(Z)-3-(4'-dimethylaminophenyl)-2-(4''-nitrophenyl)acrylonitrile | 7496-26-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-3-(4'-dimethylaminophenyl)-2-(4''-nitrophenyl)acrylonitrile
• 英文别名: (Z)-3-(4-(dimethylamino)phenyl)-2-(4-nitrophenyl)acrylonitrile；(Z)-3-[4-(dimethylamino)phenyl]-2-(4-nitrophenyl)acrylonitrile；dimethylamino-4' nitro-4 α-cyanostilbene-trans；dimethylamino-4' nitro-4 α-cyanostilbene；2-(4-nitro-phenyl)-3c-(4-dimethylamino-phenyl)-acrylonitrile；2-(4-Nitro-phenyl)-3c-(4-dimethylamino-phenyl)-acrylonitril；(Z)-3-(4-dimethylaminophenyl)-2-(4-nitrophenyl)prop-2-enenitrile；(Z)-3-[4-(dimethylamino)phenyl]-2-(4-nitrophenyl)prop-2-enenitrile
• CAS: 7496-26-6；60004-48-0；2900-71-2
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: BLOQCELCRSCRAK-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-(4'-dimethylaminophenyl)-2-(4''-nitrophenyl)acrylonitrile 生成
  参考文献：
  名称：

  Walkow, F.; Epperlein, J.; Mustroph, H., Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 5, p. 799 - 807

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯乙腈 、 对二甲氨基苯甲醛 在 silica chloride 作用下， 以 乙醇 为溶剂， 反应 1.8h， 以85%的产率得到(Z)-3-(4'-dimethylaminophenyl)-2-(4''-nitrophenyl)acrylonitrile
  参考文献：
  名称：

  Z-丙烯腈衍生物的 立体选择性合成：催化和乙酰胆碱酯酶抑制研究†

  摘要：

  在本研究中，合成了一个（Z）-丙烯腈类似物的聚焦库（库A和B），通常通过对硝基苯乙腈与适当取代的芳族醛（1a–i）和3-之间的便捷的Knoevenagel缩合来访问甲酰基色酮（3a–c）。这种新的合成环保方法极大地提高了合成效率（83-92％的收率），高纯度，在不使用高毒性试剂进行合成的情况下最大程度地减少了化学废物的产生，并且更明显地，它提高了选择性用于（Z）-丙烯腈衍生物。通过进行理论计算，发现在（ž与（E）-异构体相比，化合物2b的）-异构体稳定2.61kcal mol -1。测试所有化合物的乙酰胆碱酯酶（AChE）抑制作用。化合物2a和4c表现出最强的抑制作用，IC 50值分别为0.20μM和0.22μM。发现苯环A对位的甲氧基对于抑制AChE是必不可少的。

  DOI：

  10.1039/c3nj01384g

文献信息

• 一类基于氰基苯乙烯的聚集诱导发光材料及其制备方法和应用
  申请人：豫章师范学院

  公开号：CN115368275A

  公开（公告）日：2022-11-22

  本发明涉及一类基于氰基苯乙烯的聚集诱导发光材料及其制备方法和应用。所述聚集诱导发光材料具有如下式(I)所示结构，其中，R1独立地为C1‑18烷基胺基、C1‑18烷基氧基中的一种；R2独立地为氢、C1‑3烷基、卤素、羟基中的一种；R3独立地为卤素、芳基、杂芳基、氨基、硝基、烷基氧基中的一种。本发明所合成材料可以对氯化氢气体和氨气进行特异性传感识别，具有良好的稳定性和快速响应性。此外，该聚集诱导发光材料还可以实现信息加密和解密应用，具有合成及纯化简单、成本低廉和多次重复利用等优点。
• Synthesis and evaluation of (Z)-2,3-diphenylacrylonitrile analogs as anti-cancer and anti-microbial agents
  作者：Mohammad Sayed Alam、Young-Joo Nam、Dong-Ung Lee

  DOI：10.1016/j.ejmech.2013.08.031

  日期：2013.11

  In the present study, a series of (Z)-2,3-diphenylacrylonitrile analogs were synthesized and then evaluated in terms of their cytotoxic activities against four human cancer cell lines, e.g. lung cancer (A549), ovarian cancer (SK-OV-3), skin cancer (SK-MEL-2), and colon cancer (HCT15), as well as anti-microbial activities against three microbes, e.g. Staphylococcus aureus, Salmonella typhi, and Aspergillus niger. The title compounds were synthesized by Knoevenagel condensation reaction of benzyl cyanide or pnitrobenzyl cyanide with substituted benzaldehydes in good yields. Most of the compounds exhibited significant suppressive activities against the growth of all cancer cell lines. Compound 3c was most active in inhibiting the growth of A549, SK-OV-3, SK-MEL-2, and HCT15 cells lines with IC50 values of 0.57, 0.14, 0.65, and 0.34 mg/mL, respectively, followed by compounds 3f, 3i, and 3h. Compound 3c exhibited 2.4 times greater cytotoxic activity against HCT15 cells, whereas it showed similar potency against SK-OV-3 cells to that of the standard anti-cancer agent doxorubicin. Structure activity relationship study revealed that electron-donating groups at the para-position of phenyl ring B were more favorable for improved cytotoxic activity, whereas the presence of electron-withdrawing groups was unfavorable compare to unsubstituted acrylonitrile. An optimal electron density on phenyl ring A of (Z)-2,3-diphenylacrylonitrile analogs was crucial for their cytotoxic activities against human cancer cell lines used in the present study. Qualitative structure cytotoxic activity relationships were studied using physicochemical parameters; a good correlation between calculated polar surface area (PSA), a lipophobic parameter, and cytotoxic activity was found. Moreover, all compounds showed significant anti-bacterial activities against S. typhi, whereas compound 3k showed potent inhibition against both S. aureus and S. typhi bacterial strains. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Merckx, Bulletin des Societes Chimiques Belges, 1949, vol. 58, p. 460,468
  作者：Merckx

  DOI：——

  日期：——
• (<i>Z</i>)-2-(2-Bromophenyl)-3-{[4-(1-methyl-piperazine)amino]phenyl}acrylonitrile (DG172): An Orally Bioavailable PPARβ/δ-Selective Ligand with Inverse Agonistic Properties
  作者：Sonja Lieber、Frithjof Scheer、Wolfgang Meissner、Simone Naruhn、Till Adhikary、Sabine Müller-Brüsselbach、Wibke E. Diederich、Rolf Müller

  DOI：10.1021/jm2017122

  日期：2012.3.22

  The ligand-regulated nuclear receptor peroxisome proliferator-activated receptor beta/delta (PPAR beta/delta) is a potential pharmacological target due to its role in disease-related biological processes. We used TR-FRET-based competitive ligand binding and coregulator interaction assays to screen 2693 compounds of the Open Chemical Repository of the NCl/NIH Developmental Therapeutics Program for inhibitory PPAR beta/delta ligands. One compound, (Z)-3-(4-dimethylamino-phenyl)-2-phenyl-acrylonitrile, was used for a systematic SAR study. This led to the design of derivative 37, (Z)-2-(2-bromopheny1)-3-[4-(1-methyl-piperazine)amino]phenyl}acrylonitrile (DG172), a novel PPAR beta/delta-selective ligand showing high binding affinity (IC50 = 27 nM) and potent inverse agonistic properties. 37 selectively inhibited the agonist-induced activity of PPAR beta/delta, enhanced transcriptional corepressor recruitment, and down-regulated transcription of the PPAR beta/delta target gene Angptl4 in mouse myoblasts (IC50 = 9.5 nM). Importantly, 37 was bioavailable after oral application to mice with peak plasma levels in the concentration range of its maximal inhibitory potency, suggesting that 37 will be an invaluable tool to elucidate the functions and therapeutic potential of PPAR beta/delta.
• Tinant, B.; Touillaux, R.; Declercq, J. P., Bulletin des Societes Chimiques Belges, 1983, vol. 92, # 2, p. 101 - 110
  作者：Tinant, B.、Touillaux, R.、Declercq, J. P.、Meerssche, M. Van、Leroy, G.、Weiler J.

  DOI：——

  日期：——