4-[(1E,3E)-4-(4-carboxynaphthalen-1-yl)-2,3-dinitrobuta-1,3-dienyl]naphthalene-1-carboxylic acid | 1007557-02-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 4-[(1E,3E)-4-(4-carboxynaphthalen-1-yl)-2,3-dinitrobuta-1,3-dienyl]naphthalene-1-carboxylic acid
• CAS: 1007557-02-9
• 化学式: C₂₆H₁₆N₂O₈
• 分子量: 484.422
• InChiKey: CPRFPYPAGLAGEI-RNIAWFEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (1E,3E)-1,4-bis(4-tert-butoxycarbonyl-1-naphthyl)-2,3-dinitro-1,3-butadiene 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到4-[(1E,3E)-4-(4-carboxynaphthalen-1-yl)-2,3-dinitrobuta-1,3-dienyl]naphthalene-1-carboxylic acid
  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

文献信息

• Design, synthesis, and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: Toward a structure/activity correlation
  作者：Giovanni Petrillo、Maria A. Mariggiò、Cinzia Aiello、Cinzia Cordazzo、Carla Fenoglio、Stefano Morganti、Michela Croce、Egon Rizzato、Domenico Spinelli、Massimo Maccagno、Lara Bianchi、Claudia Prevosto、Cinzia Tavani、Maurizio Viale

  DOI：10.1016/j.bmc.2007.09.042

  日期：2008.1

  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.