2-(3,4-dimethoxybenzoyl)cyclohexanecarboxylic acid | 439660-78-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3,4-dimethoxybenzoyl)cyclohexanecarboxylic acid
• 英文别名: 2-[1-(3,4-dimethoxy-phenyl)-methanoyl]-cyclohexanecarboxylic acid；2-(3,4-Dimethoxybenzoyl)[cis]cyclohexanecarboxylic acid；2-(3,4-Dimethoxy-benzoyl)-cyclohexanecarboxylic acid；2-(3,4-dimethoxybenzoyl)cyclohexane-1-carboxylic acid
• CAS: 439660-78-3
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: SUBXEIQUVGKQGF-UHFFFAOYSA-N

物化性质

• 沸点：
  475.1±45.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-(3,4-dimethoxybenzoyl)cyclohexanecarboxylic acid 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.67h， 生成 2-(2-bromobutyl)-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one
  参考文献：
  名称：

  Design, synthesis and evaluation of dual pharmacology β2-adrenoceptor agonists and PDE4 inhibitors

  摘要：

  A novel series of formoterol-phthalazinone hybrids were synthesised and evaluated as dual pharmacology beta(2)-adrenoceptor agonists and PDE4 inhibitors. Most of the hybrids displayed high beta(2)-adrenoceptor agonist and moderate PDE4 inhibitory activities. The most potent compound, (R, R)-11c, exhibited agonist (EC50 = 1.05 nM, pEC(50) = 9.0) and potent PDE4B2 inhibitory activities (IC50 = 0.092 mu M). (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.11.028
• 作为产物：
  描述：

  邻苯二甲醚 、 六氢苯酐 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(3,4-dimethoxybenzoyl)cyclohexanecarboxylic acid
  参考文献：
  名称：

  Dual β2-adrenoceptor agonists-PDE4 inhibitors for the treatment of asthma and COPD

  摘要：

  We designed and synthesized a novel class of dual pharmacology bronchodilators targeting both beta 2-adrenoceptor and PDE4 by applying a multivalent approach. The most potent dual pharmacology molecule, compound 29, possessed good inhibitory activity on PDE4B2 (IC50 = 0.278 mu M, which was more potent than phthalazinone, IC50 = 0.520 mu M) and possessed excellent relaxant effects on tracheal rings precontracted by histamine (pEC(50) = 9.3). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.013

文献信息

• [EN] PHTHALAZINONE-DERIVATIVES AS PDE4 INHIBITORS<br/>[FR] DERIVES DE PHTALAZINONE UTILISES EN TANT QU'INHIBITEURS DE PDE4
  申请人：ALTANA PHARMA AG

  公开号：WO2005075457A1

  公开（公告）日：2005-08-18

  The compounds of a certain formula (1), in which R1, R2, R3, R9 and n have the meanings as given in the description, are novel effective PDE4 inhibitors.

  某种化学式（1）的化合物，其中R1、R2、R3、R9和n的含义如描述中所示，是新型有效的PDE4抑制剂。
• [EN] PIPERIDINE-N-OXIDE-DERIVATIVES<br/>[FR] DERIVES DE N-OXYDE DE PIPERIDINE
  申请人：ALTANA PHARMA AG

  公开号：WO2004018450A1

  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指示的含义，是新颖有效的PDE4抑制剂。
• Phthalazinones
  申请人：Byk Gulden Lomberg Chemische Fabrik GmbH

  公开号：US06103718A1

  公开（公告）日：2000-08-15

  Compounds of formula I wherein R1, R2, R3, R4 and R5 have the means set forth in the description are selective cyclic nucleotide phosphodiesterase (PDE) inhibitors (specifically of type 4), which are effective bronchial therapeutics.

  式I中的化合物，其中R1、R2、R3、R4和R5具有描述中所述的平均值，是选择性环核苷酸磷酸二酯酶（特别是类型4）抑制剂，对支气管治疗具有有效作用。
• Piperidine-n-oxide-derivatives
  申请人：Sterk Jan Geert

  公开号：US20060166995A1

  公开（公告）日：2006-07-27

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

  某一公式（1）的化合物，其中给定的取代基具有描述中所给的含义，是新颖有效的PDE4抑制剂。
• PHTHALAZINONE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：Kagayama Kohei

  公开号：US20090042879A1

  公开（公告）日：2009-02-12

  The present invention provides a novel compound having an excellent PDE4 inhibitory activity and TNF-α production-suppressing activity, and also provides a preventive and therapeutic agent for atopic dermatitis or the like. The present invention includes a novel phthalazinone derivative of the following general structural formula [1] or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising it as an active ingredient. In the structural formula [1], the partial structure bridging the 6-position and the 7-position represents a single bond or a double bond; R 1 and R 2 are the same or different and each represents alkyl or the like; Y represents phenylene or the like; Z represents alkylene or the like; and R 3 represents a mono- to tri-cyclic saturated or unsaturated cyclic amino group or the like optionally substituted with R 31 and R 32 , wherein R 31 and R 32 represent alkyl or the like.

  本发明提供了一种具有优异的PDE4抑制活性和TNF-α产生抑制活性的新型化合物，同时还提供了预防和治疗特应性皮炎或类似疾病的药物。本发明包括以下一般结构式[1]的新型邻苯二酮衍生物或其药学上可接受的盐，以及包含其作为活性成分的制药组合物。在结构式[1]中，连接6位和7位的部分结构代表单键或双键；R1和R2相同或不同，分别代表烷基或类似物；Y代表苯撑基或类似物；Z代表烷基或类似物；R3代表单环至三环饱和或不饱和环状氨基或类似物，可选地被R31和R32取代，其中R31和R32代表烷基或类似物。