(E)-S-methyl 5-(1-(3,7-dimethyl-2-oxo-2,3-dihydrobenz[d]oxazol-5-yl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)pent-1-enyl)-2-methoxy-3-methylbenzothioate | 1034197-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: (E)-S-methyl 5-(1-(3,7-dimethyl-2-oxo-2,3-dihydrobenz[d]oxazol-5-yl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)pent-1-enyl)-2-methoxy-3-methylbenzothioate
• 英文别名: (E)-S-methyl 5-(1-(3,7-dimethyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)pent-1-enyl)-2-methoxy-3-methylbenzothioate；S-methyl 5-[(E)-1-(3,7-dimethyl-2-oxo-1,3-benzoxazol-5-yl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)pent-1-enyl]-2-methoxy-3-methylbenzenecarbothioate
• CAS: 1034197-06-2
• 化学式: C₂₇H₂₉N₃O₅S
• 分子量: 507.61
• InChiKey: OIXOQSQILWVOGS-AWQFTUOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-iodo-3,7-dimethyl-3H-benzoxazol-2-one 、 S-methyl 2-methoxy-3-methyl-5-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-tributylstannylpent-1-enyl]benzenecarbothioate 在 copper(l) iodide 、 四(三苯基膦)钯 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以4%的产率得到(E)-S-methyl 5-(1-(3,7-dimethyl-2-oxo-2,3-dihydrobenz[d]oxazol-5-yl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)pent-1-enyl)-2-methoxy-3-methylbenzothioate
  参考文献：
  名称：

  Crystallographic Study of a Novel Subnanomolar Inhibitor Provides Insight on the Binding Interactions of Alkenyldiarylmethanes with Human Immunodeficiency Virus-1 Reverse Transcriptase

  摘要：

  Two crystal structures have been solved for separate complexes of alkenyldiarylmethane (ADAM) nonnucleoside reverse transcriptase inhibitors (NNRTI) 3 and 4 with HIV-1 reverse transcriptase (RT). The structures reveal inhibitor binding is exclusively hydrophobic in nature and the shape of the inhibitor-bound NNRTI binding pocket is unique among other reported inhibitor-RT crystal structures. Primarily, ADAMs 3 and 4 protrude from a large gap in the back side of the binding pocket, placing portions of the inhibitors unusually close to the polymerase active site and allowing 3 to form a weak hydrogen bond with Lys223. The lack of additional stabilizing interactions, beyond the observed hydrophobic surface contacts, between 4 and RT is quite perplexing given the extreme potency of the compound (IC50 <= 1 nM). ADAM 4 was designed to be hydrolytically stable in blood plasma, and an investigation of its hydrolysis in rat plasma demonstrated it has a significantly prolonged half-life in comparison to ADAM lead compounds 1 and 2.

  DOI：

  10.1021/jm901167t