1-chloro-10H-indolo[3,2-b]quinoline | 1268525-74-1

• 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: 1-chloro-10H-indolo[3,2-b]quinoline
• CAS: 1268525-74-1
• 化学式: C₁₅H₉ClN₂
• 分子量: 252.703
• InChiKey: YUQLHBDUKKULNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-chloro-10H-indolo[3,2-b]quinoline 、 三氟甲烷磺酸甲酯 以 甲苯 为溶剂， 反应 24.0h， 以71%的产率得到1-chloro-5-methyl-10H-indolo[3,2-b]quinolin-5-ium triflate
  参考文献：
  名称：

  Identification of 3-phenylaminoquinolinium and 3-phenylaminopyridinium salts as new agents against opportunistic fungal pathogens

  摘要：

  Previous studies on the indoloquinoline alkaloid, cryptolepine (2), revealed that it has antii-nfective properties among other activities. Using Structure-activity relationship (SAR) techniques, several ring-opened analogs of cryptolepine (3-phenylaminopyridinium and 3-phenylaminoquinolinium derivatives) were designed to improve the potency and lower the cytotoxicity shown by several of the precursor agents. Results indicate that these ring-opened analogs constitute new anti-infective agents with over a 100-fold potency and several fold lower cytotoxicity than cryptolepine from which they are derived. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.10.065
• 作为产物：
  描述：

  1-chloro-10H-indolo[3,2-b]quinoline-11-carboxylic acid 以 paraffin oil 为溶剂， 反应 3.0h， 生成 1-chloro-10H-indolo[3,2-b]quinoline
  参考文献：
  名称：

  Identification of 3-phenylaminoquinolinium and 3-phenylaminopyridinium salts as new agents against opportunistic fungal pathogens

  摘要：

  Previous studies on the indoloquinoline alkaloid, cryptolepine (2), revealed that it has antii-nfective properties among other activities. Using Structure-activity relationship (SAR) techniques, several ring-opened analogs of cryptolepine (3-phenylaminopyridinium and 3-phenylaminoquinolinium derivatives) were designed to improve the potency and lower the cytotoxicity shown by several of the precursor agents. Results indicate that these ring-opened analogs constitute new anti-infective agents with over a 100-fold potency and several fold lower cytotoxicity than cryptolepine from which they are derived. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.10.065

文献信息

• [EN] QUINDOLINE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE QUINDOLINE ET LEURS UTILISATIONS
  申请人：UNIV ARIZONA

  公开号：WO2020160175A1

  公开（公告）日：2020-08-06

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a quindoline (or similar) structure which function as stabilizers of G-quadruplex (G4) formation, and their use as therapeutics for the treatment of cancer (e.g., castration-resistant prostate cancer), and other conditions mediated by G4 stabilization.

  这项发明属于药物化学领域。具体而言，该发明涉及一类新型具有喹啉（或类似）结构的小分子，其作为G-四链体（G4）形成的稳定剂，并且它们作为治疗癌症（例如去势抵抗性前列腺癌）和其他通过G4稳定介导的疾病的治疗药物的用途。
• Condensed quinoline system compound and process of preparation thereof
  申请人：MECT CORPORATION

  公开号：EP0376166A1

  公开（公告）日：1990-07-04

  Novel condensed quinoline system compounds such as indenoquinoline system compounds, indoloquinoline system compounds, benzothienoquinoline system compounds and benzofuranoquinoline system compounds, and a process for preparation of these compounds are provided. The present invention is also directed to salts of the above compounds. The compounds of the present invention are effective for inhibition of KB-cell growth and prolongation of life span in cancer implanted mice.

  本发明提供了新型缩合喹啉系化合物，如茚并喹啉系化合物、吲哚并喹啉系化合物、苯并噻吩并喹啉系化合物和苯并呋喃并喹啉系化合物，以及制备这些化合物的工艺。本发明还涉及上述化合物的盐类。本发明的化合物可有效抑制 KB 细胞的生长，延长癌症植入小鼠的寿命。
• QUINDOLINE COMPOUNDS AND USES THEREOF
  申请人：Arizona Board of Regents on Behalf of the University of Arizona

  公开号：US20220098210A1

  公开（公告）日：2022-03-31

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a quindoline (or similar) structure which function as stabilizers of G-quadruplex (G4) formation, and their use as therapeutics for the treatment of cancer (e.g., castration-resistant prostate cancer), and other conditions mediated by G4 stabilization.
• [EN] CRYPTOLEPINE ANALOGS WITH HYPOGLYCEMIC ACTIVITY<br/>[FR] ANALOGUES DE CRYPTOLEPINE A ACTIVITE HYPOGLYCEMIQUE
  申请人：SHAMAN PHARMACEUTICALS, INC.

  公开号：WO1996010015A1

  公开（公告）日：1996-04-04

  (EN) Novel cryptolepine analogs useful as hypoglycemic agents and methods for their use as hypoglycemic agents, for example, in the treatment of diabetes, and a method for their synthesis are described. As hypoglycemic agents, the novel cryptolepine analogs are useful for the treatment of insulin-dependent diabetes mellitus (IDDM or Type I) and non-insulin dependent diabetes mellitus (NIDDM or Type II).(FR) Nouveaux analogues de cryptolépine utiles comme agents hypoglycémiques, méthodes d'utilisation de ces analogues comme agents hypoglycémiques, par exemple, pour le traitement du diabète, et méthodes de synthèse de ces analogues. En tant qu'agents hypoglycémiques, ces nouveaux analogues de cryptolépine se révèlent utiles pour le traitement du diabète sucré insulino-dépendant (IDDM ou Type I) et du diabète sucré non insulino-dépendant (NIDDM OU Type II).