5-amino-3-(4-nitrobenzyl)-4-isothiazolecarbonitrile | 607713-72-4

• 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: 5-amino-3-(4-nitrobenzyl)-4-isothiazolecarbonitrile
• 英文别名: 5-Amino-3-[(4-nitrophenyl)methyl]-1,2-thiazole-4-carbonitrile
• CAS: 607713-72-4
• 化学式: C₁₁H₈N₄O₂S
• 分子量: 260.276
• InChiKey: UCEASZPWLMYVNO-UHFFFAOYSA-N

物化性质

• 沸点：
  396.0±34.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-amino-3-(4-nitrobenzyl)-4-isothiazolecarbonitrile 、 原甲酸三乙酯 在 硫酸氢铵 、 氨 、 lithium methanolate 作用下， 以 乙醇 、 甲醇 为溶剂， 生成 3-(4-nitrobenzyl)isothiazolo[5,4-d]pyrimidin-4-amine
  参考文献：
  名称：

  Isothiazolopyrimidines and isoxazolopyrimidines as novel multi-targeted inhibitors of receptor tyrosine kinases

  摘要：

  A series of isothiazolopyrimidines and isoxazolopyrimidines were synthesized and identified as potent KDR inhibitors. SAR studies led to isothiazolopyrimidine urea analogs that potently inhibit VEGFR tyrosine kinases (KDR enzymatic and cellular IC50 values below 10 nM) as well as cKIT and TIE2. The selected compounds 8 and 13 display 56% and 48% oral bioavailability in mice, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.057
• 作为产物：
  描述：

  2-(4-硝基苯基)乙酰氯 在 ammonium hydroxide 、 sodium hydroxide 、 O,S-diethyl-dithiophosphoric acid 、 五氯化磷 、 苄基三乙基氯化铵 、 双氧水 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 5-amino-3-(4-nitrobenzyl)-4-isothiazolecarbonitrile
  参考文献：
  名称：

  Isothiazolopyrimidines and isoxazolopyrimidines as novel multi-targeted inhibitors of receptor tyrosine kinases

  摘要：

  A series of isothiazolopyrimidines and isoxazolopyrimidines were synthesized and identified as potent KDR inhibitors. SAR studies led to isothiazolopyrimidine urea analogs that potently inhibit VEGFR tyrosine kinases (KDR enzymatic and cellular IC50 values below 10 nM) as well as cKIT and TIE2. The selected compounds 8 and 13 display 56% and 48% oral bioavailability in mice, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.057

文献信息

• Thiopyrimidine and isothiazolopyrimidine kinase inhibitors
  申请人：——

  公开号：US20040014756A1

  公开（公告）日：2004-01-22

  Compounds having the formula 1 are useful for inhibiting protein tyrosine kinases. The present invention also discloses methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  具有以下化学式的化合物对抑制蛋白酪氨酸激酶具有用处。本发明还公开了制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。
• Thiopyrimidine and isothiazolopyrimidine Kinase Inhibitors
  申请人：Michaelides R. Michael

  公开号：US20060276490A1

  公开（公告）日：2006-12-07

  Compounds having the formula are useful for inhibiting protein tyrosine kinases. The present invention also discloses methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  具有公式的化合物对于抑制蛋白酪氨酸激酶是有用的。本发明还揭示了制备该化合物的方法，含有该化合物的组合物以及使用该化合物的治疗方法。
• THIOPYRIMIDINE AND ISOTHIAZOLOPYRIMIDINE KINASE INHIBITORS
  申请人：AbbVie Inc.

  公开号：EP1487841B1

  公开（公告）日：2014-01-15
• US7560552B2
  申请人：——

  公开号：US7560552B2

  公开（公告）日：2009-07-14
• Isothiazolopyrimidines and isoxazolopyrimidines as novel multi-targeted inhibitors of receptor tyrosine kinases
  作者：Zhiqin Ji、Asma A. Ahmed、Daniel H. Albert、Jennifer J. Bouska、Peter F. Bousquet、George A. Cunha、Keith B. Glaser、Jun Guo、Junling Li、Patrick A. Marcotte、Maria D. Moskey、Lori J. Pease、Kent D. Stewart、Melinda Yates、Steven K. Davidsen、Michael R. Michaelides

  DOI：10.1016/j.bmcl.2006.05.057

  日期：2006.8

  A series of isothiazolopyrimidines and isoxazolopyrimidines were synthesized and identified as potent KDR inhibitors. SAR studies led to isothiazolopyrimidine urea analogs that potently inhibit VEGFR tyrosine kinases (KDR enzymatic and cellular IC50 values below 10 nM) as well as cKIT and TIE2. The selected compounds 8 and 13 display 56% and 48% oral bioavailability in mice, respectively. (c) 2006 Elsevier Ltd. All rights reserved.