiadiazolo- and [1,2,4]oxadiazolo- substituted 2,4-dicyclopropylamino-6-phenoxy-s-triazines

Hashmi¹,

Kishore²

2016

Arkivoc

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“…It can be emphasized that there exists continuous demand for drugs of new structural classes with novel mechanisms of action other than isoniazid, rifampicin and pyridazinamide. Hence, discovery and development of novel, more active and less-toxic anti-TB agents is an imperative task for medicinal researchers 107 . …”

Section: Antitubercular Activitymentioning

confidence: 99%

Medicinal significance of benzothiazole scaffold: an insight view

Sharma

Sinhmar

Sharma

et al. 2012

Journal of Enzyme Inhibition and Medicinal Chemistry

218

106

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Synthesis and evaluation of antitubercular activity of imidazo[2,1-b][1,3,4]thiadiazole derivatives

Cited by 136 publications

References 15 publications

3D QSAR Studies on Some 5-(1H-Indol-5-yl)-1, 3, 4-Thiadiazol-2 Amines as Potential PIM-1 Inhibitors

3D QSAR Studies on Some 5-(1H-Indol-5-yl)-1, 3, 4-Thiadiazol-2 Amines as Potential PIM-1 Inhibitors

Design, synthesis and characterization of [1,3,4]thiadiazolo- and [1,2,4]oxadiazolo- substituted 2,4-dicyclopropylamino-6-phenoxy-s-triazines

Medicinal significance of benzothiazole scaffold: an insight view

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