1-cinnamoyl-6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione | 1312679-82-5

• 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: 1-cinnamoyl-6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione
• 英文别名: 6-iodo-1-[(E)-3-phenylprop-2-enoyl]-3,1-benzoxazine-2,4-dione
• CAS: 1312679-82-5
• 化学式: C₁₇H₁₀INO₄
• 分子量: 419.175
• InChiKey: JBEYNWMZFUBJSJ-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-cinnamoyl-6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione 在 氨 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以88%的产率得到5-iodo-2-{[(2E)-3-phenylprop-2-enoyl]amino}benzamide
  参考文献：
  名称：

  Synthesis, antiproliferative activity, and mechanism of action of a series of 2-{[(2E)-3-phenylprop-2-enoyl]amino}benzamides

  摘要：

  Several new 2-{[(2E)-3-phenylprop-2-enoyl]amino}benzamides 12a-s and 17t-v were synthesized by stirring in pyridine the (E)-3-(2-R1-3-R2-4-R3-phenyl)acrylic acid chlorides 11c-k and 11t-v with the appropriate anthranilamide derivatives 10a-c or the 5-iodoanthranilic acid 13. Some of the synthesized compounds were evaluated for their in vitro antiproliferative activity against the full NCI tumor cell line panel derived from nine clinically isolated cancer types (leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast). COMPARE analysis, effects on tubulin polymerization in cells and with purified tubulin, and effects on cell cycle distribution for 17t, the most active of the series, indicate that these new antiproliferative compounds act as antitubulin agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.067
• 作为产物：
  描述：

  3-苯基-2-丙烯酰氯 在 吡啶 作用下， 反应 44.75h， 生成 1-cinnamoyl-6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione
  参考文献：
  名称：

  Synthesis, antiproliferative activity, and mechanism of action of a series of 2-{[(2E)-3-phenylprop-2-enoyl]amino}benzamides

  摘要：

  Several new 2-{[(2E)-3-phenylprop-2-enoyl]amino}benzamides 12a-s and 17t-v were synthesized by stirring in pyridine the (E)-3-(2-R1-3-R2-4-R3-phenyl)acrylic acid chlorides 11c-k and 11t-v with the appropriate anthranilamide derivatives 10a-c or the 5-iodoanthranilic acid 13. Some of the synthesized compounds were evaluated for their in vitro antiproliferative activity against the full NCI tumor cell line panel derived from nine clinically isolated cancer types (leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast). COMPARE analysis, effects on tubulin polymerization in cells and with purified tubulin, and effects on cell cycle distribution for 17t, the most active of the series, indicate that these new antiproliferative compounds act as antitubulin agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.067