methyl 4-chloro-2-(3-(bromomethyl)phenylacetamido)benzoate | 142327-14-8

• 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: methyl 4-chloro-2-(3-(bromomethyl)phenylacetamido)benzoate
• 英文别名: Methyl 2-(3-bromomethylphenylacetamido)-4-chlorobenzoate；methyl 2-[[2-[3-(bromomethyl)phenyl]acetyl]amino]-4-chlorobenzoate
• CAS: 142327-14-8
• 化学式: C₁₇H₁₅BrClNO₃
• 分子量: 396.668
• InChiKey: VIURPKFNETYEIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-chloro-2-(3-(bromomethyl)phenylacetamido)benzoate 在 双(三甲基硅烷基)氨基钾 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 L 703717
  参考文献：
  名称：

  3'-（芳甲基）-和3'-（芳氧基）-3-苯基-4-羟基喹啉-2（1H）-ones：NMDA受体上甘氨酸位点的口服活性拮抗剂。

  摘要：

  DOI：

  10.1021/jm00036a002
• 作为产物：
  描述：

  3-(溴甲基)苯乙酸 在 草酰氯 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 methyl 4-chloro-2-(3-(bromomethyl)phenylacetamido)benzoate
  参考文献：
  名称：

  3'-（芳甲基）-和3'-（芳氧基）-3-苯基-4-羟基喹啉-2（1H）-ones：NMDA受体上甘氨酸位点的口服活性拮抗剂。

  摘要：

  DOI：

  10.1021/jm00036a002

文献信息

• Hydroxyquinolone derivatives
  申请人：Merck, Sharp & Dohme Limited

  公开号：US05559125A1

  公开（公告）日：1996-09-24

  A class of 4-hydroxy-2-(1H)-quinolone derivatives, substituted at the 3-position by an optionally substituted aryl substituent, are selective non-competitive antagonists of NMDA receptors and/or are antagonists of AMPA receptors, and are therefore of utility in the treatment of conditions, such as neurodegenerative disorders, convulsions or schizophrenia, which require the administration of an NMDA and/or AMPA receptor antagonist.

  一类4-羟基-2-(1H)-喹啉衍生物，其在3位被可选择取代的芳基取代基所取代，是NMDA受体的选择性非竞争性拮抗剂和/或AMPA受体的拮抗剂，因此在治疗需要给予NMDA和/或AMPA受体拮抗剂的疾病，如神经退行性疾病、惊厥或精神分裂症等方面具有实用价值。
• Hydroxyquinolone derivatives compounds which have pharmaceutical utility
  申请人：Merck Sharpe & Dohme Ltd.

  公开号：US05348962A1

  公开（公告）日：1994-09-20

  This present invention relates to a class of 4-hydroxy-2-(1H)-quinolones which are substituted in the 3-position by an optionally substituted aryl substituent. These compounds are selective non-competitive antagonists of N-methyl-D-aspartate (NMDA) receptors.

  本发明涉及一类4-羟基-2-(1H)-喹啉衍生物，其在3位被一个可选择取代的芳基取代基所取代。这些化合物是选择性的非竞争性N-甲基-D-天冬氨酸（NMDA）受体拮抗剂。
• Development of N-[11C]methylamino 4-hydroxy-2(1H)-quinolone derivatives as PET radioligands for the glycine-binding site of NMDA receptors
  作者：Takeshi Fuchigami、Terushi Haradahira、Noriko Fujimoto、Yumiko Nojiri、Takahiro Mukai、Fumihiko Yamamoto、Takashi Okauchi、Jun Maeda、Kazutoshi Suzuki、Tetsuya Suhara、Hiroshi Yamaguchi、Mikako Ogawa、Yasuhiro Magata、Minoru Maeda

  DOI：10.1016/j.bmc.2009.06.014

  日期：2009.8

  In this study, we synthesized and evaluated several amino 4-hydroxy-2(1H)-quinolone (4HQ) derivatives as new PET radioligand candidates for the glycine site of the NMDA receptors. Among these ligands, we discovered that 7-chloro-4-hydroxy-3-3-(4-methylaminobenzyl) phenyl}-2-(1H)-quinolone (12) and 5-ethyl-7-chloro-4-hydroxy-3-(3-methylaminophenyl)-2(1H)-quinolone (32) have high affinity for the glycine site (K-i values; 11.7 nM for 12 and 11.8 nM for 32). In vitro autoradiography experiments indicated that [C-11]12 and [C-11]32 showed high specific binding in the brain slices, which were strongly inhibited by both glycine agonists and antagonists. In vivo brain uptake of these C-11-labeled 4HQs were examined in normal mice. Cerebellum to blood ratio of accumulation, of both [C-11]12 and [C-11]32 at 30 min were 0.058, which were slightly higher than those of cerebrum to blood ratio (0.043 and 0.042, respectively). These results indicated that [C-11]12 and [C-11]32 have poor blood brain barrier permeability. Although the plasma protein-binding ratio of [C-11]32 was much lower than methoxy analogs (71% vs 94-98%, respectively), [C-11]32 still binds with plasma protein strongly. It is conjectured that still acidic moiety and high affinity with plasma protein of [C-11]32 may prevent in vivo brain uptake. In conclusion, [C-11]12 and [C-11]32 are unsuitable for imaging cerebral NMDA receptors. (C) 2009 Elsevier Ltd. All rights reserved.
• US5348962A
  申请人：——

  公开号：US5348962A

  公开（公告）日：1994-09-20
• US5559125A
  申请人：——

  公开号：US5559125A

  公开（公告）日：1996-09-24