2-ethoxy-4-(2-nitro-cis-propenyl)-phenol | 15804-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-ethoxy-4-(2-nitro-cis-propenyl)-phenol
• 英文别名: 2-Aethoxy-4-(2-nitro-cis-propenyl)-phenol；2-ethoxy-4-[(E)-2-nitroprop-1-enyl]phenol
• CAS: 15804-77-0
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: PPZCVPJQPOPRLZ-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙基香兰素 、 硝基乙烷 在 ammonium acetate 作用下， 反应 24.0h， 生成 2-ethoxy-4-(2-nitro-cis-propenyl)-phenol
  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 OF ι-NITROSTYRENES¹
  作者：CATHERINE B. GAIRAUD、GERALD R. LAPPIN

  DOI：10.1021/jo01129a001

  日期：1953.1
• 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.