(Z)-3-氯-3-(3-硝基苯基)丙烯醛 | 1036272-08-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: (Z)-3-氯-3-(3-硝基苯基)丙烯醛
• 英文名称: (Z)-3-chloro-3-(3-nitrophenyl)acrylaldehyde
• 英文别名: (Z)-3-(3-nitrophenyl)-3-chloroacrylaldehyde；m-nitro-β-chlorocinnamaldehyde；(Z)-3-chloro-3-(3-nitrophenyl)prop-2-enal
• CAS: 1036272-08-8
• 化学式: C₉H₆ClNO₃
• 分子量: 211.605
• InChiKey: CMZSPDJDJCPJKW-WTKPLQERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dithiocarbonic acid O-ethyl ester S-[2-oxo-2-(3,4,5-trimethoxyphenyl)-ethyl] ester 、 (Z)-3-氯-3-(3-硝基苯基)丙烯醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以43%的产率得到[5-(3-Nitrophenyl)thiophen-2-yl]-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of thiophene analogues of chalcones

  摘要：

  Chalcones are characterized by possessing an enone moiety between two aromatic rings. A series of chalcone-like agents, in which the double bond of the enone system is embedded within a thiophene ring, were synthesized and evaluated for antiproliferative activity and inhibition of tubulin assembly and colchicine binding to tubulin. The replacement of the double bond with a thiophene maintains antiproliferative activity and therefore must not significantly alter the relative conformation of the two aryl rings. The synthesized compounds were found to inhibit the growth of several cancer cell lines at nanomolar to low micromolar concentrations. In general, all compounds having significant antiproliferative activity inhibited tubulin polymerization with an IC50 < 2 mu M. Several of these compounds caused K562 cells to arrest in the G2/M phase of the cell cycle. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.026
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 间硝基苯乙酮 在 三氯氧磷 作用下， 以69 %的产率得到(Z)-3-氯-3-(3-硝基苯基)丙烯醛
  参考文献：
  名称：

  CYP450抑制剂新型异恶唑衍生物的合成、晶体结构和分子对接研究，寻找抗癌药物

  摘要：

  摘要 本工作报道了一些新型异恶唑衍生物的合成及其与CYP450家族酶的分子对接，以厄洛替尼、吉西他滨和酮康唑为参比药物进行。合成了8种3,4-取代苯基3-氯丙烯醛的异恶唑衍生物和1种肉桂醛的异恶唑衍生物。与标准药物厄洛替尼、吉西他滨和酮康唑相比，所有九种化合物的分子对接研究显示出良好的对接分数。发现 4-OH 和 4-F 衍生物对本工作中正在研究的所有六种 CYP450 蛋白均具有很强的亲和力。4-F 和 3-NO 2衍生物可能是 CYP1A2 的合适先导化合物抑制剂，其次是 4-OH 衍生物。具有显着结合亲和力的 4-OH 衍生物对 CYP1A2、CYP2C9、CYP2C8、CYP2C19 和 CYP2D6 表现出令人鼓舞的抑制作用。目前对这九种3,4-取代苯基3-氯丙烯醛异恶唑衍生物的预测需要在体内和体外条件下进一步研究，以确定最佳治疗效果。根据文献调查，异恶唑衍生物的合成是丙烯醛衍生

  DOI：

  10.1080/07391102.2022.2142667

文献信息

• US4125563A
  申请人：——

  公开号：US4125563A

  公开（公告）日：1978-11-14
• Design, synthesis, and biological evaluation of thiophene analogues of chalcones
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Carlota Lopez Cara、Olga Cruz-Lopez、Delia Preti、Manlio Tolomeo、Stefania Grimaudo、Antonella Di Cristina、Nicola Zonta、Jan Balzarini、Andrea Brancale、Taradas Sarkar、Ernest Hamel

  DOI：10.1016/j.bmc.2008.04.026

  日期：2008.5

  Chalcones are characterized by possessing an enone moiety between two aromatic rings. A series of chalcone-like agents, in which the double bond of the enone system is embedded within a thiophene ring, were synthesized and evaluated for antiproliferative activity and inhibition of tubulin assembly and colchicine binding to tubulin. The replacement of the double bond with a thiophene maintains antiproliferative activity and therefore must not significantly alter the relative conformation of the two aryl rings. The synthesized compounds were found to inhibit the growth of several cancer cell lines at nanomolar to low micromolar concentrations. In general, all compounds having significant antiproliferative activity inhibited tubulin polymerization with an IC50 < 2 mu M. Several of these compounds caused K562 cells to arrest in the G2/M phase of the cell cycle. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis, crystal structure and molecular docking study of novel isoxazole derivatives as CYP450 inhibitors in search of anticancer agents
  作者：Sachin Sudhakar Wazalwar、Anita Ravindra Banpurkar、Franc Perdih

  DOI：10.1080/07391102.2022.2142667

  日期：——

  optimum therapeutic efficacy. Synthesis of the isoxazole derivatives is the first known report of the Knoevenagal condensation of acrylaldehyde derivatives to form isoxazole derivatives as per the literature survey. A detailed crystal structure study of five analogues gives insight into the solid-state structural features of this new framework with isoxazole moieties. Communicated by Ramaswamy H. Sarma

  摘要 本工作报道了一些新型异恶唑衍生物的合成及其与CYP450家族酶的分子对接，以厄洛替尼、吉西他滨和酮康唑为参比药物进行。合成了8种3,4-取代苯基3-氯丙烯醛的异恶唑衍生物和1种肉桂醛的异恶唑衍生物。与标准药物厄洛替尼、吉西他滨和酮康唑相比，所有九种化合物的分子对接研究显示出良好的对接分数。发现 4-OH 和 4-F 衍生物对本工作中正在研究的所有六种 CYP450 蛋白均具有很强的亲和力。4-F 和 3-NO 2衍生物可能是 CYP1A2 的合适先导化合物抑制剂，其次是 4-OH 衍生物。具有显着结合亲和力的 4-OH 衍生物对 CYP1A2、CYP2C9、CYP2C8、CYP2C19 和 CYP2D6 表现出令人鼓舞的抑制作用。目前对这九种3,4-取代苯基3-氯丙烯醛异恶唑衍生物的预测需要在体内和体外条件下进一步研究，以确定最佳治疗效果。根据文献调查，异恶唑衍生物的合成是丙烯醛衍生