Methyl (2z,4e)-2-methylsulphanyl-5-(1-naphthyl)-4-nitro-2,4-pentadienoate | 1007557-04-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl (2z,4e)-2-methylsulphanyl-5-(1-naphthyl)-4-nitro-2,4-pentadienoate
• 英文别名: methyl (2Z,4E)-2-methylsulfanyl-5-naphthalen-1-yl-4-nitropenta-2,4-dienoate
• CAS: 1007557-04-1
• 化学式: C₁₇H₁₅NO₄S
• 分子量: 329.376
• InChiKey: VLMKZNBQNUZLNC-DECHVDIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-萘基溴化镁, 0.5M IN METHF 、 methyl (2Z,4E)-2-methylthio-4-nitro-5-pyrrolidino-2,4-pentadienoate 以 四氢呋喃 为溶剂， 反应 0.75h， 以78%的产率得到Methyl (2z,4e)-2-methylsulphanyl-5-(1-naphthyl)-4-nitro-2,4-pentadienoate
  参考文献：
  名称：

  Design, synthesis, and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: Toward a structure/activity correlation

  摘要：

  On the grounds of previous encouraging results on the antitumor activity of (1E,3E)-1,4-bis(1-naphthyl)-2,3-dinitro-1, 3-butadiene (1), we have designed and synthesized two new molecules [(1E,3E)-1,4-bis(4-carboxy-1-naphthyl)-2,3-dinitro-1,3-butadiene (2) and methyl (2Z,4E)-2-methylsulfanyl-5-(1-naphthyl)-4-nitro-2,4-pentadienoate (3)] characterized by a common naphthyl-nitrobutadiene array but with different structural properties, with the aim of approaching to some structure-activity correlation. When 2 and 3 were analyzed in vitro for their inhibition of cell proliferation and pro-apoptotic properties, the carboxyderivative 2 did not furnish appreciable results. In contrast, 3 (which contains only one of the two naphthyinitroethenyl moieties of the original compound 1) showed remarkable activities in the range of micromolar concentrations (in six over eight cell lines its IC(50)s are in the 1-3 mu M range), with a significant improvement compared to 1. In particular, 3 proved able to bind to DNA, to upregulate p53, to block cells in the G2/M phase of their cycle, and to induce apoptosis. Thus, very interestingly, the performance of 3 with respect to 1 shows that a single 1-(1-naphthyl)-2-nitroethene moiety is able to ensure better (on four out of eight of the cell lines tested) or comparable levels of activity. This result suggests that the 'molecular-simplification strategy' could furnish a useful instrument for future design in our antitumor research. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.042