N-(p-methylbenzoyl)-L-isoleucine | 1160565-44-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(p-methylbenzoyl)-L-isoleucine
• 英文别名: (2S,3S)-3-methyl-2-(4-methylbenzamido)pentanoic acid；(2S,3S)-3-methyl-2-[(4-methylbenzoyl)amino]pentanoic acid
• CAS: 1160565-44-5
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: OBFLRUJYNBSPOM-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二氯(1,10-亚铁试剂)钯(II) 、 N-(p-methylbenzoyl)-L-isoleucine 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 [palladium(II)(1,10-phenanthroline)(N-benzoyl-L-isoleucine)]
  参考文献：
  名称：

  Synthesis, characterization, and cytotoxicity of mixed-ligand complexes of palladium(II) with 1,10-phenanthroline and N-carbonyl-L-isoleucine dianion

  摘要：

  Three novel palladium(II) complexes [Pd(Phen)(Bzile)] (I), [Pd(Phen)(p-mBzile)] (II), and [Pd(Phen)(p-NBzile)] center dot H2O (III), where Bzile = N-benzoyl-L-isolecine), p-MBzile = N-(p-methylbenzoyl)-L-isolecine), p-NBzile = N-(p-nitrobenzoyl)-L-isolecine), have been synthesized and characterized by elemental analysis, ES-MS, and IR. The crystal and molecular structure of the complex II has been determined by single crystal X-ray diffraction. The cytotoxicity was tested against carcinoma cell lines: KB, BGC-823, Bel-7402 and HL-60 by MTT assay. The results indicated that these complexes exerted cytotoxicity, but none of them showed higher cytotoxicity than cisplatin. The cytotoxicity against HL-60, BGC-823, Bel-7402 and KB cell lines decreases in the sequence: p-MBzile > Bzile > p-NBzile. It suggests that the acylated groups have important impact on the cytotoxicity of complexes.

  DOI：

  10.1134/s1070328414020122
• 作为产物：
  描述：

  L-异亮氨酸 、 以 水 、 乙腈 为溶剂， 反应 1.0h， 以38 mg的产率得到N-(p-methylbenzoyl)-L-isoleucine
  参考文献：
  名称：

  N-2-硝基苯肼基溴衍生的腈亚胺重排形成酰胺键

  摘要：

  我们报告了如何利用源自N -2-硝基苯基肼基溴的高反应性腈亚胺的重排来轻松构建酰胺键。发现该酰胺化反应广泛适用于伯、仲和叔酰胺的合成，是合成降脂剂苯扎贝特的关键步骤。这种方法的正交性和官能团耐受性以未受保护的氨基酸的N-酰化为例。

  DOI：

  10.1021/acs.orglett.1c03993

文献信息

• Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from <i>N</i>-2-Nitrophenyl Hydrazonyl Bromides
  作者：Mhairi Boyle、Keith Livingstone、Martyn C. Henry、Jessica M. L. Elwood、J. Daniel Lopez-Fernandez、Craig Jamieson

  DOI：10.1021/acs.orglett.1c03993

  日期：2022.1.14

  rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance

  我们报告了如何利用源自N -2-硝基苯基肼基溴的高反应性腈亚胺的重排来轻松构建酰胺键。发现该酰胺化反应广泛适用于伯、仲和叔酰胺的合成，是合成降脂剂苯扎贝特的关键步骤。这种方法的正交性和官能团耐受性以未受保护的氨基酸的N-酰化为例。
• Synthesis, characterization, and cytotoxicity of mixed-ligand complexes of palladium(II) with 1,10-phenanthroline and N-carbonyl-L-isoleucine dianion
  作者：J. C. Zhang、L. W. Wang、S. Y. Liu、F. F. Zhang、J. L. Du、L. W. Li、S. X. Wang、S. H. Li、G. Q. Zhou

  DOI：10.1134/s1070328414020122

  日期：2014.2

  Three novel palladium(II) complexes [Pd(Phen)(Bzile)] (I), [Pd(Phen)(p-mBzile)] (II), and [Pd(Phen)(p-NBzile)] center dot H2O (III), where Bzile = N-benzoyl-L-isolecine), p-MBzile = N-(p-methylbenzoyl)-L-isolecine), p-NBzile = N-(p-nitrobenzoyl)-L-isolecine), have been synthesized and characterized by elemental analysis, ES-MS, and IR. The crystal and molecular structure of the complex II has been determined by single crystal X-ray diffraction. The cytotoxicity was tested against carcinoma cell lines: KB, BGC-823, Bel-7402 and HL-60 by MTT assay. The results indicated that these complexes exerted cytotoxicity, but none of them showed higher cytotoxicity than cisplatin. The cytotoxicity against HL-60, BGC-823, Bel-7402 and KB cell lines decreases in the sequence: p-MBzile > Bzile > p-NBzile. It suggests that the acylated groups have important impact on the cytotoxicity of complexes.