3-Methoxycarbonyl-2-nitro-bicyclo<2.2.1>hepten-(5) | 76954-18-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-Methoxycarbonyl-2-nitro-bicyclo<2.2.1>hepten-(5)
• 英文别名: methyl 3-exo-nitrobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate；(±)-2,3-trans-methyl 3-nitrobicyclo[2.2.1]hept-5-ene-2-carboxylate；methyl 3-exo-nitrobicyclo[2.2.1]hept-5-ene-2-endo-carboxylate
• CAS: 76954-18-2；76986-03-3；99094-79-8
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: GWUGMNRQLYMFJV-ULAWRXDQSA-N

物化性质

• 沸点：
  295.4±40.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  环戊二烯 、 1,4-dimethyl but-2-enedioate 以68%的产率得到
  参考文献：
  名称：

  Discovery of a Novel, First-in-Class, Orally Bioavailable Azaindole Inhibitor (VX-787) of Influenza PB2

  摘要：

  In our effort to develop agents for the treatment of influenza, a phenotypic screening approach utilizing a cell protection assay identified a series of azaindole based inhibitors of the cap-snatching function of the PB2 subunit of the influenza A viral polymerase complex. Using a bDNA viral replication assay (Wagaman, P. C.; Leong, M. A.; Simmen, K. A. Development of a novel influenza A antiviral assay. J. Virol. Methods 2002, 105, 105-114) in cells as a direct measure of antiviral activity, we discovered a set of cyclohexyl carboxylic acid analogues, highlighted by VX-787 (2). Compound 2 shows strong potency versus multiple influenza A strains, including pandemic 2009 H1N1 and avian H5N1 flu strains, and shows an efficacy profile in a mouse influenza model even when treatment was administered 48 h after infection. Compound 2 represents a first-in-class, orally bioavailable, novel compound that offers potential for the treatment of both pandemic and seasonal influenza and has a distinct advantage over the current standard of care treatments including potency, efficacy, and extended treatment window.

  DOI：

  10.1021/jm5007275

文献信息

• Highly constrained bicyclic VLA-4 antagonists
  作者：Linda L. Chang、Quang Truong、George A. Doss、Malcolm MacCoss、Kathryn Lyons、Ermengilda McCauley、Richard Mumford、Gail Forrest、Stella Vincent、John A. Schmidt、William K. Hagmann

  DOI：10.1016/j.bmcl.2006.11.011

  日期：2007.2

  VLA-4 is implicated in several inflammatory and autoimmune disease states. A series of cyclic P-amino acids (beta-aa) was studied as VLA-4 antagonists. Binding affinity was highly dependent on the dihedral angle (phi) between the amino and the carboxyl termini of the beta-aa. Compound 5m where the beta-aa is embedded in a bicycle possesses the most preferred phi (120 degrees). It is a potent and bioavailable VLA-4 antagonist (VCAM-Ig alpha 4 beta 1 IC50 = 54 nM, rat po F = 49%). (c) 2006 Elsevier Ltd. All rights reserved.
• Michael, Joseph P.; Blom, Norman F.; Glintenkamp, Lueta-Ann, Journal of the Chemical Society. Perkin transactions I, 1991, # 8, p. 1855 - 1862
  作者：Michael, Joseph P.、Blom, Norman F.、Glintenkamp, Lueta-Ann

  DOI：——

  日期：——