3-(4-羟基-5-氧代-3-苯基-2H-呋喃-2-基)丙酸 | 105364-56-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 3-(4-羟基-5-氧代-3-苯基-2H-呋喃-2-基)丙酸
• 英文名称: (+)-WS 3681
• 英文别名: 3-(4-hydroxy-5-oxo-3-phenyl-2H-furan-2-yl)propanoic acid
• CAS: 105364-56-5
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: PPZVSYXNLXFYAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-羟基-5-氧代-3-苯基-2H-呋喃-2-基)丙酸 在 吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 3-hydroxy-5-(3-hydroxypropyl)-4-phenyl-2(5H)-furanone
  参考文献：
  名称：

  Structure and synthesis of WF 3681, a novel aldose reductase inhibitor

  摘要：

  DOI：

  10.1016/s0040-4039(00)84436-6
• 作为产物：
  描述：

  苯丙酮酸 在 盐酸 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 3-(4-羟基-5-氧代-3-苯基-2H-呋喃-2-基)丙酸
  参考文献：
  名称：

  An efficient synthesis of WF-3681, A novel aldose reductase inhibitor, and its related compounds.

  摘要：

  WF-3681（1a）是一种醛糖还原酶抑制剂，其相关化合物（1b-1j）是以苯丙酮酸酯和ω-甲酰基烷酸酯的醛醇缩合为关键步骤合成的。

  DOI：

  10.1248/cpb.35.2594

文献信息

• New furanone derivatives, process for preparation thereof and use thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04585789A1

  公开（公告）日：1986-04-29

  Described are compounds of the formula: ##STR1## Wherein A is a lower alkylene group; R.sup.1 is a carboxy, hydroxy, lower alkoxycarbonyl, lower alkoxycarbonylamino, phenyl(lower)alkyloxy, benzoyloxy or lower alkanoyloxy group; R.sup.2 is a hydrogen or halogen atom or a halo(lower)alkyl group; R.sup.3 is a hydrogen or halogen atom; R.sup.4 is hydroxy, lower alkoxy, lower alkanoyloxy or lower alkoxycarbonyloxy group; and R.sup.5 is a hydrogen or halogen atom; Q is the number of double bonds which is equal to 0 or 1; n is an integer of 0 or 1, provided that when Q is 0, n is 1 and when Q is 1, n is 0.

  描述了以下化合物的结构：##STR1## 其中A是较低的烷基烯基；R.sup.1是羧基、羟基、较低的烷氧羰基、较低的烷氧羰氨基、苯基(较低)烷氧基、苯甲酰氧基或较低的烷酰氧基；R.sup.2是氢原子或卤素原子或卤(较低)烷基基团；R.sup.3是氢原子或卤素原子；R.sup.4是羟基、较低的烷氧基、较低的烷酰氧基或较低的烷氧羰基氧基；R.sup.5是氢原子或卤素原子；Q是双键数，等于0或1；n是0或1的整数，但当Q为0时，n为1，当Q为1时，n为0。
• Synthesis and aldose reductase-inhibitory activities of structural analogues of WF-3681, a novel aldose reductase inhibitor.
  作者：TAKAYUKI NAMIKI、YUKIHISA BABA、YASUTAKA SUZUKI、MOTOAKI NISHIKAWA、KOZO SAWADA、YOSHIKUNI ITOH、TERUO OKU、YOSHIHIKO KITAURA、MASASHI HASHIMOTO

  DOI：10.1248/cpb.36.1404

  日期：——

  Various analogues of WF-3681 (1a), a novel aldose reductase inhibitor, were synthesized and examined for aldose reductase-inhibitory activity. It was found that the carboxylic acid function is necessary and the side-chain length is important for the activity. Furthermore, the lipophilicities of the benzene ring and the enol ether group are significant for increasing the activity.

  合成了多种WF-3681（1a）的类似物，这是一种新型的醛糖还原酶抑制剂，并对其醛糖还原酶抑制活性进行了研究。结果发现，羧酸基团是必要的，侧链长度对活性也很重要。此外，苯环和烯醇醚基团的脂溶性对提高活性具有重要意义。
• Pharmaceutical preparation for prevention and/or treatment for cataract
  申请人：Kikkoman Corporation

  公开号：US05698585A1

  公开（公告）日：1997-12-16

  In order to prevent or treat cataract, present invention features 3(2H)-furanone derivatives having 3(2H)-furanone skeleton as a main structure and/or pharmaceutically acceptable salts thereof, pharmaceutical preparations containing the derivatives and/or the salts thereof, treatment methods of cataract, and their use. The 3(2H)-furanone derivatives have excellent effects for the prevention and/or treatment of cataract, for instance, senile cataract caused by oxidation disorder. Particularly, the pharmaceutical preparations have good effect for the prevention and/or treatment of cataract when they are administrated as ophtalmics.

  为了预防或治疗白内障，本发明涉及具有3(2H)-呋喃酮骨架作为主要结构和/或其药用可接受盐的3(2H)-呋喃酮衍生物，含有这些衍生物和/或其盐的药物制剂，白内障的治疗方法，以及它们的用途。这些3(2H)-呋喃酮衍生物对于预防和/或治疗白内障具有出色的效果，例如由氧化失调引起的老年性白内障。特别是，当这些药物制剂作为眼科用药进行给药时，对于预防和/或治疗白内障有良好效果。
• Furanone derivatives, process for preparation thereof and use thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04797417A1

  公开（公告）日：1989-01-10

  The invention relates to novel furanone derivatives, having an aldose reductase-inhibitory activity, of the formula ##STR1## wherein A is a lower alkylene group, R.sup.1 is a carboxy, hydroxy, protected hydroxy or lower alkoxycarbonyl group, R.sup.2 is a hydrogen or halogen atom or a halo (lower) alkyl group, and R.sup.3 is a hydrogen atom or a hydroxy, carboxy, lower alkoxy or lower alkoxycarbonyl group.

  本发明涉及一种新型呋喃酮衍生物，具有醛糖还原酶抑制活性，其化学式为##STR1##其中A是较低的烷基烃基，R.sup.1是羧基、羟基、保护羟基或较低的烷氧卡波尼基，R.sup.2是氢或卤素原子或卤代（较低）烷基基团，而R.sup.3是氢原子或羟基、羧基、较低的烷氧基或较低的烷氧卡波尼基。
• New furanone derivatives, process for the preparation thereof and use thereof
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0099692A1

  公开（公告）日：1984-02-01

  The present invention provides compounds of the formula:- wherein A is a lower alkylene group; R' is a carboxy, hydroxy, protected hydroxy, lower alkoxycarbonyl, lower alkoxycarbonylamino or lower alkanoyloxy group; R2 is a hydrogen or halogen atom or a halo (lower) - alkyl group; R3 is a hydrogen or halogen atom; R4 is a hydrogen atom or a hydroxy, carboxy, lower alkoxy, lower alkanoyloxy or lower alkoxycarbonyloxy group and R5 is a hydrogen or halogen atom or R4 and R5 together represent the group =CH2; F is the number of double bonds which is equal to 0 or 1 and n is an integer of 0 or 1, with the proviso that when F is 0 then n is 1 and when F is 1 then n is 0; and the pharmaceutically- acceptable salts thereof. The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them. Futhermore, the present invention is concerned with the use of these compounds for the treatment of diabetic cataract and/or neuropathy.

  本发明提供式如下的化合物 其中 A 是低级亚烷基；R'是羧基、羟基、保护羟基、低级烷氧基羰基、低级烷氧基羰基氨基或低级烷酰氧基；R2 是氢原子或卤素原子或卤代（低级）-烷基；R3 是氢原子或卤素原子；R4是氢原子或羟基、羧基、低级烷氧基、低级烷酰氧基或低级烷氧基羰基，R5是氢原子或卤素原子或R4和R5共同代表基团＝CH2；F是双键的数目，等于0或1，n是0或1的整数，但当F为0时，n为1，当F为1时，n为0；及其药学上可接受的盐。 本发明还提供了制备这些化合物和含有这些化合物的药物组合物的工艺。此外，本发明还涉及使用这些化合物治疗糖尿病性白内障和/或神经病变。