2-amino-4-(4-methoxyphenyl)-8-[(E)-(4-methoxy-phenyl)methylidene]-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile | 1313510-63-2

• 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: 2-amino-4-(4-methoxyphenyl)-8-[(E)-(4-methoxy-phenyl)methylidene]-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: (E)-2-amino-8-(4-methoxybenzylidene)-4-(4-methoxyphenyl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；(8E)-2-amino-4-(4-methoxyphenyl)-8-[(4-methoxyphenyl)methylidene]-4,5,6,7-tetrahydrochromene-3-carbonitrile
• CAS: 1313510-63-2
• 化学式: C₂₅H₂₄N₂O₃
• 分子量: 400.477
• InChiKey: ICMMKYOFRYNIBJ-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(4-methoxyphenyl)-8-[(E)-(4-methoxy-phenyl)methylidene]-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 、 benzohydroximoyl chloride 在 三乙胺 作用下， 以 苯 为溶剂， 反应 5.0h， 以52%的产率得到4-(4-methoxyphenyl)-8-[(E)-(4-methoxyphenyl)-methylidene]-3-(3-phenyl-1,2,4-oxadiazol-5-yl)-5,6,7,8-tetrahydro-4H-chromen-2-ylamine
  参考文献：
  名称：

  1,2,4-恶二唑-吡喃吡啶/色烯杂化物的新型分枝杆菌活性，由腈的化学选择性1,3-偶极环加成反应产生

  摘要：

  由苯并氢氧亚甲基氯和三乙胺就地生成的腈的1，3-偶极环加成反应生成2-氨基吡咯并吡啶-3-甲腈和2-氨基氧化烯-3-甲腈的化学选择性提供了新的1,2,4-恶二唑-吡喃吡啶/色烯杂化物中等产量的杂环。这些化合物针对结核分枝杆菌H37Rv（MTB）的体外筛选显示，1,2,4-恶二唑-吡喃并吡啶杂化物相对于1,2,4-恶二唑-色烯杂化物表现出增强的活性。在筛选的化合物中，3- [3-（4-氯苯基）-1,2,4-恶二唑-5-基] -4-（2,4-二氯苯基）-8-[（E）-（2,4 -（二氯苯基）-亚甲基] -6-甲基-5,6,7,8-四氢-4 H-吡喃并[3,2- c] pyridin-2-amine（MIC：0.31μM）的活性是标准抗结核药的1.2倍，15.2倍和24.6倍。分别为异烟肼，环丙沙星和乙胺丁醇。

  DOI：

  10.1016/j.bmc.2011.04.033
• 作为产物：
  描述：

  环己酮 在 哌啶 、 sodium hydroxide 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 26.0h， 生成 2-amino-4-(4-methoxyphenyl)-8-[(E)-(4-methoxy-phenyl)methylidene]-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  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

• 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.
• Antimycobacterial activity of novel 1,2,4-oxadiazole-pyranopyridine/chromene hybrids generated by chemoselective 1,3-dipolar cycloadditions of nitrile oxides
  作者：Raju Ranjith Kumar、Subbu Perumal、J. Carlos Menéndez、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2011.04.033

  日期：2011.6

  The 1,3-dipolar cycloaddition of nitrile oxides generated in situ from benzohydroximinoyl chloride and triethylamine to 2-aminopyranopyridine-3-carbonitriles and 2-aminochromene-3-carbonitriles occurred chemoselectively furnishing novel 1,2,4-oxadiazole-pyranopyridine/chromene hybrid heterocycles in moderate yields. In vitro screening of these compounds against Mycobacterium tuberculosis H37Rv (MTB)

  由苯并氢氧亚甲基氯和三乙胺就地生成的腈的1，3-偶极环加成反应生成2-氨基吡咯并吡啶-3-甲腈和2-氨基氧化烯-3-甲腈的化学选择性提供了新的1,2,4-恶二唑-吡喃吡啶/色烯杂化物中等产量的杂环。这些化合物针对结核分枝杆菌H37Rv（MTB）的体外筛选显示，1,2,4-恶二唑-吡喃并吡啶杂化物相对于1,2,4-恶二唑-色烯杂化物表现出增强的活性。在筛选的化合物中，3- [3-（4-氯苯基）-1,2,4-恶二唑-5-基] -4-（2,4-二氯苯基）-8-[（E）-（2,4 -（二氯苯基）-亚甲基] -6-甲基-5,6,7,8-四氢-4 H-吡喃并[3,2- c] pyridin-2-amine（MIC：0.31μM）的活性是标准抗结核药的1.2倍，15.2倍和24.6倍。分别为异烟肼，环丙沙星和乙胺丁醇。