t-butyl N-(carbobenzyloxy)-9-azabicyclo[2.2.1]heptane-1-carboxylate | 182137-48-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: t-butyl N-(carbobenzyloxy)-9-azabicyclo[2.2.1]heptane-1-carboxylate
• 英文别名: 7-(benzyloxycarbonyl)-1-carboxy-7-azabicyclo[2.2.1]heptane tert-butyl ester；7-Benzyl 1-tert-butyl 7-azabicyclo[2.2.1]heptane-1,7-dicarboxylate；7-O-benzyl 1-O-tert-butyl 7-azabicyclo[2.2.1]heptane-1,7-dicarboxylate
• CAS: 182137-48-0
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: NVPNMUKHXNVSAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  t-butyl N-(carbobenzyloxy)-9-azabicyclo[2.2.1]heptane-1-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 生成 tert-butyl 7-azabicyclo[2.2.1 ]heptane-1-carboxylate
  参考文献：
  名称：

  7-氮杂双环庚烷羧酸：硼精氨酸凝血酶抑制剂中的脯氨酸替代物。

  摘要：

  描述了凝血酶抑制剂3的合成，该凝血酶抑制剂3结合有构象约束的7-氮杂双环庚烷羧酸（1）作为脯氨酸的替代物。抑制常数（Ki（凝血酶）= 2.9 nM）表示1是脯氨酸在β-turn三肽模拟物形成中的合理替代。

  DOI：

  10.1021/ol990294x
• 作为产物：
  描述：

  (2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到t-butyl N-(carbobenzyloxy)-9-azabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  跨环烷基化的构象约束7-氮杂双环庚烷氨基酸的手性合成。

  摘要：

  报道了一种新的方法，用于光学纯的1-羧基-7-氮杂双环庚烷氨基酸的手性制备，以产生拟肽作为构象探针。所述方法允许通过使用硫代内酰胺硫化物收缩和跨环烷基化序列作为关键的CC键形成步骤，从L-谷氨酸开始，对这些氨基酸类似物进行多谱图制备。该路线提供了通往两个常见中间体的途径，即7-（苄氧羰基）-1-羧基-7-氮杂双环[2.2.1] -3-庚烷和（1S，4R）-7-（苄氧羰基）-1-羧基-7-氮杂双环[2.2.1] -3-庚酮叔丁酯，分别用于修饰对称和手性氨基酸同源物。后者中间体的C-1羧基单元的脱羧也证明该方法适用于短时，

  DOI：

  10.1021/jo960759m

文献信息

• [EN] DIHYDROXYPYRIMIDINE CARBOXAMIDE INHIBITORS OF HIV INTEGRASE<br/>[FR] INHIBITEURS DE L'INTEGRASE DU VIH A BASE DE DIHYDROXYPYRIMIDINE CARBOXAMIDE
  申请人：ANGELETTI P IST RICHERCHE BIO

  公开号：WO2003035076A1

  公开（公告）日：2003-05-01

  4,5-Dihydroxypyrimidine-6-carboxamides of formula (I); are described as inhibitors of HIV integrase and inhibitors of HIV replication, wherein R?1, R2, R3 and R4¿ are defined herein. These compounds are useful in the prevention and treatment of infection by HIV and in the prevention, delay in the onset, and treatment of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of preventing, treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.

  公式为（I）的4,5-二羟基嘧啶-6-羧酰胺被描述为HIV整合酶抑制剂和HIV复制抑制剂，其中R?1，R2，R3和R4¿在此定义。这些化合物对于预防和治疗HIV感染以及预防、延迟发病和治疗艾滋病非常有用。这些化合物作为化合物本身或药物可接受的盐的形式用于对抗HIV感染和艾滋病。这些化合物及其盐可作为药物组合中的成分，可选地与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。还描述了预防、治疗或延迟艾滋病发病的方法以及预防或治疗HIV感染的方法。
• Dihydroxypyrimidine carboxamide inhibitors of hiv integrase
  申请人：Di Francesco E. Maria

  公开号：US20050075356A1

  公开（公告）日：2005-04-07

  4,5-Dihydroxypyrimidine-6-carboxamides of formula (I); are described as inhibitors of HIV integrase and inhibitors of HIV replication, wherein R 1 , R 2 , R 3 and R 4 are defined herein. These compounds are useful in the prevention and treatment of infection by HIV and in the prevention, delay in the onset, and treatment of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of preventing, treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.

  本文描述了式（I）的4,5-二羟基嘧啶-6-羧酰胺类化合物作为HIV整合酶抑制剂和HIV复制抑制剂，其中R1，R2，R3和R4在此定义。这些化合物在预防和治疗HIV感染以及预防，延迟发病和治疗艾滋病方面非常有用。这些化合物可作为化合物本身或作为药物可接受的盐的形式用于对抗HIV感染和艾滋病。这些化合物及其盐可作为药物组合物中的成分，可选择与其他抗病毒药物，免疫调节剂，抗生素或疫苗组合使用。还描述了预防，治疗或延迟艾滋病发病的方法以及预防或治疗HIV感染的方法。
• Dihydroxypyrimidine carboxamide inhibitors of HIV integrase
  申请人：Di Francesco E. Maria

  公开号：US20070083045A1

  公开（公告）日：2007-04-12

  4,5-Dihydroxypyrimidine-6-carboxamides of formula: are described as inhibitors of HIV integrase and inhibitors of HIV replication, wherein R 1 , R 2 , R 3 and R 4 are defined herein. These compounds are useful in the prevention and treatment of infection by HIV and in the prevention, delay in the onset, and treatment of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of preventing, treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.

  本文描述了式子中R1，R2，R3和R4被定义的4,5-二羟基嘧啶-6-羧酰胺化合物，其作为HIV整合酶抑制剂和HIV复制抑制剂。这些化合物对于预防和治疗HIV感染以及预防、延迟AIDS发病和治疗AIDS非常有用。这些化合物可以作为化合物本身或药物可接受的盐形式用于对抗HIV感染和AIDS。这些化合物及其盐可以与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用，作为制药组合物的成分。本文还描述了预防、治疗或延迟AIDS发病以及预防或治疗HIV感染的方法。
• Tricyclic ureas: A new class of HIV-1 protease inhibitors
  作者：Wei Han、Jeffrey C. Pelletier、C.Nicholas Hodge

  DOI：10.1016/s0960-894x(98)00659-3

  日期：1998.12

  A new class of tricyclic ureas containing a conformationally constrained proline was designed with the aid of molecular modeling. Efficient stereoselective intermolecular pinacol coupling represented the highlight of the synthesis. These rigid cyclic ureas are active towards HIV-1 protease, with 9 being the most potent compound (Ki = 9 nM) despite interacting with only three side chain binding pockets of HIV protease. (C) 1998 The DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.
• DIHYDROXYPYRIMIDINE CARBOXAMIDE INHIBITORS OF HIV INTEGRASE
  申请人：Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A.

  公开号：EP1441734A1

  公开（公告）日：2004-08-04