3-(R)-[((2S)-2-(2-phenyl-1H-indol-3-yl)-1-methylcarbamoyl)-ethylcarbamoyl]-5-methyl hexanoic acid | 1078156-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(R)-[((2S)-2-(2-phenyl-1H-indol-3-yl)-1-methylcarbamoyl)-ethylcarbamoyl]-5-methyl hexanoic acid
• CAS: 1078156-38-3
• 化学式: C₂₆H₃₁N₃O₄
• 分子量: 449.55
• InChiKey: PKCFIJOYZBUOHX-GCJKJVERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  111.29
• 氢给体数：
  4.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(4-bromophenyl)benzenesulfonylhydrazine hydrochloride 、 3-(R)-[((2S)-2-(2-phenyl-1H-indol-3-yl)-1-methylcarbamoyl)-ethylcarbamoyl]-5-methyl hexanoic acid 在 N-甲基吗啉 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以35%的产率得到N'-{3-(R)-[(2S)-2-(2-phenyl-1H-indol-3-yl)-1-(methylcarbamoyl)-ethylcarbamoyl]-5-methyl hexanoyl}-N-4-(4-bromophenyl)benzenesulfonylhydrazide
  参考文献：
  名称：

  Introduction of the 4-(4-bromophenyl)benzenesulfonyl group to hydrazide analogs of Ilomastat leads to potent gelatinase B (MMP-9) inhibitors with improved selectivity

  摘要：

  Hydrazide derivatives of Ilomastat, carrying either aryl groups or distinct alkyl and arylsulfonyl moieties were synthesized and evaluated for their MMP inhibitory activity. Potent and selective MMP-9 inhibition (IC50 = 3 nM) was observed for compound 3m (arylsulfonyl group: 4-(4-Br-C6H4)-C6H4-SO2-). Interaction with the S-2 enzyme subsite is mainly responsible for the inhibitory properties of this derivative as confirmed by molecular docking computation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.041
• 作为产物：
  描述：

  3-(R)-[((2S)-2-(2-phenyl-1H-indol-3-yl)-1-methylcarbamoyl)-ethylcarbamoyl]-5-methyl tert-butylhexanoate 在 三氟乙酸 、 1,4-二巯基-2,3-丁二醇 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以64%的产率得到3-(R)-[((2S)-2-(2-phenyl-1H-indol-3-yl)-1-methylcarbamoyl)-ethylcarbamoyl]-5-methyl hexanoic acid
  参考文献：
  名称：

  Introduction of the 4-(4-bromophenyl)benzenesulfonyl group to hydrazide analogs of Ilomastat leads to potent gelatinase B (MMP-9) inhibitors with improved selectivity

  摘要：

  Hydrazide derivatives of Ilomastat, carrying either aryl groups or distinct alkyl and arylsulfonyl moieties were synthesized and evaluated for their MMP inhibitory activity. Potent and selective MMP-9 inhibition (IC50 = 3 nM) was observed for compound 3m (arylsulfonyl group: 4-(4-Br-C6H4)-C6H4-SO2-). Interaction with the S-2 enzyme subsite is mainly responsible for the inhibitory properties of this derivative as confirmed by molecular docking computation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.041