ethyl 5-(4-amino-phenyl)isoxazole-3-carboxylate | 908802-68-6

• 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: ethyl 5-(4-amino-phenyl)isoxazole-3-carboxylate
• 英文别名: Ethyl 5-(4-aminophenyl)isoxazole-3-carboxylate；ethyl 5-(4-aminophenyl)-1,2-oxazole-3-carboxylate
• CAS: 908802-68-6
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: XNPRZYLIFFJCCW-UHFFFAOYSA-N

物化性质

• 沸点：
  427.3±35.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-amino-phenyl)isoxazole-3-carboxylate 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 59.0h， 生成 ethyl 4-(5-(4-guanidinophenyl)isoxazole-3-carboxamido)benzoate hydrochloride
  参考文献：
  名称：

  Design and synthesis of phenylisoxazole derivatives as novel human acrosin inhibitors

  摘要：

  Human acrosin is an attractive target for the discovery of novel male contraceptives. Isoxazole derivative ISO-1, a small-molecule weak human acrosin inhibitor, was used as the starting point for lead optimization. After two rounds of structure-based inhibitor design, a highly potent inhibitor B6 (IC50 = 1.44 mu M) was successfully identified, which showed good selectivity over trypsin and represents one of the most active human acrosin inhibitors up to date. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.118
• 作为产物：
  描述：

  ethyl 4-(4-nitrophenyl)-2,4-dioxobutanoate 在 tin(II) chloride dihdyrate 、 盐酸羟胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 10.0h， 生成 ethyl 5-(4-amino-phenyl)isoxazole-3-carboxylate
  参考文献：
  名称：

  Design and synthesis of phenylisoxazole derivatives as novel human acrosin inhibitors

  摘要：

  Human acrosin is an attractive target for the discovery of novel male contraceptives. Isoxazole derivative ISO-1, a small-molecule weak human acrosin inhibitor, was used as the starting point for lead optimization. After two rounds of structure-based inhibitor design, a highly potent inhibitor B6 (IC50 = 1.44 mu M) was successfully identified, which showed good selectivity over trypsin and represents one of the most active human acrosin inhibitors up to date. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.118

文献信息

• 异噁唑类新型顶体酶抑制剂及其制备方法
  申请人：中国人民解放军第二军医大学

  公开号：CN104119287B

  公开（公告）日：2016-04-20

  本发明涉及一类新型的顶体酶抑制剂、其制备方法及其在制备男性抗生育药物中的应用。具体的，本发明涉及一类如式Ⅰ所示的新型的顶体酶抑制剂，其中各取代基的定义如说明书中所述。本发明还涉及所述顶体酶抑制剂的制备方法及其在制备男性抗生育药物中的应用。
• Use of the Nitrile Oxide Cycloaddition (NOC) Reaction for Molecular Probe Generation: A New Class of Enzyme Selective Histone Deacetylase Inhibitors (HDACIs) Showing Picomolar Activity at HDAC6
  作者：Alan P. Kozikowski、Subhasish Tapadar、Doris N. Luchini、Ki Hwan Kim、Daniel D. Billadeau

  DOI：10.1021/jm8002894

  日期：2008.8.1

  as the CAP group has been synthesized using nitrile oxide cycloaddition chemistry. An HDAC6 selective inhibitor having a potency of approximately 2 picomolar was identified. Some of the compounds were examined for their ability to block pancreatic cancer cell growth and found to be about 10-fold more potent than SAHA. This research provides valuable, new molecular probes for use in exploring HDAC biology

  已经使用腈氧化物环加成化学合成了一系列含有苯基异恶唑作为 CAP 基团的基于异羟肟酸酯的 HDAC 抑制剂。鉴定了效力约为2皮摩尔的HDAC6选择性抑制剂。检查了一些化合物阻断胰腺癌细胞生长的能力，发现其效力比 SAHA 强约 10 倍。这项研究为探索 HDAC 生物学提供了有价值的新分子探针。
• Isoxazole moiety in the linker region of HDAC inhibitors adjacent to the Zn-chelating group: Effects on HDAC biology and antiproliferative activity
  作者：Subhasish Tapadar、Rong He、Doris N. Luchini、Daniel D. Billadeau、Alan P. Kozikowski

  DOI：10.1016/j.bmcl.2009.04.058

  日期：2009.6

  A series of hydroxamic acid based histone deacetylase inhibitors 6-15, containing an isoxazole moiety adjacent to the Zn-chelating hydroxamic acid, is reported herein. Some of these compounds showed nanomolar activity in the HDAC isoform inhibitory assay and exhibited micro molar inhibitory activity against five pancreatic cancer cell lines. (C) 2009 Elsevier Ltd. All rights reserved.