4-methyl-7-[3-(4-phenyl-piperazin-1-yl)-propoxy]-chromen-2-one | 39577-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-methyl-7-[3-(4-phenyl-piperazin-1-yl)-propoxy]-chromen-2-one
• 英文别名: 7-[3-(4-phenyl-1-piperazinyl)-propoxy]-4-methyl-2H-1-benzopyran-2-one；4-methyl-7-[3-(4-phenylpiperazin-1-yl)propoxy]chromen-2-one
• CAS: 39577-23-6
• 化学式: C₂₃H₂₆N₂O₃
• 分子量: 378.471
• InChiKey: ZYBLSQVXWVJACW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-苯基哌嗪 在 sodium hydroxide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 73.0h， 生成 4-methyl-7-[3-(4-phenyl-piperazin-1-yl)-propoxy]-chromen-2-one
  参考文献：
  名称：

  Phenylpiperazine derivatives with strong affinity for 5HT1A, D2A and D3 receptors

  摘要：

  Four 7-[3-(4-phenyl-1-piperazinyl)propoxy]coumarins were synthesized. The affinities of these compounds for DA (D-2A, D-3) and 5HT(1A) receptors were evaluated for their ability to displace [H-3]-raclopride and [H-3]-8-OH-DPAT respectively from their specific binding sites. The affinities of the target compounds were all in the nanomolar range and followed the order 5-HT1A > D-2 > D-3 (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00646-5

文献信息

• Aminoalkoxybenzopyranones and processes for the production thereof
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0175541A1

  公开（公告）日：1986-03-26

  Aminoalkoxybenzopyranones of the formula or a pharmaceutically acceptable acid addition salt thereof; wherein n is an integer from 2-5; R is hydrogen, lower alkyl, trofluoromethyl, or lower alkoxy; R1 is a radical of the formula in which --- represents a single or double bond, Ar is phenyl or phenyl substituted by lower alkyl, lower alkoxy, lower thioalkoxy, halogen, or trifluoromethyl, and in which Het is chosen from the following heterocyclic radicals (a) 2-, 3-, or 4-pyridinyl or 2-, 3-, or 4-pyridinyl substituted by lower alkyl, lower alkoxy, or halogen, (b) 2-, 4-, or 5-pyrimidinyl, or 2-, 4-, or 5-pyrimidinyl substituted by lower alkyl, lower alkoxy, or halogen, (c) 2-pyrazinyl or 2-pyrazinyl substituted by lower alkyl, lower alkoxy, or halogen, (d) 2- or 3-thienyl, or 2- or 3-thienyl substituted by lower alkyl or halogen, (e) 2- or 3-furanyl, or 2-or 3-furanyl substituted by lower alkyl or halogen, or (f) 2- or 5-thiazolyl or 2- or 5-thiazolyl substituted by lower alkyl or halogen; with the exclusion of the compound in which n is 3, R is methyl, and R, is a radical of the formula Also described are processes for producing the compounds, and pharmaceutical compositions comprising the compounds.

  式中的氨基烷氧基苯并吡喃酮 或其药学上可接受的酸加成盐； 其中 n 是 2-5 之间的整数 R 是氢、低级烷基、三氟甲基或低级烷氧基； R1 是式中的一个基团 其中 --- 代表单键或双键，Ar 是苯基或被低级烷基、低级烷氧基、低级硫代烷氧基、卤素或三氟甲基取代的苯基，其中 Het 选自以下杂环基 (a) 2-、3-或 4-吡啶基或被低级烷基、低级烷氧基或卤素取代的 2-、3-或 4-吡啶基， (b) 2-、4-或 5-嘧啶基或被低级烷基、低级烷氧基或卤素取代的 2-、4-、(c) 2-吡嗪基，或被低级烷基、低级烷氧基或卤素取代的 2-吡嗪基， (d) 2-或 3-噻吩基，或被低级烷基或卤素取代的 2-或 3-噻吩基， (e) 2-或 3-呋喃基，或被低级烷基或卤素取代的 2-或 3-呋喃基，或 (f) 2-或 5-噻唑基，或被低级烷基或卤素取代的 2-或 5-噻唑基；其中 n 为 3、R 为甲基、R 为式中自由基的化合物除外。 还描述了生产这些化合物的工艺和包含这些化合物的药物组合物。
• New arylpiperazine derivatives with high affinity for α1A, D2 and 5-HT2A receptors
  作者：J.C González-Gómez、L Santana、E Uriarte、J Brea、M Villazón、M.I Loza、M De Luca、M.E Rivas、G.Y Montenegro、J.A Fontenla

  DOI：10.1016/s0960-894x(02)00933-2

  日期：2003.1

  A series of novel long-chain arylpiperazines bearing a coumarin fragment was synthesized and the compounds were evaluated for their affinity at alpha(1), D-2 and 5-HT2A receptors. Most of the new compounds showed high affinity for the three types of receptors alpha(1A), D-2 and 5-HT2A which depends, fundamentally, on the substitution of the N-4 of the piperazine ring. From the series emerged compound 6, which had an haloperidol-like profile at D-2 and 5HT(2A) receptors (pK(i) values of 7.93 and 6.76 respectively). The higher alpha(1A) receptor affinity (pA(2) = 9.07) of this compound could contribute to a more atypical antipsychotic profile than the haloperidol. (C) 2002 Elsevier Science Ltd. All rights reserved.
• DEWALD, HORACE A.;WISE, LAWRENCE D.;HEFFNER, THOMAS G.
  作者：DEWALD, HORACE A.、WISE, LAWRENCE D.、HEFFNER, THOMAS G.

  DOI：——

  日期：——
• US4701456A
  申请人：——

  公开号：US4701456A

  公开（公告）日：1987-10-20
• Phenylpiperazine derivatives with strong affinity for 5HT1A, D2A and D3 receptors
  作者：Carmen Terán、Lourdes Santana、Eugenio Uriarte、Yagamare Fall、Lena Unelius、Bo-Ragnar Tolf

  DOI：10.1016/s0960-894x(98)00646-5

  日期：1998.12

  Four 7-[3-(4-phenyl-1-piperazinyl)propoxy]coumarins were synthesized. The affinities of these compounds for DA (D-2A, D-3) and 5HT(1A) receptors were evaluated for their ability to displace [H-3]-raclopride and [H-3]-8-OH-DPAT respectively from their specific binding sites. The affinities of the target compounds were all in the nanomolar range and followed the order 5-HT1A > D-2 > D-3 (C) 1998 Elsevier Science Ltd. All rights reserved.