1-(4-hydroxy-3-methoxy-phenyl)-pentan-1-one | 114515-51-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-hydroxy-3-methoxy-phenyl)-pentan-1-one
• 英文别名: 1-(4-Hydroxy-3-methoxy-phenyl)-pentan-1-on；1-(4-Hydroxy-3-methoxyphenyl)pentan-1-one
• CAS: 114515-51-4
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: HLDFNGHNRQVEBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxy-3-methoxy-phenyl)-pentan-1-one 、 1,3-二溴丙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 1-[4-(3-Bromopropoxy)-3-methoxyphenyl]pentan-1-one
  参考文献：
  名称：

  3-[[(Aryloxy)alkyl]piperidinyl]-1,2-Benzisoxazoles as D2/5-HT2 Antagonists with Potential Atypical Antipsychotic Activity: Antipsychotic Profile of Iloperidone (HP 873)

  摘要：

  A series of 3-[[(aryloxy)alkyl]piperidinyl]-1,2-benzisoxazoles was synthesized and evaluated as potential antipsychotic D-2/5-HT2 antagonists. Most of these compounds showed potent antipsychotic-like activity in an apomorphine-induced climbing mouse paradigm, with many also showing preferential mesolimbic activity, as indicated by their weaker effects in an apomorphine-induced stereotypy model. In receptor binding assays, many displayed a moderate affinity for the D-2 receptor coupled with a significantly greater affinity for the 5-HT2 receptor. a property that has been suggested as necessary for atypicality. From this series, compound 45, 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone (iloperidone, HP 873), was further evaluated in a battery of in vivo and in vitro assays. This compound showed a 300-fold greater potency in inhibition of climbing than in inhibition of stereotypy or induction of catalepsy, and when evaluated chronically in an electrophysiological model, 45 caused a depolarization blockade of dopamine neurons in the A10 area of the rat brain but not in the A9 area. Additionally, it showed positive activity in a social interaction paradigm, suggesting potential efficacy;against asociality, a component of the negative symptoms of schizophrenia. In chronic ex vivo studies, 45, similar to clozapine, caused a down regulation of 5-HT2 receptors but had no effect on the number of D-2 receptors. Compound 45 is currently undergoing clinical evaluation.

  DOI：

  10.1021/jm00007a009
• 作为产物：
  描述：

  乙酰香兰素 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 苯 为溶剂， 反应 5.0h， 生成 1-(4-hydroxy-3-methoxy-phenyl)-pentan-1-one
  参考文献：
  名称：

  Suri, O. P.; Bindra, R. S.; Satti, N. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 587 - 588

  摘要：

  DOI：

文献信息

• THE SYNTHESIS OF SOME NEW COMPOUNDS RELATED TO APOCYNIN AND APOCYNOL¹
  作者：Henry P. Howells、B. H. Little、H. P. Andersen

  DOI：10.1021/ja01373a047

  日期：1930.10
• XLII.—The variation of phenol coefficients in homologous series of phenols
  作者：Charles Edward Coulthard、Joseph Marshall、Frank Lee Pyman

  DOI：10.1039/jr9300000280

  日期：——
• SURI, O. P.;BINDRA, R. S.;SATTI, N. K.;KHAJURIA, R. K., INDIAN J. CHEM., 26,(1987) N 6, 587-588
  作者：SURI, O. P.、BINDRA, R. S.、SATTI, N. K.、KHAJURIA, R. K.

  DOI：——

  日期：——
• Suri, O. P.; Bindra, R. S.; Satti, N. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 587 - 588
  作者：Suri, O. P.、Bindra, R. S.、Satti, N. K.、Khajuria, R. K.

  DOI：——

  日期：——
• 3-[[(Aryloxy)alkyl]piperidinyl]-1,2-Benzisoxazoles as D2/5-HT2 Antagonists with Potential Atypical Antipsychotic Activity: Antipsychotic Profile of Iloperidone (HP 873)
  作者：Joseph T. Strupczewski、Kenneth J. Bordeau、Yulin Chiang、Edward J. Glamkowski、Paul G. Conway、Roy Corbett、Harold B. Hartman、Mark R. Szewczak、Carole A. Wilmot、Grover C. Helsley

  DOI：10.1021/jm00007a009

  日期：1995.3

  A series of 3-[[(aryloxy)alkyl]piperidinyl]-1,2-benzisoxazoles was synthesized and evaluated as potential antipsychotic D-2/5-HT2 antagonists. Most of these compounds showed potent antipsychotic-like activity in an apomorphine-induced climbing mouse paradigm, with many also showing preferential mesolimbic activity, as indicated by their weaker effects in an apomorphine-induced stereotypy model. In receptor binding assays, many displayed a moderate affinity for the D-2 receptor coupled with a significantly greater affinity for the 5-HT2 receptor. a property that has been suggested as necessary for atypicality. From this series, compound 45, 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone (iloperidone, HP 873), was further evaluated in a battery of in vivo and in vitro assays. This compound showed a 300-fold greater potency in inhibition of climbing than in inhibition of stereotypy or induction of catalepsy, and when evaluated chronically in an electrophysiological model, 45 caused a depolarization blockade of dopamine neurons in the A10 area of the rat brain but not in the A9 area. Additionally, it showed positive activity in a social interaction paradigm, suggesting potential efficacy;against asociality, a component of the negative symptoms of schizophrenia. In chronic ex vivo studies, 45, similar to clozapine, caused a down regulation of 5-HT2 receptors but had no effect on the number of D-2 receptors. Compound 45 is currently undergoing clinical evaluation.