7-chloro-N-(3-(4-phenylpiperazin-1-yl)propyl)quinolin-4-amine | 1228697-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 7-chloro-N-(3-(4-phenylpiperazin-1-yl)propyl)quinolin-4-amine
• 英文别名: 7-chloro-N-[3-(4-phenylpiperazin-1-yl)propyl]quinolin-4-amine
• CAS: 1228697-77-5
• 化学式: C₂₂H₂₅ClN₄
• 分子量: 380.92
• InChiKey: RANAESZULQGHTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  31.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(7-chloroquinolin-4-ylamino)propyl methanesulfonate 、 N-苯基哌嗪 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以53%的产率得到7-chloro-N-(3-(4-phenylpiperazin-1-yl)propyl)quinolin-4-amine
  参考文献：
  名称：

  Design and synthesis of chloroquine analogs with anti-breast cancer property

  摘要：

  A series of chloroquine (CQ) analogs were designed and synthesized in a repositioning approach to develop compounds with high anti-breast cancer property. The compounds were then examined for their antiproliferative effects on two human breast tumor cell lines and a matching non-cancer cell line. Although many of them showed substantial antiproliferative effects on breast cancer cells examined, two compounds, 7-chloro-N-(3-(4-(7-(trifluoromethyl)quinolin-4-yl)piperazin-1-yl)propyl)quinolin-4-amine (14) and (3[4-(7-chloro-quinolin-4-yl)-piperazin-1-yl]-propyl)-(7-trifluoromethyl-quinolin-4-yl)-amine (26), emerged as the most active among this series. They were particularly potent against MCF7 cells when compared to CQ and cisplatin, a widely prescribed anti-cancer drug. The results suggest that these CQ analogs could serve as bases for the development of a new group of effective cancer chemotherapeutics. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.046

文献信息

• [EN] MODIFIED CHLOROQUINES WITH SINGLE RING MOIETY OR FUSED RING MOIETY<br/>[FR] CHLOROQUINES MODIFIÉES PAR UN GROUPEMENT MONOCYCLIQUE OU UN GROUPEMENT À CYCLES FUSIONNÉS
  申请人：DESIGNMEDIX INC

  公开号：WO2010065932A1

  公开（公告）日：2010-06-10

  The disclosure provides modified chloroquine compounds having single ring or fused ring moieties. Also provided are pharmaceutical compositions comprising such compounds, methods of using such compounds to inhibit or treat diseases or conditions caused by chloroquine-resistant (CQR) and chloroquine-sensitive (CQS) malaria parasites and other CQ-susceptible microorganisms, and processes and intermediates useful for preparing such compounds.

  该披露提供了具有单环或融合环基团的改良氯喹化合物。还提供了包含这些化合物的药物组合物，使用这些化合物抑制或治疗由氯喹耐药（CQR）和氯喹敏感（CQS）疟疾寄生虫以及其他氯喹敏感微生物引起的疾病或病症的方法，以及用于制备这些化合物的过程和中间体。
• MODIFIED CHLOROQUINES WITH SINGLE RING MOIETY OR FUSED RING MOIETY
  申请人：Designmedix, Inc.

  公开号：EP2379505A1

  公开（公告）日：2011-10-26
• US8658648B2
  申请人：——

  公开号：US8658648B2

  公开（公告）日：2014-02-25
• Design and synthesis of chloroquine analogs with anti-breast cancer property
  作者：V.R. Solomon、Changkun Hu、Hoyun Lee

  DOI：10.1016/j.ejmech.2010.05.046

  日期：2010.9

  A series of chloroquine (CQ) analogs were designed and synthesized in a repositioning approach to develop compounds with high anti-breast cancer property. The compounds were then examined for their antiproliferative effects on two human breast tumor cell lines and a matching non-cancer cell line. Although many of them showed substantial antiproliferative effects on breast cancer cells examined, two compounds, 7-chloro-N-(3-(4-(7-(trifluoromethyl)quinolin-4-yl)piperazin-1-yl)propyl)quinolin-4-amine (14) and (3[4-(7-chloro-quinolin-4-yl)-piperazin-1-yl]-propyl)-(7-trifluoromethyl-quinolin-4-yl)-amine (26), emerged as the most active among this series. They were particularly potent against MCF7 cells when compared to CQ and cisplatin, a widely prescribed anti-cancer drug. The results suggest that these CQ analogs could serve as bases for the development of a new group of effective cancer chemotherapeutics. (C) 2010 Elsevier Masson SAS. All rights reserved.