(R)-2-(2-fluoro-4-phenylphenyl)propionic acid | 68285-18-7

• 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: (R)-2-(2-fluoro-4-phenylphenyl)propionic acid
• 英文别名: (r)-(-)-2-(3-Fluorobiphenyl-4yl)propanoic acid；(2R)-2-(2-fluoro-4-phenylphenyl)propanoic acid
• CAS: 68285-18-7
• 化学式: C₁₅H₁₃FO₂
• 分子量: 244.265
• InChiKey: ICKWGFYFODTQTL-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R,S)-N-flurbiprofenyl-1,2,4-triazole 在 Novozym 435 、 水 作用下， 以 甲基叔丁基醚 为溶剂， 生成 (R)-2-(2-fluoro-4-phenylphenyl)propionic acid 、 (S)-N-flurbiprofenyl-1,2,4-triazole
  参考文献：
  名称：

  （R，S）-偶氮内酯作为新型底物在有机溶剂中用于脂肪酶催化的水解拆分

  摘要：

  偶氮化合物，即N-酰基唑，作为通用的酰化试剂已在文献中充分表征，其中唑结构不仅可以充当更好的离去基团，还可以使羰基碳更具亲电性，并易于发生亲核攻击。因此，期望在开发用于制备光学纯的羧酸的新的拆分方法的开发中结合这种独特的性质和脂肪酶的拆分能力。以南极假丝酵母脂肪酶B（CALB）-在有机溶剂中催化（R，S）-N-丙烯烯基唑的水解为模型系统，（R，S）-N-profenyl-1,2,4-三唑代替其相应的酯类似物被用作制备光学纯的profen（即2-芳基丙酸）的最佳底物。在45°C下水饱和的甲基叔丁基醚（MTBE）中的（R，S）-偶氮内酯的结构反应性相关性以及彻底的动力学分析进一步用于阐明四面体加合物的限速形成在酰化步骤中，没有CN键断裂或具有适度的CN键断裂与CO键形成协同作用。容易制备底物，高酶反应性和对映体选择性以及通过水萃取容易回收产物和残留底物的优势证明了使用（R，S）-偶氮内酯作为酶促拆分过程的新型底物。

  DOI：

  10.1002/adsc.200900391

文献信息

• NOVEL TREATMENT OF MULTIPLE SCLEROSIS (MS)
  申请人：Fraunhofer Gesellschaft zur Förderung der angewandten Forschung e.V.

  公开号：EP2635271A1

  公开（公告）日：2013-09-11
• Novel Treatment of Multiple Sclerosis (MS)
  申请人：Tegeder Irmgard

  公开号：US20130309199A1

  公开（公告）日：2013-11-21

  The present invention relates to the use of an R-enantiomer of a compound according to the following formula (I) (I), wherein R 1 or R 2 is a group selected from H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , and —CH 2 CH 2 CH 2 CH 3 or can be taken together with another to give a cyclopropyl ring, a cyclobutyl ring, a cyclopentyl ring, or a cyclohexyl ring, R 3 is a group selected from —COOH, —COOR 6 , —CONH 2 , —CONHR 6 , —CONR 6 R 7 , —CONHSO 2 R 6 , —COO—(CH 2 ) 3 —CH 2 OH, —COO—(CH 2 ) 4 —ONO 2 , —COO—PhOCH 3 —C 2 H 2 —COO—(CH 2 ) 4 —ONO 2 , tetrazolyl, and a —COOH bioisostere, R 4 or R 5 is a group selected from —Cl, —F, —Br, —I, —CF 3 , —OCF 3 , —SCF 3 , —OCH 3 , —OCH 2 CH 3 , —CN, —CH═CH 2 , —CH 2 OH, and —NO 2 , R 6 of R 7 is a group selected from —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , and —CH 2 CH 2 CH 2 CH 3 , and m or n is an integer selected from 0, 1, 2, and 3, or a nitro-variant of said compound, and pharmaceutically acceptable salts of said compound, preferably Tarenflurbil (R-Flurbiprofen), for use in the treatment of multiple sclerosis (MS).
• [EN] NOVEL TREATMENT OF MULTIPLE SCLEROSIS (MS)<br/>[FR] NOUVEAU TRAITEMENT DE LA SCLÉROSE EN PLAQUES (MS)
  申请人：UNIV JW GOETHE FRANKFURT MAIN

  公开号：WO2012059541A1

  公开（公告）日：2012-05-10

  The present invention relates to the use of an R-enantiomer of a compound according to the following formula (I) (I), wherein R1 or R2 is a group selected from H, -CH3, -CH2CH3, -CH2CH2CH3, and - CH2CH2CH2CH3 or can be taken together with another to give a cyclopropyl ring, a cyclobutyl ring, a cyclopentyl ring, or a cyclohexyl ring, R3 is a group selected from -COOH, - COOR6, -CONH2, -CONHR6, -CONR6R7, -CONHSO2R6, -COO-(CH2)3-CH2OH, -COO- (CH2)4-ONO2, -COO-PhOCH3-C2H2-COO-(CH2)4-ONO2, tetrazolyl, and a -COOH bioisostere, R4 or R5 is a group selected from -Cl, -F, -Br, -I, -CF3, -OCF3, -SCF3, -OCH3, - OCH2CH3, -CN, -CH=CH2, -CH2OH, and -NO2, R6 ot R7 is a group selected from -CH3, - CH2CH3, -CH2CH2CH3, and -CH2CH2CH2CH3, and m or n is an integer selected from 0, 1, 2, and 3, or a nitro-variant of said compound, and pharmaceutically acceptable salts of said compound, preferably Tarenflurbil (R-Flurbiprofen), for use in the treatment of multiple sclerosis (MS).
• [EN] (R)-FLURIPROFEN FOR THE PREVENTION AND/OR TREATMENT OF DIABETES<br/>[FR] (R)-FLURIPROFÈNE POUR LA PRÉVENTION ET/OU LE TRAITEMENT DU DIABÈTE
  申请人：FRAUNHOFER GES FORSCHUNG

  公开号：WO2017080989A1

  公开（公告）日：2017-05-18

  The present invention relates to a compound being an (R)-enantiomer of a compound according to the following formula (I), wherein Rl or R2 is a group selected from H, -CH3, -CH2CH3, -CH2CH2CH3, and CH2CH2CH2CH3 or can be taken together with another to give a cyclopropyl ring, a cyclobutyl ring, a cyclopentyl ring, or a cyclohexyl ring, R3 is a group selected from -COOH, -COOR6, -CONH2, -CONHR6, -CONR6R7, -CONHS02R6, -COO-(CH2)3-CH20H, -COO- (CH2)4-ON02, -COO-PhOCH3-C2H2-COO-(CH2)4-ON02, tetrazolyl, and a -COOH bioisostere, R4 or R5 is a group selected from -CI, -F, -Br, -I, -CF3, -OCF3, -SCF3, -OCH3, - OCH2CH3, -CN, -CH=CH2, -CH20H, and -N02, R6 or R7 is a group selected from -CH3, - CH2CH3, -CH2CH2CH3, and -CH2CH2CH2CH3, and m or n is an integer selected from 0, 1, 2, and 3, a nitro-variant of said compound, or pharmaceutically acceptable salts of said compound for use in preventing and/or treating diabetes in a subject in need thereof. Moreover, also encompassed by the invention is a composition comprising said compound, nitro-variant, or pharmaceutically acceptable salts and at least one additional therapeutic agent for prevention and/or treatment of diabetes.