(E)-benzyl 3-(2-nitrophenyl)acrylate | 1385030-49-8

• 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: (E)-benzyl 3-(2-nitrophenyl)acrylate
• 英文别名: benzyl (E)-3-(2-nitrophenyl)prop-2-enoate
• CAS: 1385030-49-8
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: GRALYQYKHDVZHR-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-benzyl 3-(2-nitrophenyl)acrylate 在 二苯基膦叠氮化物 、 氯化铵 、 三乙胺 、 锌 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Inhibition of cellular proliferation and induction of apoptosis in human lung adenocarcinoma A549 cells by T-type calcium channel antagonist

  摘要：

  The anti-proliferative and apoptotic activities of new T-type calcium channel antagonist, 6e (BK10040) on human lung adenocarcinoma A549 cells were investigated. The MTT assay results indicated that BK10040 was cytotoxic against human lung adenocarcinoma (A549) and pancreatic cancer (MiaPaCa2) cells in a dose-dependent manner with IC50 of 2.25 and 0.93 mu M, respectively, which is ca. 2-fold more potent than lead compound KYS05090 despite of its decreased T-type calcium channel blockade. As a mode of action for cytotoxic effect of BK10040 on lung cancer (A549) cells, this cancer cell death was found to have the typical features of apoptosis, as evidenced by the accumulation of positive cells for annexin V. In addition, BK10040 triggered the activations of caspases 3 and 9, and the cleavages of poly (ADP-ribose) polymerase (PARP). Moreover, the treatment with z-VAD-fmk (a broad spectrum caspase inhibitor) significantly prevented BK10040-induced apoptosis. Based on these results, BK10040 may be used as a potential therapeutic agent for human lung cancer via the potent apoptotic activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.071
• 作为产物：
  描述：

  苯甲醇 、 (Z)-2-bromo-3-(2-nitrophenyl)acrylaldehyde 在 1,3-二苄基-1H-苯并[D]咪唑-3-氯化物 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以62%的产率得到(E)-benzyl 3-(2-nitrophenyl)acrylate
  参考文献：
  名称：

  NHC-catalyzed C–O or C–N bond formation: efficient approaches to α,β-unsaturated esters and amides

  摘要：

  简单高效的NHC催化转化，通过C-O或C-N键形成，将溴代烯酸或α,β-二溴代烯酸高立体选择性地转化为α,β-不饱和酯或酰胺。NHC催化的过程在温和条件下进行。起始原料易于获得，避免使用外部氧化剂，以及产品的实用价值，都使这一策略具有吸引力。

  DOI：

  10.1039/c2cc32862c

文献信息

• NHC-catalyzed C–O or C–N bond formation: efficient approaches to α,β-unsaturated esters and amides
  作者：Bo Zhang、Peng Feng、Yuxin Cui、Ning Jiao

  DOI：10.1039/c2cc32862c

  日期：——

  Simple and efficient NHC-catalyzed transformations of bromoenal or α,β-dibromoenal into α,β-unsaturated esters or amides with high stereoselectivity through C–O or C–N bond formation have been demonstrated. The NHC-catalyzed processes occur under mild conditions. The ready availability of the starting materials, avoidance of external oxidants and the usefulness of the products all make the strategy attractive.

  简单高效的NHC催化转化，通过C-O或C-N键形成，将溴代烯酸或α,β-二溴代烯酸高立体选择性地转化为α,β-不饱和酯或酰胺。NHC催化的过程在温和条件下进行。起始原料易于获得，避免使用外部氧化剂，以及产品的实用价值，都使这一策略具有吸引力。
• Inhibition of cellular proliferation and induction of apoptosis in human lung adenocarcinoma A549 cells by T-type calcium channel antagonist
  作者：Doo Li Choi、Sun Jeong Jang、Sehyeon Cho、Hye-Eun Choi、Hong-Kun Rim、Kyung-Tae Lee、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2014.01.071

  日期：2014.3

  The anti-proliferative and apoptotic activities of new T-type calcium channel antagonist, 6e (BK10040) on human lung adenocarcinoma A549 cells were investigated. The MTT assay results indicated that BK10040 was cytotoxic against human lung adenocarcinoma (A549) and pancreatic cancer (MiaPaCa2) cells in a dose-dependent manner with IC50 of 2.25 and 0.93 mu M, respectively, which is ca. 2-fold more potent than lead compound KYS05090 despite of its decreased T-type calcium channel blockade. As a mode of action for cytotoxic effect of BK10040 on lung cancer (A549) cells, this cancer cell death was found to have the typical features of apoptosis, as evidenced by the accumulation of positive cells for annexin V. In addition, BK10040 triggered the activations of caspases 3 and 9, and the cleavages of poly (ADP-ribose) polymerase (PARP). Moreover, the treatment with z-VAD-fmk (a broad spectrum caspase inhibitor) significantly prevented BK10040-induced apoptosis. Based on these results, BK10040 may be used as a potential therapeutic agent for human lung cancer via the potent apoptotic activity. (C) 2014 Elsevier Ltd. All rights reserved.