N-(3-cyano-4,5,6,7,8,9-hexahydrocycloocta[b]thiophen-2-yl)-2-(2-imino-4-oxo-1,3-thiazolidin-5-yl)acetamide | 665023-96-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(3-cyano-4,5,6,7,8,9-hexahydrocycloocta[b]thiophen-2-yl)-2-(2-imino-4-oxo-1,3-thiazolidin-5-yl)acetamide
• CAS: 665023-96-1
• 化学式: C₁₆H₁₈N₄O₂S₂
• 分子量: 362.477
• InChiKey: UHGFFXIIDPVSJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-cyano-4,5,6,7,8,9-hexahydrocycloocta[b]thiophen-2-yl)-2-(2-imino-4-oxo-1,3-thiazolidin-5-yl)acetamide 在 CHIRALPAK IA column 作用下， 以 乙醇 、 正己烷 为溶剂， 生成 2-[(5S)-2-amino-4-oxo-1,3-thiazol-5-yl]-N-(3-cyano-4,5,6,7,8,9-hexahydrocycloocta[b]thiophen-2-yl)acetamide 、 2-[(5R)-2-amino-4-oxo-1,3-thiazol-5-yl]-N-(3-cyano-4,5,6,7,8,9-hexahydrocycloocta[b]thiophen-2-yl)acetamide
  参考文献：
  名称：

  Virtual ligand screening of α-glucosidase: Identification of a novel potent noncarbohydrate mimetic inhibitor

  摘要：

  5-Thiazoleacetamide derivatives of AR122 and AR125 were screened as alpha-glucosidase inhibitors by in silico high-throughput screening from commercial drug-like small compound libraries. Inhibition of alpha-glucosidase with AR122 and AR125 is time dependent: with no preincubation, AR122 and AR125 are relatively moderate inhibitors, but interestingly, after a 120 min incubation, they were 50-fold more potent (AR122: IC50 = 2.47 mu M and AR125: IC50 = 27.1 mu M). Plots of ln [residual alpha-glucosidase activity %] versus preincubation time show a pseudo-first order kinetics for both inhibitors. Through dialysis of enzyme-inhibitor complexes, no activity recovery was shown. These results suggest that AR122 and AR125 constitute a new class of noncarbohydrate mimetic inhibitor with an irreversible mechanism. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.084