(2E)-3-(3-hydroxy-4-methoxyphenyl)-1-(3-hydroxy-5-methoxyphenyl)prop-2-en-1-one | 1312835-97-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-3-(3-hydroxy-4-methoxyphenyl)-1-(3-hydroxy-5-methoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-(3-hydroxy-4-methoxyphenyl)-1-(3-hydroxy-5-methoxyphenyl)prop-2-en-1-one
• CAS: 1312835-97-4
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: ZPDRRRPQEDFFBY-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  异香兰素 、 1-(3-羟基-5-甲氧基-苯基)-乙酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 以72%的产率得到(2E)-3-(3-hydroxy-4-methoxyphenyl)-1-(3-hydroxy-5-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, biological evaluation, and docking studies of gigantol analogs as calmodulin inhibitors

  摘要：

  Several analogs of gigantol (1) were synthesized to evaluate their effect on the complexes Ca(2+)-calmodulin (CaM) and Ca(2+)-CaM-CaM sensitive phosphodiesterase 1 (PDE1). The compounds belong to four structural groups including, 1,2-diphenylethanes (2-11), diphenylmethanes (13-15), 1,3-diphenylpropenones (16-18), and 1,3-diphenylpropanes (20-22). In vitro enzymatic studies showed that all compounds except 11 inhibited the complex Ca(2+)-CaM-PDE1 with IC(50) values ranging from 9 to 146 mu M. On the other hand, all analogs but 11,12 and 15 quenched the extrinsic fluorescence of the CaM biosensor hCaM-M124C-mBBr to different extent, then revealing different affinities to CaM; their affinity constants (K(m)) values were in the range of 3-80 mu M. Molecular modeling studies indicated that all these compounds bound to CaM at the same site that the classical inhibitors trifluoperazine (TFP) and chlorpromazine (CPZ). Some of these analogs could be worthy candidates for developing new anti-tumor, local anesthetics, antidepressants, antipsychotic, or smooth muscle relaxant drugs, with anti-CaM properties due to their good affinity to CaM and the straightforwardness of their synthesis. In addition they could be valuable tools for the study of Ca(2+)-CaM functions. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.057

文献信息

• 3,4-METHYLENEDIOXY-SUBSTITUTED CHALCONES AS THERAPEUTIC AGENTS
  申请人：Potter Gerard Andrew

  公开号：US20100028262A1

  公开（公告）日：2010-02-04

  The present invention pertains to the use of a compounds for the manufacture of a medicament for use in the treatment of a proliferative condition, wherein the compounds have the following formula: wherein: each of R B2 , R B3 , R B4 , and R B5 is independently —H, —OH, or —OMe; each of R 1 and R 2 is independently: —H, optionally substituted C 1-4 alkyl, or optionally substituted C 5-20 aryl; R A3 is —H, —OH, —OC(═O)R E , —OS(═O) 2 OH, or —OP(═O)(OH) 2 ; R E is: —H, optionally substituted C 1-6 alkyl, optionally substituted C 3-20 heterocyclyl, or optionally substituted C 5-20 aryl; or a pharmaceutically acceptable salt, solvate, amide, ester, ether, chemically protected form, or prodrug thereof. The present invention also pertains to such compounds, pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, for both diagnosis and treatment of, for example, proliferative conditions, such as cancer, and inflammatory conditions.

  本发明涉及使用化合物制备药物，用于治疗增殖性疾病，其中该化合物具有以下结构式：其中：RB2、RB3、RB4和RB5中的每一个独立地为—H、—OH或—OMe；R1和R2中的每一个独立地为—H、可选地取代的C1-4烷基或可选地取代的C5-20芳基；RA3为—H、—OH、—OC(═O)RE、—OS(═O)2OH或—OP(═O)(OH)2；RE为：—H、可选地取代的C1-6烷基、可选地取代的C3-20杂环基或可选地取代的C5-20芳基；或其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式或前药。本发明还涉及这种化合物、包含这种化合物的药物组合物以及这种化合物和组合物的使用，无论是在体内还是体外，用于诊断和治疗增殖性疾病（例如癌症）和炎症性疾病。
• Synthesis, biological evaluation, and docking studies of gigantol analogs as calmodulin inhibitors
  作者：Adelfo Reyes-Ramírez、Martha Leyte-Lugo、Mario Figueroa、Trinidad Serrano-Alba、Martín González-Andrade、Rachel Mata

  DOI：10.1016/j.ejmech.2011.03.057

  日期：2011.7

  Several analogs of gigantol (1) were synthesized to evaluate their effect on the complexes Ca(2+)-calmodulin (CaM) and Ca(2+)-CaM-CaM sensitive phosphodiesterase 1 (PDE1). The compounds belong to four structural groups including, 1,2-diphenylethanes (2-11), diphenylmethanes (13-15), 1,3-diphenylpropenones (16-18), and 1,3-diphenylpropanes (20-22). In vitro enzymatic studies showed that all compounds except 11 inhibited the complex Ca(2+)-CaM-PDE1 with IC(50) values ranging from 9 to 146 mu M. On the other hand, all analogs but 11,12 and 15 quenched the extrinsic fluorescence of the CaM biosensor hCaM-M124C-mBBr to different extent, then revealing different affinities to CaM; their affinity constants (K(m)) values were in the range of 3-80 mu M. Molecular modeling studies indicated that all these compounds bound to CaM at the same site that the classical inhibitors trifluoperazine (TFP) and chlorpromazine (CPZ). Some of these analogs could be worthy candidates for developing new anti-tumor, local anesthetics, antidepressants, antipsychotic, or smooth muscle relaxant drugs, with anti-CaM properties due to their good affinity to CaM and the straightforwardness of their synthesis. In addition they could be valuable tools for the study of Ca(2+)-CaM functions. (C) 2011 Elsevier Masson SAS. All rights reserved.