spiro[1,2,3,4-tetrahydronaphthalenyl-1,4'-pyrrolidin]-2'-one | 111140-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: spiro[1,2,3,4-tetrahydronaphthalenyl-1,4'-pyrrolidin]-2'-one
• 英文别名: 3,4-dihydrospiro((2H)-naphthalene-1,3'-pyrrolidin)-5'-one；spiro[1,2,3,4-tetrahydronaphthalene-1,3''-(tetrahydro-1''H-pyrrole)]-5''-one；spiro[2,3-dihydro-1H-naphthalene-4,4'-pyrrolidine]-2'-one
• CAS: 111140-74-0
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: LDOLUWJSBOPVET-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153.5 °C(Solv: chloroform (67-66-3); ligroine (8032-32-4))
• 沸点：
  417.8±34.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  spiro[1,2,3,4-tetrahydronaphthalenyl-1,4'-pyrrolidin]-2'-one 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 3,4-二氢-2H-螺[萘-1,3'-吡咯烷
  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：

  1-氰基四氢化萘 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium ethanolate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 79.0h， 生成 spiro[1,2,3,4-tetrahydronaphthalenyl-1,4'-pyrrolidin]-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

文献信息

• Spiro Hydantoin Aldose Reductase Inhibitors
  作者：Reinhard Sarges、Rodney C. Schnur、John L. Belletire、Michael J. Peterson

  DOI：10.1021/jm00396a037

  日期：1988.1

  formation from glucose, catalyzed by the enzyme aldose reductase, is believed to play a role in the development of certain chronic complications of diabetes mellitus. Spiro hydantoins derived from five- and six-membered ketones fused to an aromatic ring or ring system inhibit aldose reductase isolated from calf lens. In vivo these compounds are potent inhibitors of sorbitol formation in sciatic nerves of

  据信由醛糖还原酶催化的葡萄糖形成山梨醇在糖尿病的某些慢性并发症的发生中起作用。源自与芳香族环或环系统融合的五元和六元酮的螺乙内酰脲抑制从小牛晶状体分离的醛糖还原酶。在体内，这些化合物是链脲佐剂化大鼠坐骨神经中山梨醇形成的有效抑制剂。在衍生自6-卤代的2,3-二氢-4H-1-苯并吡喃-4-酮（4-苯并二氢吡喃酮）的螺旋乙内酰脲中可达到最佳的体内活性。在2,4-二氢-6-氟螺[4H-1-苯并吡喃-4,4'-咪唑烷] -2'，5'-二酮中，活性仅存在于4S异构体化合物115（CP-45,634，USAN ：山梨醇）。该化合物目前正用于测试人体，
• SARGES, REINHARD;SCHNUR, RODNEY C.;BELLETIRE, JOHN L.;PETERSON, MICHAEL J+, J. MED. CHEM., 31,(1988) N 1, 230-243
  作者：SARGES, REINHARD、SCHNUR, RODNEY C.、BELLETIRE, JOHN L.、PETERSON, MICHAEL J+

  DOI：——

  日期：——
• 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.