6-(3,4-dimethoxybenzoyl)cyclohex-3-enecarboxylic acid | 439660-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(3,4-dimethoxybenzoyl)cyclohex-3-enecarboxylic acid
• 英文别名: (4aS,8aR)-2-(3,4-Dimethoxybenzoyl)-1,2,3,6-tetrahydrobenzoic acid；cis-2-(-)-(3,4-Dimethoxybenzoyl)-1,2,3,6-tetrahydrobenzoic acid；6-(3,4-Dimethoxy-benzoyl)-cyclohex-3-enecarboxylic acid；6-(3,4-dimethoxybenzoyl)cyclohex-3-ene-1-carboxylic acid
• CAS: 439660-85-2
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: IVDZZBBOYNNPHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(3,4-dimethoxybenzoyl)cyclohex-3-enecarboxylic acid 在 一水合肼 作用下， 以 乙醇 为溶剂， 以63%的产率得到4-(3,4-dimethoxyphenyl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one
  参考文献：
  名称：

  Stereoselective inhibition of serotonin re-uptake and phosphodiesterase by dual inhibitors as potential agents for depression

  摘要：

  Multi-target compounds where more than one functional activity is incorporated into the same molecule may have advantages in treating disease states. Selective serotonin re-uptake inhibitors (SSRIs)(a) (i.e., (R)- and (S)-norfluoxetine) were chemically linked to a PDE4 inhibitor via a five carbon bridge. The new dual PDE4 inhibitor/SSRIs (i.e., (R)-8 and (S)-8) showed moderately potent but highly selective serotonin re-uptake inhibition (IC50 values of 173 and 42 nM, respectively) in vitro. The dual PDE4 inhibitor/SSRIs (R)-8 and (S)-8 also inhibited PDE4D2 (i.e., K-i values of 106 and 253 nM, respectively). Due to the synergistic functional activity, PDE4 inhibitor/SSRIs may be effective in treating diseases such as depression. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.10.065
• 作为产物：
  描述：

  3,4-Dimethoxyphenylmagnesium bromide 、 cis-1,2,3,6-tetrahydrophthalic anhydride 在 盐酸 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以10%的产率得到6-(3,4-dimethoxybenzoyl)cyclohex-3-enecarboxylic acid
  参考文献：
  名称：

  Stereoselective inhibition of serotonin re-uptake and phosphodiesterase by dual inhibitors as potential agents for depression

  摘要：

  Multi-target compounds where more than one functional activity is incorporated into the same molecule may have advantages in treating disease states. Selective serotonin re-uptake inhibitors (SSRIs)(a) (i.e., (R)- and (S)-norfluoxetine) were chemically linked to a PDE4 inhibitor via a five carbon bridge. The new dual PDE4 inhibitor/SSRIs (i.e., (R)-8 and (S)-8) showed moderately potent but highly selective serotonin re-uptake inhibition (IC50 values of 173 and 42 nM, respectively) in vitro. The dual PDE4 inhibitor/SSRIs (R)-8 and (S)-8 also inhibited PDE4D2 (i.e., K-i values of 106 and 253 nM, respectively). Due to the synergistic functional activity, PDE4 inhibitor/SSRIs may be effective in treating diseases such as depression. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.10.065

文献信息

• [EN] PIPERIDINE-DERIVATIVES AS PDE4 INHIBITORS<br/>[FR] DERIVES DE PIPERIDINE UTILISES COMME INHIBITEURS DE LA PHOSPODIESTERASE-4 (PDE4)
  申请人：ALTANA PHARMA AG

  公开号：WO2004018449A1

  公开（公告）日：2004-03-04

  The compounds of a certain formula (1), in which the given substituents have the meanings as indicated in the description, are novel effective PDE4 inhibitors.

  具有特定化学式（1）的化合物，其中给定的取代基具有描述中所指示的含义，是新颖有效的PDE4抑制剂。
• [EN] PIPERIDINE-PYRIDAZONES AND PHTHALAZONES AS PDE4 INHIBITORS<br/>[FR] PIPERIDINE-PYRIDAZONES ET PHTHALAZONES EN TANT QU'INHIBITEURS DE PDE4
  申请人：ALTANA PHARMA AG

  公开号：WO2004017974A1

  公开（公告）日：2004-03-04

  The compounds of a certain formula 1, in which the given substituents have the meanings as indicated in the description, are novel effective PDE4 inhibitors.

  某种化学式为1的化合物，其中给定的取代基具有描述中所示的含义，是新颖有效的PDE4抑制剂。
• Piperidine-pyridazones and phthalazones as pde4 inhibitors
  申请人：Sterk Geert Jan

  公开号：US20060094710A1

  公开（公告）日：2006-05-04

  The compounds of a certain formula 1, in which the given substituents have the meanings as indicated in the description, are novel effective PDE4 inhibitors.

  某种化学式为1的化合物，其中给定的取代基具有描述中指定的含义，是新颖有效的PDE4抑制剂。
• Phthalatyinone-piperidino-derivatives as pde4 inhibitors
  申请人：——

  公开号：US20040067946A1

  公开（公告）日：2004-04-08

  The compounds of a formula I, in which the given substituents have the meanings as given in the description, are novel effective PDE4 inhibitors. 1

  在化学式I中，给定的取代基具有描述中给出的含义，这些化合物是新颖的有效PDE4抑制剂。
• Compounds effective as beta-2 adrenoreceptor agonists as well pde4-inhibitors
  申请人：——

  公开号：US20030195215A1

  公开（公告）日：2003-10-16

  The compounds of formula I in which Ar 1 , A, R6, R7, R8 and Ar 2 have the meanings as given in the description are novel effective bronchial therapeutics. 1

  式I的化合物中，其中Ar1、A、R6、R7、R8和Ar2的含义如描述所示，是一种新型有效的支气管治疗剂。