N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocycloprop[f]isoindol-2(1H)-yl)-4-nitrobenzamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocycloprop[f]isoindol-2(1H)-yl)-4-nitrobenzamide
• 英文别名: N-[(1S,2S,6R,7R,8R,10S)-3,5-dioxo-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-en-4-yl]-4-nitrobenzamide
• 化学式: C₁₈H₁₅N₃O₅
• 分子量: 353.334
• InChiKey: AGTXHHZRNMTLHL-VWLPUNTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环庚三烯 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 4.5h， 生成 N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocycloprop[f]isoindol-2(1H)-yl)-4-nitrobenzamide
  参考文献：
  名称：

  N-(3,3a,4,4a,5,5a,6,6a-Octahydro-1,3-dioxo-4,6- ethenocycloprop[f]isoindol-2-(1H)-yl)carboxamides:  Identification of Novel Orthopoxvirus Egress Inhibitors

  摘要：

  A series of novel, potent orthopoxvirus egress inhibitors was identified during high-throughput screening of the ViroPharma small molecule collection. Using structure-activity relationship information inferred from early hits, several compounds were synthesized, and compound 14 was identified as a potent, orally bioavailable first-in-class inhibitor of orthopoxvirus egress from infected cells. Compound 14 has shown comparable efficaciousness in three murine orthopoxvirus models and has entered Phase I clinical trials.

  DOI：

  10.1021/jm061484y

文献信息

• <i>N</i>-(3,3a,4,4a,5,5a,6,6a-Octahydro-1,3-dioxo-4,6- ethenocycloprop[f]isoindol-2-(1<i>H</i>)-yl)carboxamides:  Identification of Novel Orthopoxvirus Egress Inhibitors
  作者：Thomas R. Bailey、Susan R. Rippin、Elizabeth Opsitnick、Christopher J. Burns、Daniel C. Pevear、Marc S. Collett、Gerry Rhodes、Sanjeev Tohan、John W. Huggins、Robert O. Baker、Earl R. Kern、Kathy A. Keith、Dongcheng Dai、Guang Yang、Dennis Hruby、Robert Jordan

  DOI：10.1021/jm061484y

  日期：2007.4.1

  A series of novel, potent orthopoxvirus egress inhibitors was identified during high-throughput screening of the ViroPharma small molecule collection. Using structure-activity relationship information inferred from early hits, several compounds were synthesized, and compound 14 was identified as a potent, orally bioavailable first-in-class inhibitor of orthopoxvirus egress from infected cells. Compound 14 has shown comparable efficaciousness in three murine orthopoxvirus models and has entered Phase I clinical trials.