3-(4-chlorophenyl)-2-cyano-5-oxo-5-phenyl-N-phenylpentanamide | 896720-63-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3-(4-chlorophenyl)-2-cyano-5-oxo-5-phenyl-N-phenylpentanamide
• 英文别名: 3-(4-chlorophenyl)-2-cyano-5-oxo-N,5-diphenylpentanamide
• CAS: 896720-63-1
• 化学式: C₂₄H₁₉ClN₂O₂
• 分子量: 402.88
• InChiKey: KIIBAGMBUNSBLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-2-cyano-5-oxo-5-phenyl-N-phenylpentanamide 在 溴 、 溶剂黄146 作用下， 反应 3.0h， 以82%的产率得到2-bromo-4-(4-chlorophenyl)-6-phenyl-N-phenyl-3-pyridinecarboxamide
  参考文献：
  名称：

  Novel synthesis of nicotinamide derivatives of cytotoxic properties

  摘要：

  A variety of 2-substituted-4,6-diaryl-3-pyridinecarboxamides 5 were synthesized through aromatic nucleophilic substitution reaction of secondary amines with 2-bromo analogues 4. The latter were obtained via bromination of 2-cyano-3,5-diaryl-5-oxo-N-substituted pentamides 3 in glacial acetic acid. Moreover, pentamide derivatives 3 were prepared through base-catalyzed Michael addition of cyanacetanilides 2 with 1,3-diaryl-2-propen-l-ones 1. Otherwise, reaction of 2-bromo-3-pyridinecarboxamides 4 with primary aromatic amines in refluxing pyridine afforded the corresponding 2-(arylamino)-3-pyridinecarboxamides 6 besides the unexpected 2-unsubstituted amino analogues 7. Antitumor properties of the synthesized pyridinecarboxamides utilizing 59 different human tumor cell lines, representing leukemia, melanoma, and cancers of the lung, colon, brain, ovary, breast, prostate as well as kidney, were screened. Many of the tested compounds show considerable in vitro antitumor properties especially 5c and 7a, which reveal moderate activities against most of the used human tumor cell lines. It has also been achieved that, all the tested nicotinamide derivatives reveal promising antitumor properties against MDA-MB-231/ATCC (breast cancer). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.031
• 作为产物：
  描述：

  2-氰基乙酰苯胺 、 (E)-beta-(4-氯苯基)丙烯酰苯 在 吗啉 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以80%的产率得到3-(4-chlorophenyl)-2-cyano-5-oxo-5-phenyl-N-phenylpentanamide
  参考文献：
  名称：

  Novel synthesis of nicotinamide derivatives of cytotoxic properties

  摘要：

  A variety of 2-substituted-4,6-diaryl-3-pyridinecarboxamides 5 were synthesized through aromatic nucleophilic substitution reaction of secondary amines with 2-bromo analogues 4. The latter were obtained via bromination of 2-cyano-3,5-diaryl-5-oxo-N-substituted pentamides 3 in glacial acetic acid. Moreover, pentamide derivatives 3 were prepared through base-catalyzed Michael addition of cyanacetanilides 2 with 1,3-diaryl-2-propen-l-ones 1. Otherwise, reaction of 2-bromo-3-pyridinecarboxamides 4 with primary aromatic amines in refluxing pyridine afforded the corresponding 2-(arylamino)-3-pyridinecarboxamides 6 besides the unexpected 2-unsubstituted amino analogues 7. Antitumor properties of the synthesized pyridinecarboxamides utilizing 59 different human tumor cell lines, representing leukemia, melanoma, and cancers of the lung, colon, brain, ovary, breast, prostate as well as kidney, were screened. Many of the tested compounds show considerable in vitro antitumor properties especially 5c and 7a, which reveal moderate activities against most of the used human tumor cell lines. It has also been achieved that, all the tested nicotinamide derivatives reveal promising antitumor properties against MDA-MB-231/ATCC (breast cancer). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.031

文献信息

• Unusual michael reaction of 3-(4-Chlorophenyl)-1-phenylprop-2-en-1-one with 3-amino-N-phenyl-3-thioxopropanamide
  作者：V. D. Dyachenko、D. A. Krasnikov

  DOI：10.1134/s1070428012070111

  日期：2012.7

  3-(4-Chlorophenyl)-1-phenylprop-2-en-1-one reacted with 3-amino-N-phenyl-3-thioxopropanamide under basic conditions in ethanol to give a mixture of 3-(4-chlorophenyl)-2-cyano-5-oxo-N,5-diphenylpentanamide and 3-(4-chlorophenyl)-1,5-diphenylpentane-1,5-dione. The structure of the former was determined by X-ray analysis. The reaction of the same compounds in DMSO in the presence of sodium hydroxide produced 4-(4-chlorophenyl)-N,6-diphenyl-2-thioxo-1,2,3,4-tetrahydropyridine-3-carboxamide.