Ethyl 6-(2-methoxyphenyl)-4-oxo-4H-pyran-2-carboxylate | 76781-70-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Ethyl 6-(2-methoxyphenyl)-4-oxo-4H-pyran-2-carboxylate
• 英文别名: ethyl 6-(2-methoxyphenyl)-4-oxopyran-2-carboxylate
• CAS: 76781-70-9
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: CJDYKNKPRHBQNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 6-(2-methoxyphenyl)-4-oxo-4H-pyran-2-carboxylate 在 盐酸 、 氨 作用下， 生成 4-hydroxy-6-(2-methoxyphenyl)pyridin-2-carboxylic acid
  参考文献：
  名称：

  Antiallergic agents. 2. N-(1H-Tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides

  摘要：

  A new series of N-(1H-tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides was prepared to determine the effects of substituents on the benzene and pyridine rings on antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) assay after oral administration. One member of this series, N-(1H-tetrazol-5-yl)-4-methyl-6-[4-(methylamino)-phenyl]-2- pyridinecarboxamide (231), has an ED50 value of 0.8 mg/kg po and is 85 times more potent than disodium cromoglycate (DSCG) on intravenous administration. Further evaluation of 231 as a clinically useful antiallergic agent is in progress.

  DOI：

  10.1021/jm00364a026
• 作为产物：
  描述：

  Ethyl 5,6-dibromo-2,4-dioxo-6-(2-methoxyphenyl)-hexanoate 在 potassium acetate 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 生成 Ethyl 6-(2-methoxyphenyl)-4-oxo-4H-pyran-2-carboxylate
  参考文献：
  名称：

  6-Substituted pyranone compounds and their use as pharmaceuticals

  摘要：

  该化合物的结构式为##STR1##其中R.sup.1为COOR.sup.5、CONHR.sup.5、氰基、5-四唑基或R.sup.6，其中R.sup.5为氢或C.sub.1-8烷基，R.sup.6为苯基或萘基，苯基或萘基可以选择性地被一个或多个取代基取代，所述取代基选自卤素、C.sub.1-6烷基、C.sub.1-4烷氧基、羟基、苄氧基、硝基、三氟甲基、羧基、C.sub.1-4烷基磺基、C.sub.1-4烷基磺酰基、N(R.sup.5).sub.2、NHCOR.sup.5和SR.sup.5；R.sup.2为R.sup.6或--CH.dbd.CH--R.sup.6，当R.sup.1为COOR.sup.5、CONHR.sup.5、氰基或5-四唑基时，或者当R.sup.1为R.sup.6时，R.sup.2为--CH.dbd.CH--R.sup.6；R.sup.3为氢、C.sub.1-6烷基、卤素、羟基或--OCH.sub.2 R.sup.6；R.sup.4为氢、C.sub.1-6烷基或卤素；以及它们的盐。这些化合物具有药理特性，特别是在治疗哮喘等即时超敏症状方面具有用途。

  公开号：

  US04304728A1

文献信息

• US4304728A
  申请人：——

  公开号：US4304728A

  公开（公告）日：1981-12-08
• US4448787A
  申请人：——

  公开号：US4448787A

  公开（公告）日：1984-05-15
• US4471129A
  申请人：——

  公开号：US4471129A

  公开（公告）日：1984-09-11
• Antiallergic agents. 2. N-(1H-Tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides
  作者：Yasushi Honma、Kuniyuki Oda、Tomiki Hashiyama、Kyoji Hanamoto、Hideo Nakai、Hirozumi Inoue、Akihiko Ishida、Mikio Takeda、Yasutoshi Ono、Kei Tsuzurahara

  DOI：10.1021/jm00364a026

  日期：1983.10

  A new series of N-(1H-tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides was prepared to determine the effects of substituents on the benzene and pyridine rings on antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) assay after oral administration. One member of this series, N-(1H-tetrazol-5-yl)-4-methyl-6-[4-(methylamino)-phenyl]-2- pyridinecarboxamide (231), has an ED50 value of 0.8 mg/kg po and is 85 times more potent than disodium cromoglycate (DSCG) on intravenous administration. Further evaluation of 231 as a clinically useful antiallergic agent is in progress.
• 6-Substituted pyranone compounds and their use as pharmaceuticals
  申请人：Lilly Industries Limited

  公开号：US04304728A1

  公开（公告）日：1981-12-08

  Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or R.sup.6, where R.sup.5 is hydrogen or C.sub.1-8 alkyl and R.sup.6 is phenyl or naphthyl, the phenyl or naphthyl group being optionally substituted by one or more group selected from halogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy, hydroxy, benzyloxy, nitro, trifluoromethyl, carboxyl, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, N(R.sup.5).sub.2, NHCOR.sup.5 and SR.sup.5 ; R.sup.2 is R.sup.6 or --CH.dbd.CH--R.sup.6 when R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano or 5-tetrazolyl, or R.sup.2 is --CH.dbd.CH--R.sup.6 when R.sup.1 is R.sup.6 ; R.sup.3 is hydrogen, C.sub.1-6 alkyl, halogen, hydroxy or --OCH.sub.2 R.sup.6 ; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. The compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.

  该化合物的结构式为##STR1##其中R.sup.1为COOR.sup.5、CONHR.sup.5、氰基、5-四唑基或R.sup.6，其中R.sup.5为氢或C.sub.1-8烷基，R.sup.6为苯基或萘基，苯基或萘基可以选择性地被一个或多个取代基取代，所述取代基选自卤素、C.sub.1-6烷基、C.sub.1-4烷氧基、羟基、苄氧基、硝基、三氟甲基、羧基、C.sub.1-4烷基磺基、C.sub.1-4烷基磺酰基、N(R.sup.5).sub.2、NHCOR.sup.5和SR.sup.5；R.sup.2为R.sup.6或--CH.dbd.CH--R.sup.6，当R.sup.1为COOR.sup.5、CONHR.sup.5、氰基或5-四唑基时，或者当R.sup.1为R.sup.6时，R.sup.2为--CH.dbd.CH--R.sup.6；R.sup.3为氢、C.sub.1-6烷基、卤素、羟基或--OCH.sub.2 R.sup.6；R.sup.4为氢、C.sub.1-6烷基或卤素；以及它们的盐。这些化合物具有药理特性，特别是在治疗哮喘等即时超敏症状方面具有用途。