2-(((2-methoxyphenyl)amino)methylene)malononitrile | 24115-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(((2-methoxyphenyl)amino)methylene)malononitrile
• 英文别名: <(2-Methoxy-anilino-)-methylen>-malonsaeuredinitril；[(2-Methoxyanilino)methylene]malononitrile；2-[(2-methoxyanilino)methylidene]propanedinitrile
• CAS: 24115-30-8
• 化学式: C₁₁H₉N₃O
• mdl: MFCD00486934
• 分子量: 199.212
• InChiKey: DWKZOLIDAMOONJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(((2-methoxyphenyl)amino)methylene)malononitrile 在 氨 、 三氯氧磷 作用下， 以 乙醇 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 4-chloro-5-(2-methoxyphenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile
  参考文献：
  名称：

  9-Deazapurines as Broad-Spectrum Inhibitors of the ABC Transport Proteins P-Glycoprotein, Multidrug Resistance-Associated Protein 1, and Breast Cancer Resistance Protein

  摘要：

  P-Glycoprotein (P-gp, ABCB1), multidrug resistance-associated protein 1 (MRP1, ABCC1), and breast cancer resistance protein (BCRP, ABCG2) are the three major ABC transport proteins conferring resistance to many structurally diverse anticancer agents, leading to the phenomenon called multidrug resistance (MDR). Much effort has been put into the development of clinically useful compounds to reverse MDR. Broad-spectrum inhibitors of ABC transport proteins can be of great use in cancers that simultaneously coexpress two or three transporters. In this work, we continued our effort to generate new, potent, nontoxic, and multiply effective inhibitors of the three major ABC transporters. The best compound was active in a very low micromolar concentration range against all three transporters and restored sensitivity toward daunorubicin (P-gp and MRP1) and SN-38 (BCRP) in A2780/ADR (P-gp), H69AR (MRP1), and MDCK II BCRP (BCRP) cells. Additionally, the compound is a noncompetitive inhibitor of daunorubicin (MRP1), calcein AM (P-gp), and pheophorbide A (BCRP) transport.

  DOI：

  10.1021/acs.jmedchem.7b00788
• 作为产物：
  描述：

  邻甲氧基苯胺 、 乙氧基亚甲基丙二腈 以 乙醇 为溶剂， 反应 1.0h， 生成 2-(((2-methoxyphenyl)amino)methylene)malononitrile
  参考文献：
  名称：

  9-Deazapurines as Broad-Spectrum Inhibitors of the ABC Transport Proteins P-Glycoprotein, Multidrug Resistance-Associated Protein 1, and Breast Cancer Resistance Protein

  摘要：

  P-Glycoprotein (P-gp, ABCB1), multidrug resistance-associated protein 1 (MRP1, ABCC1), and breast cancer resistance protein (BCRP, ABCG2) are the three major ABC transport proteins conferring resistance to many structurally diverse anticancer agents, leading to the phenomenon called multidrug resistance (MDR). Much effort has been put into the development of clinically useful compounds to reverse MDR. Broad-spectrum inhibitors of ABC transport proteins can be of great use in cancers that simultaneously coexpress two or three transporters. In this work, we continued our effort to generate new, potent, nontoxic, and multiply effective inhibitors of the three major ABC transporters. The best compound was active in a very low micromolar concentration range against all three transporters and restored sensitivity toward daunorubicin (P-gp and MRP1) and SN-38 (BCRP) in A2780/ADR (P-gp), H69AR (MRP1), and MDCK II BCRP (BCRP) cells. Additionally, the compound is a noncompetitive inhibitor of daunorubicin (MRP1), calcein AM (P-gp), and pheophorbide A (BCRP) transport.

  DOI：

  10.1021/acs.jmedchem.7b00788

文献信息

• Copper-Catalyzed Three-Component Reaction: Solvent-Controlled Regioselective Synthesis of 4-Amino- and 6-Amino-2-iminopyridines
  作者：Fenguo Zhou、Xu Liu、Ning Zhang、Yongjiu Liang、Rui Zhang、Xiaoqing Xin、Dewen Dong

  DOI：10.1021/ol4028368

  日期：2013.11.15

  Regioselective synthesis of multisubstituted 4-amino- and 6-amino-2-iminopyridines has been developed via the copper-catalyzed three-component reaction based on the reaction conditions selection. The reaction of sulfonyl azides, alkynes, and 2-[(amino)methylene]malononitriles catalyzed by copper(I) iodide in tetrahydrofuran at room temperature afforded substituted 4-amino-2-iminopyridines, whereas

  基于反应条件的选择，通过铜催化的三组分反应，已经开发了多取代的4-氨基-和6-氨基-2-亚氨基吡啶的区域选择性合成。在室温下，碘化铜（I）在四氢呋喃中催化磺酰叠氮化物，炔烃和2-[（（氨基）亚甲基]丙二腈）的反应，得到取代的4-氨基-2-亚氨基吡啶，而在N，N-二甲基甲酰胺中则为50在N 2的℃下，它产生取代的6-氨基-2-亚氨基吡啶为主要产物。
• Enamine Derivatives of Malonic Acid with Pharmacologic Activities
  作者：Arthur A. Santilli、William F. Bruce、T. S. Osdene

  DOI：10.1021/jm00331a015

  日期：1964.1
• 9-Deazapurines as Broad-Spectrum Inhibitors of the ABC Transport Proteins P-Glycoprotein, Multidrug Resistance-Associated Protein 1, and Breast Cancer Resistance Protein
  作者：Katja Stefan、Sven Marcel Schmitt、Michael Wiese

  DOI：10.1021/acs.jmedchem.7b00788

  日期：2017.11.9

  P-Glycoprotein (P-gp, ABCB1), multidrug resistance-associated protein 1 (MRP1, ABCC1), and breast cancer resistance protein (BCRP, ABCG2) are the three major ABC transport proteins conferring resistance to many structurally diverse anticancer agents, leading to the phenomenon called multidrug resistance (MDR). Much effort has been put into the development of clinically useful compounds to reverse MDR. Broad-spectrum inhibitors of ABC transport proteins can be of great use in cancers that simultaneously coexpress two or three transporters. In this work, we continued our effort to generate new, potent, nontoxic, and multiply effective inhibitors of the three major ABC transporters. The best compound was active in a very low micromolar concentration range against all three transporters and restored sensitivity toward daunorubicin (P-gp and MRP1) and SN-38 (BCRP) in A2780/ADR (P-gp), H69AR (MRP1), and MDCK II BCRP (BCRP) cells. Additionally, the compound is a noncompetitive inhibitor of daunorubicin (MRP1), calcein AM (P-gp), and pheophorbide A (BCRP) transport.