4-({5-[(4-methylphenyl)ethynyl]-2-furoyl}amino)butanoic acid | 223465-86-9

• 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: 4-({5-[(4-methylphenyl)ethynyl]-2-furoyl}amino)butanoic acid
• 英文别名: 4-[[5-[2-(4-Methylphenyl)ethynyl]furan-2-carbonyl]amino]butanoic acid
• CAS: 223465-86-9
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: YCRQYHUVWWOTEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  79.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-({5-[(4-methylphenyl)ethynyl]-2-furoyl}amino)butanoic acid 在 盐酸 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-p-Tolylethynyl-furan-2-carboxylic acid (3-hydroxycarbamoyl-propyl)-amide
  参考文献：
  名称：

  Novel matrix metalloproteinase inhibitors: Generation of lead compounds by the in silico fragment-based approach

  摘要：

  Generation of structurally new matrix metalloproteinase inhibitors was successfully carried out using an in silico technique. In order to identify the small fragment interacting with residues in the S1' pocket of MMP-1 through hydrogen bonds, we performed in silico screening using the LUDI program. As a result, acetyl-L-alanyl-(N-methyl)amide (AC-L-Ala-NHMe) was selected to link with another fragment, hydroxamic acid that interacted with catalytic zinc. By this approach, the L-glutamic acid derivative 2b was discovered to be a new type of matrix metalloproteinase inhibitor. Further transformation to reduce its peptidic nature and improve activity yielded nonpeptidic lead compounds as inhibitors of MMP-1, -2, -3, and -9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.051
• 作为产物：
  描述：

  ethyl 4-({5-[(4-methylphenyl)ethynyl]-2-furoyl}amino)butanoate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到4-({5-[(4-methylphenyl)ethynyl]-2-furoyl}amino)butanoic acid
  参考文献：
  名称：

  Novel matrix metalloproteinase inhibitors: Generation of lead compounds by the in silico fragment-based approach

  摘要：

  Generation of structurally new matrix metalloproteinase inhibitors was successfully carried out using an in silico technique. In order to identify the small fragment interacting with residues in the S1' pocket of MMP-1 through hydrogen bonds, we performed in silico screening using the LUDI program. As a result, acetyl-L-alanyl-(N-methyl)amide (AC-L-Ala-NHMe) was selected to link with another fragment, hydroxamic acid that interacted with catalytic zinc. By this approach, the L-glutamic acid derivative 2b was discovered to be a new type of matrix metalloproteinase inhibitor. Further transformation to reduce its peptidic nature and improve activity yielded nonpeptidic lead compounds as inhibitors of MMP-1, -2, -3, and -9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.051

文献信息

• Novel matrix metalloproteinase inhibitors: Generation of lead compounds by the in silico fragment-based approach
  作者：Kanji Takahashi、Masahiro Ikura、Hiromu Habashita、Minoru Nishizaki、Tsuneyuki Sugiura、Shingo Yamamoto、Shingo Nakatani、Koji Ogawa、Hiroyuki Ohno、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2005.04.051

  日期：2005.7

  Generation of structurally new matrix metalloproteinase inhibitors was successfully carried out using an in silico technique. In order to identify the small fragment interacting with residues in the S1' pocket of MMP-1 through hydrogen bonds, we performed in silico screening using the LUDI program. As a result, acetyl-L-alanyl-(N-methyl)amide (AC-L-Ala-NHMe) was selected to link with another fragment, hydroxamic acid that interacted with catalytic zinc. By this approach, the L-glutamic acid derivative 2b was discovered to be a new type of matrix metalloproteinase inhibitor. Further transformation to reduce its peptidic nature and improve activity yielded nonpeptidic lead compounds as inhibitors of MMP-1, -2, -3, and -9. (c) 2005 Elsevier Ltd. All rights reserved.