3-chloro-N-(quinolin-5-yl)propanamide | 16880-67-4

• 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-chloro-N-(quinolin-5-yl)propanamide
• 英文别名: 3-chloro-N-quinolin-5-yl-propionamide；3-chloro-propionic acid-[5]quinolylamide；3-Chlor-propionsaeure-[5]chinolylamid；5-(3-chloropropionamido)quinoline；3-chloro-N-quinolin-5-ylpropanamide
• CAS: 16880-67-4
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: UZWQFPKJPFLRLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-N-(quinolin-5-yl)propanamide 、 3-氨基丙基三乙基硅烷 在 三乙胺 作用下， 以 xylene 为溶剂， 生成 N-Quinolin-5-yl-3-(3-triethylsilanyl-propylamino)-propionamide; hydrochloride
  参考文献：
  名称：

  Nitrogenous organosilicon compounds. 140. Synthesis and pharmacology of triethylsilylpropylaminoalkanecarboxylic quinolylamides

  摘要：

  DOI：

  10.1007/bf00769644
• 作为产物：
  描述：

  5-氨基喹啉 、 3-氯丙酰氯 在 乙醚 作用下， 生成 3-chloro-N-(quinolin-5-yl)propanamide
  参考文献：
  名称：

  Gaind et al., Journal of the Indian Chemical Society, 1940, vol. 17, p. 619,621

  摘要：

  DOI：

文献信息

• Quinoline derivatives
  申请人：Mitsui Toatsu Chemicals, Incorporated

  公开号：US05405843A1

  公开（公告）日：1995-04-11

  Heterocyclic compounds useful as anticancer drug potentiaters having a potentiating effect on the incorporation of anticancer drugs into cancer cells are disclosed, the compounds each synthesized by, for example, reacting a epoxy compound obtained by reacting a heterocyclic compound with an epihalogenohydrin, with an amine derivative.

  本发明揭示了一种用作抗癌药物增强剂的杂环化合物，具有增强抗癌药物并入癌细胞的作用，例如，通过将与环杂化合物反应的环氧化合物与胺衍生物反应合成。
• Heterocyclic compounds and anticancer-drug potentiaters conaining them
  申请人：Mitsui Toatsu Chemicals Inc.

  公开号：US05204348A1

  公开（公告）日：1993-04-20

  Novel heterocyclic compounds, which are represented by the following general formula, useful as anticancer drug potentiaters having a potentiating effect on the incorporation of anticancer drugs into cancer cells, the compounds each synthesized by, for example, reacting a epoxy compound obtained by reacting a heterocyclic compound with an epihalogenohydrin, with an amine derivative.

  以下是通用式所代表的新型杂环化合物，可用作抗癌药物增强剂，对抗癌药物在癌细胞内的纳入具有增强作用，这些化合物可以通过例如将异环化合物与环氧卤代醇反应得到的环氧化合物与胺衍生物反应而合成。
• Discovery of new potent protein arginine methyltransferase 5 (PRMT5) inhibitors by assembly of key pharmacophores from known inhibitors
  作者：Kongkai Zhu、Jia-Li Song、Hong-Rui Tao、Zhi-Qiang Cheng、Cheng-Shi Jiang、Hua Zhang

  DOI：10.1016/j.bmcl.2018.10.026

  日期：2018.12

  Protein arginine methyltransferase 5 (PRMT5) is an epigenetics related enzyme that has been validated as a promising therapeutic target for human cancer. Up to now, two small molecule PRMT5 inhibitors has been put into phase I clinical trial. In the present study, a series of candidate molecules were designed by combining key pharmacophores of formerly reported PRMT5 inhibitors. The in vitro PRMT5 inhibitory testing of compound 4b14 revealed an IC50 of 2.71 mu M, exhibiting high selectivity over PRMT1 and PRMT4 (> 70-fold selective). As expected, 4b14 exhibited potent anti-proliferative activity against a panel of leukemia and lymphoma cells, including MV4-11, Pfeiffer, SU-DHL-4 and KARPAS-422. Besides, 4b14 showed significant cell cycle arrest and apoptosis-inducing effects, as well as reduced the cellular symmetric arginine dimethylation level of SmD3 protein. Finally, affinity profiling analysis indicated that hydrophobic interactions, pi-pi stacking and cation-pi actions made the major contributions to the overall binding affinity. This scaffold provides a new chemical template for further development of better lead compounds targeting PRMT5.
• Novel heterocyclic compounds and anticancer-drug reinforcing agents containing them as effective components
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0363212B1

  公开（公告）日：1995-01-04
• US5112817A
  申请人：——

  公开号：US5112817A

  公开（公告）日：1992-05-12