2-[2-bromo-6-fluoro-4-{(2-oxocyclopentyl)methyl}phenyl]propanoic acid | 1377934-90-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-[2-bromo-6-fluoro-4-{(2-oxocyclopentyl)methyl}phenyl]propanoic acid
• 英文别名: 2-[2-Bromo-6-fluoro-4-[(2-oxocyclopentyl)methyl]phenyl]propanoic acid
• CAS: 1377934-90-1
• 化学式: C₁₅H₁₆BrFO₃
• 分子量: 343.193
• InChiKey: YTWMTGXABKKVSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-bromo-6-fluoro-4-{(2-oxocyclopentyl)methyl}phenyl]propanoic acid 在 4-二甲氨基吡啶 、 trans-bromo(N-succinimidyl)-bis(triphenylphosphine)palladium(II) 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成
  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
• 作为产物：
  描述：

  Methyl 2-(2-bromo-6-fluoro-4-methylphenyl)acetate 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 水 、 potassium carbonate 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 四氯化碳 、 丙酮 为溶剂， 反应 12.25h， 生成 2-[2-bromo-6-fluoro-4-{(2-oxocyclopentyl)methyl}phenyl]propanoic acid
  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）。
• 2-FLUOROPHENYLPROPIONIC ACID DERIVATIVE
  申请人：LTT Bio-Pharma Co., Ltd.

  公开号：EP2799424A1

  公开（公告）日：2014-11-05

  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.)]

  本研究提供了新型 2-氟苯基丙酸衍生物，这些衍生物具有出色的消炎/镇痛效果，同时还能避免胃肠道紊乱等副作用，即下式 (I) 所代表的 2-氟苯基丙酸衍生物或其药学上可接受的盐类、 [其中，R1 代表氢原子、卤素原子或取代或未取代的苯基，X 代表-CH2-、-NH-、-O-或-S-，Y 具体代表基团 (II) (其中，Z1 代表 -CO-、-CH(OH)- 或 -CH2-，n 代表 1 或 2 的整数）]。
• US9221786B2
  申请人：——

  公开号：US9221786B2

  公开（公告）日：2015-12-29
• 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
  作者：Naoki Yamakawa、Shintaro Suemasu、Yoshinari Okamoto、Ken-ichiro Tanaka、Tomoaki Ishihara、Teita Asano、Keishi Miyata、Masami Otsuka、Tohru Mizushima

  DOI：10.1021/jm300049g

  日期：2012.6.14

  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.