(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one | 16635-71-5

• 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: (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one
• 英文别名: 3,4-Methylendioxy-5'-methyl-2'-hydroxy-chalkon；2'-Hydroxy-5'-methyl-3,4-methylendioxy-chalkon；3-benzo[1,3]dioxol-5-yl-1-(2-hydroxy-5-methyl-phenyl)-propenone；2'-hydroxy-5'-methyl-3,4-methylenedioxy-trans-chalcone；3-(Benzo[1,3]dioxol-5-yl)-1-(5-methyl-2-hydroxyphenyl)-2-propen-1-one；2'-Hydroxy-5'-methyl-3,4-methylendioxy-trans-chalkon；(E)-3-(1,3-benzodioxol-5-yl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one
• CAS: 16635-71-5
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: XTKNYLGLYDBLBO-ZZXKWVIFSA-N

物化性质

• 熔点：
  211-212 °C
• 沸点：
  481.4±45.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以67%的产率得到2-(benzo[d][1,3]dioxol-5-yl)-3-hydroxy-6-methyl-4H-chromen-4-one
  参考文献：
  名称：

  SAR Studies and Biological Characterization of a Chromen-4-one Derivative as an Anti-Trypanosoma brucei Agent

  摘要：

  Chemical modulation of the flavonol 2-(benzo[d] [1,3]dioxo1-5-y1)-chromen-4-one (1), a promising anti-Trypanosomatid agent previously identified, was evaluated through a phenotypic screening approach. Herein, we have performed structure activity relationship studies around hit compound 1. The pivaloyl derivative (13) showed significant anti-T. brucei activity (EC50 = 1.1 1iM) together with a selectivity index higher than 92. The early in vitro ADME-tox properties (cytotoxicity, mitochondria] toxicity, cytochrome P450 and hERG inhibition) were determined for compound 1 and its derivatives, and these led to the identification of some liabilities. The 1,3-benzodioxole moiety in the presented compounds confers better in vivo pharmacokinetic properties than those of classical flavonols. Further studies using different delivery systems could lead to an increase of compound blood levels.

  DOI：

  10.1021/acsmedchemlett.8b00565
• 作为产物：
  描述：

  胡椒醛 、 2-羟基-5-甲基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.5h， 以86.2%的产率得到(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Discovery of 2′-hydroxychalcones as autophagy inducer in A549 lung cancer cells

  摘要：

  合成了一系列2'-羟基茚酮衍生物，并研究了所有化合物对A549肺癌细胞生长的影响。

  DOI：

  10.1039/c3ob42429d

文献信息

• Ozawa et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 1178,1182
  作者：Ozawa et al.

  DOI：——

  日期：——
• Marathe, Journal of the University of Poona, Science and Technology, 1958, # 14, p. 63,66
  作者：Marathe

  DOI：——

  日期：——
• CHINCHOLKAR M. M.; KAKADE B. S.; JAMODE V. S., INDIAN J. CHEM., 1980, B 17, NO 6, 629-630
  作者：CHINCHOLKAR M. M.、 KAKADE B. S.、 JAMODE V. S.

  DOI：——

  日期：——
• JOSHI, U. K.;KELKAR, R. M.;PARADKAR, M. V., INDIAN J. CHEM., 1983, 22, N 11, 1151-1152
  作者：JOSHI, U. K.、KELKAR, R. M.、PARADKAR, M. V.

  DOI：——

  日期：——
• ESTROGEN RECEPTOR ALPHA COLIGANDS, AND METHODS OF USE THEREOF
  申请人：The Regents of the University of California

  公开号：US20190008797A1

  公开（公告）日：2019-01-10

  Provided herein is a coligand for the estrogen receptor (ER) a subunit, and methods of use thereof in treating conditions associated with ER signaling in an individual. The present ERα coligand may be a cell type-selective, allosteric modulator of ERα signaling. The ERα coligand, when administered to an individual, may modulate ER agonist-dependent signaling in a tissue-selective manner.