(R)-methyl 4-(1-azidoethyl)benzoate | 885105-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-methyl 4-(1-azidoethyl)benzoate
• 英文别名: Methyl 4-[(1R)-1-azidoethyl]benzoate
• CAS: 885105-34-0
• 化学式: C₁₀H₁₁N₃O₂
• 分子量: 205.216
• InChiKey: PNYJDKRGKXPKRX-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-methyl 4-(1-azidoethyl)benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到4-[(1R)-1-氨基乙基]-苯甲醇
  参考文献：
  名称：

  Identification of a Nonpeptidic and Conformationally Restricted Bradykinin B1 Receptor Antagonist with Anti-Inflammatory Activity

  摘要：

  We report the discovery of chroman 28, a potent and selective antagonist of human, nonhuman primate, rat, and rabbit bradykinin B1 receptors (0.4-17 nM). At 90 mg/kg s.c., 28 decreased plasma extravasation in two rodent models of inflammation. A novel method to calculate entropy is introduced and ascribed similar to 30% of the gained affinity between "flexible" 4 (K-i = 132 nM) and "rigid" 28 (K-i = 0.77 nM) to decreased conformational entropy.

  DOI：

  10.1021/jm061224g
• 作为产物：
  描述：

  4-乙酰基苯甲酸甲酯 在 dimethyl sulfide borane 、 二苯基膦叠氮化物 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.58h， 生成 (R)-methyl 4-(1-azidoethyl)benzoate
  参考文献：
  名称：

  Identification of a Nonpeptidic and Conformationally Restricted Bradykinin B1 Receptor Antagonist with Anti-Inflammatory Activity

  摘要：

  We report the discovery of chroman 28, a potent and selective antagonist of human, nonhuman primate, rat, and rabbit bradykinin B1 receptors (0.4-17 nM). At 90 mg/kg s.c., 28 decreased plasma extravasation in two rodent models of inflammation. A novel method to calculate entropy is introduced and ascribed similar to 30% of the gained affinity between "flexible" 4 (K-i = 132 nM) and "rigid" 28 (K-i = 0.77 nM) to decreased conformational entropy.

  DOI：

  10.1021/jm061224g

文献信息

• Triazoles and methods of use
  申请人：Aya Toshihiro

  公开号：US20060100213A1

  公开（公告）日：2006-05-11

  Selected compounds are effective for treatment of pain and diseases, such as inflammation mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable derivatives thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving pain, inflammation, and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  选定的化合物对于治疗疼痛和疾病，例如炎症介导性疾病具有有效性。本发明涵盖了新型化合物、类似物、前药和其药学上可接受的衍生物、制药组合物以及预防和治疗涉及疼痛、炎症等疾病和其他疾病或病况的方法。本发明还涉及制备这种化合物的过程以及在这种过程中有用的中间体。
• WO2006/44355
  申请人：——

  公开号：——

  公开（公告）日：——
• US7612060B2
  申请人：——

  公开号：US7612060B2

  公开（公告）日：2009-11-03
• Identification of a Nonpeptidic and Conformationally Restricted Bradykinin B1 Receptor Antagonist with Anti-Inflammatory Activity
  作者：Derin C. D'Amico、Toshi Aya、Jason Human、Christopher Fotsch、Jian Jeffrey Chen、Kaustav Biswas、Bobby Riahi、Mark H. Norman、Christopher A. Willoughby、Randall Hungate、Paul J. Reider、Gloria Biddlecome、Dianna Lester-Zeiner、Carlo Van Staden、Eileen Johnson、Augustus Kamassah、Leyla Arik、Judy Wang、Vellarkad N. Viswanadhan、Robert D. Groneberg、James Zhan、Hideo Suzuki、Andras Toro、David A. Mareska、David E. Clarke、Darren M. Harvey、Laurence E. Burgess、Ellen R. Laird、Benny Askew、Gordon Ng

  DOI：10.1021/jm061224g

  日期：2007.2.1

  We report the discovery of chroman 28, a potent and selective antagonist of human, nonhuman primate, rat, and rabbit bradykinin B1 receptors (0.4-17 nM). At 90 mg/kg s.c., 28 decreased plasma extravasation in two rodent models of inflammation. A novel method to calculate entropy is introduced and ascribed similar to 30% of the gained affinity between "flexible" 4 (K-i = 132 nM) and "rigid" 28 (K-i = 0.77 nM) to decreased conformational entropy.