methyl 2-amino-7-<(2-hydroxyphenyl)thio>heptanoate | 124603-81-2

• 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: methyl 2-amino-7-<(2-hydroxyphenyl)thio>heptanoate
• CAS: 124603-81-2
• 化学式: C₁₄H₂₁NO₃S
• 分子量: 283.392
• InChiKey: OMEYVLZODUWECK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.55
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-amino-7-<(2-hydroxyphenyl)thio>heptanoate 在 间氯过氧苯甲酸 作用下， 反应 16.0h， 以76%的产率得到methyl 2-amino-7-<(2-hydroxyphenyl)sulfinyl>heptanoate
  参考文献：
  名称：

  A unified approach to systematic isosteric substitution for acidic groups and application to NMDA antagonists related to 2-amino-7-phosphonoheptanoate

  摘要：

  A systematic approach to the replacement of acidic groups with potential bioisosteres is described. The strategy involves simple nucleophilic displacement of a common alkyl halide precursor with a variety of mercaptoazoles and related molecules. The mercaptoazoles and their oxidized derivatives (sulfinyl- and sulfonylazoles) represent a series of possible surrogates for acidic groups which span a pKa range from about 4.5-11.5. This simple strategy was extended to include 2-hydroxy- or 2-aminothiophenyl groups which function as relatively nonacidic isosteres for a phosphonic acid. By replacing the phosphonic acid of 2-amino-7-phosphonoheptanoate (AP-7) with these groups, we have synthesized novel N-methyl-d-aspartate (NMDA) antagonists.

  DOI：

  10.1021/jm00165a030
• 作为产物：
  描述：

  2-羟基苯硫酚 在 盐酸 、 sodium hydride 作用下， 反应 21.25h， 生成 methyl 2-amino-7-<(2-hydroxyphenyl)thio>heptanoate
  参考文献：
  名称：

  A unified approach to systematic isosteric substitution for acidic groups and application to NMDA antagonists related to 2-amino-7-phosphonoheptanoate

  摘要：

  A systematic approach to the replacement of acidic groups with potential bioisosteres is described. The strategy involves simple nucleophilic displacement of a common alkyl halide precursor with a variety of mercaptoazoles and related molecules. The mercaptoazoles and their oxidized derivatives (sulfinyl- and sulfonylazoles) represent a series of possible surrogates for acidic groups which span a pKa range from about 4.5-11.5. This simple strategy was extended to include 2-hydroxy- or 2-aminothiophenyl groups which function as relatively nonacidic isosteres for a phosphonic acid. By replacing the phosphonic acid of 2-amino-7-phosphonoheptanoate (AP-7) with these groups, we have synthesized novel N-methyl-d-aspartate (NMDA) antagonists.

  DOI：

  10.1021/jm00165a030