(5-carboxy-5-phenylpentyl)triphenylphosphonium bromide | 93943-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5-carboxy-5-phenylpentyl)triphenylphosphonium bromide
• 英文别名: 5-carboxy-5-phenylpentyltriphenylphosphonium bromide；5carboxy-5-phenylpentyltriphenylphosphonium bromide；5-Carboxy-5-phenylpentyltriphenylphosphonium bromide；(5-carboxy-5-phenylpentyl)-triphenylphosphanium;bromide
• CAS: 93943-68-1
• 化学式: Br*C₃₀H₃₀O₂P
• 分子量: 533.445
• InChiKey: AVRIVCUNRSJYAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-吡啶基(2-噻吩基)甲酮 、 (5-carboxy-5-phenylpentyl)triphenylphosphonium bromide 在 sodium hydride 作用下， 生成 2-phenyl-7-pyridin-3-yl-7-thiophen-2-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
• 作为产物：
  描述：

  6-bromo-2-phenylhexanoic acid 、 三苯基膦 在 甲苯 、 乙酸乙酯 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以to give 5-carboxy-5-phenylpentyltriphenylphosphonium bromide (21 g, 67%, m.p. 210°-215° C.)的产率得到(5-carboxy-5-phenylpentyl)triphenylphosphonium bromide
  参考文献：
  名称：

  Vinyl carboxylic acid derivatives, their production and use as

  摘要：

  化合物的式子：##STR1## 其中R.sup.1是吡啶基；R.sup.2是苯基，噻吩基，呋喃基，萘基，苯并噻吩基或吡啶基，可以有较低的烷氧基，较低的烷基，卤素，三氟甲基，较低的烯基或亚甲氧基作为取代基；R.sup.3是氢，苄基或较低的烷基；R.sup.4和R.sup.5中的一个是氢或较低的烷基，另一个是芳氧基，或较低的脂肪烃，或不超过6个碳原子的脂环烃或含取代基的芳基，或由公式--S(O).sub.m--R.sup.6（其中R.sup.6是苯基或较低的烷基；m是0至2的整数）表示的基团，或R.sup.4和R.sup.5结合成一个脂肪基；n是2至6的整数，或其药学上可接受的盐具有对生物合成血栓素A.sub.2（TXA.sub.2）的选择性抑制作用和增强前列腺素I.sub.2（PGI.sub.2）生产的效果，并可用于哺乳动物的预防和治疗因血小板聚集引起的动脉血栓形成或因心脏，脑和周围循环系统的血管痉挛引起的缺血性疾病（例如心肌梗塞，中风，肾脏，肺和其他器官的血管梗塞，消化性溃疡等）。

  公开号：

  US04518602A1

文献信息

• Vinyl carboxylic acid derivatives, their production and use as
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04518602A1

  公开（公告）日：1985-05-21

  Novel compound of the formula: ##STR1## wherein R.sup.1 is a pyridyl group; R.sup.2 is a phenyl, thienyl, furyl, naphthyl, benzothienyl or pyridyl group which may have as a substituent a lower alkoxy, a lower alkyl, a halogen, trifluoromethyl, a lower alkenyl or methylenedioxy; R.sup.3 is hydrogen, benzyl or a lower alkyl; one of R.sup.4 and R.sup.5 is hydrogen or a lower alkyl, and the other is an aryloxy, or lower aliphatic hydrocarbon, an alicyclic hydrocarbon having not more than 6 carbon atoms or an aromatic group which may have a substituent, or a group represented by the formula, --S(O).sub.m --R.sup.6 (in which R.sup.6 is phenyl or a lower alkyl group; m is an integer of 0 to 2), or R.sup.4 and R.sup.5 each combine with the other to represent one alkylene group; n is an integer of 2 to 6, or a pharmaceutically acceptable salt thereof has a selective inhibitory action on bio-synthesis of thromboxane A.sub.2 (TXA.sub.2) and an effect of enhancing the production of prostaglandin I.sub.2 (PGI.sub.2), and can be used in mammals for to prevention and treatment of arterial thrombosis caused by platelet aggregation or ischemic diseases caused by vasospasms in cardiac, cerebral and peripheral circulatory system (e.g. cardian infarction, apoplexy, infarct of blood vessels in kidney, lung and other organs, pectic ulcer, etc.).

  化合物的式子：##STR1## 其中R.sup.1是吡啶基；R.sup.2是苯基，噻吩基，呋喃基，萘基，苯并噻吩基或吡啶基，可以有较低的烷氧基，较低的烷基，卤素，三氟甲基，较低的烯基或亚甲氧基作为取代基；R.sup.3是氢，苄基或较低的烷基；R.sup.4和R.sup.5中的一个是氢或较低的烷基，另一个是芳氧基，或较低的脂肪烃，或不超过6个碳原子的脂环烃或含取代基的芳基，或由公式--S(O).sub.m--R.sup.6（其中R.sup.6是苯基或较低的烷基；m是0至2的整数）表示的基团，或R.sup.4和R.sup.5结合成一个脂肪基；n是2至6的整数，或其药学上可接受的盐具有对生物合成血栓素A.sub.2（TXA.sub.2）的选择性抑制作用和增强前列腺素I.sub.2（PGI.sub.2）生产的效果，并可用于哺乳动物的预防和治疗因血小板聚集引起的动脉血栓形成或因心脏，脑和周围循环系统的血管痉挛引起的缺血性疾病（例如心肌梗塞，中风，肾脏，肺和其他器官的血管梗塞，消化性溃疡等）。
• Vinyl carboxylic acid derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0111997B1

  公开（公告）日：1991-04-10
• US4518602A
  申请人：——

  公开号：US4518602A

  公开（公告）日：1985-05-21
• 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.