Rapid, microwave-accelerated synthesis and anti-osteoporosis activities evaluation of Morusin scaffolds and Morusignin L scaffolds. Issue 11 (1st June 2017)

• Record Type: Journal Article
• Authors: Lin, Bing; Huang, Jun-Fei; Liu, Xiong-Wei; Ma, Xi-Tao; Liu, Xiong-Li; Lu, Yi; Zhou, Ying; Guo, Feng-Min; Feng, Ting-Ting
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 11(2017)
• Page Start: 2389
• Page End: 2396
• Publication Date: 2017-06-01
• Subjects: Morusin -- Morusignin L -- TRAP enzyme -- Bone resorption -- Anti-osteoporosis activity; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.04.018
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Highlights: Morusin scaffolds and Morusignin L scaffolds were synthesized. A rapid, microwave-accelerated cyclization was used as the key step. Their in vitro anti-osteoporosis activities have been demonstrated. Abstract: Described herein is a facile and efficient methodology toward the synthesis of Morusin scaffolds and Morusignin L scaffolds4 –9 and12 via a novel three-step approach (Michael addition or prenylation, cyclization and cyclization) and use a rapid, microwave-accelerated cyclization as the key step. Furthermore, their biological activities have been preliminarily demonstrated by in vitro evaluation for anti-osteoporosis activity. These Morusin, Morusignin L and newly synthesized compounds5b, 6a, 8e, 8f greatly exhibited the highest potency, especially at the 10 −5 mol/L (P < 0.01), and had good in vitro anti-osteoporosis activities using the commercially available standard drug Ipriflavone as a positive control. The mechanisms associated with anti-osteoporosis effects of these compounds may be through the inhibition of TRAP enzyme activity and bone resorption in osteoclasts, and promotion effect of osteoblast proliferation in vitro . The results indicated that Morusin scaffolds and Morusignin L scaffolds may be useful leads for further anti-osteoporosis activity screenings.