ethyl (Z)-3-(3,5-dimethoxyanilino)-2-phenyl-2-propenoate | 327592-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (Z)-3-(3,5-dimethoxyanilino)-2-phenyl-2-propenoate
• 英文别名: (Z)-ethyl 3-((3,5-dimethoxyphenyl)amino)-2-phenylacrylate；ethyl (Z)-3-(3,5-dimethoxyanilino)-2-phenylprop-2-enoate
• CAS: 327592-94-9
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: LJTHXNNNORYCIT-AQTBWJFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-3-(3,5-dimethoxyanilino)-2-phenyl-2-propenoate 在 cerium(III) chloride heptahydrate 、 sodium iodide 作用下， 以 二苯醚 、 联苯 、 乙腈 为溶剂， 反应 8.0h， 生成 5-hydroxy-7-methoxy-3-phenylquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones

  摘要：

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.047
• 作为产物：
  描述：

  苯乙酸乙酯 在 sodium hydride 作用下， 以 乙醚 、 甲苯 、 mineral oil 为溶剂， 反应 24.0h， 生成 ethyl (Z)-3-(3,5-dimethoxyanilino)-2-phenyl-2-propenoate
  参考文献：
  名称：

  Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones

  摘要：

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.047

文献信息

• Pharmaceutical compositions comprising 4-quinolones for treating cancers
  申请人：Laboratoire L. Lafon

  公开号：US06645983B1

  公开（公告）日：2003-11-11

  A non-cytotoxic pharmaceutical composition acting on the proliferation of clonogenic cells in malignant tumors and including an efficient amount of a compound selected among the compounds of formula (I) and (Ia).

  一种非细胞毒性药物组合物，对恶性肿瘤中克隆细胞的增殖起作用，包括在式(I)和(Ia)的化合物中选择的有效量的化合物。
• A new cytotoxic quinolone alkaloid and a pentacyclic steroidal glycoside from the stem bark of Crataeva nurvala: Study of anti-proliferative and apoptosis inducing property
  作者：Sadhna Sinha、Priyanka Mishra、Hina Amin、Bilal Rah、Debasis Nayak、Anindya Goswami、Naresh Kumar、Ram Vishwakarma、Sabari Ghosal

  DOI：10.1016/j.ejmech.2012.12.017

  日期：2013.2

  Chemical investigation of stem bark of Crataeva nurvala afforded 5,7-dimethoxy-3-phenyl-1-ethyl-1,4-dihydro-4-quinolone and a steroidal glycoside with unprecedented pentacyclic ring system named crataemine (1a) and crataenoside (2) respectively. The structures of the compounds were determined by spectroscopic analysis. A series of compounds with modification at position 1 of 1a (1a-1c) were prepared. All compounds were screened for cytotoxic activity against HeLa, PC-3 and MCF-7 cells. Only la and 2 showed potency against all three cells. Mechanism based study for activity of the compounds demonstrated that it could block the migration of more aggressive HeLa and PC-3 cells and prevent their colony formation ability as well. The compounds potentiated apoptosis in HeLa and PC-3 cells in a significant manner. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones
  作者：Santosh Rajput、Christopher R. Gardner、Timothy W. Failes、Greg M. Arndt、David StC. Black、Naresh Kumar

  DOI：10.1016/j.bmc.2013.11.047

  日期：2014.1

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.