[(7-chloroquinolin-4-yl)oxy]butan-1-ol | 1033132-55-6

• 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: [(7-chloroquinolin-4-yl)oxy]butan-1-ol
• 英文别名: 4-{(7-chloroquinolin-4-yl)oxy}butanol；O-(7-chloro-4-quinolyl)-1,4-butanediol；4-(7-chloroquinolin-4-yl)oxybutan-1-ol
• CAS: 1033132-55-6
• 化学式: C₁₃H₁₄ClNO₂
• 分子量: 251.713
• InChiKey: PQFKNECNAFPRLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  [(7-chloroquinolin-4-yl)oxy]butan-1-ol 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 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 、 1,4-丁二醇 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 18.0h， 以66%的产率得到[(7-chloroquinolin-4-yl)oxy]butan-1-ol
  参考文献：
  名称：

  4-N-, 4-S-, and 4-O-Chloroquine Analogues: Influence of Side Chain Length and Quinolyl Nitrogen pK_a on Activity vs Chloroquine Resistant Malaria

  摘要：

  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.

  DOI：

  10.1021/jm701478a

文献信息

• Quinoline‐Conjugated Ruthenacarboranes: Toward Hybrid Drugs with a Dual Mode of Action
  作者：Marta Gozzi、Blagoje Murganic、Dijana Drača、John Popp、Peter Coburger、Danijela Maksimović‐Ivanić、Sanja Mijatović、Evamarie Hey‐Hawkins

  DOI：10.1002/cmdc.201900349

  日期：2019.12.17

  ,1,2-RuC2 B9 H10 ] (4) showed a dual mode of action against the LN229 (human glioblastoma) cell line, where it inhibited tumor-promoting autophagy, and strongly inhibited cell proliferation, de facto blocking cellular division. These results, together with the tendency to spontaneously form nanoparticles in aqueous solution, make complex 4 a very promising drug candidate for further studies in vivo

  自噬在癌症中的作用通常很复杂，从促进肿瘤到抑制肿瘤。在这项研究中，设计了两种新型杂化分子，其中含有与已知的自噬调节剂（即喹啉衍生物）缀合的钌碳硼烷片段。复合物 closo-[3-(η6 -p-cymene)-1-(quinolin-8-yl-acetate)-3,1,2-RuC2 B9 H10 ] (4) 显示出针对 LN229 的双重作用模式（人胶质母细胞瘤）细胞系，它抑制肿瘤促进自噬，并强烈抑制细胞增殖，事实上阻止细胞分裂。这些结果，加上在水溶液中自发形成纳米颗粒的倾向，使得复合物 4 成为一种非常有前途的候选药物，可用于进一步的体内研究，用于治疗易发生自噬的胶质母细胞瘤。
• 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
• 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：——