7-(1,3-Benzodioxol-5-yl)-7-pyridin-3-ylhept-6-enoic acid | 89667-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 7-(1,3-Benzodioxol-5-yl)-7-pyridin-3-ylhept-6-enoic acid
• CAS: 89667-54-9
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: CYUMKTIXQHGAKU-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C
• 沸点：
  536.6±39.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (5-羧基戊基)三苯基溴化磷 、 3,4-(methylenedioxy)phenyl 3-pyridyl ketone 在 sodium hydride 作用下， 生成 (Z)-7-Benzo[1,3]dioxol-5-yl-7-pyridin-3-yl-hept-6-enoic acid 、 7-(1,3-Benzodioxol-5-yl)-7-pyridin-3-ylhept-6-enoic acid
  参考文献：
  名称：

  Thromboxane synthetase inhibitors (TXSI). Design, synthesis, and evaluation of a novel series of .omega.-pyridylalkenoic acids

  摘要：

  A novel series of omega-pyridylalkenoic acids has been prepared by applying the Wittig reaction. Modifications were made in the omega-aryl moiety, the alkylene chain length, the alpha-methylene group adjacent to the carbonyl group, and the carboxyl group of the molecule. The compounds were tested as inhibitors of thromboxane synthetase in an in vitro assay and in ex vivo experiments with the rat. Most members of this new class of thromboxane synthetase inhibitors (TXSI) showed good activity in both assay systems. (E)-7-Phenyl-7-(3-pyridyl)-6-heptenoic acid (9c; CV-4151) was one of the most potent compounds in in vitro enzyme inhibition (IC50 = 2.6 X 10(-8) M) and, when orally administered, the most potent and long acting in the inhibition of blood thromboxane A2 production in the rat. New conceptual models I-III for the enzyme-substrate (prostaglandin H2, PGH2) and the enzyme-TXSI interactions are proposed for understanding the molecular design and structure-activity relations.

  DOI：

  10.1021/jm00381a005

文献信息

• Process for producing substituted vinyl pyridines
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0337640A1

  公开（公告）日：1989-10-18

  An improved process for producing a substituted vinyl pyridine compound of the general formula: wherein R¹ is pyridyl group; R² is an optionally substituted aromatic or heterocyclic group; R³ is a lower alkyl group, hydroxymethyl group, nitroxymethyl group, a nitrogen containing 5 membered ring-methyl group, an acetal-methyl group, a trialkylsilyloxymethyl group, an alkyl- or aryl­sulfonyloxymethyl group, an alkyl- or aryl-sulfonylamino­carbonyloxymethyl group, an acyloxymethyl group, an alkoxycarbonyloxymethyl group, a halogenomethyl group, an alkoxymethyl group, an aryl-oxymethyl group, cyano group, an optionally substituted carbamoyl group, an optionally substituted carbamoyloxymethyl group, an optionally substituted thiocarbamoyloxymethyl group, carboxyl group or an alkoxycarbonyl group; and n is an integer of 1 to 22, which comprises reacting a compound of the general formula: wherein R¹ and R² are as defined above, with a compound of the general formula: (C₆H₅)₃P⁺-CH₂CH₂R³·X⁻ wherein R³ is as defined above and X is a halogen atom, in a tertiary alcohol in the presence of a metallic hydride or a tertiary alkoxide of an alkali metal.

  一种生产通式为取代乙烯基吡啶化合物的改进工艺： 其中R¹是吡啶基；R²是任选取代的芳香族或杂环基团；R³是低级烷基、羟甲基、硝基、含氮五元环甲基、缩醛甲基、三烷基硅氧基甲基、烷基或芳基磺酰氧基甲基、烷基或芳基磺酰氨基羰基氧基甲基、酰氧基甲基、卤代甲基、烷氧基甲基、芳基氧基甲基、氰基、任选取代的氨基甲酰基、任选取代的氨基甲酰氧基甲基、任选取代的硫代氨基甲酰氧基甲基、羧基或烷氧基羰基；和 n 是 1 至 22 的整数，其中包括使通式如下的化合物发生反应： 其中 R¹ 和 R² 如上定义，与通式化合物反应： (c₆h₅)₃p⁺-ch₂ch₂r³-x- 其中 R³ 如上定义，X 为卤素原子。
• Vinyl carboxylic acid derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0098690B1

  公开（公告）日：1987-09-09
• US4727078A
  申请人：——

  公开号：US4727078A

  公开（公告）日：1988-02-23
• US4760068A
  申请人：——

  公开号：US4760068A

  公开（公告）日：1988-07-26
• Thromboxane synthetase inhibitors (TXSI). Design, synthesis, and evaluation of a novel series of .omega.-pyridylalkenoic acids
  作者：Kaneyoshi Kato、Shigenori Ohkawa、Shinji Terao、Zenichi Terashita、Kohei Nishikawa

  DOI：10.1021/jm00381a005

  日期：1985.3

  A novel series of omega-pyridylalkenoic acids has been prepared by applying the Wittig reaction. Modifications were made in the omega-aryl moiety, the alkylene chain length, the alpha-methylene group adjacent to the carbonyl group, and the carboxyl group of the molecule. The compounds were tested as inhibitors of thromboxane synthetase in an in vitro assay and in ex vivo experiments with the rat. Most members of this new class of thromboxane synthetase inhibitors (TXSI) showed good activity in both assay systems. (E)-7-Phenyl-7-(3-pyridyl)-6-heptenoic acid (9c; CV-4151) was one of the most potent compounds in in vitro enzyme inhibition (IC50 = 2.6 X 10(-8) M) and, when orally administered, the most potent and long acting in the inhibition of blood thromboxane A2 production in the rat. New conceptual models I-III for the enzyme-substrate (prostaglandin H2, PGH2) and the enzyme-TXSI interactions are proposed for understanding the molecular design and structure-activity relations.