methyl (3R,6R)-6-<(acethylthio)methyl>-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate | 150198-31-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: methyl (3R,6R)-6-<(acethylthio)methyl>-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate
• 英文别名: methyl (3R,6R)-6-[(acethylthio)methyl]-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate
• CAS: 150198-31-5
• 化学式: C₁₆H₂₇NO₄S₂
• 分子量: 361.527
• InChiKey: OZOQBEKEUGBDSV-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (3R,6R)-6-<(acethylthio)methyl>-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以93%的产率得到(3R,6R)-6-(mercaptomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid
  参考文献：
  名称：

  Heterocyclic lactam derivatives as dual angiotensin converting enzyme and neutral endopeptidase 24.11 inhibitors

  摘要：

  A series of 13- and 14-membered ring lactam derivatives 9a,b, 10, 11, and 12a-c was prepared from L-cysteine. Compounds 9a,b and 12a,b were tested in vitro for inhibition of neutral endopeptidase 24.11 (NEP) and angiotensin converting enzyme (ACE) inhibition. The structure-activity profile of the series is discussed. Compound 9b, a 13-membered ring macrocyclic lactam, had an NEP IC50 Of 18 nM and an ACE IC50 of 12 nM in vitro and showed dual plasma inhibition after intravenous or oral administration.

  DOI：

  10.1021/jm00076a010
• 作为产物：
  描述：

  dimethyl (2R)-2-amino-12-carboxy-4-thia-1,13-tridecanedicarboxylate hydrochloride 在 哌啶 、 吡啶 、 sodium hydroxide 、 五氟苯酚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl (3R,6R)-6-<(acethylthio)methyl>-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate
  参考文献：
  名称：

  Heterocyclic lactam derivatives as dual angiotensin converting enzyme and neutral endopeptidase 24.11 inhibitors

  摘要：

  A series of 13- and 14-membered ring lactam derivatives 9a,b, 10, 11, and 12a-c was prepared from L-cysteine. Compounds 9a,b and 12a,b were tested in vitro for inhibition of neutral endopeptidase 24.11 (NEP) and angiotensin converting enzyme (ACE) inhibition. The structure-activity profile of the series is discussed. Compound 9b, a 13-membered ring macrocyclic lactam, had an NEP IC50 Of 18 nM and an ACE IC50 of 12 nM in vitro and showed dual plasma inhibition after intravenous or oral administration.

  DOI：

  10.1021/jm00076a010