3-[3-[(7-Chloro-4-quinolyl)amino]propyl]-2-thioxo-thiazolidin-4-one | 1430804-48-0

• 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: 3-[3-[(7-Chloro-4-quinolyl)amino]propyl]-2-thioxo-thiazolidin-4-one
• 英文别名: 3-[3-[(7-chloroquinolin-4-yl)amino]propyl]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 1430804-48-0
• 化学式: C₁₅H₁₄ClN₃OS₂
• 分子量: 351.881
• InChiKey: SAOORLRASZJGDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[3-[(7-Chloro-4-quinolyl)amino]propyl]-2-thioxo-thiazolidin-4-one 、 对二甲氨基苯甲醛 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 以74%的产率得到(5Z)-3-[3-[(7-chloro-4-quinolyl)amino]propyl]-5-[(4-dimethylaminophenyl)methylene]-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a new class of 4-aminoquinoline–rhodanine hybrid as potent anti-infective agents

  摘要：

  Synthesis of novel 4-aminoquinoline-rhodanine hybrid using inexpensive starting materials via easy to operate methodology, and their biological activity is reported. All the compounds were screened for their in vitro antimalarial activity against chloroquine-resistant (1(1) and chloroquine-sensitive (3D7) strains of Plasmodium falciparum, and their cytotoxicity toward VERO cell line. Compounds 9, 19, 21 and 23 exhibited excellent antimalarial activity with IC50 value ranging from 13.2 to 45.5 nM against chloroquine-resistant (K1) strain. Biochemical studies revealed that inhibition of hemozoin formation is the primary mechanism of action of these analogs for their antimalarial activity. Additionally, some derivatives (14, 18 and 26) of this series also exhibited the antimycobacterial activity against H(37)Rv strain of Mycobacterium tuberculosis with MIC value of 6.25 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.017
• 作为产物：
  描述：

  4,7-二氯喹啉 以 乙腈 为溶剂， 反应 4.0h， 生成 3-[3-[(7-Chloro-4-quinolyl)amino]propyl]-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a new class of 4-aminoquinoline–rhodanine hybrid as potent anti-infective agents

  摘要：

  Synthesis of novel 4-aminoquinoline-rhodanine hybrid using inexpensive starting materials via easy to operate methodology, and their biological activity is reported. All the compounds were screened for their in vitro antimalarial activity against chloroquine-resistant (1(1) and chloroquine-sensitive (3D7) strains of Plasmodium falciparum, and their cytotoxicity toward VERO cell line. Compounds 9, 19, 21 and 23 exhibited excellent antimalarial activity with IC50 value ranging from 13.2 to 45.5 nM against chloroquine-resistant (K1) strain. Biochemical studies revealed that inhibition of hemozoin formation is the primary mechanism of action of these analogs for their antimalarial activity. Additionally, some derivatives (14, 18 and 26) of this series also exhibited the antimycobacterial activity against H(37)Rv strain of Mycobacterium tuberculosis with MIC value of 6.25 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.017

文献信息

• Synthesis and biological evaluation of a new class of 4-aminoquinoline–rhodanine hybrid as potent anti-infective agents
  作者：Kuldeep Chauhan、Moni Sharma、Juhi Saxena、Shiv Vardan Singh、Priyanka Trivedi、Kumkum Srivastava、Sunil K. Puri、J.K. Saxena、Vinita Chaturvedi、Prem. M.S. Chauhan

  DOI：10.1016/j.ejmech.2013.01.017

  日期：2013.4

  Synthesis of novel 4-aminoquinoline-rhodanine hybrid using inexpensive starting materials via easy to operate methodology, and their biological activity is reported. All the compounds were screened for their in vitro antimalarial activity against chloroquine-resistant (1(1) and chloroquine-sensitive (3D7) strains of Plasmodium falciparum, and their cytotoxicity toward VERO cell line. Compounds 9, 19, 21 and 23 exhibited excellent antimalarial activity with IC50 value ranging from 13.2 to 45.5 nM against chloroquine-resistant (K1) strain. Biochemical studies revealed that inhibition of hemozoin formation is the primary mechanism of action of these analogs for their antimalarial activity. Additionally, some derivatives (14, 18 and 26) of this series also exhibited the antimycobacterial activity against H(37)Rv strain of Mycobacterium tuberculosis with MIC value of 6.25 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.