7-chloro-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one | 133999-06-1

• 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: 7-chloro-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one
• 英文别名: 7-Chloro-4,4-dimethyl-1,3-dihydroquinolin-2-one
• CAS: 133999-06-1
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: XOCSIBQQEXKLPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-chloro-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以68%的产率得到7-chloro-4, 4-dimethyl-3,4-dihydro-1H-quinoline-2-thione
  参考文献：
  名称：

  Synthesis and anticancer activity of aminodihydroquinoline analogs: Identification of novel proapoptotic agents

  摘要：

  A series of 2-aminodihydroquinoline analogs were synthesized and their in vitro cytotoxicities against metastatic breast adenocarcinoma cell line MDA-MB-231 were tested. Five out of 16 compounds exhibited promising activity and structure-activity relationship revealed major role of dialkylaminoethyl substituents on dihydroquinoline ring for the activity. Two compounds, 5f and 5h, presented cytotoxicity with IC50 values of about 2 mu M when the compounds were treated to the cells without serum. The cell proliferation was inhibited mildly when the cells cultured with serum. Flow cytometry analyses showed that those compounds arrested the cells at G2/M checkpoint when the cell cycle is active while they induce apoptosis when the cell growth is restricted due to the absence of growth factors. These results suggest the two novel compounds may have anticancer activity through cell cycle arrest and pro apoptosis mechanism. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.038
• 作为产物：
  描述：

  3-甲基-巴豆酸-(3-氯-苯胺) 在 aluminum (III) chloride 作用下， 以 邻二氯苯 为溶剂， 反应 4.0h， 以81%的产率得到7-chloro-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one
  参考文献：
  名称：

  Synthesis and anticancer activity of aminodihydroquinoline analogs: Identification of novel proapoptotic agents

  摘要：

  A series of 2-aminodihydroquinoline analogs were synthesized and their in vitro cytotoxicities against metastatic breast adenocarcinoma cell line MDA-MB-231 were tested. Five out of 16 compounds exhibited promising activity and structure-activity relationship revealed major role of dialkylaminoethyl substituents on dihydroquinoline ring for the activity. Two compounds, 5f and 5h, presented cytotoxicity with IC50 values of about 2 mu M when the compounds were treated to the cells without serum. The cell proliferation was inhibited mildly when the cells cultured with serum. Flow cytometry analyses showed that those compounds arrested the cells at G2/M checkpoint when the cell cycle is active while they induce apoptosis when the cell growth is restricted due to the absence of growth factors. These results suggest the two novel compounds may have anticancer activity through cell cycle arrest and pro apoptosis mechanism. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.038

文献信息

• [EN] HETEROCYCLIC SUBSTITUTED PIPERAZINES FOR THE TREATMENT OF SCHIZOPHRENIA<br/>[FR] PIPERAZINES HETEROCYCLIQUES SUBSTITUEES POUR LE TRAITEMENT DE LA SCHIZOPHRENIE
  申请人：WARNER LAMBERT CO

  公开号：WO2004026864A1

  公开（公告）日：2004-04-01

  This invention relates to compounds of the formula 1 wherein X, Y, Z, A, R', R2, R3, R4, R9, W' and W2 are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system and other disorders.

  本发明涉及式1的化合物，其中X、Y、Z、A、R'、R2、R3、R4、R9、W'和W2如规范中定义，包含它们的药物组合物以及它们在治疗中枢神经系统和其他疾病中的用途。
• Heterocyclic substituted piperazines for the treatment of schizophrenia
  申请人：——

  公开号：US20040138230A1

  公开（公告）日：2004-07-15

  This invention relates to compounds of the formula 1 1 wherein X, Y, Z, A, R 1 , R 2 , R 3 , R 4 , R 9 , W 1 and W 2 are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system and other disorders.

  本发明涉及式子11的化合物，其中X、Y、Z、A、R1、R2、R3、R4、R9、W1和W2如规范中定义的那样，包含它们的药物组合物以及它们在治疗中枢神经系统和其他疾病中的应用。
• HETEROCYCLIC SUBSTITUTED PIPERAZINES FOR THE TREATMENT OF SCHIZOPHRENIA
  申请人：Warner-Lambert Company LLC

  公开号：EP1546143A1

  公开（公告）日：2005-06-29
• Synthesis and anticancer activity of aminodihydroquinoline analogs: Identification of novel proapoptotic agents
  作者：Eun Lee、SeulAa Han、Guo Hua Jin、Hwa Jin Lee、Woo-Young Kim、Jae-Ha Ryu、Raok Jeon

  DOI：10.1016/j.bmcl.2013.04.038

  日期：2013.7

  A series of 2-aminodihydroquinoline analogs were synthesized and their in vitro cytotoxicities against metastatic breast adenocarcinoma cell line MDA-MB-231 were tested. Five out of 16 compounds exhibited promising activity and structure-activity relationship revealed major role of dialkylaminoethyl substituents on dihydroquinoline ring for the activity. Two compounds, 5f and 5h, presented cytotoxicity with IC50 values of about 2 mu M when the compounds were treated to the cells without serum. The cell proliferation was inhibited mildly when the cells cultured with serum. Flow cytometry analyses showed that those compounds arrested the cells at G2/M checkpoint when the cell cycle is active while they induce apoptosis when the cell growth is restricted due to the absence of growth factors. These results suggest the two novel compounds may have anticancer activity through cell cycle arrest and pro apoptosis mechanism. (c) 2013 Elsevier Ltd. All rights reserved.