N-(4-chlorophenyl)-2-methyl-4-phenylquinoline-3-carboxamide

• 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: N-(4-chlorophenyl)-2-methyl-4-phenylquinoline-3-carboxamide
• 化学式: C₂₃H₁₇ClN₂O
• 分子量: 372.854
• InChiKey: JJHDDKKGBZDLHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  N-(4-chlorophenyl)-2-methyl-4-phenylquinoline-3-carboxamide 在 Oxone 、 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以84%的产率得到2-(4-chlorophenyl)-9-phenyl-1H-pyrrolo[3,4-b]quinoline-1,3(2H)-dione
  参考文献：
  名称：

  铜（I）催化的酰胺化和苄基C（sp 3）-H键的连续氧化：1 H-吡咯并[3,4- b ]喹啉-1,3（2 H）-二酮的合成

  摘要：

  开发了一种有效的铜（I）催化的分子内芳基甲基C（sp 3）–H直接氧化酰胺化反应，用于制备药物样的1 H-吡咯并[3,4- b ]喹啉-1,3（2 H）-二酮类化合物可从2-甲基-3-氨基甲酰基喹啉中轻松获得。

  DOI：

  10.1016/j.tet.2016.05.059
• 作为产物：
  描述：

  2-氨基二苯甲酮 在 4-十二烷基苯磺酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 生成 N-(4-chlorophenyl)-2-methyl-4-phenylquinoline-3-carboxamide
  参考文献：
  名称：

  Design, development of new synthetic methodology, and biological evaluation of substituted quinolines as new anti-tubercular leads

  摘要：

  Two series of quinoline-based compounds were designed, synthesised and evaluated for anti-tubercular activity against Mycobacterium tuberculosis H(37)Rv (ATCC 27294 strain). A new method for Friedlander quinoline synthesis has been developed in water under the catalytic influence of the Bronsted acid surfactant DBSA. Among the forty-two compounds tested for anti-TB activity, twenty-three compounds exhibited significant activity against the growth of M. tuberculosis (MIC 0.02-6.25 mu g/mL). In particular, the compounds 3b and 3c displayed excellent anti-TB activity with MIC values of 0.2 and 0.39 mu g/mL, respectively, and are more potent than the standard drugs E, Cfx and Z that are clinically used to treat TB. The cytotoxicity of the compounds with MIC <= 6.25 mu g/mL was evaluated against Human Embryonic Kidney 293T cell lines and all of the active compounds were found to be nontoxic (<50% inhibition). The results suggest that the synthesised substituted quinolines are promising leads for development of new drug to treat TB. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.082

文献信息

• Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines via Friedlander hetero-annulation reaction
  作者：B. Palakshi Reddy、P. Iniyavan、S. Sarveswari、V. Vijayakumar

  DOI：10.1016/j.cclet.2014.06.026

  日期：2014.12

  Abstract Reusable acidic nickel oxide nanoparticles have been synthesized, characterized and applied as a catalyst to convert 2-aminoaryl ketones and β-ketoesters/ketones into the corresponding quinolines in good yields with high selectivity. This could serve as a simple and convenient procedure for the Friedlander annulations.

  摘要合成，表征了可重复使用的酸性氧化镍纳米颗粒，并将其用作催化剂，以高收率，高选择性将2-氨基芳基酮和β-酮​​酸酯/酮转化为相应的喹啉。这可以用作Friedlander环空的简单方便的过程。
• Design, development of new synthetic methodology, and biological evaluation of substituted quinolines as new anti-tubercular leads
  作者：Babita Tanwar、Asim Kumar、Perumal Yogeeswari、Dharmarajan Sriram、Asit K. Chakraborti

  DOI：10.1016/j.bmcl.2016.10.082

  日期：2016.12

  Two series of quinoline-based compounds were designed, synthesised and evaluated for anti-tubercular activity against Mycobacterium tuberculosis H(37)Rv (ATCC 27294 strain). A new method for Friedlander quinoline synthesis has been developed in water under the catalytic influence of the Bronsted acid surfactant DBSA. Among the forty-two compounds tested for anti-TB activity, twenty-three compounds exhibited significant activity against the growth of M. tuberculosis (MIC 0.02-6.25 mu g/mL). In particular, the compounds 3b and 3c displayed excellent anti-TB activity with MIC values of 0.2 and 0.39 mu g/mL, respectively, and are more potent than the standard drugs E, Cfx and Z that are clinically used to treat TB. The cytotoxicity of the compounds with MIC <= 6.25 mu g/mL was evaluated against Human Embryonic Kidney 293T cell lines and all of the active compounds were found to be nontoxic (<50% inhibition). The results suggest that the synthesised substituted quinolines are promising leads for development of new drug to treat TB. (C) 2016 Elsevier Ltd. All rights reserved.
• Copper(I)-catalysed amidation and successive oxidation of benzylic C(sp3)–H bond: synthesis of 1H-pyrrolo[3,4-b]quinoline-1,3(2H)-diones
  作者：Xiangqian Yan、Zhiguo Zhang、Guisheng Zhang、Nana Ma、Qingfeng Liu、Tongxin Liu、Lei Shi

  DOI：10.1016/j.tet.2016.05.059

  日期：2016.7

  An efficient copper(I)-catalysed intramolecular arylmethyl C(sp3)–H direct oxidative amidation reaction has been developed for the preparation of drug-like 1H-pyrrolo[3,4-b]quinoline-1,3(2H)-diones from readily available 2-methyl-3-carbamoyl-quinolines.

  开发了一种有效的铜（I）催化的分子内芳基甲基C（sp 3）–H直接氧化酰胺化反应，用于制备药物样的1 H-吡咯并[3,4- b ]喹啉-1,3（2 H）-二酮类化合物可从2-甲基-3-氨基甲酰基喹啉中轻松获得。