(4R,S)-2,3-dihydro-6-fluoro-2(R)-methylspiro<4H-benzopyran-4,4'-2'-phenyloxazolidin>-5'-one | 1134785-09-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4R,S)-2,3-dihydro-6-fluoro-2(R)-methylspiro<4H-benzopyran-4,4'-2'-phenyloxazolidin>-5'-one
• 英文别名: 2,3-dihydro-6-fluoro-2(R)-methyl-2'-phenylspiro[4H-benzopyran-4,4'-oxazolidin]-5'-one；6-fluoro-2(R)-methylspiro[chroman-4,4'-phenylaxazolidine-5'-one]；(4R,S)-2,3-dihydro-6-fluoro-2(R)-methylspiro(4H-benzopyran-4,4'-2'-phenyloxazolidin)-5'-one；(2'R)-6'-fluoro-2'-methyl-2-phenylspiro[1,3-oxazole-4,4'-2,3-dihydrochromene]-5-one
• CAS: 1134785-09-3
• 化学式: C₁₈H₁₄FNO₃
• 分子量: 311.312
• InChiKey: SDQFSBSOAXXHHL-SSJGJQFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,S)-2,3-dihydro-6-fluoro-2(R)-methylspiro<4H-benzopyran-4,4'-2'-phenyloxazolidin>-5'-one 在 氯化亚砜 、 α-chymotrypsin 作用下， 以 盐酸 、 甲醇 、 水 、 溶剂黄146 、 sodium chloride 为溶剂， 反应 87.0h， 生成 (2R,4S)-6-氟-2-甲基螺[色满-4,5'-咪唑烷]-2',4'-二酮
  参考文献：
  名称：

  Novel synthesis of the aldose reductase inhibitor sorbinil via amidoalkylation, intramolecular oxazolidin-5-one alkylation and chymotrypsin resolution

  摘要：

  DOI：

  10.1021/jo00392a017
• 作为产物：
  描述：

  (R)-2-(4-fluorophenoxy)propanol 在 甲烷磺酸 、 溴 、 乙酸酐 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 20.0h， 生成 (4R,S)-2,3-dihydro-6-fluoro-2(R)-methylspiro<4H-benzopyran-4,4'-2'-phenyloxazolidin>-5'-one
  参考文献：
  名称：

  Novel synthesis of the aldose reductase inhibitor sorbinil via amidoalkylation, intramolecular oxazolidin-5-one alkylation and chymotrypsin resolution

  摘要：

  DOI：

  10.1021/jo00392a017

文献信息

• [EN] TOPICAL TREATMENT OF CATARACTS IN DOGS<br/>[FR] TRAITEMENT TOPIQUE DE LA CATARACTE CHEZ LES CHIENS
  申请人：KADOR PETER F

  公开号：WO2010065024A1

  公开（公告）日：2010-06-10

  The topical treatment of cataracts in dogs is a composition having an aldose reductase inhibitor (ARI) in a topical carrier. The ARI is preferably 2R,4S-6-fluoro-2-methyl-spiro[chroman-4,4'-imidazolidine]-2',5'-dione, referred to as 2R-methyl sorbinil. The topical carrier is formed from EDTA and deionized water containing about 2.5% carbomer, 1.5% glycerin, 0.02% EDTA and 0.1% benzalkonium chloride mixed to form a uniform emulsion. The concentration of the ARI in the topical carrier is preferably about 5-6%. The treatment includes administering to a dog an effective amount of the composition for preventing the formation of cataracts, reversing the formation of cataracts, and for treating diabetic retinopathy and pathological conditions resulting from diabetes affecting the cornea, iris, ciliary bodies, etc. The composition is preferably administered in the form of about two to four eye drops daily.

  翻译结果如下： 犬白内障的局部治疗是一种具有醛糖还原酶抑制剂（ARI）的局部载体的组合物。 ARI 最好是 2R，4S-6-氟-2-甲基-螺[色酮-4,4'-咪唑啉]-2'，5'-二酮，称为 2R-甲基索比林。局部载体由 EDTA 和去离子水形成，含约 2.5％ 的卡波姆，1.5％ 的甘油，0.02％ 的 EDTA 和 0.1％ 的苯扎氯铵混合形成均匀乳液。 ARI 在局部载体中的浓度最好约为5-6％。治疗包括向犬中投与有效量的该组合物，以预防白内障的形成，逆转白内障的形成，并治疗糖尿病视网膜病变和糖尿病影响角膜，虹膜，睫状体等的病理情况。该组合物最好以每日约两到四滴眼药水的形式投与。
• Spectral assignments for the aldose reductase inhibitor 4(S)-2,3-dihydro-6-fluoro-2(R)-methylspiro[chroman-4,4′-imidazoline]-2′,5′-dione and its synthetic intermediates
  作者：Mingan Wang、Manoj K. Mishra、Wenjun Zhu、Peter F. Kador

  DOI：10.1002/mrc.1697

  日期：2005.12

  The 1H and 13C NMR chemical shifts of the aldose reductase inhibitor 4(S)‐2,3‐dihydro‐6‐fluoro‐2(R)‐methylspiro[chroman‐4,4′‐imidazoline]‐2′,5′‐dione, methylsorbinil, and its seven synthetic intermediates, have been completely assigned on the basis of DEPT, COSY, g‐HSQC and g‐HMBC. All CF coupling constants from one‐bond to four‐bond in the 13C NMR spectra and HF and HH coupling constants from three‐bond

  醛糖还原酶抑制剂 4(S)-2,3-dihydro-6-fluoro-2(R)-methylspiro[chroman-4,4'-imidazoline]-2',5'-的 1H 和 13C NMR 化学位移二酮、甲基山梨醇及其七种合成中间体已完全基于 DEPT、COSY、g-HSQC 和 g-HMBC 进行分配。获得了13C NMR光谱中从单键到四键的所有CF耦合常数以及1H光谱中从三键到四键的HF和HH耦合常数。版权所有 © 2005 John Wiley & Sons, Ltd.
• Topical treatment of cataracts in dogs
  申请人：Kador Peter F.

  公开号：US20090082415A1

  公开（公告）日：2009-03-26

  The topical treatment of cataracts in dogs is a composition having an aldose reductase inhibitor (ARI) in a topical carrier. The ARI is preferably 2R,4S-6-fluoro-2-methyl-spiro[chroman-4,4′-imidazolidine]-2′,5′-dione, referred to as 2R-methyl sorbinil, having the structure: The topical carrier is formed from EDTA and deionized water containing about 2.5% carbomer, 1.5% glycerin, 0.02% EDTA and 0.1% benzalkonium chloride mixed to form a uniform emulsion. The concentration of the ARI in the topical carrier is preferably about 5-6%. The treatment includes administering to a dog an effective amount of the composition for preventing the formation of cataracts, reversing the formation of cataracts, and for treating diabetic retinopathy and pathological conditions resulting from diabetes affecting the cornea, iris, ciliary bodies, etc. The composition is preferably administered in the form of about two to four eye drops daily.

  犬类白内障的局部治疗是一种具有醛糖还原酶抑制剂（ARI）的局部载体组成的药物。 ARI 最好是 2R,4S-6-氟-2-甲基-螺[色酮-4,4'-咪唑啉]-2',5'-二酮，称为 2R-甲基索比林，其结构式为：局部载体由 EDTA 和去离子水组成，含有约2.5％的卡波姆，1.5％的甘油，0.02％的 EDTA 和 0.1％苯扎氯铵混合形成均匀乳液。在局部载体中的 ARI 浓度最好约为5-6％。治疗包括向犬类施用有效量的该组成物，以预防白内障的形成，逆转白内障的形成，并治疗糖尿病视网膜病变和由糖尿病影响角膜，虹膜，睫状体等的病理情况。该组成物最好以每天约两到四滴眼药水的形式施用。
• URBAN, FRANK J.
  作者：URBAN, FRANK J.

  DOI：——

  日期：——
• DIRLAM, NANCY L.;MOORE, B. S.;URBAN, F. J., J. ORG. CHEM., 52,(1987) N 16, 3587-3591
  作者：DIRLAM, NANCY L.、MOORE, B. S.、URBAN, F. J.

  DOI：——

  日期：——