3-methyladamantane-1-acetic acid chloride | 120081-34-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 3-methyladamantane-1-acetic acid chloride
• 英文别名: 2-(3-Methyl-1-adamantyl)acetyl chloride
• CAS: 120081-34-7
• 化学式: C₁₃H₁₉ClO
• 分子量: 226.746
• InChiKey: BCHMHMJVIDFKQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-二羟基蒽醌 、 3-methyladamantane-1-acetic acid chloride 在 吡啶 作用下， 以47%的产率得到(3-Methyl-adamantan-1-yl)-acetic acid 2-[2-(3-methyl-adamantan-1-yl)-acetoxy]-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester
  参考文献：
  名称：

  Synthesis and antiviral activity of anthraquinone esters

  摘要：

  DOI：

  10.1007/bf00765210
• 作为产物：
  描述：

  3-甲基三环[3.3.1.13,7]癸烷-1-基乙酸 在 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-methyladamantane-1-acetic acid chloride
  参考文献：
  名称：

  Synthesis and SAR of Adatanserin:  Novel Adamantyl Aryl- and Heteroarylpiperazines with Dual Serotonin 5-HT_1A and 5-HT₂ Activity as Potential Anxiolytic and Antidepressant Agents

  摘要：

  Several novel functionalized adamantyl aryl- and heteroarylpiperazine derivatives were prepared and examined in various receptor binding and behavioral tests to determine their serotonin receptor activities. Many compounds demonstrated modest to high affinity for 5-HT1A receptors, with compounds 9, 13, 23, 33, 34, and 43 being the most potent at this site. Compound 1, 2-[4-(2-pyrimidinyl)-1-piperazinyl] ethyl adamantyl-1-carboxylate, demonstrated relatively high affinity for 5-HT1A receptors (K-i = 8 nM) and acceptable selectivity versus D-2 receptors (K-i = 708 mM); however, it lacked in vivo activity in serotonergic behavioral models. In contrast, compounds 9 (WY-50,324, SEB-324, adatanserin), adamantyl-1-carboxylic acid 2-[4-(2-pyrimidinyl)-1-piperazinyl]ethylamide, and 13, adamantyl-1-carboxylic acid 2-[4-(2-methoxyphenyl)-1-piperazinyl] ethylamide, demonstrated high affinity for 5-HT1A binding sites (K-i = 1 nM for both) and moderate affinity for 5-HT2 receptors (K-i = 73 and 75 nM, respectively). Both compounds also demonstrated partial 5-HT1A agonist activity in vivo in rat serotonin syndrome and 5-HT2 antagonist activity in quipazine- and DOI-induced head shake paradigms. The selective 5-HT1A partial agonist and 5-HT2 antagonist activity of 9 was accompanied by significant anxiolytic activity in an animal conflict model. On the basis of this profile, compound 9 entered development as a combined anxiolytic and antidepressant agent.

  DOI：

  10.1021/jm9806704

文献信息

• Adamantyl- and fluorenyl-arylpiperazines and -arylpiperidines
  申请人：American Home Products Corp.

  公开号：US04797489A1

  公开（公告）日：1989-01-10

  The compounds ##STR1## wherein R.sup.1 is 1-adamantyl, 3-methyl-1-adamantyl, 9-fluorenyl or 1-fluorenyl; n is 0 or 1; m is 1, 2, 3, 4 or 5; and X is ##STR2## where R.sup.2 is phenyl, benzyl, pyridinyl, pyrimidinyl, pyrazinyl or substituted phenyl or benzyl in which the substituent is alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo, cyano, nitro or trifluoromethyl, ##STR3## where R.sup.3 is hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo, cyano or nitro; or pharmaceutically acceptable salts thereof are useful antidepressant and/or anxiolytic agents.

  化合物##STR1##中，其中R.sup.1是1-金刚烷基，3-甲基-1-金刚烷基，9-芴基或1-芴基；n为0或1；m为1、2、3、4或5；X为##STR2##其中R.sup.2是苯基，苄基，吡啶基，嘧啶基，吡嗪基或取代苯基或苄基，其中取代基是1到6个碳原子的烷基，1到6个碳原子的烷氧基，卤素，氰基，硝基或三氟甲基，##STR3##其中R.sup.3是氢，1到6个碳原子的烷基，1到6个碳原子的烷氧基，卤素，氰基或硝基；或其药学上可接受的盐是有用的抗抑郁和/或抗焦虑剂。
• LITVINOVA, L. A.;ANDRONATI, S. A.;LEMPART, G. V.;ISAEV, S. D.;YASINSKAYA,+, XIM.-FARMATS. ZH., 1983, 17, N 2, 147-148
  作者：LITVINOVA, L. A.、ANDRONATI, S. A.、LEMPART, G. V.、ISAEV, S. D.、YASINSKAYA,+

  DOI：——

  日期：——
• US4797489A
  申请人：——

  公开号：US4797489A

  公开（公告）日：1989-01-10
• Synthesis and SAR of Adatanserin:  Novel Adamantyl Aryl- and Heteroarylpiperazines with Dual Serotonin 5-HT_1A and 5-HT₂ Activity as Potential Anxiolytic and Antidepressant Agents
  作者：Magid A. Abou-Gharbia、Wayne E. Childers、Horace Fletcher、Georgia McGaughey、Usha Patel、Michael B. Webb、John Yardley、Terrance Andree、Carl Boast、Robert J. Kucharik、Karen Marquis、Herman Morris、Rosemary Scerni、John A. Moyer

  DOI：10.1021/jm9806704

  日期：1999.12.1

  Several novel functionalized adamantyl aryl- and heteroarylpiperazine derivatives were prepared and examined in various receptor binding and behavioral tests to determine their serotonin receptor activities. Many compounds demonstrated modest to high affinity for 5-HT1A receptors, with compounds 9, 13, 23, 33, 34, and 43 being the most potent at this site. Compound 1, 2-[4-(2-pyrimidinyl)-1-piperazinyl] ethyl adamantyl-1-carboxylate, demonstrated relatively high affinity for 5-HT1A receptors (K-i = 8 nM) and acceptable selectivity versus D-2 receptors (K-i = 708 mM); however, it lacked in vivo activity in serotonergic behavioral models. In contrast, compounds 9 (WY-50,324, SEB-324, adatanserin), adamantyl-1-carboxylic acid 2-[4-(2-pyrimidinyl)-1-piperazinyl]ethylamide, and 13, adamantyl-1-carboxylic acid 2-[4-(2-methoxyphenyl)-1-piperazinyl] ethylamide, demonstrated high affinity for 5-HT1A binding sites (K-i = 1 nM for both) and moderate affinity for 5-HT2 receptors (K-i = 73 and 75 nM, respectively). Both compounds also demonstrated partial 5-HT1A agonist activity in vivo in rat serotonin syndrome and 5-HT2 antagonist activity in quipazine- and DOI-induced head shake paradigms. The selective 5-HT1A partial agonist and 5-HT2 antagonist activity of 9 was accompanied by significant anxiolytic activity in an animal conflict model. On the basis of this profile, compound 9 entered development as a combined anxiolytic and antidepressant agent.
• Synthesis and antiviral activity of anthraquinone esters
  作者：L. A. Litvinova、S. A. Andronati、G. V. Lempart、S. D. Isaev、O. G. Yasinskaya、V. V. Ivanova

  DOI：10.1007/bf00765210

  日期：1983.2