3-[4-Hydroxy-5-oxo-3-(3-trifluoromethyl-phenyl)-2,5-dihydro-furan-2-yl]-propionic acid | 90055-39-3

• 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: 3-[4-Hydroxy-5-oxo-3-(3-trifluoromethyl-phenyl)-2,5-dihydro-furan-2-yl]-propionic acid
• 英文别名: 3-[4-hydroxy-5-oxo-3-[3-(trifluoromethyl)phenyl]-2H-furan-2-yl]propanoic acid
• CAS: 90055-39-3
• 化学式: C₁₄H₁₁F₃O₅
• 分子量: 316.234
• InChiKey: UNXMDEUJVLEOMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-[4-Hydroxy-5-oxo-3-(3-trifluoromethyl-phenyl)-2,5-dihydro-furan-2-yl]-propionic acid ethyl ester 在 盐酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.0h， 以89%的产率得到3-[4-Hydroxy-5-oxo-3-(3-trifluoromethyl-phenyl)-2,5-dihydro-furan-2-yl]-propionic acid
  参考文献：
  名称：

  Synthesis and aldose reductase-inhibitory activities of structural analogues of WF-3681, a novel aldose reductase inhibitor.

  摘要：

  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。

  DOI：

  10.1248/cpb.36.1404

文献信息

• 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。
• New furanone derivatives, processes for preparation thereof and use thereof
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0189272A2

  公开（公告）日：1986-07-30

  The present invention provides compounds of the general formula: wherein R1 is a hydroxyl or protected hydroxyl group or a carboxyl group or a lower alkoxycarbonyl or benzyloxy radical, R2 is a hydrogen or halogen atom or a halo(lower)alkyl radical, R3 is a hydrogen atom, a hydroxyl group or a lower alkoxy radical and A is a lower alkylene radical; and the pharmaceutically acceptable salts thereof. The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them and is also concerned with the use thereof.

  本发明提供通式如下的化合物：其中 R1 是羟基或受保护羟基或羧基或低级烷氧基羰基或苄氧基基团，R2 是氢原子或卤素原子或卤代（低级）烷基基团，R3 是氢原子、羟基或低级烷氧基基团，A 是低级亚烷基基团；以及它们的药学上可接受的盐；本发明还提供制备这些化合物和含有它们的药物组合物的工艺，并涉及它们的用途。
• NAMIKI, TAKAYUKI;BABA, YUKIHISA;SUZUKI, YASUTAKA;NISHIKAWA, MOTOAKI;SAWAD+, CHEM. AND PHARM. BULL, 36,(1988) N 4, C. 1404-1414
  作者：NAMIKI, TAKAYUKI、BABA, YUKIHISA、SUZUKI, YASUTAKA、NISHIKAWA, MOTOAKI、SAWAD+

  DOI：——

  日期：——
• US4585789A
  申请人：——

  公开号：US4585789A

  公开（公告）日：1986-04-29
• 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。