2-amino-4-(benzo[d][1,3]dioxol-5-yl)-6-phenylnicotinonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-4-(benzo[d][1,3]dioxol-5-yl)-6-phenylnicotinonitrile
• 英文别名: 2-amino-4-benzo[1,3]dioxol-5-yl-6-phenyl-nicotinonitrile；2-amino-4-(1,3-benzodioxol-5-yl)-6-phenylpyridine-3-carbonitrile
• 化学式: C₁₉H₁₃N₃O₂
• 分子量: 315.331
• InChiKey: YYXSAHAQWKXVIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(benzo[d][1,3]dioxol-5-yl)-6-phenylnicotinonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-Aminomethyl-4-benzo[1,3]dioxol-5-yl-6-phenyl-pyridin-2-ylamine
  参考文献：
  名称：

  Aminomethylpyridines as DPP-IV inhibitors

  摘要：

  In a novel series of DPP-IV inhibitors, a large increase of inhibitory activity was achieved by optimisation of aromatic substituents and conformational restriction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.049
• 作为产物：
  描述：

  (苯并[3,4-d]1,3-二氧杂烷-5-亚甲基)甲烷-1,1-二甲腈 、 苯乙酮 在 ammonium acetate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 2-amino-4-(benzo[d][1,3]dioxol-5-yl)-6-phenylnicotinonitrile
  参考文献：
  名称：

  Aminomethylpyridines as DPP-IV inhibitors

  摘要：

  In a novel series of DPP-IV inhibitors, a large increase of inhibitory activity was achieved by optimisation of aromatic substituents and conformational restriction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.049

文献信息

• Synthesis of Some Polysubstituted Nicotinonitriles and Derived Pyrido[2,3-<i>d</i>]pyrimidines as<i>In Vitro</i>Cytotoxic and Antimicrobial Candidates
  作者：Hassan M. Faidallah、Sherif A. F. Rostom、Khalid A. Khan

  DOI：10.1155/2016/2135893

  日期：——

  The synthesis of polysubstituted pyridines, in addition to some derived pyrido[2,3-d]pyrimidine ring systems supported with chemotherapeutically active functionalities, is described. They were evaluated for their in vitro cytotoxic effects against three different human tumor cell lines (human colon carcinoma HT29, hepatocellular carcinoma Hep-G2, and Caucasian breast adenocarcinoma MCF7). Nine compounds

  描述了多取代吡啶的合成，以及一些衍生的带有化学治疗活性官能团的吡啶并 [2,3-d] 嘧啶环系统。评估了它们对三种不同人类肿瘤细胞系（人类结肠癌 HT29、肝细胞癌 Hep-G2 和白种人乳腺癌 MCF7）的体外细胞毒性作用。九种化合物显示出不同的细胞毒性潜力，其中烷硫基类似物 33、34 和 37 是最活跃的成员，对结肠癌 HT29 细胞系的活性几乎是阿霉素的两倍。此外，相同的三种类似物显示出明显不同的细胞毒性特征，因为它们对正常未转化的人包皮成纤维细胞 Hs27 细胞系的生长表现出边缘抑制作用。同时，19 种化合物能够对革兰氏阳性菌和革兰氏阴性菌表现出显着的抗菌活性，以及​​中等的抗真菌活性。吡啶并 [2,3-d] 嘧啶-2(1H)-硫酮 30 及其烷硫基衍生物 33 和 34 是最活跃的抗菌成员，与氨苄西林对金黄色葡萄球菌、大肠杆菌和铜绿假单胞菌具有同等效力，以及对白色念珠菌的显着抗真菌活性。化合物
• 2-Amino-6-furan-2-yl-4-substituted Nicotinonitriles as A_2A Adenosine Receptor Antagonists
  作者：Monica Mantri、Olivier de Graaf、Jacobus van Veldhoven、Anikó Göblyös、Jacobien K. von Frijtag Drabbe Künzel、Thea Mulder-Krieger、Regina Link、Henk de Vries、Margot W. Beukers、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm701594y

  日期：2008.8.1

  A2A adenosine receptor antagonists usually have bi- or tricyclic N aromatic systems with varying substitution patterns to achieve desired receptor affinity and selectivity. Using a pharmacophore model designed by overlap of nonxanthine type of previously known A2A antagonists, we synthesized a new class of compounds having a 2-amino nicotinonitrile core moiety. From our data, we conclude that the presence of at least one furan group rather than phenyl is beneficial for high affinity on the A2A adenosine receptor. Compounds 39 (LUF6050) and 44 (LUF6080) of the series had Ki values of 1.4 and 1.0 nM, respectively, with reasonable selectivity toward the other adenosine receptor subtypes, A,, A2B, and A3. The high affinity of 44 was corroborated in a cAMP second messenger assay, yielding subnanomolar potency for this compound.
• Aminomethylpyridines as DPP-IV inhibitors
  作者：Jens-Uwe Peters、Silja Weber、Stéphane Kritter、Peter Weiss、Angelina Wallier、Daniel Zimmerli、Markus Boehringer、Matthias Steger、Bernd-Michael Loeffler

  DOI：10.1016/j.bmcl.2004.04.049

  日期：2004.7

  In a novel series of DPP-IV inhibitors, a large increase of inhibitory activity was achieved by optimisation of aromatic substituents and conformational restriction. (C) 2004 Elsevier Ltd. All rights reserved.