2-氨基金刚烷-2-甲酸叔丁酯 | 502937-07-7

• 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
• 中文名称: 2-氨基金刚烷-2-甲酸叔丁酯
• 英文名称: tert-butyl 2-aminoadamantane-2-carboxylate
• CAS: 502937-07-7
• 化学式: C₁₅H₂₅NO₂
• 分子量: 251.369
• InChiKey: PCSWAFUARBKFHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  2-氨基金刚烷-2-甲酸叔丁酯 在 哌啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 N-{(2S)-1-[(2-hydroxycarbonyl)-2-adamantylamino]-3-(4-hydroxyphenyl)-1-oxo-propan-2-yl} 1-(6-guanidinohexyl)-6-(5-guanidinopentyloxy)indole-2-carboxamide bis(trifluoroacetate)
  参考文献：
  名称：

  Synthesis and Biological Studies of Novel Neurotensin(8–13) Mimetics

  摘要：

  Novel neurotensin (NT) (8-13) (Arg(8)-Arg(9)-Pro(10)-Tyr(11)-Ile(12)-Leu(13)) mimetics 3, 4 were designed by adopting all intrinsic functional groups of the native neurotensin(8-13) and using a substituted indole as a template to mimic the pharmacophore of NT(8-13). Biological studies at subtype 1 of the NT receptor showed that 3 has a 55 and 580 nM binding affinity at rat and human neurotensin receptors, respectively, As a comparison. compounds 5 and 6 were also synthesized. The binding difference between 3, 4 and 5, 6 argues the importance of the carboxylic group in achieving higher potency NT(8-13) mimetics. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00342-5
• 作为产物：
  描述：

  2-cyanoadamantan-2-ol 在 盐酸 、 ammonium hydroxide 、 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 38.0h， 生成 2-氨基金刚烷-2-甲酸叔丁酯
  参考文献：
  名称：

  CN117209390

  摘要：

  公开号：
• 作为试剂：
  描述：

  1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carbonyl chloride 、 2-氨基金刚烷-2-甲酸叔丁酯 在 2-氨基金刚烷-2-甲酸叔丁酯 作用下， 以89的产率得到tert-butyl 2-(1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxamido)adamantane-2-carboxylate
  参考文献：
  名称：

  Bioorg. Med. Chem. 2013, 21, 4378-4387

  摘要：

  DOI：

文献信息

• A Machine-Assisted Flow Synthesis of SR48692: A Probe for the Investigation of Neurotensin Receptor-1
  作者：Claudio Battilocchio、Benjamin J. Deadman、Nikzad Nikbin、Matthew O. Kitching、Ian R. Baxendale、Steven V. Ley

  DOI：10.1002/chem.201300696

  日期：2013.6.10

  Here we report the direct comparison of a conventional batch mode synthesis of Meclinertant (SR48692, 1), a neurotensin receptor‐1 antagonist, with its machine‐assisted flow chemistry alternative. By using these enabling tools, combined with solid‐supported reagents and scavengers, many process advantages were observed. Care, however, must be taken not to convert these techniques into expensive solutions

  这里，我们报告Meclinertant（SR48692，的常规分批方式合成的直接比较1），神经降压素受体-1拮抗剂，以其机器辅助流动化学替代。通过使用这些辅助工具，再加上固体支持的试剂和清除剂，可以观察到许多工艺优势。但是，必须注意不要将这些技术转换为不存在的问题的昂贵解决方案。
• Conjugate comprising a neurotensin receptor ligand
  申请人：3B Pharmaceuticals GmbH

  公开号：EP2954933A1

  公开（公告）日：2015-12-16

  The present invention is related to a conjugate comprising a structure of general formula (I)         [TM1] - [AD1] - [LM] - [AD2] - [TM2]     (I), wherein TM1 is a first targeting moiety, wherein the first targeting moiety is capable of binding to a first target, AD1 is a first adapter moiety or is absent, LM is a linker moiety or is absent, AD2 is a second adapter moiety or is absent, and TM2 is a second targeting moiety, wherein the second targeting moiety is capable of binding to a second target; wherein the first targeting moiety and/or the second targeting moiety is a compound of formula (II): wherein R1 is selected from the group consisting of hydrogen, methyl and cyclopropylmethyl; AA-COOH is an amino acid selected from the group consisting of 2-amino-2-adamantane carboxylic acid, cyclohexylglycine and 9-amino-bicyclo[3.3.1]nonane-9-carboxylic acid; R2 is selected from the group consisting of (C1-C6)alkyl, (C3-C8)cycloalkyl, (C3C8)cycloalkylmethyl, halogen, nitro and trifluoromethyl; ALK is (C2-C5)alkylidene; R3, R4 and R5 are each and independently selected from the group consisting of hydrogen and (C1-C4)alkyl under the proviso that one of R3, R4 and R5 is of the following formula (III) wherein ALK' is (C2-C5)alkylidene; R6 is selected from the group consisting of hydrogen and (C1-C4)alkyl; and R7 is a bond; or a pharmacologically acceptable salt, solvate or hydrate thereof.

  本发明涉及一种包含一般式（I）结构的结合物，其中TM1是第一靶向基团，第一靶向基团能够结合到第一个靶标，AD1是第一适配基团或者不存在，LM是连接基团或者不存在，AD2是第二适配基团或者不存在，TM2是第二靶向基团，第二靶向基团能够结合到第二个靶标；其中第一靶向基团和/或第二靶向基团是式（II）化合物之一：其中R1选自氢、甲基和环丙基甲基组成的群；AA-COOH是选自2-氨基-2-环戊烷羧酸、环己基甘氨酸和9-氨基-双环[3.3.1]壬烷-9-羧酸组成的氨基酸；R2选自（C1-C6）烷基、（C3-C8）环烷基、（C3-C8）环烷基甲基、卤素、硝基和三氟甲基的群；ALK是（C2-C5）烷基亚基；R3、R4和R5各自独立地选自氢和（C1-C4）烷基，但是在R3、R4和R5中的一个符合以下式（III）：其中ALK'是（C2-C5）烷基亚基；R6选自氢和（C1-C4）烷基；R7是键；或其药理学上可接受的盐、溶剂或水合物。
• Conjugate comprising a neurotensin receptor ligand and use thereof
  申请人：3B Pharmaceuticals GmbH

  公开号：EP2954934A1

  公开（公告）日：2015-12-16

  The present invention is related to a conjugate comprising a structure of general formula (1)         [TM1] - [AD1] - [LM] - [AD2] - [TM2]     (1), wherein TM1 is a first targeting moiety, wherein the first targeting moiety is capable of binding to a first target, AD1 is a first adapter moiety or is absent, LM is a linker moiety or is absent, AD2 is a second adapter moiety or is absent, and TM2 is a second targeting moiety, wherein the second targeting moiety is capable of binding to a second target; wherein the first targeting moiety and/or the second targeting moiety is a compound of formula (2): wherein R1 is selected from the group consisting of hydrogen, methyl and cyclopropylmethyl; AA-COOH is an amino acid selected from the group consisting of 2-amino-2-adamantane carboxylic acid, cyclohexylglycine and 9-amino-bicyclo[3.3.1]nonane-9-carboxylic acid; R2 is selected from the group consisting of (C1-C6)alkyl, (C3-C8)cycloalkyl, (C3C8)cycloalkylmethyl, halogen, nitro and trifluoromethyl; ALK is (C2-C5)alkylidene; R3, R4 and R5 are each and independently selected from the group consisting of hydrogen and (C1-C4)alkyl under the proviso that one of R3, R4 and R5 is of the following formula (3) wherein ALK' is (C2-C5)alkylidene; R6 is selected from the group consisting of hydrogen and (C1-C4)alkyl; and R7 is a bond; or a pharmacologically acceptable salt, solvate or hydrate thereof.

  本发明涉及一种包含通式（1）结构的共轭物 [TM1] - [AD1] - [LM] - [AD2] - [TM2] (1)、 其中 TM1 是第一靶向分子，其中第一靶向分子能够与第一靶点结合、 AD1 是第一适配基团或不存在、 LM 是连接分子或不存在、 AD2 是第二适配基团或不存在，以及 TM2 是第二靶向分子，其中第二靶向分子能与第二靶点结合； 其中第一靶向分子和/或第二靶向分子为式（2）化合物： 其中 R1 选自由氢、甲基和环丙基甲基组成的组； AA-COOH 是一种氨基酸，选自由 2-氨基-2-金刚烷羧酸、环己基甘氨酸和 9-氨基-双环[3.3.1]壬烷-9-羧酸组成的组； R2 选自(C1-C6)烷基、(C3-C8)环烷基、(C3C8)环烷基甲基、卤素、硝基和三氟甲基组成的组； ALK 是（C2-C5）亚烷基； R3、R4 和 R5 各自独立地选自氢和(C1-C4)烷基组成的组，但 R3、R4 和 R5 中的一个必须符合下式 (3) 其中 ALK' 是 (C2-C5) 亚烷基； R6 选自氢和（C1-C4）烷基组成的组；以及 R7 是键； 或其药理学上可接受的盐、溶液或水合物。
• Neurotensin receptor ligands
  申请人：3B Pharmaceuticals GmbH

  公开号：US10961199B2

  公开（公告）日：2021-03-30

  The present invention is related to a compound of formula (I) wherein R1 is selected from the group consisting of hydrogen, methyl and cyclopropylmethyl; AA-COOH is an amino acid selected from the group consisting of 2-amino-2-adamantane carboxylic acid, cyclohexylglycine and 9-amino-bicyclo[3.3.1]nonane-9-carboxylic acid; R2 is selected from the group consisting of (C1-C6)alkyl, (C3-C8)cycloalkyl, (C3-C5)cycloalkylmethyl, halogen, nitro and trifluoromethyl; ALK is (C2-C5)alkylidene; R3, R4 and R5 are each and independently selected from the group consisting of hydrogen and (C1-C4)alkyl under the proviso that one of R3, R4 and R5 is of the formula (II) wherein ALK′ is (C2-C5)alkylidene; R6 is selected from the group consisting of hydrogen and (C1-C4)alkyl; and R7 is selected from the group consisting of H and an Effector moiety; or a pharmacologically acceptable salt, solvate or hydrate thereof.

  本发明涉及式(I)化合物 其中 R1 选自氢、甲基和环丙基甲基组成的组；AA-COOH 是选自 2-氨基-2-金刚烷羧酸、环己基甘氨酸和 9-氨基-双环[3.3.1]壬烷-9-羧酸组成的组的氨基酸；R2 选自(C1-C6)烷基、(C3-C8)环烷基、(C3-C5)环烷基组成的组。R2选自由(C1-C6)烷基、(C3-C8)环烷基、(C3-C5)环烷基甲基、卤素、硝基和三氟甲基组成的组；ALK为(C2-C5)亚烷基；R3、R4和R5各自独立地选自由氢和(C1-C4)烷基组成的组，但R3、R4和R5中的一个为式(II)，其中ALK′为(C2-C5)亚烷基；R6 选自由氢和（C1-C4）烷基组成的组；以及 R7 选自由 H 和效应分子组成的组；或其药理学上可接受的盐、溶液或水合物。
• The synthesis of neurotensin antagonist SR 48692 for prostate cancer research
  作者：I.R. Baxendale、S. Cheung、M.O. Kitching、S.V. Ley、J.W. Shearman

  DOI：10.1016/j.bmc.2013.04.075

  日期：2013.7

  An improved synthesis of the molecule SR 48692 is presented and its use as a neurotensin antagonist biological probe for use in cancer research is described. The preparation includes an number of enhanced chemical conversions and strategies to overcome some of the limiting synthetic transformations in the original chemical route. (C) 2013 Elsevier Ltd. All rights reserved.