S-(7-chloro-4-quinolyl)-2-(N,N-diethylamino)ethanethiol

• 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: S-(7-chloro-4-quinolyl)-2-(N,N-diethylamino)ethanethiol
• 英文别名: 7-chloro-4-(2-diethylamino-ethylmercapto)-quinoline；7-Chlor-4-(2-diaethylamino-aethylmercapto)-chinolin；S-(7-chloro-4-quinolyl)-2-(N,N-diethylamino)ethanethioll；2-(7-chloroquinolin-4-yl)sulfanyl-N,N-diethylethanamine
• 化学式: C₁₅H₁₉ClN₂S
• 分子量: 294.848
• InChiKey: CKKMSPRSSCZILT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-二乙基氯乙胺 、 7-Chloro-1H-quinoline-4-thione 在 sodium hydroxide 作用下， 以 丁酮 为溶剂， 生成 S-(7-chloro-4-quinolyl)-2-(N,N-diethylamino)ethanethiol
  参考文献：
  名称：

  Synthesis of aza mono, bi and tricyclic compounds. Evaluation of their anti MDR activity

  摘要：

  Anti MDR activity of a series of acridine, pyridoquinoline, quinoline and pyridine analogous amines was evaluated. Interesting activity is displayed by tricyclic compounds. Besides ring size, influence of the side chain was studied. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01422-8

文献信息

• Antimalarial Quinolines and Methods of Use Thereof
  申请人：Wolf Christian

  公开号：US20110045100A1

  公开（公告）日：2011-02-24

  One aspect of the invention relates to substitute quinolines with antimalarial activity, and compositions and kits comprising at least one of them. Another aspect of the invention relates to methods for the treatment or prevention or both of malaria comprising administering to a subject a therapeutically effective amount of such a compound. Importantly, a number of the compounds show excellent potency against both chloroquine-sensitive and chloroquine-resistant strains.

  本发明的一个方面涉及具有抗疟活性的替代喹啉，以及包含至少其中之一的组合物和试剂盒。另一个方面涉及用这种化合物向受试者施用治疗有效量的方法，以治疗或预防疟疾。重要的是，其中一些化合物对氯喹敏感和氯喹耐药菌株都表现出极高的效力。
• 4-<i>N</i>-, 4-<i>S</i>-, and 4-<i>O</i>-Chloroquine Analogues: Influence of Side Chain Length and Quinolyl Nitrogen p<i>K</i>_a on Activity vs Chloroquine Resistant Malaria
  作者：Jayakumar K. Natarajan、John N. Alumasa、Kimberly Yearick、Kekeli A. Ekoue-Kovi、Leah B. Casabianca、Angel C. de Dios、Christian Wolf、Paul D. Roepe

  DOI：10.1021/jm701478a

  日期：2008.6.1

  Using predictions from heme-quinoline antimalarial complex structures, previous modifications of chloroquine (CQ), and hypotheses for chloroquine resistance (CQR), we synthesize and assay CQ analogues that test structure-function principles. We vary side chain length for both monoethyl and diethyl 4-N CQ derivatives. We alter the pK(a) of the quinolyl N by introducing alkylthio or alkoxy substituents into the 4 position and vary side chain length for these analogues. We introduce an additional titratable amino group to the side chain of 4-O analogues with promising CQR strain selectivity and increase activity while retaining selectivity. We solve atomic resolution structures for complexes formed between representative 4-N, 4-S, and 4-O derivatives vs mu-oxo dimeric heme, measure binding constants for monomeric vs dimeric heme, and quantify hemozoin (Hz) formation inhibition in vitro. The data provide additional insight for the design of CQ analogues with improved activity vs CQR malaria.
• [EN] ANTIMALARIAL QUINOLINES AND METHODS OF USE THEREOF<br/>[FR] QUINOLÉINES ANTIPALUDIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV GEORGETOWN

  公开号：WO2009148659A3

  公开（公告）日：2010-02-25
• Some Dialkylaminoalkylmercaptoquinolines
  作者：Henry. Gilman、Mary Alys. Plunkett

  DOI：10.1021/ja01179a026

  日期：1949.11.19
• Some Dialkylaminoalkyl Sulfides and Ethers Derived from Quinoline and Acridine Heterocycles
  作者：R. O. Clinton、C. M. Suter

  DOI：10.1021/ja01182a017

  日期：1948.2