N-benzo[1,3]dioxol-4-ylmethyl-N'-(7-chloroquinolin-4-yl)propane-1,3-diamine | 1224301-09-0

• 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: N-benzo[1,3]dioxol-4-ylmethyl-N'-(7-chloroquinolin-4-yl)propane-1,3-diamine
• 英文别名: N-(1,3-benzodioxol-4-ylmethyl)-N'-(7-chloroquinolin-4-yl)propane-1,3-diamine
• CAS: 1224301-09-0
• 化学式: C₂₀H₂₀ClN₃O₂
• 分子量: 369.851
• InChiKey: OFSBGWQDFBFFGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzo[1,3]dioxol-4-ylmethyl-N'-(7-chloroquinolin-4-yl)propane-1,3-diamine 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 N-benzo[1,3]dioxol-4-ylmethyl-N'-(7-chloroquinolin-4-yl)propane-1,3-diamine hydrochloride
  参考文献：
  名称：

  Development of a New Generation of 4-Aminoquinoline Antimalarial Compounds Using Predictive Pharmacokinetic and Toxicology Models

  摘要：

  Among the known antimalarial drugs, chloroquine (CQ) and other 4-aminoquinolines have shown high potency and good bioavailability. Yet complications associated with drug resistance necessitate the discovery of effective new antimalarial agents. ADMET prediction studies were employed to evaluate a library of new molecules based on the 4-aminoquinolone-related structure of CQ. Extensive in vitro screening and in vivo pharmacokinetic studies in mice helped to identify two lead molecules, 18 and 4, with promising in vitro therapeutic efficacy, improved ADMET properties, low risk for drug drug interactions, and desirable pharmacokinetic profiles. Both 18 and 4 are highly potent antimalarial compounds, with IC(50) values of 5.6 and 17.3 nM, respectively, against the W2 (CQ-resistant) strain of Plasmodium falciparum (for CQ, IC(50) = 382 nM). When tested in mice, these compounds were found to have biological half-lives and plasma exposure values similar to or higher than those of CQ; they are therefore desirable candidates to pursue in future clinical trials.

  DOI：

  10.1021/jm100057h
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N-benzo[1,3]dioxol-4-ylmethyl-N'-(7-chloroquinolin-4-yl)propane-1,3-diamine
  参考文献：
  名称：

  Development of a New Generation of 4-Aminoquinoline Antimalarial Compounds Using Predictive Pharmacokinetic and Toxicology Models

  摘要：

  Among the known antimalarial drugs, chloroquine (CQ) and other 4-aminoquinolines have shown high potency and good bioavailability. Yet complications associated with drug resistance necessitate the discovery of effective new antimalarial agents. ADMET prediction studies were employed to evaluate a library of new molecules based on the 4-aminoquinolone-related structure of CQ. Extensive in vitro screening and in vivo pharmacokinetic studies in mice helped to identify two lead molecules, 18 and 4, with promising in vitro therapeutic efficacy, improved ADMET properties, low risk for drug drug interactions, and desirable pharmacokinetic profiles. Both 18 and 4 are highly potent antimalarial compounds, with IC(50) values of 5.6 and 17.3 nM, respectively, against the W2 (CQ-resistant) strain of Plasmodium falciparum (for CQ, IC(50) = 382 nM). When tested in mice, these compounds were found to have biological half-lives and plasma exposure values similar to or higher than those of CQ; they are therefore desirable candidates to pursue in future clinical trials.

  DOI：

  10.1021/jm100057h