2-amino-4-(furan-2-yl)-6-phenylnicotinonitrile | 77607-68-2

• 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-(furan-2-yl)-6-phenylnicotinonitrile
• 英文别名: 2-Amino-4-furan-2-yl-6-phenyl-nicotinonitrile；2-amino-4-(furan-2-yl)-6-phenylpyridine-3-carbonitrile
• CAS: 77607-68-2
• 化学式: C₁₆H₁₁N₃O
• 分子量: 261.283
• InChiKey: UPNSGUUFOFSFEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  148 °C
• 沸点：
  480.6±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-(furan-2-yl)-6-phenylnicotinonitrile 在 氢氧化钾 作用下， 以 二苯醚 为溶剂， 反应 31.0h， 生成 5-Furan-2-yl-3-(2-methoxy-phenyl)-7-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  SYNTHESIS OF RIBONUCLEOSIDES OF 2-THIOXOPYRIDO [2,3-d]PYRIMIDINES BY PHASE TRANSFER CATALYSIS AND THEIR ANTIMICROBIAL ACTIVITY

  摘要：

  The ribonucleosides viz; 2-thioxo-3,5,7-trisubstituted-1-(2,3,5-tri-O-benzoyl-beta -D-ribofuranosyl)pyrido[2,3-d]pyrimidine-4 (1H)-ones have been synthesized via phase transfer ribosylation of 2-thioxo- 3,5,7-trisubstituted pyrido[2,3-d]pyrimidine-4(IH)-ones with 2,3,5-tri-O-benzoyl-beta -D- ribofuranosyl bromide in biphasic solvent such as CH2Cl2-50% aqueous NaOH using tetrabutylammonium bromide as phase transfer catalysis (PTC). The synthesized compounds have been characterized by elemental analyses, spectral data and screened for their antimicrobial activity.

  DOI：

  10.1080/10426509808033729
• 作为产物：
  描述：

  (2-呋喃亚甲基)丙二腈 、 苯乙酮 在 ammonium acetate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 2-amino-4-(furan-2-yl)-6-phenylnicotinonitrile
  参考文献：
  名称：

  2-Amino-6-furan-2-yl-4-substituted Nicotinonitriles as A_2A Adenosine Receptor Antagonists

  摘要：

  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.

  DOI：

  10.1021/jm701594y

文献信息

• Synthesis of Some Novel Pyrido[2,3-<i>d</i> ]pyrimidine and Pyrido[3,2-<i>e</i> ][1,3,4]triazolo and Tetrazolo[1,5-<i>c</i> ]pyrimidine Derivatives as Potential Antimicrobial and Anticancer Agents
  作者：Elsayed Mohmoud AbedelRehim、Mohamed AbdEllatif

  DOI：10.1002/jhet.3058

  日期：2018.2

  A novel series of pyrido[2,3‐d]pyrimidines 3a–d, 4a–d, 5a–d, 6a–d, and 7a–d; pyrido[3,2‐e][1,3,4]triazolo; and tetrazolo[1,5‐c]pyrimidines 10a–d and 11a–d was synthesized through different chemical reactions starting from 2‐amino‐3‐cyano‐4,6‐diarylpyridines. The newly synthesized heterocycles were characterized by elemental analysis, IR, 1H‐NMR, 13C‐NMR, and mass spectral data. Compounds have been

  一系列新颖的吡啶并[2,3- d ]嘧啶3a - d，4a - d，5a - d，6a - d和7a - d；pyrido [3,2- e ] [1,3,4]三唑; 从2-氨基-3-氰基-4-4，6-二芳基吡啶开始，通过不同的化学反应合成了四唑并[1,5– c ]嘧啶10a – d和11a – d。通过元素分析，IR，1 H-NMR，13对新合成的杂环进行了表征C-NMR和质谱数据。已经对化合物的抗菌和抗真菌活性进行了筛选。数据表明，给电子基团（例如对甲氧基苯基）的存在增加了抗菌活性。同样，这些化合物对结肠和肝癌细胞也显示出抗癌活性。
• Synthesis and Antimicrobial Evaluation of Some Novel Pyrido[2,3-<i>d</i>] Pyrimidine Derivatives and Their Ribofuranosides
  作者：Sangeeta Bhargava、Lokesh Kumar Rajwanshi

  DOI：10.1002/jhet.3203

  日期：2018.8

  4‐imino‐3,5,7‐trisubstituted pyrido[2,3‐d] pyrimidin‐2(1H)‐ones 3a–c and 4‐imino‐3,5,7‐trisubstituted pyrido[2,3‐d]pyrimidin‐2(1H)‐thiones 4a–c, respectively. The ribofuranosides, namely, 4‐imino‐3,5,7‐trisubstituted‐1‐(2′,3′,5′‐tri‐O‐benzoyl‐β‐d‐ribofuranosyl) pyrido[2,3‐d]pyrimidin‐2(1H)‐ones 7a–c and 4‐imino‐3,5,7‐trisubstituted‐1‐(2′,3′,5′‐tri‐O‐benzoyl‐β‐D‐ribofuranosyl) pyrido[2,3‐d]pyri‐midin‐2(1H)‐thiones

  用芳基异氰酸酯和芳基异硫氰酸酯处理的2-氨基3-氰基-4,6-二取代吡啶2a-c提供了4-亚氨基-3,5,7-三取代吡啶[2,3 - d ]嘧啶2（1 H）分别是3a–c和4–亚氨基-3,5,7-三取代吡啶并[2,3 – d ]嘧啶2（1 H）–硫酮4a–c。呋喃核糖核苷，即4-亚氨基-3,5,7-三取代-1-（2'，3'，5'-三-O-苯甲酰基-β - d-呋喃呋喃糖基）吡啶基[2,3- d ]嘧啶‐2（1 H）‐7a –c和4‐亚氨基‐3,5,7‐三取代‐1‐（2 '，3 '，5 ' -三- ö -benzoyl- β -D-呋喃核糖基）吡啶并[2,3- d ]螨-midin-2（1 ħ）-thiones 8A-C ，由三甲基硅烷衍生物的缩合合成3A- c和4a–c与β - d-呋喃呋喃糖基-1-乙酸酯2,3,5-三苯甲酸酯。通过元素分析，IR，1 H NMR和13 C NMR光谱确定
• β-Cyclodextrin: a supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1<i>H</i>)-one
  作者：Bijeta Mitra、Gyan Chandra Pariyar、Pranab Ghosh

  DOI：10.1039/d0ra09562a

  日期：——

  proficient promoter for the metal-free one-pot multi-component synthesis of a vast range of highly functionalized bioactive heterocyclic moiety, 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1H)-one, from easily available precursor aldehydes. The main endeavor of these protocols is to explore this organic supramolecule in one-pot multi-component synthesis. Absence of metal catalyst or toxic

  β-环糊精是一种绿色且广泛使用的超分子催化剂，已被探索作为一种高效的促进剂，用于无金属一锅多组分合成各种高功能化生物活性杂环部分，2-氨基-4,6-二苯基烟腈和 2,3-二氢喹唑啉-4(1 H )-酮，来自容易获得的前体醛。这些协议的主要努力是在一锅多组分合成中探索这种有机超分子。没有金属催化剂或有毒酸和苛刻的反应条件，优异的官能团耐受性，廉价、绿色和环境安全的方案是这项工作的关键优势。
• Novel Bu4N+Br− catalyzed one-pot multi-component synthesis of 2-amino nicotinonitriles in aqueous medium
  作者：C. Kurumurthy、R. Naresh Kumar、T. Yakaiah、P. Shanthan Rao、B. Narsaiah

  DOI：10.1007/s11164-013-1424-5

  日期：2015.5

  An efficient single-pot strategy for 2-amino nicotinonitrile derivatives 5 has been developed by multi-component reaction of arylaldehydes 1, methylketones 2, malononitrile 3, and ammonium acetate 4 using tetrabutyl ammonium bromide as catalyst in aqueous medium.

  以四丁基溴化铵为催化剂，在水介质中通过芳基醛 1、甲基酮 2、丙二腈 3 和醋酸铵 4 的多组分反应，开发出了一种高效的单锅法制备 2-氨基烟腈衍生物 5。
• Method of using aminocyanopyridine compounds as mitogen activated protein kinase-activated protein kinase-2 inhibitors
  申请人：Pharmacia Corporation

  公开号：US20040127519A1

  公开（公告）日：2004-07-01

  A method is described for inhibiting mitogen activated protein kinase-activated protein kinase-2 in a subject in need of such inhibition, where the method involves administering to the subject an anminocyanopyridine MK-2 inhibiting compound, or a pharmaceutically acceptable salt thereof.

  本文描述了一种抑制需要抑制的受试者中的有丝分裂原活化蛋白激酶激活蛋白激酶-2的方法，其中该方法涉及向受试者给予一种抑制MK-2的氨基氰基吡啶化合物或其药学上可接受的盐。