[2-methoxy-4-[(E)-2-nitroethenyl]phenyl] 3-fluorobenzoate | 1256376-69-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: [2-methoxy-4-[(E)-2-nitroethenyl]phenyl] 3-fluorobenzoate
• CAS: 1256376-69-8
• 化学式: C₁₆H₁₂FNO₅
• 分子量: 317.273
• InChiKey: OMZCAJXSEGOGKB-BQYQJAHWSA-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：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-甲氧基-4-[(e)-2-硝基乙烯基]苯酚 、 间氟苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 [2-methoxy-4-[(E)-2-nitroethenyl]phenyl] 3-fluorobenzoate
  参考文献：
  名称：

  The synthesis and biologic evaluation of anti-platelet and cytotoxic β-nitrostyrenes

  摘要：

  Our previous studies demonstrated that two cytotoxic beta-nitrostyrene derivatives, 3,4-methylenedioxy-beta-nitrostyrene (MNS) and 4-O-benzoyl-3-methoxy-beta-nitrostyrene (BMNS) exhibit potent anti-platelet activities. In this study, a series of beta-nitrostyrenes were synthesized and subjected to anti-platelet aggregation assay and cytotoxicity assay. The mono-and di-substitutions on the B ring of BMNS tended to increase the anti-platelet activity and decrease the cytotoxic activity. Of these, compounds 19 and 24 exhibited the most potent inhibitory effects on thrombin-and collagen-induced platelet aggregation (IC(50) <= 0.7 mu M) without significant cytotoxicity on a human cancer cell line (up to 20 mu M). Further studies indicated that compounds 19 and 24 inhibited platelet aggregation via prevention of glycoprotein IIb/IIIa activation. The potent and novel effects of BMNS derivatives make them attractive candidates for the development of new anti-platelet agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.039

文献信息

• The synthesis and biologic evaluation of anti-platelet and cytotoxic β-nitrostyrenes
  作者：Pei-Wen Hsieh、Yu-Ting Chang、Wen Yin Chuang、Hsin-Chu Shih、Shin-Zan Chiang、Chin-Chung Wu

  DOI：10.1016/j.bmc.2010.08.039

  日期：2010.11

  Our previous studies demonstrated that two cytotoxic beta-nitrostyrene derivatives, 3,4-methylenedioxy-beta-nitrostyrene (MNS) and 4-O-benzoyl-3-methoxy-beta-nitrostyrene (BMNS) exhibit potent anti-platelet activities. In this study, a series of beta-nitrostyrenes were synthesized and subjected to anti-platelet aggregation assay and cytotoxicity assay. The mono-and di-substitutions on the B ring of BMNS tended to increase the anti-platelet activity and decrease the cytotoxic activity. Of these, compounds 19 and 24 exhibited the most potent inhibitory effects on thrombin-and collagen-induced platelet aggregation (IC(50) <= 0.7 mu M) without significant cytotoxicity on a human cancer cell line (up to 20 mu M). Further studies indicated that compounds 19 and 24 inhibited platelet aggregation via prevention of glycoprotein IIb/IIIa activation. The potent and novel effects of BMNS derivatives make them attractive candidates for the development of new anti-platelet agents. (C) 2010 Elsevier Ltd. All rights reserved.