(5-Bromo-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-benzo[4,5]thieno[2,3-c]pyran-1-yl)-acetic acid ethyl ester | 873922-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (5-Bromo-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-benzo[4,5]thieno[2,3-c]pyran-1-yl)-acetic acid ethyl ester
• CAS: 873922-30-6
• 化学式: C₁₉H₂₂BrFO₃S
• 分子量: 429.35
• InChiKey: MWWYEKPWKDECAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (5-Bromo-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-benzo[4,5]thieno[2,3-c]pyran-1-yl)-acetic acid ethyl ester 在 N-甲基吡咯烷酮 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.25h， 生成 [(1R)-5-cyano-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-[1]benzothieno[2,3-c]pyran-1-yl]acetic acid
  参考文献：
  名称：

  Design and synthesis of 3,4-dihydro-1H-[1]-benzothieno[2,3-c]pyran and 3,4-dihydro-1H-pyrano[3,4-b]benzofuran derivatives as non-nucleoside inhibitors of HCV NS5B RNA dependent RNA polymerase

  摘要：

  A novel class of HCV NS513 RNA dependent RNA polymerase inhibitors containing 3,4-dihydro-1H-[1]-benzothieno[2,3-c]pyran and 3,4-dihydro-1H-pyrano[3,4-b]benzofuran scaffolds were designed and synthesized. Optimization of the alkyl substituent in the pyran ring showed preference for an n-propyl group, while 5,8-disubstitution pattern is preferred for the aromatic region. Analog 19 displayed potent activity with an IC50 of 50 nM against HCV NS513 enzyme and was selective over a panel of polymerases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.114
• 作为产物：
  描述：

  4-Bromo-5-fluoro-7-methyl-benzo[b]thiophen-3-one 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (5-Bromo-6-fluoro-8-methyl-1-propyl-3,4-dihydro-1H-benzo[4,5]thieno[2,3-c]pyran-1-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Design and synthesis of 3,4-dihydro-1H-[1]-benzothieno[2,3-c]pyran and 3,4-dihydro-1H-pyrano[3,4-b]benzofuran derivatives as non-nucleoside inhibitors of HCV NS5B RNA dependent RNA polymerase

  摘要：

  A novel class of HCV NS513 RNA dependent RNA polymerase inhibitors containing 3,4-dihydro-1H-[1]-benzothieno[2,3-c]pyran and 3,4-dihydro-1H-pyrano[3,4-b]benzofuran scaffolds were designed and synthesized. Optimization of the alkyl substituent in the pyran ring showed preference for an n-propyl group, while 5,8-disubstitution pattern is preferred for the aromatic region. Analog 19 displayed potent activity with an IC50 of 50 nM against HCV NS513 enzyme and was selective over a panel of polymerases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.114