8-ethoxycarbonyl-3-phenyl-8-azabicyclo[3.2.1]oct-2-ene | 861853-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 8-ethoxycarbonyl-3-phenyl-8-azabicyclo[3.2.1]oct-2-ene
• 英文别名: Ethyl 3-phenyl-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate
• CAS: 861853-59-0
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: PQZZXMJOKXYTSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-ethoxycarbonyl-3-phenyl-8-azabicyclo[3.2.1]oct-2-ene 在 一水合肼 、 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 3.0h， 以29%的产率得到3-phenyl-2-nortropene
  参考文献：
  名称：

  Synthesis and monoamine transporter affinity of 3α-arylmethoxy-3β-arylnortropanes

  摘要：

  A series of 3-arylnortrop-2-enes and 3 alpha-arylmethoxy-3 beta-arylnortropanes were synthesized and evaluated for binding affinity at monoamine transporters. The 3-(3,4-dichlorophenyl)nortrop-2-ene (6e) exhibited high affinity for the SERT (K-i = 0.3 nM). The 3 alpha-arylmethoxy-3 beta-arylnortropanes were generally SERT selective with the 3 alpha-(3,4-dichlorophenylmethoxy)-3 beta phenylnortrop-2-ene (7c) possessing subnanomolar potency (K-i = 0.061 nM). However, 3 alpha-(3,4-dichlorophenylmethoxy)-3 beta-phenylnortrop-2-ene (7b) exhibited high affinity at all three transporters [(DAT K-i = 22 nM), (SERT K-i = 6 nM) and (NET K-i = 101 nM)]. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.087
• 作为产物：
  描述：

  8-ethoxycarbonyl-3α-hydroxy-3-β-phenyl-8-azabicyclo[3.2.1]octane 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以68%的产率得到8-ethoxycarbonyl-3-phenyl-8-azabicyclo[3.2.1]oct-2-ene
  参考文献：
  名称：

  Synthesis and monoamine transporter affinity of 3α-arylmethoxy-3β-arylnortropanes

  摘要：

  A series of 3-arylnortrop-2-enes and 3 alpha-arylmethoxy-3 beta-arylnortropanes were synthesized and evaluated for binding affinity at monoamine transporters. The 3-(3,4-dichlorophenyl)nortrop-2-ene (6e) exhibited high affinity for the SERT (K-i = 0.3 nM). The 3 alpha-arylmethoxy-3 beta-arylnortropanes were generally SERT selective with the 3 alpha-(3,4-dichlorophenylmethoxy)-3 beta phenylnortrop-2-ene (7c) possessing subnanomolar potency (K-i = 0.061 nM). However, 3 alpha-(3,4-dichlorophenylmethoxy)-3 beta-phenylnortrop-2-ene (7b) exhibited high affinity at all three transporters [(DAT K-i = 22 nM), (SERT K-i = 6 nM) and (NET K-i = 101 nM)]. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.087

文献信息

• 2,6-Disubstituted piperiddines as modulators
  申请人：Yang Lihu

  公开号：US20070179158A1

  公开（公告）日：2007-08-02

  The present invention is further directed to compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 and R 22 are as defined herein) which are modulators of chemokine receptor activity and are useful in the prevention or treatment of certain inflammatory and immunoregulatory disorders and diseases, allergic diseases, atopic conditions including allergic rhinitis, dermatitis, conjunctivitis, and asthma, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which chemokine receptors are involved.

  本发明进一步涉及具有以下结构的化合物（I）：其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R16、R17、R18、R19、R20、R21和R22如本文所定义），这些化合物是趋化因子受体活性的调节剂，并且在预防或治疗某些炎症和免疫调节性疾病、过敏性疾病、包括过敏性鼻炎、皮炎、结膜炎和哮喘等特应性疾病，以及风湿性关节炎和动脉粥样硬化等自身免疫病理学方面是有用的。本发明还涉及包含这些化合物的药物组合物以及这些化合物和组合物在预防或治疗涉及趋化因子受体的疾病中的用途。
• US7410961B2
  申请人：——

  公开号：US7410961B2

  公开（公告）日：2008-08-12
• Synthesis and monoamine transporter affinity of 3α-arylmethoxy-3β-arylnortropanes
  作者：Harneet Kaur、Sari Izenwasser、Abha Verma、Dean Wade、Amy Housman、Edwin D. Stevens、David L. Mobley、Mark L. Trudell

  DOI：10.1016/j.bmcl.2009.10.087

  日期：2009.12

  A series of 3-arylnortrop-2-enes and 3 alpha-arylmethoxy-3 beta-arylnortropanes were synthesized and evaluated for binding affinity at monoamine transporters. The 3-(3,4-dichlorophenyl)nortrop-2-ene (6e) exhibited high affinity for the SERT (K-i = 0.3 nM). The 3 alpha-arylmethoxy-3 beta-arylnortropanes were generally SERT selective with the 3 alpha-(3,4-dichlorophenylmethoxy)-3 beta phenylnortrop-2-ene (7c) possessing subnanomolar potency (K-i = 0.061 nM). However, 3 alpha-(3,4-dichlorophenylmethoxy)-3 beta-phenylnortrop-2-ene (7b) exhibited high affinity at all three transporters [(DAT K-i = 22 nM), (SERT K-i = 6 nM) and (NET K-i = 101 nM)]. (C) 2009 Elsevier Ltd. All rights reserved.