7-(3-(cyclohexylamino)-2-hydroxypropoxy)-3-(3,4-dimethoxyphenyl)-4H-chromen-4-one | 1182706-80-4

• 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: 7-(3-(cyclohexylamino)-2-hydroxypropoxy)-3-(3,4-dimethoxyphenyl)-4H-chromen-4-one
• 英文别名: 7-[3-(Cyclohexylamino)-2-hydroxypropoxy]-3-(3,4-dimethoxyphenyl)-4H-chromen-4-one；7-[3-(cyclohexylamino)-2-hydroxypropoxy]-3-(3,4-dimethoxyphenyl)chromen-4-one
• CAS: 1182706-80-4
• 化学式: C₂₆H₃₁NO₆
• 分子量: 453.535
• InChiKey: PSBRBCLZHLONKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(3,4-dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)-4H-chromen-4-one 、 环己胺 在 水 、 methanol-dichloromethane 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以to give the title compound 6c (0.24 g, 54% yield)的产率得到7-(3-(cyclohexylamino)-2-hydroxypropoxy)-3-(3,4-dimethoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Isoflavone derivatives and pharmaceutical compositions comprising the same

  摘要：

  提供一种异黄酮衍生物。该异噁唑衍生物具有以下式子：其中R1和R2，独立地，包括C1-C12烷基，可选地取代氧环丙烷、硫环丙烷、氮杂环丙烷、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，可选地取代氧环丙烷、硫环丙烷、氮杂环丙烷、氨基、环氨基、氨基羟基或环氨基羟基。本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学上可接受的盐和药学上可接受的载体。

  公开号：

  US07618998B2

文献信息

• Isoflavone derivatives and pharmaceutical compositions comprising the same
  申请人：Kaosiung Medical University

  公开号：US07618998B2

  公开（公告）日：2009-11-17

  An isoflavone derivative is provided. The isoxazole derivative has following formula: wherein R1 and R2, independently, include C1-C12 alkyl optionally substituted with oxirane, thiirane, aziridine, amino, cycloamino, aminohydroxy or cycloaminohydroxy, and R3 includes hydrogen, hydroxy or C1-C12 alkoxy optionally substituted with oxirane, thiirane, aziridine, amino, cycloamino, aminohydroxy or cycloaminohydroxy. The invention also provides a pharmaceutical composition for treatment of osteoporosis including an isoflavone derivative or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

  提供一种异黄酮衍生物。该异噁唑衍生物具有以下式子：其中R1和R2，独立地，包括C1-C12烷基，可选地取代氧环丙烷、硫环丙烷、氮杂环丙烷、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，可选地取代氧环丙烷、硫环丙烷、氮杂环丙烷、氨基、环氨基、氨基羟基或环氨基羟基。本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学上可接受的盐和药学上可接受的载体。
• 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
• ISOFLAVONE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：TZENG Cherng-Chyi

  公开号：US20090215767A1

  公开（公告）日：2009-08-27

  An isoflavone derivative is provided. The isoxazole derivative has following formula: wherein R 1 and R 2 , independently, include C 1 -C 12 alkyl optionally substituted with oxirane, thiirane, aziridine, amino, cycloamino, aminohydroxy or cycloaminohydroxy, and R 3 includes hydrogen, hydroxy or C 1 -C 12 alkoxy optionally substituted with oxirane, thiirane, aziridine, amino, cycloamino, aminohydroxy or cycloaminohydroxy. The invention also provides a pharmaceutical composition for treatment of osteoporosis including an isoflavone derivative or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

  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。