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ID: ALA2346568

Journal: Bioorg Med Chem

Title: Discovery and structure-activity relationship of thienopyridine derivatives as bone anabolic agents.

Authors: Saito K, Nakao A, Shinozuka T, Shimada K, Matsui S, Oizumi K, Yano K, Ohata K, Nakai D, Nagai Y, Naito S.

Abstract: A cell-based assay was performed for the discovery of novel bone anabolic agents. Alkaline phosphatase (ALPase) activity of ST2 cells was utilized as an indicator of osteoblastic differentiation, and thienopyridine derivative 1 was identified as a hit compound. 3-Aminothieno[2,3-b]pyridine-2-carboxamide was confirmed to be a necessary core structure for the enhancement of ALPase activity, and then optimization of the C4-substituent on the thienopyridine ring was carried out. Introduction of cyclic amino groups to the C4-position of the thienopyridine ring improved the activity. Especially, N-phenyl-homopiperazine derivatives were found to be strong enhancers of ALPase among this new series. Furthermore, 3-amino-4-(4-phenyl-1,4-diazepan-1-yl)thieno[2,3-b]pyridine-2-carboxamide (15k) was orally administered to ovariectomized (OVX) rats over 6 weeks for evaluating the effects on areal bone mineral density (aBMD), and statistically significant improvements in aBMD were observed from the dosage of 10 mg/kg/day.

CiteXplore: 23453217

DOI: 10.1016/j.bmc.2013.01.071