methyl 4-<2-<5-<<(cyclopentyloxy)carbonyl>amino>-2-(methylamino)phenyl>-2-oxoethyl>-3-methoxybenzoate | 127973-92-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 4-<2-<5-<<(cyclopentyloxy)carbonyl>amino>-2-(methylamino)phenyl>-2-oxoethyl>-3-methoxybenzoate
• 英文别名: methyl 4-[2-[5-(cyclopentyloxycarbonylamino)-2-(methylamino)phenyl]-2-oxoethyl]-3-methoxybenzoate
• CAS: 127973-92-6
• 化学式: C₂₄H₂₈N₂O₆
• 分子量: 440.496
• InChiKey: XMLWNIXAMAPMLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-<2-<5-<<(cyclopentyloxy)carbonyl>amino>-2-(methylamino)phenyl>-2-oxoethyl>-3-methoxybenzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以62%的产率得到4-<2-<5-<<(cyclopentyloxy)carbonyl>amino>-2-(methylamino)phenyl>-2-oxoethyl>-3-methoxybenzoic acid
  参考文献：
  名称：

  Synthesis and in vitro LTD4 antagonist activity of bicyclic and monocyclic cyclopentylurethane and cyclopentylacetamide N-arylsulfonyl amides

  摘要：

  The dissociation constants (KB) at the LTD4 receptor on guinea pig trachea of a series of monocyclic and bicyclic cyclopentylurethane and cyclopentylacetamide N-arylsulfonyl amides have been measured. The KB was found to be remarkably tolerant of changes in the electronic constitution and lipophilicity of the bicyclic ring system (template). Thus, N-[4[[6-[[(cyclopentyloxy)carbonyl]amino]benzimidazol-1- yl]methyl]-3-methoxybenzoyl]benzenesulfonamide (11a) and N-[4-[[5-[[(cyclopentyloxy)carbonyl]amino]benzo[b]thien-3- yl]methyl]-3-methoxybenzoyl]benzene-sulfonamide (25a) had closely similar affinities (pKB, 9.20 and 9.31, respectively; LTE4 as agonist). It has been shown that the hetero-ring of the template need not be aromatic in order to achieve high affinity, since indoline 31 and 2,3-dihydrobenz-1,4-oxazines 37a-c had pKBs greater than 9. Further, it has been shown that an o-aminophenone (see 42 and Figure 3) can function as a template; the template in 42 [see iii] is bicyclic by virtue of the presence of an intramolecular hydrogen bond. In contrast, when the template is a phenyl ring (48), receptor affinity is markedly reduced. These findings support the notion that central bicyclic ring system in this family of peptidoleukotriene antagonists is a molecular feature which helps to preorganize the acylamino and acidic chains and thereby facilitate the molecular recognition event.

  DOI：

  10.1021/jm00171a043
• 作为产物：
  描述：

  methyl 4-<2-<5-<<(cyclopentyloxy)carbonyl>amino>-2-(N-formyl-N-methylamino)phenyl>-2-oxoethyl>-3-methoxybenzoate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 80.0h， 以64%的产率得到methyl 4-<2-<5-<<(cyclopentyloxy)carbonyl>amino>-2-(methylamino)phenyl>-2-oxoethyl>-3-methoxybenzoate
  参考文献：
  名称：

  Synthesis and in vitro LTD4 antagonist activity of bicyclic and monocyclic cyclopentylurethane and cyclopentylacetamide N-arylsulfonyl amides

  摘要：

  The dissociation constants (KB) at the LTD4 receptor on guinea pig trachea of a series of monocyclic and bicyclic cyclopentylurethane and cyclopentylacetamide N-arylsulfonyl amides have been measured. The KB was found to be remarkably tolerant of changes in the electronic constitution and lipophilicity of the bicyclic ring system (template). Thus, N-[4[[6-[[(cyclopentyloxy)carbonyl]amino]benzimidazol-1- yl]methyl]-3-methoxybenzoyl]benzenesulfonamide (11a) and N-[4-[[5-[[(cyclopentyloxy)carbonyl]amino]benzo[b]thien-3- yl]methyl]-3-methoxybenzoyl]benzene-sulfonamide (25a) had closely similar affinities (pKB, 9.20 and 9.31, respectively; LTE4 as agonist). It has been shown that the hetero-ring of the template need not be aromatic in order to achieve high affinity, since indoline 31 and 2,3-dihydrobenz-1,4-oxazines 37a-c had pKBs greater than 9. Further, it has been shown that an o-aminophenone (see 42 and Figure 3) can function as a template; the template in 42 [see iii] is bicyclic by virtue of the presence of an intramolecular hydrogen bond. In contrast, when the template is a phenyl ring (48), receptor affinity is markedly reduced. These findings support the notion that central bicyclic ring system in this family of peptidoleukotriene antagonists is a molecular feature which helps to preorganize the acylamino and acidic chains and thereby facilitate the molecular recognition event.

  DOI：

  10.1021/jm00171a043

文献信息

• MATASSA, VICTOR G.;BROWN, FREDERICK J.;BERNSTEIN, PETER R.;SHAPIRO, HOWAR+, J. MED. CHEM., 33,(1990) N, C. 2621-2629
  作者：MATASSA, VICTOR G.、BROWN, FREDERICK J.、BERNSTEIN, PETER R.、SHAPIRO, HOWAR+

  DOI：——

  日期：——