AGR 40

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: AGR 40
• 英文别名: 3-[3-(Benzooxazol-2-ylsulfanylmethyl)-4-hydroxy-5-methoxy-phenyl]-2-cyano-acrylamide；(E)-3-[3-(1,3-benzoxazol-2-ylsulfanylmethyl)-4-hydroxy-5-methoxyphenyl]-2-cyanoprop-2-enamide
• 化学式: C₁₉H₁₅N₃O₄S
• 分子量: 381.412
• InChiKey: DAXNLYJBKOOJIV-WUXMJOGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-巯基苯并恶唑 在 哌啶 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 AGR 40
  参考文献：
  名称：

  Tyrphostins. 3. Structure-activity relationship studies of .alpha.-substituted benzylidenemalononitrile 5-S-aryltyrphostins

  摘要：

  In this study we describe an extension of our previous studies on cis-benzylidenemalononitrile tyrphostins. We have introduced S-aryl substituents in the 5 position (meta vis-a-vis the malononitrile moiety). We find that these compounds are potent blockers of EGFR kinase and its homolog HER-2 kinase. Interestingly, we find that certain S-aryltyrphostins discriminate between EGFR and HER-2 kinase in favor of the HER-2 kinase domain by almost 2 orders of magnitude. When examined in intact cells it was found that these selective S-aryltyrphostins are equipotent in inhibiting EGF dependent proliferation of NIH 3T3 harboring either the EGF receptor or the chimera EGF/neu (HER1-2). These findings suggest that the antiproliferative activity of these tyrphostins is mainly due to the inhibition of a mitogenic signaling element downstream to the growth receptor kinase.

  DOI：

  10.1021/jm00075a010

文献信息

• Tyrphostins. 3. Structure-activity relationship studies of .alpha.-substituted benzylidenemalononitrile 5-S-aryltyrphostins
  作者：Aviv Gazit、Nir Osherov、Israel Posner、Allan Bar-Sinai、Chaim Gilon、Alexander Levitzki

  DOI：10.1021/jm00075a010

  日期：1993.11

  In this study we describe an extension of our previous studies on cis-benzylidenemalononitrile tyrphostins. We have introduced S-aryl substituents in the 5 position (meta vis-a-vis the malononitrile moiety). We find that these compounds are potent blockers of EGFR kinase and its homolog HER-2 kinase. Interestingly, we find that certain S-aryltyrphostins discriminate between EGFR and HER-2 kinase in favor of the HER-2 kinase domain by almost 2 orders of magnitude. When examined in intact cells it was found that these selective S-aryltyrphostins are equipotent in inhibiting EGF dependent proliferation of NIH 3T3 harboring either the EGF receptor or the chimera EGF/neu (HER1-2). These findings suggest that the antiproliferative activity of these tyrphostins is mainly due to the inhibition of a mitogenic signaling element downstream to the growth receptor kinase.