6-(2-fluorophenyl)-4-(furan-2-yl)-2-imino-1,2-dihydropyridine-3-carbonitrile | 328087-59-8

• 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: 6-(2-fluorophenyl)-4-(furan-2-yl)-2-imino-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 2-Amino-6-(2-fluorophenyl)-4-(furan-2-yl)pyridine-3-carbonitrile
• CAS: 328087-59-8
• 化学式: C₁₆H₁₀FN₃O
• 分子量: 279.273
• InChiKey: VSOMXTIFRLWFFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 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：
  5

反应信息

• 作为反应物：
  描述：

  6-(2-fluorophenyl)-4-(furan-2-yl)-2-imino-1,2-dihydropyridine-3-carbonitrile 在 氢氧化钾 作用下， 以 二苯醚 、 乙醇 为溶剂， 生成 7-(2-fluorophenyl)-5-(furan-2-yl)-3-(2-methoxyphenyl)-2-sulfanylidene-1H-pyrido[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  SYNTHESIS OF SOME 2-THIOXOPYRIDO[2,3-d]PYRIMIDINE RIBOFURANOSIDES AND THEIR ANTIMICROBIAL ACTIVITY

  摘要：

  2-Thioxo-3,5,7-trisubstituted-1-[2',3',5'-tri-O-benzoyl-beta -D-ribofuranosyl]pyrido [2,3-d]pyrimidin-4(1H)-ones have been prepared by the condensation of trimethylsilyl derivative of w2-thioxo-3,5,7-trisubstituted pyrido[2,3-d]pyrimidin-4(IH)-ones with P-D-ribofuranose 1-acetate-2,3,5-tribenzoate in 65%-78% yield. The structure of the synthesized ribofuranosides and their precursors have been established by JR, H-1 NMR and elemental analysis. These derivatives, have been screened for their antimicrobial activity.

  DOI：

  10.1080/10426500108040270
• 作为产物：
  描述：

  (Z)-1-(2-Fluoro-phenyl)-3-furan-2-yl-propenone 、 丙二腈 在 乙酸铵 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 6-(2-fluorophenyl)-4-(furan-2-yl)-2-imino-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  合成一些新的吡啶并[2,3-d]嘧啶及其呋喃核苷作为可能的抗菌剂

  摘要：

  呋喃核苷，即4-氨基-5,7-二取代-1-[2',3',5'-三-O-苯甲酰基-α-d-呋喃核糖基]吡啶并-[2,3-d]嘧啶- 2(1H)-硫酮，通过 5,7-二取代吡啶并[2,3-d]嘧啶-2(1H)-硫酮的三甲基甲硅烷基衍生物与 β-d-呋喃核糖-1-乙酸酯-2缩合合成,3,5-三苯甲酸酯在 SnCl4 存在下。4-氨基-5,7-二取代吡啶并[2,3-d]嘧啶-2(1H)-硫酮通过2-氨基-3-氰基-4,6-的处理合成了杂环碱基。双取代吡啶与硫脲。所有合成的呋喃核糖苷及其前体的结构均已通过元素分析、IR 和 1H NMR 光谱数据确定。还提供了呋喃核苷的 13C NMR 数据。所有合成的杂环碱基及其呋喃核糖苷均已筛选出抗菌和抗真菌活性。© 2001 John Wiley & Sons, Inc. 杂原子化学 12:52–56, 2001

  DOI：

  10.1002/1098-1071(2001)12:1<52::aid-hc11>3.0.co;2-0

文献信息

• Synthesis of Some Novel 4-Imino-3,5,7-Trisubstituted Pyrido[2,3-<i>d</i>]Pyrimidine-2(1<i>H</i>)-Thiones and Their Nucleosides as Potential Therapeutic Agents
  作者：Girwar Singh、Gajendra Singh、Ashok K. Yadav、A. K. Mishra

  DOI：10.1080/10426500008076330

  日期：2000.2

  Abstract Some newer 4-imino-3,5,7-trisubstituted pyrido[2,3-d]pyrimidine-2(1H)-thiones were synthesized by the condensation of 2-amino-3-cyano-4,6-disubstituted pyridines with phenylisothiocyanate. The nucleosides viz., 4-imino-3,5,7-trisubstituted-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrido[2,3,-d]pyrimidine-2(1H)-thiones were synthesized by the condensation of trimethylsilyl derivatives of pyrido[2

  摘要 通过2-氨基-3-氰基-4,6-二取代吡啶的缩合反应合成了一些较新的4-亚氨基-3,5,7-三取代吡啶并[2,3-d]嘧啶-2(1H)-硫酮。与异硫氰酸苯酯。核苷即4-亚氨基-3,5,7-三取代-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrido[2,3,-d]pyrimidine-2 (1H)-硫酮是通过吡啶并[2,3-d]嘧啶的三甲基甲硅烷基衍生物与糖缩合合成的，即β-D-呋喃核糖1-acere-2,3,5-tribenzonte，而4-imino-3,5 ,7-三取代-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)pyrido(2,3-d]pyrimidine-2(1H)-thiones 通过缩合吡啶的三甲基甲硅烷基衍生物制备[2,3-d]-嘧啶与糖在 SnCl4 存在下。
• Four-Component Synthesis of 1,2-Dihydropyridine Derivatives and their Evaluation as Anticancer Agents
  作者：Mohamed A. O. Abdel-Fattah、Mahmoud A. M. El-Naggar、Rasha M. H. Rashied、Bernard D. Gary、Gary A. Piazza、Ashraf H. Abadi

  DOI：10.2174/1573406411208030392

  日期：2012.5.1

  Two series of compounds with the general formula of 4,6-diaryl-2-oxo-1,2 dihydropyridine-3-carbonitriles and their isosteric imino derivatives were synthesized through a one pot reaction of acetophenone, aldehyde and ammonium acetate with ethyl cyanoacetate or malononitrile, respectively. The synthesized compounds were evaluated for tumor cell growth inhibitory using the human HT-29 colon and MDA-MB-231 breast tumor cell lines. Compound 4-(2- Ethoxyphenyl)-2-imino-6-(4-fluorophenyl)-1,2-dihydropyridine-3 carbonitrile (6) showed IC50 value of 0.70 μM versus HT-29. Meanwhile, compound 4-(2-Hydroxyphenyl)-2-imino-6-(4-fluorophenyl)-1,2-dihydropyridine-3-carbonitrile (4) showed IC50 value of 4.6 μM versus MDA-MB-231. Docking compound 10 to possible molecular targets, survivin and PIM1 kinase showed appreciable interactions with both, which suggest possible targets for the antitumor activity of this novel class of anticancer compounds.

  通式为4,6-二芳基-2-氧代-1,2二氢吡啶-3-甲腈的两个系列化合物和 通过苯乙酮、醛和铵的一锅反应合成了它们的等排亚氨基衍生物 分别用氰基乙酸乙酯或丙二腈制备乙酸酯。评估合成的化合物对肿瘤细胞的作用 使用人 HT-29 结肠和 MDA-MB-231 乳腺肿瘤细胞系进行生长抑制。化合物4-(2- 乙氧基苯基)-2-亚氨基-6-(4-氟苯基)-1,2-二氢吡啶-3甲腈 (6) 的 IC50 值为 0.70 μM HT-29。同时，化合物4-(2-羟基苯基)-2-亚氨基-6-(4-氟苯基)-1,2-二氢吡啶-3-甲腈(4) 与 MDA-MB-231 相比，IC50 值为 4.6 μM。将化合物 10 与可能的分子靶点、生存素和 PIM1 激酶与两者均表现出明显的相互作用，这表明该药物的抗肿瘤活性可能是靶点 新型抗癌化合物。
• Synthesis of some new pyrido[2,3-d]pyrimidines and their ribofuranosides as possible antimicrobial agents
  作者：Neeraj Kumar、Gajendra Singh、Ashok K. Yadav

  DOI：10.1002/1098-1071(2001)12:1<52::aid-hc11>3.0.co;2-0

  日期：——

  5′-tri-O-benzoyl-α-d-ribofuranosyl]pyrido-[2,3-d] pyrimidine-2(1H)-thiones, have been synthesized by the condensation of trimethylsilyl derivatives of 5,7-disubstituted pyrido[2,3-d]pyrimidine-2(1H)-thiones with β-d-ribofuranose-1-acetate-2,3,5-tribenzoate in the presence of SnCl4. The heterocyclic bases, namely, 4-amino-5,7-disubstituted pyrido[2,3-d]pyrimidine-2(1H)-thiones, were synthesized by the treatment

  呋喃核苷，即4-氨基-5,7-二取代-1-[2',3',5'-三-O-苯甲酰基-α-d-呋喃核糖基]吡啶并-[2,3-d]嘧啶- 2(1H)-硫酮，通过 5,7-二取代吡啶并[2,3-d]嘧啶-2(1H)-硫酮的三甲基甲硅烷基衍生物与 β-d-呋喃核糖-1-乙酸酯-2缩合合成,3,5-三苯甲酸酯在 SnCl4 存在下。4-氨基-5,7-二取代吡啶并[2,3-d]嘧啶-2(1H)-硫酮通过2-氨基-3-氰基-4,6-的处理合成了杂环碱基。双取代吡啶与硫脲。所有合成的呋喃核糖苷及其前体的结构均已通过元素分析、IR 和 1H NMR 光谱数据确定。还提供了呋喃核苷的 13C NMR 数据。所有合成的杂环碱基及其呋喃核糖苷均已筛选出抗菌和抗真菌活性。© 2001 John Wiley & Sons, Inc. 杂原子化学 12:52–56, 2001
• SYNTHESIS OF SOME 2-THIOXOPYRIDO[2,3-d]PYRIMIDINE RIBOFURANOSIDES AND THEIR ANTIMICROBIAL ACTIVITY
  作者：Neeraj Kumar、Gajendra Smgh、Ashok K Yadav

  DOI：10.1080/10426500108040270

  日期：2001.8

  2-Thioxo-3,5,7-trisubstituted-1-[2',3',5'-tri-O-benzoyl-beta -D-ribofuranosyl]pyrido [2,3-d]pyrimidin-4(1H)-ones have been prepared by the condensation of trimethylsilyl derivative of w2-thioxo-3,5,7-trisubstituted pyrido[2,3-d]pyrimidin-4(IH)-ones with P-D-ribofuranose 1-acetate-2,3,5-tribenzoate in 65%-78% yield. The structure of the synthesized ribofuranosides and their precursors have been established by JR, H-1 NMR and elemental analysis. These derivatives, have been screened for their antimicrobial activity.