5,7-dimethoxy-3-phenyl-1,4-dihydro-4-quinolone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5,7-dimethoxy-3-phenyl-1,4-dihydro-4-quinolone
• 英文别名: 5,7-dimethoxy-3-phenylquinolin-4(1H)-one；5,7-Dimethoxy-3-phenyl-1,4-dihydro-4-quinolinone；5,7-dimethoxy-3-phenyl-1H-quinolin-4-one
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: YRACMPLCMQTCDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-dimethoxy-3-phenyl-1,4-dihydro-4-quinolone 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-(4-Bromophenyl)-5,7-dimethoxy-10-phenyl-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7,10-pentaen-9-one
  参考文献：
  名称：

  Facile syntheses of 7,9-dimethoxypyrrolo[3,2,1-ij]quinolin-6-ones

  摘要：

  The activated dimethoxypyrrolo[3,2,1-ij]quinolin-6-one ring system was synthesized via two approaches, starting from an indole and quinolin-4-one, respectively. Subsequent demethylation led to both monohydroxy- and dihydroxypyrrolo[3,2,1-ij]quinolin-6-ones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.089
• 作为产物：
  描述：

  Alpha-甲酰基苯乙酸乙酯 以 二苯醚 、 联苯 、 甲苯 为溶剂， 反应 20.0h， 生成 5,7-dimethoxy-3-phenyl-1,4-dihydro-4-quinolone
  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.
• COMPOSITIONS PHARMACEUTIQUES COMPRENANT DES 4-QUINOLONES POUR LE TRAITEMENT DES CANCERS
  申请人：LABORATOIRE L. LAFON

  公开号：EP1202971A2

  公开（公告）日：2002-05-08
• US6645983B1
  申请人：——

  公开号：US6645983B1

  公开（公告）日：2003-11-11
• [EN] PHARMACEUTICAL COMPOSITIONS COMPRISING 4-QUINOLONES<br/>[FR] COMPOSITIONS PHARMACEUTIQUES COMPRENANT DES 4-QUINOLONES
  申请人：LAFON LABOR

  公开号：WO2001012607A2

  公开（公告）日：2001-02-22

  La présente invention concerne une composition pharmaceutique non cytotoxique ayant une activité sur la prolifération de cellules clonogènes dans les tumeurs malignes et qui comprend une quantité efficace d'un composé choisi parmi les composés de formules (I) et (Ia) dans laquelle R1, R2, R3, R4, R5, R6 et R6a sont tels que définis à la revendication 1.