(8E)-2-amino-4-(4-methoxyphenyl)-8-[(4-methoxyphenyl)methylidene]-6-methyl-5,7-dihydro-4H-pyrano[3,2-c]pyridine-3-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (8E)-2-amino-4-(4-methoxyphenyl)-8-[(4-methoxyphenyl)methylidene]-6-methyl-5,7-dihydro-4H-pyrano[3,2-c]pyridine-3-carbonitrile
• 化学式: C₂₅H₂₅N₃O₃
• 分子量: 415.492
• InChiKey: FHJARLMXPKCCEJ-LDADJPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 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：
  80.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 sodium hydroxide 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 5.17h， 生成 (8E)-2-amino-4-(4-methoxyphenyl)-8-[(4-methoxyphenyl)methylidene]-6-methyl-5,7-dihydro-4H-pyrano[3,2-c]pyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Certain α,β-Unsaturated Ketones and Their Corresponding Fused Pyridines as Antiviral and Cytotoxic Agents

  摘要：

  A new series of 3,5-bis(arylidene)-4-piperidones, as chalcone analogues carrying variety of aryl and heteroaryl groups, pyrazolo[4,3-c]pyridines, pyrido[4,3-d]pyrimidines, and pyrido[3,2-c]-pyridines, carrying an arylidene moiety, and a series of pyrano[3,2-c]pyridines, as flavone and coumarin isosteres, were synthesized and screened for their in vitro antiviral and antitumor activities at the National Cancer Institute (NCI). Compounds 9 and 18 proved to be active against herpes simplex virus-1 (HSV-1), while compound 13 showed moderate activity against human immunodeficiency virus-1 (HIV-1). Compounds 14, 26, 28, 33, and 35 exhibited a broad spectrum antitumor activity. In addition, compounds 26, 33, and 35 proved to be of moderate selectivity toward leukemia cell lines. The pyrano[3,2-c]pyridines heterocyclic system proved to be the most active antitumors among the investigated heterocycles.

  DOI：

  10.1021/jm000038m

文献信息

• Application of MCM-41-SO3H as an Advanced Nanocatalyst for the Solvent Free Synthesis of Pyrano[3,2-c]pyridine Derivatives
  作者：Shahnaz Rostamizadeh、Nasrin Shadjou、Mohammad Hasanzadeh

  DOI：10.1002/jccs.201100667

  日期：2012.7

  MCM‐41‐SO3H, an ordered mesoporous silica material in which MCM‐41 with covalently anchored sulfonic acid groups was used as an acidic catalyst for the rapid and ‘green’ synthesis of pyrano[3,2‐c]pyridine derivatives under solvent‐free conditions. Reusability of the catalyst, high yields, short reaction times, simplicity and easy workup are advantages of this novel synthetic procedure compared to the

  MCM-41-SO 3 H，一种有序的介孔二氧化硅材料，其中具有共价锚定磺酸基团的MCM-41被用作酸性催化剂，可在以下条件下快速并“绿色”合成吡喃并[3,2-c]吡啶衍生物无溶剂条件。与文献报道的常规方法相比，该新颖的合成方法的优点是催化剂的可重复使用性，高产率，短反应时间，简单和易于后处理。
• An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles
  作者：Raju Ranjith Kumar、Subbu Perumal、Palaniappan Senthilkumar、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2007.09.095

  日期：2007.12

  An atom efficient, green protocol for the synthesis of fifteen 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro4H-pyrano[3,2-c] pyridine-3-carbonitriles in quantitative yields from the reaction of 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones with malononitrile in presence of solid sodium ethoxide under solvent-free condition is described. The compounds were tested for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant tuberculosis (MDR-TB), and Mycobacterium smegmatis using agar dilution method. 2-Amino-4-[4-(dimethylamino) phenyl]-8-(E)-[4(dimethylamino) phenyl] methylidene-6-methyl-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]-pyridine-3-carbonitrile was found to be the most potent compound (MIC: 0.43 mu M) against MTB and MDR-TB, being 100 times more active than standard, isoniazid against MDRTB. (c) 2007 Elsevier Ltd. All rights reserved.