3-((7-chloroquinolin-4-yl)oxy)propan-1-ol | 1033132-54-5

• 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-((7-chloroquinolin-4-yl)oxy)propan-1-ol
• 英文别名: O-(7-chloro-4-quinolyl)-1,3-propanediol；3-(7-Chloroquinolin-4-yl)oxypropan-1-ol
• CAS: 1033132-54-5
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: QZMPXJWFDJZJSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((7-chloroquinolin-4-yl)oxy)propan-1-ol 在 氯化亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成
  参考文献：
  名称：

  Morita-Baylis-Hillman Reaction with 7-Chloroquinoline Derivatives‑New Compounds with Potential Anticancer Activity

  摘要：

  DOI：

  10.21577/0103-5053.20200185
• 作为产物：
  描述：

  4,7-二氯喹啉 、 1,3-丙二醇 在 potassium tert-butylate 作用下， 反应 16.0h， 以96%的产率得到3-((7-chloroquinolin-4-yl)oxy)propan-1-ol
  参考文献：
  名称：

  喹啉-1,2,4-三嗪杂化物作为抗疟药的设计、合成和生物学评价

  摘要：

  一系列新的 1,2,4-三嗪-喹啉杂化物被设计、合成和评估为抗疟药。1,2,4-三嗪-喹啉杂化物的结构通过IR、NMR、HRMS和单晶X射线衍射研究得到证实。化合物5f具有单斜晶系和Cc空间群，化合物5j和5n具有单斜晶系和P 21空间群。化合物5a - 5m均表现出与β-血红素形成相关的良好抑制活性。化合物5c对β-血红素形成的抑制活性最好，IC 50值为 4.54 ± 0.16 µM。

  DOI：

  10.1016/j.molstruc.2022.133982

文献信息

• Synthesis and antimalarial activity of new chloroquine analogues carrying a multifunctional linear side chain
  作者：Daniel P. Iwaniuk、Eric D. Whetmore、Nicholas Rosa、Kekeli Ekoue-Kovi、John Alumasa、Angel C. de Dios、Paul D. Roepe、Christian Wolf

  DOI：10.1016/j.bmc.2009.08.003

  日期：2009.9

  We report the synthesis and in vitro antimalarial activity of several new 4-amino- and 4-alkoxy-7-chloroquinolines carrying a linear dibasic side chain. Many of these chloroquine analogues have submicromolar antimalarial activity versus HB3 (chloroquine sensitive) and Dd2 (chloroquine resistant strain of Plasmodium falciparum) and low resistance indices were obtained in most cases. Importantly, compounds

  我们报告了几种带有线性二元侧链的新 4-氨基和 4-烷氧基-7-氯喹啉的合成和体外抗疟活性。许多这些氯喹类似物对 HB3（对氯喹敏感）和 Dd2（恶性疟原虫的氯喹抗性菌株）具有亚微摩尔的抗疟活性，并且在大多数情况下获得了低抗性指数。重要的是，化合物11-15和24被证明比氯喹更有效地对抗 Dd2。侧链结构的分支证明对抗 CQR 菌株的活性有害。
• 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.
• Morita-Baylis-Hillman Reaction with 7-Chloroquinoline Derivatives‑New Compounds with Potential Anticancer Activity
  作者：João Paulo Oliveira、Guilherme Caleffi、Everton Silva、Maísa Coelho、Aleff Castro、Rhuan Mendes、Tayná Olegário、Claudio Lima-Junior、Mario Vasconcellos、Júlia Souza、Sílvia Souza、Gardênia Militão、Boniek Vaz、Ruver Ramalho

  DOI：10.21577/0103-5053.20200185

  日期：——
• Design, synthesis and biological evaluation of quinoline-1,2,4-triazine hybrids as antimalarial agents
  作者：Yuan-Yuan Feng、Chang-E Dong、Rui Li、Xiao-Qing Zhang、Wei Wang、Xing-Rui Zhang、Wei-Wei Liu、Da-Hua Shi

  DOI：10.1016/j.molstruc.2022.133982

  日期：2023.1

  A series of new hybrids of 1,2,4-triazine-quinoline were designed, synthesized and assessed as antimalarial agents. The structures of the 1,2,4-triazine-quinoline hybrids were confirmed by IR, NMR, HRMS and single-crystal X-ray diffraction studies. The compound 5f had the monoclinic crystal system and Cc space group, 5j and 5n had the monoclinic crystal system and P21 space group. Compounds 5a-5m all

  一系列新的 1,2,4-三嗪-喹啉杂化物被设计、合成和评估为抗疟药。1,2,4-三嗪-喹啉杂化物的结构通过IR、NMR、HRMS和单晶X射线衍射研究得到证实。化合物5f具有单斜晶系和Cc空间群，化合物5j和5n具有单斜晶系和P 21空间群。化合物5a - 5m均表现出与β-血红素形成相关的良好抑制活性。化合物5c对β-血红素形成的抑制活性最好，IC 50值为 4.54 ± 0.16 µM。