4-Amino-8-benzyliden-3-cyan-4-phenyl-5.6.7.8-tetrahydro-4-chroman | 54105-27-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4-Amino-8-benzyliden-3-cyan-4-phenyl-5.6.7.8-tetrahydro-4-chroman
• 英文别名: (8E)-2-amino-8-benzylidene-4-phenyl-4,5,6,7-tetrahydrochromene-3-carbonitrile
• CAS: 54105-27-0
• 化学式: C₂₃H₂₀N₂O
• 分子量: 340.425
• InChiKey: NFPMGUPGOPWSQV-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Amino-8-benzyliden-3-cyan-4-phenyl-5.6.7.8-tetrahydro-4-chroman 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以60%的产率得到3-amino-9-benzylideno-4-phenyl-1,4-dihydrocyclohexano--pyrano<2,3-c>pyrazole
  参考文献：
  名称：

  Assy, M. G.; Youssif, Sh. A.; Ouf, N. H., Polish Journal of Chemistry, 1995, vol. 69, # 6, p. 896 - 901

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮 在 哌啶 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 4-Amino-8-benzyliden-3-cyan-4-phenyl-5.6.7.8-tetrahydro-4-chroman
  参考文献：
  名称：

  Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents

  摘要：

  Twenty-four new compounds were prepared, taking curcumin as a lead, in order to explore their antioxidant and antitumor properties. The capacities of these derivatives to scavenge the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS(.+)), and to protect human red blood cells (RBCs) from oxidative haemolysis were investigated. In addition, the percentage viability of different cell lines (Hep G2, WI38, VERO and MCF-7) was tested. The result of the antitumor testing was generally in accordance with those of the antioxidant assays. Compounds which bear o-methoxy substitution to the 4-hydroxy function in the phenyl ring (7g, 5g and 3g) exhibited significantly higher ABTS(.+)-scavenging, antihaemolysis, and antitumor activities than other derivatives. In addition, molecular modelling studies were carried out for biologically active and inactive compounds, to study the structure-activity relationship, with the aim to elucidate which portions of the molecules are critical for the antioxidant and antitumor activity.

  DOI：

  10.1007/s00044-012-0116-9

文献信息

• A novel synthetic route to phenyl-substituted pyridines synthesis of [1] benzopyrano[4,3-b]pyridines, [1]benzothiopyrano[4,3-b]bpyridines and pyrido[3,2-b][1,4]benzothiazines(1-azaphenothiazines)
  作者：D.V. Tyndall、T. Al Nakib、M.J. Meegan

  DOI：10.1016/0040-4039(88)85265-1

  日期：——

  4-diphenyl-2-methoxypyridine-3-carbonitrile. This reaction has been applied to a general synthesis of phenyl-substituted [1]benzopyrano[4,3-pyridines, [1]benzothiopyrano[4,3-]pyridines and pyrido[3,2- [1,4]benzothiazines(1-azaphenothiazines).

  1，3-二苯基丙烯酮与丙二腈在碱中的反应得到1，4-二苯基-2-甲氧基吡啶-3-甲腈。该反应已应用于一般合成苯基取代的[1]苯并吡喃并[4,3-吡啶]，[1]苯并噻吩并吡喃并[ 4,3- ]吡啶和吡啶并[3,2- [1,4]苯并噻嗪（1 -氮杂吩噻嗪）。
• Clean, One‐Pot Synthesis of 4<i>H</i>‐Pyran Derivatives Catalyzed by Hexadecyltrimethyl Ammonium Bromide in Aqueous Media
  作者：Tong‐Shou Jin、Li‐Bin Liu、Ying Zhao、Tong‐Shuang Li

  DOI：10.1081/scc-200064898

  日期：2005.7

  Abstract An efficient and convenient synthetic route to 4H‐pyran derivatives in water in the presence of hexadecyltrimethyl ammonium bromide (HTMAB) as catalyst is described. This method provides several advantages such as environment friendliness, high yields, and a simple workup procedure. In addition, water was chosen as a green solvent.

  摘要 描述了在十六烷基三甲基溴化铵 (HTMAB) 作为催化剂存在下，在水中有效、方便地合成 4H-吡喃衍生物的路线。该方法具有多种优点，例如环境友好、产量高和后处理程序简单。此外，选择水作为绿色溶剂。
• Synthesis of 2‐Aminopyran Derivatives and 3‐Arylpropionitrile Derivatives Catalyzed by KF/Al₂O₃
  作者：Xiang‐shan Wang、Da‐qing Shi、Ya Du、Yan Zhou、Shu‐jiang Tu

  DOI：10.1081/scc-120030692

  日期：2004.12.31

  A series of 2-cyano-3-aryl-3-(3,4-dihydro-1(2H)-naphthalene-one-2-yl) propionitrile derivatives and 2-aminopyran derivatives were synthesized by the KF-Al2O3-catalyzed reaction of malononitrile with 2-arylmethylidene-3,4-dihydro-1(2H)-naphthalenone, 2,6-biarylmethylidene cyclohexanone, or 2,5-biarylmethylidene cyclopenanone in DMF at room temperature. The structure of the later was confirmed by x-ray analysis.
• TYNDALL, D. V.;AL, NAKIB T.;MEEGAN, M. J., TETRAHEDRON LETT., 29,(1988) N 22, C. 2703-2706
  作者：TYNDALL, D. V.、AL, NAKIB T.、MEEGAN, M. J.

  DOI：——

  日期：——
• Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents
  作者：Said M. Bayomi、Hassan A. El-Kashef、Mahmoud B. El-Ashmawy、Magda N. A. Nasr、Magda A. El-Sherbeny、Farid A. Badria、Laila A. Abou-zeid、Mariam A. Ghaly、Naglaa I. Abdel-Aziz

  DOI：10.1007/s00044-012-0116-9

  日期：2013.3

  Twenty-four new compounds were prepared, taking curcumin as a lead, in order to explore their antioxidant and antitumor properties. The capacities of these derivatives to scavenge the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS(.+)), and to protect human red blood cells (RBCs) from oxidative haemolysis were investigated. In addition, the percentage viability of different cell lines (Hep G2, WI38, VERO and MCF-7) was tested. The result of the antitumor testing was generally in accordance with those of the antioxidant assays. Compounds which bear o-methoxy substitution to the 4-hydroxy function in the phenyl ring (7g, 5g and 3g) exhibited significantly higher ABTS(.+)-scavenging, antihaemolysis, and antitumor activities than other derivatives. In addition, molecular modelling studies were carried out for biologically active and inactive compounds, to study the structure-activity relationship, with the aim to elucidate which portions of the molecules are critical for the antioxidant and antitumor activity.