6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone | 1002113-03-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone
• 英文别名: 6-(3-(4-Methoxyphenyl)-1-oxo-2-propenyl)-2(3H)-benzoxazolone；6-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-3H-1,3-benzoxazol-2-one
• CAS: 1002113-03-2
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: CLXFTNRFNACNSF-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone 、 二甲胺 以 乙醇 为溶剂， 反应 24.0h， 以72%的产率得到3-[(dimethylamino)methyl]-6-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-1,3-benzoxazol-2-one
  参考文献：
  名称：

  Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones

  摘要：

  A series of 12 new Mannich bases with chalcone core structure were synthesized as potential antineoplastic agents, via N-aminomethylation of two parent 6-(3 -aryl-2-propenoyl)-2(3 H)-benzoxazolones. The newly synthesized compounds as well as the chalcone prototypes were evaluated for cytotoxicity in the human pre-B-cell leukemia cell line BV-173 using the MTT-dye reduction assay. The tested compounds exhibited concentration-dependent cytotoxic effects at low micromolar concentrations. Ten of the Mannich bases characterized by significant activity in BV-173 were further evaluated against the chronic myeloid leukemia cell line K-562 and were found to suppress the growth of these cells at relatively higher concentrations as compared to the former tumor model. Selected Mannich bases induced programmed cell death in BV-173 at a concentration of 2.5 mu M as evidenced by the encountered DNA-laddering. Taken together our data suggest that the presented heterocyclic chalcone derived Mannich bases necessitate detailed pharmacological evaluation in order to define further the structure activity relationships, in a larger spectrum of tumor models and to elucidate the mechanisms implicated in the observed cytotoxic effects. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.019
• 作为产物：
  描述：

  2-苯并唑啉酮 在 C₃H₇NO*AlCl₃ 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone
  参考文献：
  名称：

  新的杂环查耳酮。第 6 部分。 5-或 6-(3-芳基-2-丙烯酰基)-2(3H)-苯并恶唑酮的合成和细胞毒活性

  摘要：

  摘要 通过 5-乙酰基-2(3H)-苯并恶唑酮或 6-乙酰基-2(3H)-苯并恶唑酮与适当的醛类的 Claisen-Schmidt 缩合，合成了许多带有恶唑环的查耳酮。使用 MTT 染料还原测定法评估了查耳酮对几种肿瘤细胞系 - BV-173（人 B 细胞前体白血病）、MCF-7 和 MDA-MB-231（人乳腺癌）的细胞毒性活性。测试的化合物在微摩尔浓度下表现出浓度依赖性细胞毒作用。将 BV-173 肿瘤细胞系暴露于化合物 3f 会导致基因组 DNA 的强烈单核小体和寡核小体片段化，正如“细胞死亡检测”ELISA 试剂盒所证明的那样，这明确表明细胞毒性模式涉及细胞凋亡的诱导受试化合物的作用。

  DOI：

  10.1515/hc-2012-0081

文献信息

• New heterocyclic chalcones. Part 6. Synthesis and cytotoxic activities of 5- or 6-(3-aryl- 2-propenoyl)-2(3<i>H</i>)-benzoxazolones
  作者：Yordanka B. Ivanova、Georgi T. Momekov、Ognyan I. Petrov

  DOI：10.1515/hc-2012-0081

  日期：2013.3.1

  Abstract A number of chalcones bearing an oxazole cycle were synthesized by Claisen-Schmidt condensation of 5-acetyl-2(3H)-benzoxazolone or 6-acetyl-2(3H)-benzoxazolone and the appropriate aldehydes. The chalcones were evaluated for cytotoxic activity against several tumor cell lines – BV-173 (human B cell precursor leukemia), MCF-7 and MDA-MB-231 (human breast adenocarcinoma) using the MTT-dye reduction

  摘要 通过 5-乙酰基-2(3H)-苯并恶唑酮或 6-乙酰基-2(3H)-苯并恶唑酮与适当的醛类的 Claisen-Schmidt 缩合，合成了许多带有恶唑环的查耳酮。使用 MTT 染料还原测定法评估了查耳酮对几种肿瘤细胞系 - BV-173（人 B 细胞前体白血病）、MCF-7 和 MDA-MB-231（人乳腺癌）的细胞毒性活性。测试的化合物在微摩尔浓度下表现出浓度依赖性细胞毒作用。将 BV-173 肿瘤细胞系暴露于化合物 3f 会导致基因组 DNA 的强烈单核小体和寡核小体片段化，正如“细胞死亡检测”ELISA 试剂盒所证明的那样，这明确表明细胞毒性模式涉及细胞凋亡的诱导受试化合物的作用。
• Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones
  作者：Y. Ivanova、G. Momekov、O. Petrov、M. Karaivanova、V. Kalcheva

  DOI：10.1016/j.ejmech.2007.02.019

  日期：2007.11

  A series of 12 new Mannich bases with chalcone core structure were synthesized as potential antineoplastic agents, via N-aminomethylation of two parent 6-(3 -aryl-2-propenoyl)-2(3 H)-benzoxazolones. The newly synthesized compounds as well as the chalcone prototypes were evaluated for cytotoxicity in the human pre-B-cell leukemia cell line BV-173 using the MTT-dye reduction assay. The tested compounds exhibited concentration-dependent cytotoxic effects at low micromolar concentrations. Ten of the Mannich bases characterized by significant activity in BV-173 were further evaluated against the chronic myeloid leukemia cell line K-562 and were found to suppress the growth of these cells at relatively higher concentrations as compared to the former tumor model. Selected Mannich bases induced programmed cell death in BV-173 at a concentration of 2.5 mu M as evidenced by the encountered DNA-laddering. Taken together our data suggest that the presented heterocyclic chalcone derived Mannich bases necessitate detailed pharmacological evaluation in order to define further the structure activity relationships, in a larger spectrum of tumor models and to elucidate the mechanisms implicated in the observed cytotoxic effects. (C) 2007 Elsevier Masson SAS. All rights reserved.