methyl 2-[4-(bromomethyl)-2-fluorophenyl]propionate | 1241405-31-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 2-[4-(bromomethyl)-2-fluorophenyl]propionate
• 英文别名: methyl 2-(4-bromomethyl-2-fluorophenyl)propanoate；Methyl 2-[4-(bromomethyl)-2-fluorophenyl]-propionate；methyl 2-[4-(bromomethyl)-2-fluorophenyl]propanoate
• CAS: 1241405-31-1
• 化学式: C₁₁H₁₂BrFO₂
• 分子量: 275.117
• InChiKey: AIYULPBMPZFWSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-[4-(bromomethyl)-2-fluorophenyl]propionate 在 盐酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 生成 2-fluoroloxoprofen
  参考文献：
  名称：

  一种洛索洛芬衍生物

  摘要：

  本发明提供一种胃肠道副作用低并提高生物利用度的洛索洛芬衍生物。

  公开号：

  CN109134262A
• 作为产物：
  描述：

  methyl 2-(2-fluoro-4-hydroxyphenyl)propanoate 在 N-溴代丁二酰亚胺(NBS) 、 (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride 、 偶氮二异丁腈 、 三乙胺 作用下， 以 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 methyl 2-[4-(bromomethyl)-2-fluorophenyl]propionate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Derivatives of 2-{2-Fluoro-4-[(2-oxocyclopentyl)methyl]phenyl}propanoic Acid: Nonsteroidal Anti-Inflammatory Drugs with Low Gastric Ulcerogenic Activity

  摘要：

  We previously reported that 2-fluoroloxoprofen has lower gastric ulcerogenic activity than loxoprofen, a nonsteroidal anti-inflammatory drug (NSAID) without selectivity for COX-2. We synthesized derivatives of 2-fluoroloxoprofen and studied their properties. Compared to 2-fluoroloxoprofen, one derivative, 1 la, exhibited higher anti-inflammatory activity and an equivalent ulcerogenic effect. These results suggest that 11a could be therapeutically beneficial for use as an NSAID.

  DOI：

  10.1021/jm300049g

文献信息

• 2-FLUOROPHENYL PROPIONIC ACID DERIVATIVES
  申请人：LTT BIO-PHARMA CO., LTD.

  公开号：US20140330026A1

  公开（公告）日：2014-11-06

  Provided are novel 2-fluorophenyl propionic acid derivatives which have excellent anti-inflammatory/analgesic effects while avoiding side effects such as gastrointestinal disorders, namely 2-fluorophenyl propionic acid derivatives represented by the formula (I) below or pharmaceutically acceptable salts thereof, [wherein, R 1 represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group, X represents —CH 2 —, —NH—, —O—, or —S—, and Y specifically represents group (II) (wherein, Z 1 represents —CO—, —CH(OH)—, or —CH 2 —, and n represents an integer of 1 or 2.)]

  提供了具有出色抗炎/镇痛效果且避免胃肠道疾病等副作用的新型2-氟苯丙酸衍生物，即由下面的式(I)所代表的2-氟苯丙酸衍生物或其药学上可接受的盐，其中，R1代表氢原子、卤原子或取代或未取代的苯基，X代表—CH2—、—NH—、—O—或—S—，Y具体表示群（II）（其中，Z1代表—CO—、—CH(OH)—或—CH2—，n代表1或2的整数）。
• LOXOPROFEN DERIVATIVE AND PHARMACEUTICAL PREPARATION CONTAINING THE SAME
  申请人：Mizushima Toru

  公开号：US20120016158A1

  公开（公告）日：2012-01-19

  There is provided a novel loxoprofen derivative that has no side effect such as a gastrointestinal disorder and also has excellent anti-inflammatory and analgesic effects and is represented by the following formula (I) or (II): (wherein R 1 and R 2 each represent a halogen atom or a substituted or unsubstituted phenyl group) or a pharmacologically acceptable salt thereof. In the derivative, the halogen atom is selected from a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom, and a substituent of the substituted phenyl group is a halogen atom, a hydroxyl group, a substituted or unsubstituted lower alkyl group, a lower alkylthio group, a lower alkoxy group, a nitro group, an amino group, or a carboxyl group.

  提供了一种新型洛索洛芬衍生物，该衍生物没有胃肠道障碍等副作用，同时具有优秀的抗炎和镇痛作用，其化学结构如下所示（式中R1和R2分别代表卤素原子或取代或未取代的苯基），或其药学上可接受的盐。在该衍生物中，卤素原子可选自氯原子、溴原子、氟原子和碘原子，取代苯基的取代基为卤素原子、羟基、取代或未取代的较低烷基基团、较低烷基硫基团、较低烷氧基团、硝基基团、氨基或羧基。
• 2-fluorophenyl propionic acid derivatives
  申请人：LTT BIO-PHARMA CO., LTD.

  公开号：US09221786B2

  公开（公告）日：2015-12-29

  Provided are novel 2-fluorophenyl propionic acid derivatives which have excellent anti-inflammatory/analgesic effects while avoiding side effects such as gastrointestinal disorders, namely 2-fluorophenyl propionic acid derivatives represented by the formula (I) below or pharmaceutically acceptable salts thereof, [wherein, R1 represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group, X represents —CH2—, —NH—, —O—, or —S—, and Y specifically represents group (II) (wherein, Z1 represents —CO—, —CH(OH)—, or —CH2—, and n represents an integer of 1 or 2.)]

  提供了一种新型的2-氟苯丙酸衍生物，具有优异的抗炎/镇痛效果，同时避免了胃肠道疾病等副作用，即由下式(I)所表示的2-氟苯丙酸衍生物或其药学上可接受的盐，[其中，R1代表氢原子、卤原子或取代或未取代的苯基，X代表—CH2—、—NH—、—O—或—S—，而Y具体代表群(II)(其中，Z1代表—CO—、—CH(OH)—或—CH2—，n代表1或2的整数)。]
• Properties and Synthesis of 2-{2-Fluoro (or Bromo)-4-[(2-oxocyclopentyl)methyl]phenyl}propanoic Acid: Nonsteroidal Anti-inflammatory Drugs with Low Membrane Permeabilizing and Gastric Lesion-Producing Activities
  作者：Naoki Yamakawa、Shintaro Suemasu、Masaaki Matoyama、Ayumi Kimoto、Miho Takeda、Ken-ichiro Tanaka、Tomoaki Ishihara、Takashi Katsu、Yoshinari Okamoto、Masami Otsuka、Tohru Mizushima

  DOI：10.1021/jm101116s

  日期：2010.11.11

  We previously proposed that membrane permeabilization activity of NSAIDs is involved in NSAID-induced gastric lesions. We here synthesized derivatives of loxoprofen that have lower membrane permeabilization activity than other NSAIDs. Compared to loxoprofen, the derivatives 10a and 10b have lower membrane permeabilization activity and their oral administration produced fewer gastric lesions but showed an equivalent anti-inflammatory effect. These results suggest that 10a and 10b are likely to be therapeutically beneficial as safer NSAIDs.
• 2-FLUOROPHENYLPROPIONIC ACID DERIVATIVE
  申请人：LTT Bio-Pharma Co., Ltd.

  公开号：EP2799424B1

  公开（公告）日：2016-08-17