methyl (3-isocyanatophenyl)acetate | 153242-33-2

• 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 (3-isocyanatophenyl)acetate
• 英文别名: Methyl 3-isocyanatophenylacetate；methyl 2-(3-isocyanatophenyl)acetate
• CAS: 153242-33-2
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: CGGIIFLJNNIRDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (3-isocyanatophenyl)acetate 、 ethyl 3,4-dihydro-7-[4-(hydroxymethyl)imidazol-1-yl]-3-oxo-6-(trifluoromethyl)quinoxaline-2-carboxylate 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以75%的产率得到ethyl 3,4-dihydro-7-(4-{[3-(methoxycarbonylmethyl)phenylaminocarbonyloxy]methyl}imidazol-1-yl)-3-oxo-6-(trifluoromethyl)quinoxaline-2-carboxylate
  参考文献：
  名称：

  Design and synthesis of novel 7-heterocycle-6-trifluoromethyl-3-oxoquinoxaline-2-carboxylic acids bearing a substituted phenyl group as superior AMPA receptor antagonists with good physicochemical properties

  摘要：

  We describe the design, synthesis, and physicochemical and biological properties of a novel series of 7-heterocycle-6-trifluoromethyl-3-oxoquinoxaline-2-carboxylic acids bearing a substituted phenyl group joined through a urethane or urea linkage to the heterocycle at the 7 position. Introduction of the trifluoromethyl group at the 6 position conferred good biological activity, including neuroprotective effects, as well as good physicochemical properties. In terms of alpha-amino-3-hydroxy-5-methylisoxazole propionate receptor (AMPA-R) affinity, a urea linkage was equivalent to a urethane linkage and a pyrrole ring at the 7 position reduced affinity in comparison with an imidazole ring. Among this series, compound 14h (KRP-199), which has a 4-carboxyphenyl group joined through a urethane linkage to a 7-imidazolyl heterocycle, was found to possess high potency and selectivity for the AMPA-R in vitro and to exhibit good neuroprotective effects in vivo. Furthermore, the compound showed good physicochemical properties, including stability to light and good solubility in aqueous solutions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.060
• 作为产物：
  描述：

  3-氨基苯乙酸甲酯 、 甲烷 、 氯甲酸三氯甲酯 在 methyl (3-isocyanatophenyl)acetate 、 氩 、 二氯甲烷 作用下， 以 甲苯 为溶剂， 反应 3.25h， 以9.30 g of methyl 3-isocyanatophenylacetate are thus obtained in the form of a yellow liquid的产率得到methyl (3-isocyanatophenyl)acetate
  参考文献：
  名称：

  Pyrrolidine and thiazolidine derivatives, their preparation and

  摘要：

  本发明涉及式子的组合：##STR1##及其盐，其制备和包含它们的药物。

  公开号：

  US05610144A1
• 作为试剂：
  描述：

  3-氨基苯乙酸甲酯 、 甲烷 、 氯甲酸三氯甲酯 在 methyl (3-isocyanatophenyl)acetate 、 氩 、 二氯甲烷 作用下， 以 甲苯 为溶剂， 反应 3.25h， 以9.30 g of methyl 3-isocyanatophenylacetate are thus obtained in the form of a yellow liquid的产率得到methyl (3-isocyanatophenyl)acetate
  参考文献：
  名称：

  Pyrrolidine and thiazolidine derivatives, their preparation and

  摘要：

  本发明涉及式子的组合：##STR1##及其盐，其制备和包含它们的药物。

  公开号：

  US05610144A1

文献信息

• Potent and subtype-selective CCK-B/gastrin receptor antagonists: 2,4-dioxo-1,5-benzodiazepines with a plane of symmetry
  作者：Sanji Hagishita、Kaoru Seno、Susumu Kamata、Nobuhiro Haga、Yasunobu Ishihara、Michio Ishikawa、Mayumi Shimamura

  DOI：10.1016/s0968-0896(97)00083-7

  日期：1997.7

  relationship studies revealed that carbonylmethyl groups at both N-1 and N-5 positions and hydrophilic groups, such as the carboxyl group on the benzene ring attached to the ureido group at the C-3 position, brought about potent affinity and subtype selectivity for CCK-B/gastrin receptors. Several compounds showed excellent in vivo inhibition of gastric acid secretion induced by pentagastrin in anesthetized

  设计，合成了一系列具有对称平面的CCK-B /胃泌素受体拮抗剂，2,4-二氧代-1,5-苯并二氮杂卓衍生物，并评估了其拮抗活性。构效关系研究表明，在N-1和N-5位置上的羰基甲基和亲水基团（例如在C-3位置与脲基相连的苯环上的羧基）带来了强大的亲和力和亚型对CCK-B /胃泌素受体的选择性。在麻醉的大鼠中，几种化合物对五肽胃泌素诱导的胃酸分泌具有出色的体内抑制作用。
• Synthesis and pharmacological properties of ureidomethylcarbamoylphenylketone derivatives. A new potent and subtype-selective nonpeptide CCK-B/gastrin receptor antagonist, S-0509
  作者：Sanji Hagishita、Yasushi Murakami、Kaoru Seno、Susumu Kamata、Nobuhiro Haga、Toshiro Konoike、Yasuhiko Kanda、Ryuichi Kiyama、Takeshi Shiota、Yasunobu Ishihara、Michio Ishikawa、Mayumi Shimamura、Koji Abe、Koji Yoshimura

  DOI：10.1016/s0968-0896(97)00104-1

  日期：1997.8

  A novel series of CCK-B/gastrin receptor antagonists-ureidomethylcarbamoylphenylketone derivatives were designed, synthesized, and evaluated for activity. Structure-activity relationship studies revealed the importance of a carboxylic acid at substituent R-2 and a tert-butoxycarbonyl group at R-1 in structure A. Compound 7a (S-0509) showed remarkable affinity for the CCK-B/gastrin receptor and a subtype selectivity profile in vitro. Administration (id) of 7a led to excellent inhibition of gastric acid secretion induced by pentagastrin in anesthetized rats with an ED50 value of 0.014 mg/kg. Furthermore, 7a proved to have poor blood-brain permeability by its small effect on enhancement of morphine analgesia. Thus, S-0509 has an increase in selectivity for the peripheral effects of gastrin antagonism from the central effects of CCK-B antagonism. (C) 1997 Elsevier Science Ltd.
• US4067726A
  申请人：——

  公开号：US4067726A

  公开（公告）日：1978-01-10
• US5610144A
  申请人：——

  公开号：US5610144A

  公开（公告）日：1997-03-11
• US5633270A
  申请人：——

  公开号：US5633270A

  公开（公告）日：1997-05-27