(9-Cyano-9,10-dihydro-anthracen-9-yl)-acetic acid ethyl ester | 634152-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (9-Cyano-9,10-dihydro-anthracen-9-yl)-acetic acid ethyl ester
• 英文别名: (9-cyano-9,10-dihydroanthracen-9-yl)acetic acid ethyl ester；ethyl 2-(9-cyano-10H-anthracen-9-yl)acetate
• CAS: 634152-92-4
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: DBJMVLRNNSPTRV-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  442.4±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9-Cyano-9,10-dihydro-anthracen-9-yl)-acetic acid ethyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以68%的产率得到spiro[9,10-dihydroanthracene]-9,4'-pyrrolidine-2'-one
  参考文献：
  名称：

  Structural determinants for high 5-HT 2A receptor affinity of spiro[9,10-dihydroanthracene]-9,3 ′ -pyrrolidine (SpAMDA)

  摘要：

  The synthesis and 5-HT2A receptor affinities of ring altered derivatives of spiro[9,10-dihydroanthracene]-9,3'-pyrrolidine (4), a structurally unique tetracyclic 5-HT2A receptor antagonist, are described. The characteristics of the parent compound prove to be necessary for optimal 5-HT2A receptor affinity. However, expansion of the size of the pyrrolidine and central rings produce compounds with reasonably high 5-HT2A receptor affinities. In addition, the parent compound is shown to have high 5-HT2 receptor selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.014
• 作为产物：
  描述：

  9,10-dihydroanthracene-9-carboxamide 在 sodium ethanolate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 7.75h， 生成 (9-Cyano-9,10-dihydro-anthracen-9-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Structural determinants for high 5-HT 2A receptor affinity of spiro[9,10-dihydroanthracene]-9,3 ′ -pyrrolidine (SpAMDA)

  摘要：

  The synthesis and 5-HT2A receptor affinities of ring altered derivatives of spiro[9,10-dihydroanthracene]-9,3'-pyrrolidine (4), a structurally unique tetracyclic 5-HT2A receptor antagonist, are described. The characteristics of the parent compound prove to be necessary for optimal 5-HT2A receptor affinity. However, expansion of the size of the pyrrolidine and central rings produce compounds with reasonably high 5-HT2A receptor affinities. In addition, the parent compound is shown to have high 5-HT2 receptor selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.014

文献信息

• Selective serotonin receptor antagonists and therapeutic applications thereof
  申请人：——

  公开号：US20030232872A1

  公开（公告）日：2003-12-18

  Spiro[9,10-dihydroanthracene]-9,3′-pyrrolidine (SPAN) and derivatives thereof are provided as selective serotonin receptor antagonists. The compounds are selective, high affinity antagonists of 5-HT 2 serotonin receptors. The compounds are useful as antidepressant and antianxiety agents.

  Spiro[9,10-二氢蒽]-9,3'-吡咯烷（SPAN）及其衍生物被提供为选择性5-羟色胺受体拮抗剂。这些化合物是5-HT2 5-羟色胺受体的选择性、高亲和力拮抗剂。这些化合物可用作抗抑郁和抗焦虑药物。
• US6806283B2
  申请人：——

  公开号：US6806283B2

  公开（公告）日：2004-10-19
• Structural determinants for high 5-HT 2A receptor affinity of spiro[9,10-dihydroanthracene]-9,3 ′ -pyrrolidine (SpAMDA)
  作者：Srinivas Peddi、Bryan L Roth、Richard A Glennon、Richard B Westkaemper

  DOI：10.1016/j.bmcl.2004.02.014

  日期：2004.5

  The synthesis and 5-HT2A receptor affinities of ring altered derivatives of spiro[9,10-dihydroanthracene]-9,3'-pyrrolidine (4), a structurally unique tetracyclic 5-HT2A receptor antagonist, are described. The characteristics of the parent compound prove to be necessary for optimal 5-HT2A receptor affinity. However, expansion of the size of the pyrrolidine and central rings produce compounds with reasonably high 5-HT2A receptor affinities. In addition, the parent compound is shown to have high 5-HT2 receptor selectivity. (C) 2004 Elsevier Ltd. All rights reserved.