Design, Synthesis and Oral Glucose Tolerance Screening of Some 5-substituted benzylidene-3-(2-(2-methyl-1H -benzimidazol- 1-yl)-2-oxoethyl)-1,3-thiazolidine-2,4-dione Derivatives on Rats (original) (raw)
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SYNTHESIS AND EVALUATION OF SOME BENZOTHIAZOLE DERIVATIVES AS ANTIDIABETIC AGENTS Original Article
International Journal of Pharmacy and Pharmaceutical Sciences, 2017
Objective: The objective of the present research investigation involves synthesis and biological evaluation of antidiabetic activity of benzothiazole derivatives. Methods: A novel series of benzothiazole derivatives 7(a-l) were synthesised and synthesised compounds were characterised for different physical and chemical properties like molecular formula, molecular weight, melting point, percentage yield, Rf value, IR, 1 HNMR, 13 Results: All the synthesised derivatives showed significant biological efficacy. The compound 7d at 350 mg/kg exerted maximum glucose lowering effects whereas 7c showed minimum glucose lowering effects. All the compounds were effective, and experimental results were statistically significant at p<0.01 and p<0.05 level. CNMR and mass spectroscopy. The newly synthesised benzothiazole derivatives were subsequently assayed in vivo to investigate their hypoglycemic activity by the alloxan-induced diabetic model in rats. Conclusion: From the results, it is clear that compound 7d demonstrated potent anti-diabetic activity and would be of better use in drug development to combat the metabolic disorder in future.
Synthesis and Evaluation of Some Benzothiazole Derivatives as Antidiabetic Agents
International Journal of Pharmacy and Pharmaceutical Sciences, 2017
Objective: The objective of the present research investigation involves synthesis and biological evaluation of antidiabetic activity of benzothiazole derivatives.Methods: A novel series of benzothiazole derivatives 7(a-l) were synthesised and synthesised compounds were characterised for different physical and chemical properties like molecular formula, molecular weight, melting point, percentage yield, Rf value, IR, 1HNMR, 13CNMR and mass spectroscopy. The newly synthesised benzothiazole derivatives were subsequently assayed in vivo to investigate their hypoglycemic activity by the alloxan-induced diabetic model in rats. Results: All the synthesised derivatives showed significant biological efficacy. The compound 7d at 350 mg/kg exerted maximum glucose lowering effects whereas 7c showed minimum glucose lowering effects. All the compounds were effective, and experimental results were statistically significant at p<0.01 and p<0.05 level.Conclusion: From the results, it is clear ...
Acta poloniae pharmaceutica
The title compounds were prepared by brominating 1-acetylnaphthalene in chloroform followed by condensation with substituted benzaldehyde thiosemicarbazones using ethanol to get 4-naphthalen-1-yl-2-{2-[(substituted phenyl)methylidene]hydrazino}-1,3-thiazoles. These thiazole derivatives were then cyclized to title compounds by reacting with thiomalic acid in dioxane using ZnCl2. All the synthesized compounds were characterized on the basis of their IR, 1H NMR, and elemental analysis. The antihyperglycemic study was divided into two phases. Phase-I involved evaluation of blood glucose lowering ability of thiazolidinones in normal rats by sucrose-loaded model (SLM). Phase-II study included the evaluation of blood sugar by alloxan model.
Synthesis and Antidiabetic Evaluation of Benzothiazole Derivatives
Journal of the Korean Chemical Society, 2012
A novel series of benzothiazole derivatives were synthesized and assayed in vivo to investigate their hypoglycemic activity by streptozotocin-induced diebetic model in rat. These derivatives showed considerable biological efficacy when compared to glibenclamide, a potent and well known antidiabetic agent as a reference drug. All the compounds were effective, amongst them 3d showed more prominent activity at 100 mg/kg p.o. The experimental results are statistically significant at p<0.01 and p<0.05 level.
Asian Pacific Journal of Health Sciences, 2016
Some of derivatives containing oxadiazole and benzothiazole moieties 6(a-l) were synthesized and the structure of synthesized compounds was elucidated by IR, 1 HNMR, 13 C NMR and mass spectroscopy. This research article deals with newly synthesized benzothiazole containing oxadiazole derivatives that were assayed for investigation of their in vivo hypoglycemic activity by alloxan induced diabetic model in rat. All these derivatives showed significant biological efficacy when compared to a potent and well known antidiabetic agent (i.e. Glibenclamide). All the compounds were effective, amongst them 6f showed more prominent activity at 350 mg/kg p.o. The experimental results are statistically significant at p<0.01 and p<0.05 level.
(3-Substituted benzyl)thiazolidine-2,4-diones as structurally new antihyperglycemic agents
Bioorganic & Medicinal Chemistry Letters, 1999
A series of 3-[(2,4-dioxothiazolidin-5-yl)methyl]benzamide derivatives was prepared as part of a search for antidiabetic agents. A structure-activity relationship study of these compounds led to the identification of 5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide (KRP-297) as a candidate drug for the treatment of diabetes mellitus.
2016
Novel 1,3,4-thiadiazole substituted 2-methyl benzimidazole derivatives were designed by using various softwares such as ACD Lab ChemSketch 12.0, Molinspiration, PASS and Discovery studio. The designed molecules having required physico-chemical properties, drug likeness and obeying Lipinski’s rule of five (BT1, BT2, BT3, BT4, BT5, BT6, BT7, BT8 and BT9) were selected for the synthesis. These compounds were synthesized by conventional methods. All the synthesized compounds were confirmed based on their physicochemical parameters and their characteristic peaks in IR, 1HNMR and Mass spectroscopic studies. Based on the Libdock score, the compound BT6 was selected for in vitro antidiabetic and anti-inflammatory evaluation. The compound BT6 showed significant antidiabetic and anti-inflammatory activities. Received date: 18/11/ 2015 Accepted date: 08/02/ 2016 Published date: 12/02/2016
Revue Roumaine De Chimie, 2019
In this study, a series of new 1, 2-disubstituted benzimidazole was synthesized starting from 5, 6-dichloro-2-(4-methoxybenzyl)-1Hbenzimidazole compound which was converted to the ester and hydrazide derivative, respectively. Then, the carbothioamide derivative compounds were obtained by using several isothiocyanates. The thiadiazole derivative compounds were synthesized by closing the intramolecular ring of the carbothioamide derivatives in the presence of conc. H 2 SO 4. And also intramolecular ringing of carbothioamides in basic medium resulted in the formation of the 1,2,4-triazole derivative compounds. Moreover, 5-((5,6-dichloro-2-(4-methoxybenzyl)-1Hbenzo[d]imidazol-1-yl)methyl)-1,3,4-oxadiazole-2-thiol compound was syntesized in basic media via reaction of hydrazide derivative with CS 2. The treatment of hydrazide derivative with various salicylic aldehydes gave Schiff-based benzimidazole derivative compounds. The structural characterization of all synthesized compounds was elucidated by elemental analyses, 1 H NMR, 13 C NMR and mass spectral methods. They were also screened for their antioxidant activity and inhibitory properties on the metabolic enzymes such as urease and xanthine oxidase.
Journal of Chemistry, 2019
A simple and cheap three-step procedure for the synthesis of three (5Z)-5-[3(4)-(1H-benzimidazol-2-ylmethoxy)benzylidene]-1,3-thiazolidine-2,4-diones has been described via a SN2 reaction of generally recognized as safe hydroxybenzaldehydes and 2-(chloromethyl)-1H-benzimidazole, followed by a Knoevenagel condensation with thiazolidine-2,4-dione in moderated yields. All the newly synthesized compounds were characterized using analytical and spectral studies. In vitro treatment on adipocytes with compounds increased the mRNA expression of two proteins recognized as strategic targets in diabetes: PPARγ and GLUT-4. In silico studies were conducted in order to explain the interaction binding mode of the synthesized compounds on PPARγ. In vivo studies confirmed that compounds 1–3 have robust antihyperglycemic action linked to insulin sensitization mechanisms. The present study provides three compounds with a promising antidiabetic action.