(3R)-3-Amino-4-(2,4,5-trifluorophenyl)-N-{4-[6-(2-methoxyethoxy)benzothiazol-2-yl]tetrahydropyran-4-yl}butanamide as a potent dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

Nitta, Akira; Fujii, H.; Sakami, Satoshi; Nishimura, Yutaka; Ohyama, Tomofumi; Satoh, Mikiya; Nakaki, Junko; Satoh, Shiho; Inada, Chifumi; Kozono, Hideki; Kumagai, Hiroki; Shimamura, Masahiro; Fukazawa, Tominaga; Kawai, Hideki

doi:10.1016/j.bmcl.2008.09.042

Cited by 37 publications

(27 citation statements)

References 38 publications

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“…The compound (3R)-3-amino-4-(2, 4, 5-trifluorophenyl)-N-{4-[6-(2-methoxyethoxy)-benzothiazol-2-yl] tetrahydropyran-4-yl}butanamide (5.3) was found to reduce the blood glucose level to a significant extent in an oral glucose tolerance test 105 .…”

Section: 12mentioning

confidence: 99%

“…The survey of literature related to benzothiazoles reveals the presence of this bicyclic ring system in various amine or terrestrial natural compounds, which have useful biological properties 23 . Benzothiazole derivatives possess a wide spectrum of biological applications such as antitumor , antimicrobial , schictosomicidal 84 , antiinflammatory [85][86][87][88][89][90][91][92][93] , anticonvulsants [94][95][96][97][98][99][100][101][102] , antidiabetic [103][104][105][106][107][108] , antipsychotic 109 and diuretic 111 etc.…”

Section: Introductionmentioning

confidence: 99%

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Untitled

2011

IJPSR

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Recently, heterocyclic compounds analogues and their derivatives have attracted strong interest in medicinal chemistry due to their biological and pharmacological properties. The small and simple benzothiazole nucleus possesses numerous biological properties like -antitumor, antimicrobial, anti-inflammatory, anticonvulsant, and antidiabetic activities. These activities are also possessed by its substituted derivatives as well. The present review focuses on some commonly used easy procedures to synthesize the benzothiazole moiety and its derivatives, which comprise of different biological activities.

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Section: 12mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Untitled

2011

IJPSR

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“…Nitta et al reported the DPP-IV inhibitory activity of 3-amino-N-substituted-4-(substituted phenyl) butanamides in two communications [11,12] calculated as concentration required to inhibit 50 % (IC 50 ) of DPP-IV derived from human colonic carcinoma cells (Caco-2). After removing two duplicates (17,28) from the series, a dataset of 48 molecules was used in the present work (Table 1, fig.…”

Section: Biological Activity Datamentioning

confidence: 99%

Structural Requirements for some 3-amino-N-substituted-4-(substituted phenyl) Butanamides as Dipeptidyl Peptidase-IV Inhibitors Using 3D-QSAR and Molecular Docking Approaches

Ghode¹,

Jain²

2017

pharmaceutical-sciences

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Ghode and Jain: QSAR and Docking Study of Butanamide DerivativesDipeptidyl peptidase-IV is well thought out as one of the key targets for treatment of type 2 diabetes mellitus and diverse scaffolds have proven effective in designing novel dipeptidyl peptidase-IV inhibitors. To this end, three dimensional quantitative structure activity relationship analysis and molecular docking studies were performed on a set of 3-amino-N-substituted-4-(substituted phenyl) butanamides to explore the structural requirements for dipeptidyl peptidase-IV inhibitory activity using k-nearest neighbour molecular field analysis and AutoDock Vina, respectively. The compounds were arbitrarily assigned to active, moderately active and less active classes according to their biological activities. The most significant k-nearest neighbour model exhibited internal cross validation coefficient (q , concordance correlation coefficient and mean absolute error provided further confidence in the predictability of both the models. Apropos the docking results, the compounds from active, moderately active and less active classes exhibited different binding patterns. Whereas the active compounds such as 12x and 12v occupied a similar space in the active site cavity as the crystallographic ligand, sitagliptin (PDBID:1X70); the binding modes of compounds from moderately active and inactive classes were distinct from the latter. The findings of this study can provide an impetus for design of prospective potent dipeptidyl peptidase-IV inhibitorss.

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“…43 They are broadly found in bio organic and medicinal chemistry with applications in drug discovery and development for the treatment of diabetes. [44][45][46][47][48][49][50][51][52] Diabetes has become an increasing concern to the world's population. In view of these literatures, it was of considerable interest to synthesize the title compound with a hope to obtain potent biologically active and safe oral anti diabetic agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antidiabetic Evaluation of Benzothiazole Derivatives

Mariappan¹,

Prabhat²,

Sutharson³

et al. 2012

Journal of the Korean Chemical Society

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ABSTRACT. 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.

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(3R)-3-Amino-4-(2,4,5-trifluorophenyl)-N-{4-[6-(2-methoxyethoxy)benzothiazol-2-yl]tetrahydropyran-4-yl}butanamide as a potent dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

Cited by 37 publications

References 38 publications

Untitled

Untitled

Structural Requirements for some 3-amino-N-substituted-4-(substituted phenyl) Butanamides as Dipeptidyl Peptidase-IV Inhibitors Using 3D-QSAR and Molecular Docking Approaches

Synthesis and Antidiabetic Evaluation of Benzothiazole Derivatives

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