[3-(4-Methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-yl] 4-methylbenzenesulfonate | 471294-69-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: [3-(4-Methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-yl] 4-methylbenzenesulfonate
• 英文别名: [3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-yl] 4-methylbenzenesulfonate
• CAS: 471294-69-6
• 化学式: C₂₈H₃₀O₇S
• 分子量: 510.608
• InChiKey: KOUJBSZWISLVSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [3-(4-Methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-yl] 4-methylbenzenesulfonate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1,2,3-Trimethoxy-5-[2-(4-methoxyphenyl)cyclopenten-1-yl]benzene
  参考文献：
  名称：

  Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues

  摘要：

  A series of 2-(3,4,5-trimethoxyphenyl)-3-arylcyclopent-2-ene-1-ones (8a-8e) and their related analogues, including pentenone 9a, pentenol 10a, pentene 12a, and furane 15, were synthesized and evaluated for cytotoxicity against murine and human tumor cell lines. Compounds 8a-c, 8e and 9a showed strong cytotoxicity with IC50 values in the range of 8-34 ng/mL. Compound 8e exhibited significant anti-tumor activity in BDF1 mice bearing Lewis lung carcinoma cells with an inhibition ratio of 59%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00321-9
• 作为产物：
  描述：

  3,4,5-trimethoxyphenylacetyl chloride 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 TEA 、 硫酸 、 溶剂黄146 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 7.5h， 生成 [3-(4-Methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-yl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues

  摘要：

  A series of 2-(3,4,5-trimethoxyphenyl)-3-arylcyclopent-2-ene-1-ones (8a-8e) and their related analogues, including pentenone 9a, pentenol 10a, pentene 12a, and furane 15, were synthesized and evaluated for cytotoxicity against murine and human tumor cell lines. Compounds 8a-c, 8e and 9a showed strong cytotoxicity with IC50 values in the range of 8-34 ng/mL. Compound 8e exhibited significant anti-tumor activity in BDF1 mice bearing Lewis lung carcinoma cells with an inhibition ratio of 59%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00321-9

文献信息

• Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues
  作者：Nguyen-Hai Nam、Yong Kim、Young-Jae You、Dong-Ho Hong、Hwan-Mook Kim、Byung-Zun Ahn

  DOI：10.1016/s0960-894x(02)00321-9

  日期：2002.8

  A series of 2-(3,4,5-trimethoxyphenyl)-3-arylcyclopent-2-ene-1-ones (8a-8e) and their related analogues, including pentenone 9a, pentenol 10a, pentene 12a, and furane 15, were synthesized and evaluated for cytotoxicity against murine and human tumor cell lines. Compounds 8a-c, 8e and 9a showed strong cytotoxicity with IC50 values in the range of 8-34 ng/mL. Compound 8e exhibited significant anti-tumor activity in BDF1 mice bearing Lewis lung carcinoma cells with an inhibition ratio of 59%. (C) 2002 Elsevier Science Ltd. All rights reserved.