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7-chloro-N-(2-(4-methylpiperazin-1-yl)ethyl)quinolin-4-amine | 1179739-55-9

中文名称
——
中文别名
——
英文名称
7-chloro-N-(2-(4-methylpiperazin-1-yl)ethyl)quinolin-4-amine
英文别名
7-chloro-N-[2-(4-methylpiperazin-1-yl)ethyl]quinolin-4-amine
7-chloro-N-(2-(4-methylpiperazin-1-yl)ethyl)quinolin-4-amine化学式
CAS
1179739-55-9
化学式
C16H21ClN4
mdl
——
分子量
304.823
InChiKey
GGBPYNWPRKJCPX-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.8
  • 重原子数:
    21
  • 可旋转键数:
    4
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.44
  • 拓扑面积:
    31.4
  • 氢给体数:
    1
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    tert-butyl 2-(4-methylpiperazin-1-yl)ethylcarbamate 在 盐酸苯酚 作用下, 以 1,4-二氧六环甲醇 为溶剂, 反应 1.0h, 生成 7-chloro-N-(2-(4-methylpiperazin-1-yl)ethyl)quinolin-4-amine
    参考文献:
    名称:
    Synthesis and Evaluation of Chirally Defined Side Chain Variants of 7-Chloro-4-Aminoquinoline To Overcome Drug Resistance in Malaria Chemotherapy
    摘要:
    摘要 一种新型 4-氨基喹啉衍生物 [( S )-7-氯- N -(4-甲基-1-(4-甲基哌嗪-1-基)戊烷-2-基)-喹啉-4-胺三磷酸酯]对耐氯喹的疟原虫具有治疗活性,已被确定作为血吸虫杀灭剂进行临床前开发。经过详细的结构-活性关系(SAR)研究后选出的先导分子具有良好的固态特性,对 体外 和 体内 实验疟疾模型具有良好的活性。体外 体外 吸收、分布、代谢和排泄(ADME)参数表明其具有良好的类药物特征。
    DOI:
    10.1128/aac.01152-16
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文献信息

  • New derivatives of 7-chloroquinolin-4-amine with antiprotozoal activity
    作者:Johanna Faist、Clemens Hinteregger、Werner Seebacher、Robert Saf、Pascal Mäser、Marcel Kaiser、Robert Weis
    DOI:10.1016/j.bmc.2016.12.006
    日期:2017.2
    Novel co-aminoacyl and -alkyl derivatives of 7-chloroquinolin-4-amine were prepared and their structures confirmed by NMR spectroscopy. Their antiprotozoal activities were examined in vitro against the sensitive NF54 strain as well as against the multiresistant K-1 strain of Plasmodium falciparum and against Trypanosoma brucei rhodesiense (STIB 900). The results were compared with the activities of clinically used drugs. Their antitypanosomal activities were only moderate whereas their antiplasmodial activities looked very promising. Some were equal or slightly more active than chloroquine against the sensitive strain. However, in comparison to chloroquine, the activity of the new compounds was decreased much less in the resistant strain. Several possessed activity against both strains in low nanomolar concentration. (C) 2016 Elsevier Ltd. All rights reserved.
  • Synthesis and Evaluation of Chirally Defined Side Chain Variants of 7-Chloro-4-Aminoquinoline To Overcome Drug Resistance in Malaria Chemotherapy
    作者:Vasantha Rao Dola、Awakash Soni、Pooja Agarwal、Hafsa Ahmad、Kanumuri Siva Rama Raju、Mamunur Rashid、Muhammad Wahajuddin、Kumkum Srivastava、W. Haq、A. K. Dwivedi、S. K. Puri、S. B. Katti
    DOI:10.1128/aac.01152-16
    日期:2017.3
    ABSTRACT

    A novel 4-aminoquinoline derivative [( S )-7-chloro- N -(4-methyl-1-(4-methylpiperazin-1-yl)pentan-2-yl)-quinolin-4-amine triphosphate] exhibiting curative activity against chloroquine-resistant malaria parasites has been identified for preclinical development as a blood schizonticidal agent. The lead molecule selected after detailed structure-activity relationship (SAR) studies has good solid-state properties and promising activity against in vitro and in vivo experimental malaria models. The in vitro absorption, distribution, metabolism, and excretion (ADME) parameters indicate a favorable drug-like profile.

    摘要 一种新型 4-氨基喹啉衍生物 [( S )-7-氯- N -(4-甲基-1-(4-甲基哌嗪-1-基)戊烷-2-基)-喹啉-4-胺三磷酸酯]对耐氯喹的疟原虫具有治疗活性,已被确定作为血吸虫杀灭剂进行临床前开发。经过详细的结构-活性关系(SAR)研究后选出的先导分子具有良好的固态特性,对 体外 和 体内 实验疟疾模型具有良好的活性。体外 体外 吸收、分布、代谢和排泄(ADME)参数表明其具有良好的类药物特征。
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