2-Amino-8(4-chlorbenzyliden)3-cyan-4(4-chlorphenyl)-5.6.7.8-tetrahydro-4-H-chromen | 54105-30-5

• 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-8(4-chlorbenzyliden)3-cyan-4(4-chlorphenyl)-5.6.7.8-tetrahydro-4-H-chromen
• 英文别名: 2-amino-8-(4-chlorobenzylidene)-4-(4-chlorophenyl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；(8E)-2-amino-4-(4-chlorophenyl)-8-[(4-chlorophenyl)methylidene]-4,5,6,7-tetrahydrochromene-3-carbonitrile
• CAS: 54105-30-5
• 化学式: C₂₃H₁₈Cl₂N₂O
• 分子量: 409.315
• InChiKey: SWTPSDIDUXZIFY-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 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：

  2-Amino-8(4-chlorbenzyliden)3-cyan-4(4-chlorphenyl)-5.6.7.8-tetrahydro-4-H-chromen 、 benzohydroximoyl chloride 在 三乙胺 作用下， 以 苯 为溶剂， 反应 5.0h， 以40%的产率得到4-(4-chlorophenyl)-8-[(E)-(4-chlorophenyl)-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：

  4-氯苯甲醛 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 2-Amino-8(4-chlorbenzyliden)3-cyan-4(4-chlorphenyl)-5.6.7.8-tetrahydro-4-H-chromen
  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

• 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 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。