9-aminomethyl-9,10-dihydro-9,10-methanoanthracene | 63293-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-aminomethyl-9,10-dihydro-9,10-methanoanthracene
• 英文别名: 1-tetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9,11,13-hexaenylmethanamine
• CAS: 63293-39-0
• 化学式: C₁₆H₁₅N
• 分子量: 221.302
• InChiKey: IZUFWQBEJCIXMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-aminomethyl-9,10-dihydro-9,10-methanoanthracene 在 乙酸酐 作用下， 以 乙醇 为溶剂， 生成 9-acetylaminomethyl-9,10-dihydro-9,10-methanoanthracene
  参考文献：
  名称：

  Organic tricyclic compounds

  摘要：

  新型9-氨基烷基-甲基蒽的化学式为：其中A为C.sub.1 -C.sub.4烷基或C.sub.3 -C.sub.4烯基，R.sub.1和R.sub.2分别为氢、C.sub.1 -C.sub.4烷基、C.sub.3 -C.sub.4烯基、C.sub.3 -C.sub.4炔基、C.sub.3 -C.sub.6环烷基(C.sub.1 -C.sub.3)烷基、ar(C.sub.1 -C.sub.3)烷基或多卤(C.sub.2 -C.sub.4)烷基，或者与相邻氮原子结合时，它们可以形成一个含氮的5至7元杂环，该环可能含有额外的杂原子，以及它们的无毒盐。这些化合物可用作抗焦虑、抗抑郁、镇静剂、抗组织胺和抗过敏药物，并可通过一种新型关键中间体制备，即9-甲酰基-9,10-二氢-9,10-甲基蒽，通过各种方法制备。

  公开号：

  US04224344A1
• 作为产物：
  描述：

  9,10-二氢-9,10-亚甲基蒽-9-羧酸 在 氯化亚砜 、 硼烷四氢呋喃络合物 、 氨 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 9.5h， 生成 9-aminomethyl-9,10-dihydro-9,10-methanoanthracene
  参考文献：
  名称：

  Geometry−Affinity Relationships of the Selective Serotonin Receptor Ligand 9-(Aminomethyl)-9,10-dihydroanthracene

  摘要：

  With the exception of its two aromatic rings and basic nitrogen atom, 9-(aminomethyl)-9,10-dihydroanthracene (AMDA; 1) is remarkably devoid of the pharmacophore features usually associated with high-affinity receptor ligands such as the heteroatom hydrogen bonding features of the endogenous ligand serotonin. AMDA does contain a phenylethylamine skeleton within a tricyclic ring system, and the presence of the second aromatic group is necessary for optimal receptor affinity. The structural requirements for the binding of AMDA at 5-HT2A receptors were investigated with respect to the geometric relationship between the two aromatic rings. It appears that the geometry of the AMDA parent is in the optimal range for fold angle between aromatic moieties. Evaluation of conformationally constrained derivatives of AMDA suggests that a chain extended trans, gauche form is most likely responsible for high affinity.

  DOI：

  10.1021/jm010354g

文献信息

• 9-Formyl-9,10-dihydro-9,10-methanoanthracene
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04358620A1

  公开（公告）日：1982-11-09

  Novel 9-aminoalkyl-methanoanthracenes of the formula: ##STR1## wherein A is C.sub.1 -C.sub.4 alkylene or C.sub.3 -C.sub.4 alkenylene and R.sub.1 and R.sub.2 are each hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.6 cycloalkyl(C.sub.1 -C.sub.3)alkyl, ar(C.sub.1 -C.sub.3)alkyl or polyhalo(C.sub.2 -C.sub.4)alkyl or, when taken together with the adjacent nitrogen atom, they may form a 5 to 7-membered nitrogen-containing heterocyclic ring which may contain an additional hetero atom, and their non-toxic salts, which are useful as anti-anxiety, anti-depressant, major tranquilizer, anti-histamine and anti-allergy drugs and can be prepared through a novel key intermediate, i.e. 9-formyl-9,10-dihydro-9,10-methanoanthracene, by various methods.

  公式如下：##STR1## 其中A为C.sub.1-C.sub.4烷基或C.sub.3-C.sub.4烯基，R.sub.1和R.sub.2分别为氢、C.sub.1-C.sub.4烷基、C.sub.3-C.sub.4烯基、C.sub.3-C.sub.4炔基、C.sub.3-C.sub.6环烷基(C.sub.1-C.sub.3)烷基、ar(C.sub.1-C.sub.3)烷基或多卤素(C.sub.2-C.sub.4)烷基，或者与相邻的氮原子一起形成一个含氮杂环的5-7元环，该杂环可以包含一个额外的杂原子，其非毒性盐可用作抗焦虑、抗抑郁、镇静剂、抗组胺和抗过敏药物，可以通过一种新的关键中间体即9-甲酰基-9,10-二氢-9,10-甲基蒽制备。
• US4224344A
  申请人：——

  公开号：US4224344A

  公开（公告）日：1980-09-23
• US4358620A
  申请人：——

  公开号：US4358620A

  公开（公告）日：1982-11-09
• Organic tricyclic compounds
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04224344A1

  公开（公告）日：1980-09-23

  Novel 9-aminoalkyl-methanoanthracenes of the formula: ##STR1## wherein A is C.sub.1 -C.sub.4 alkylene or C.sub.3 -C.sub.4 alkenylene and R.sub.1 and R.sub.2 are each hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.6 cycloalkyl(C.sub.1 -C.sub.3)alkyl, ar(C.sub.1 -C.sub.3)alkyl or polyhalo(C.sub.2 -C.sub.4)alkyl or, when taken together with the adjacent nitrogen atom, they may form a 5 to 7-membered nitrogen-containing heterocyclic ring which may contain an additional hetero atom, and their non-toxic salts, which are useful as anti-anxiety, anti-depressant, major tranquilizer, anti-histamine and anti-allergy drugs and can be prepared through a novel key intermediate, i.e., 9-formyl-9,10-dihydro-9,10-methanoanthracene, by various methods.

  新型9-氨基烷基-甲基蒽的化学式为：其中A为C.sub.1 -C.sub.4烷基或C.sub.3 -C.sub.4烯基，R.sub.1和R.sub.2分别为氢、C.sub.1 -C.sub.4烷基、C.sub.3 -C.sub.4烯基、C.sub.3 -C.sub.4炔基、C.sub.3 -C.sub.6环烷基(C.sub.1 -C.sub.3)烷基、ar(C.sub.1 -C.sub.3)烷基或多卤(C.sub.2 -C.sub.4)烷基，或者与相邻氮原子结合时，它们可以形成一个含氮的5至7元杂环，该环可能含有额外的杂原子，以及它们的无毒盐。这些化合物可用作抗焦虑、抗抑郁、镇静剂、抗组织胺和抗过敏药物，并可通过一种新型关键中间体制备，即9-甲酰基-9,10-二氢-9,10-甲基蒽，通过各种方法制备。
• Geometry−Affinity Relationships of the Selective Serotonin Receptor Ligand 9-(Aminomethyl)-9,10-dihydroanthracene
  作者：Scott P. Runyon、Srinivas Peddi、Jason E. Savage、Bryan L. Roth、Richard A. Glennon、Richard B. Westkaemper

  DOI：10.1021/jm010354g

  日期：2002.4.1

  With the exception of its two aromatic rings and basic nitrogen atom, 9-(aminomethyl)-9,10-dihydroanthracene (AMDA; 1) is remarkably devoid of the pharmacophore features usually associated with high-affinity receptor ligands such as the heteroatom hydrogen bonding features of the endogenous ligand serotonin. AMDA does contain a phenylethylamine skeleton within a tricyclic ring system, and the presence of the second aromatic group is necessary for optimal receptor affinity. The structural requirements for the binding of AMDA at 5-HT2A receptors were investigated with respect to the geometric relationship between the two aromatic rings. It appears that the geometry of the AMDA parent is in the optimal range for fold angle between aromatic moieties. Evaluation of conformationally constrained derivatives of AMDA suggests that a chain extended trans, gauche form is most likely responsible for high affinity.