3-(4-(3-(cyclopropylamino)-2-hydroxypropoxy)phenyl)-7-methoxy-4H-chromen-4-one | 1182706-76-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-(4-(3-(cyclopropylamino)-2-hydroxypropoxy)phenyl)-7-methoxy-4H-chromen-4-one
• 英文别名: 3-[4-[3-(Cyclopropylamino)-2-hydroxypropoxy]phenyl]-7-methoxychromen-4-one
• CAS: 1182706-76-8
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: QRONGSZTGATKJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-methoxy-3-(4-(oxiran-2-ylmethoxy)phenyl)-4H-chromen-4-one 、 环丙胺 以 乙醇 为溶剂， 反应 4.0h， 以78%的产率得到3-(4-(3-(cyclopropylamino)-2-hydroxypropoxy)phenyl)-7-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  ISOFLAVONE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME

  摘要：

  提供了一种异黄酮衍生物。该异噁唑衍生物具有以下结构式：其中R1和R2独立地包括C1-C12烷基，可选择地取代为环氧丙烷、硫代环氧丙烷、环氮丙烷、氨基、环氨基、氨基羟基或环氨基羟基；R3包括氢、羟基或C1-C12烷氧基，可选择地取代为环氧丙烷、硫代环氧丙烷、环氮丙烷、氨基、环氨基、氨基羟基或环氨基羟基。该发明还提供了一种用于治疗骨质疏松症的药物组合物，包括一种异黄酮衍生物或其药用盐以及一种药学上可接受的载体。

  公开号：

  US20090215767A1

文献信息

• Synthesis and anti-osteoporotic evaluation of certain 3-amino-2-hydroxypropoxyisoflavone derivatives
  作者：Chih-Hua Tseng、Yeh-Long Chen、Chih-Ming Lu、Chih-Kuang Wang、Yin-Tung Tsai、Ru-Wei Lin、Chain-Fu Chen、Yu-Fang Chang、Gwo-Jaw Wang、Mei-Ling Ho、Cherng-Chyi Tzeng

  DOI：10.1016/j.ejmech.2009.02.025

  日期：2009.9

  We report herein the synthesis and anti-osteoporotic evaluation of certain 3-amino-2-hydroxypropoxyisoflavone derivatives. The results indicated that 3-(3,4-dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)-4H-chromen-4-one (4) and 3-4-[3-(cyclohexylamino)-2-hydroxypropoxy]phenyl}-7-methoxy-4H-chromen-4-one (5a) exhibited significant inhibitory effects on osteoclast activity (TRAP activity in RAW 264.7 with an ED50 of 0.56 and 2.28 mu M respectively). Both compounds have also exhibited very strong osteogenic effects, approximately a 10-fold effect of Ipriflavone on mineralization of osteoblasts; (MC3T3E1 cells, a preosteoblast cell line derived from calvaria of C57BL/6 mice). Results indicated the potency on enhancing mineralization in D1 cells (a bone marrow mesenchymal cell line derived from BALB/c mice) decreased in an order 4 > Ipriflavone > Sa. However, the potency on enhancing mineralization in human adipose tissue derived stem cells (hADSCs) decreased in an order Sa > 4 > Raloxifene > Ipriflavone. Compound 5a has been found to be non-cytotoxic and especially active in the enhancement of mineralization in human adipose tissue derived stem cells. Therefore, Sa was selected as a potential lead for further structural optimization. (C) 2009 Published by Elsevier Masson SAS.
• US7618998B2
  申请人：——

  公开号：US7618998B2

  公开（公告）日：2009-11-17