(E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid | 144562-61-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid
• 英文别名: (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenic acid；(E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(3-pyridyl)pentyl]-2-propenoic acid；(E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(3-pyridyl)pentyl]-2-propenic acid；(2E)-2-[(4-methoxy-2,5-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylidene]-7-pyridin-3-ylheptanoic acid
• CAS: 144562-61-8
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: WWYFKRSBSWBEGV-SFQUDFHCSA-N

物化性质

• 沸点：
  601.8±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid 在 sodium disulfite 作用下， 以 水 、 乙酸乙酯 为溶剂， 以66%的产率得到(E)-3-(2,5-Dihydroxy-4-methoxy-3,6-dimethylphenyl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid
  参考文献：
  名称：

  Structure−Activity Relationships of (E)-3-(1,4-Benzoquinonyl)-2-[(3-pyridyl)- alkyl]-2-propenoic Acid Derivatives That Inhibit Both 5-Lipoxygenase and Thromboxane A₂ Synthetase

  摘要：

  As part of our research for the development of novel antiinflammatory drug candidates, we have designed and synthesized a series of (E)-3-(1,4-benzoquinonyl)-2-[(3-pyridyl)alkyl]-2-propenoic acid derivatives as dual inhibitors of 5-lipoxygenase (5-LO) and thromboxane (TX) A(2) synthetase. In order to increase the absorption after oral administration, we introduced a carboxylic acid moiety into the 1,4-benzoquinone skeleton, which has 5-LO-inhibitory character. Introduction of a 3-pyridylalkyl group at the double bond of the 1,4-benzoquinonyl propenoic acid moiety afforded good to moderate inhibitory activities against the production of leukotriene (LT) Bq and TXA(2) while not significantly inhibiting that of prostaglandin E(2) by glycogen-induced peritoneal cells of rat (in vitro). The length of the methylene chain of the 3-pyridylalkyl group influenced the inhibition of LTB(4) and TXB(2) production. An increase of lipophilicity by introducing a more lipophilic alkoxy group did not markedly increase the inhibitory activity on LTB(4) production. The position of an alkoxy group on the 1,4-benzoquinone skeleton played an important role in TXA(2) synthetase inhibition. Compounds such as 20c (E6700) with an appropriate alkoxy group and proper length of methylene side chain, together with a polar substituent (carboxylic acid), showed good inhibition of both 5-LO and TXA(2) synthetase and possess a variety of pharmacologically beneficial effects.

  DOI：

  10.1021/jm950725r
• 作为产物：
  描述：

  (E)-3-(2,4,5-Trimethoxy-3,6-dimethylphenyl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以74%的产率得到(E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid
  参考文献：
  名称：

  Structure−Activity Relationships of (E)-3-(1,4-Benzoquinonyl)-2-[(3-pyridyl)- alkyl]-2-propenoic Acid Derivatives That Inhibit Both 5-Lipoxygenase and Thromboxane A₂ Synthetase

  摘要：

  As part of our research for the development of novel antiinflammatory drug candidates, we have designed and synthesized a series of (E)-3-(1,4-benzoquinonyl)-2-[(3-pyridyl)alkyl]-2-propenoic acid derivatives as dual inhibitors of 5-lipoxygenase (5-LO) and thromboxane (TX) A(2) synthetase. In order to increase the absorption after oral administration, we introduced a carboxylic acid moiety into the 1,4-benzoquinone skeleton, which has 5-LO-inhibitory character. Introduction of a 3-pyridylalkyl group at the double bond of the 1,4-benzoquinonyl propenoic acid moiety afforded good to moderate inhibitory activities against the production of leukotriene (LT) Bq and TXA(2) while not significantly inhibiting that of prostaglandin E(2) by glycogen-induced peritoneal cells of rat (in vitro). The length of the methylene chain of the 3-pyridylalkyl group influenced the inhibition of LTB(4) and TXB(2) production. An increase of lipophilicity by introducing a more lipophilic alkoxy group did not markedly increase the inhibitory activity on LTB(4) production. The position of an alkoxy group on the 1,4-benzoquinone skeleton played an important role in TXA(2) synthetase inhibition. Compounds such as 20c (E6700) with an appropriate alkoxy group and proper length of methylene side chain, together with a polar substituent (carboxylic acid), showed good inhibition of both 5-LO and TXA(2) synthetase and possess a variety of pharmacologically beneficial effects.

  DOI：

  10.1021/jm950725r

文献信息

• Quinone derivatives
  申请人：Eisai Co., Ltd.

  公开号：US05329010A1

  公开（公告）日：1994-07-12

  The present invention is a quinone derivative which exhibits excellent therapeutic activity represented by the general formula (I) or a pharmacologically acceptable salt thereof: ##STR1## wherein A stands for a group represented by the formula: ##STR2## (wherein R.sup.3, R.sup.4 and R.sup.5 is the same or different from each other and each stand for a hydrogen atom, a hydroxyl group, a lower alkyl group, a lower alkoxy group, an alkoxyalkyl group, an alkoxyalkoxy group, a cycloalkylalkoxy group, a thiol group or a thioalkyl group, with the proviso that R.sup.3 and R.sup.4 are each a lower alkoxy group R.sup.1 stands for a heteroarylalkyl group; and B stands for a carboxyl group or a protected carboxyl group.

  本发明涉及一种喹酮衍生物，其具有优异的治疗活性，其通式（I）或其药理学上可接受的盐表示为：##STR1##其中A代表由以下公式表示的基团：##STR2##（其中R.sup.3，R.sup.4和R.sup.5相同或不同，分别代表氢原子，羟基，低碳基，低烷氧基，烷氧基烷基，烷氧基烷氧基，环烷烷氧基，硫醇基或硫代烷基，但R.sup.3和R.sup.4分别为低烷氧基；R.sup.1代表杂环烷基烷基；B代表羧基或保护羧基。
• AGENT FOR PREVENTION AND DEPRESSION OF DRY COUGHING CAUSED BY ANGIOTENSIN CONVERTING ENZYME INHIBITORS
  申请人：KISSEI PHARMACEUTICAL CO., LTD.

  公开号：EP0875254A1

  公开（公告）日：1998-11-04

  The present invention is to provide an agent for the prevention and depression of dry coughing caused by angiotensin converting enzyme inhibitors which comprises a thromboxane synthetase inhibitor or thromboxane receptor antagonist as the active ingredient. Administering the drug is effective in preventing and depressing dry coughing caused by angiotensin converting enzyme inhibitors. For example, the use of the drug in combination with ozagrel hydrochloride was found to be effective in significantly dry coughing in hypertonic patients suffering from dry coughing attributable to the administration of captopril.

  本发明旨在提供一种预防和抑制由血管紧张素转换酶抑制剂引起的干咳的药物，其活性成分包括血栓素合成酶抑制剂或血栓素受体拮抗剂。服用该药物可有效预防和抑制血管紧张素转换酶抑制剂引起的干咳。例如，对于因服用卡托普利而引起干咳的高渗患者，将该药物与盐酸奥扎格雷联合使用可有效明显缓解干咳。
• MEDICINAL COMPOSITIONS
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1161956A1

  公开（公告）日：2001-12-12

  The present invention relates to a granular pharmaceutical composition comprising a drug having a disagreeable taste, a wax and a sugar alcohol; a method for preparing the same; and a pharmaceutical product for oral administration, comprising the granular composition. The product excellently masks a disagreeable taste possessed by a drug and provides good sensation upon oral administration, and therefore is easily ingested by even the elderly, children, and patients suffering dysphagia. Moreover, the product is suitable for administration using tube.

  本发明涉及一种颗粒状药物组合物，该组合物由具有异味的药物、蜡和糖醇组成；一种制备该组合物的方法；以及一种包含该颗粒状组合物的口服药物。该产品能很好地掩盖药物的异味，并在口服时提供良好的感觉，因此即使是老人、儿童和吞咽困难患者也很容易摄入。此外，该产品还适合使用软管给药。
• JPH07330605A
  申请人：——

  公开号：JPH07330605A

  公开（公告）日：1995-12-19
• JPH0733739A
  申请人：——

  公开号：JPH0733739A

  公开（公告）日：1995-02-03