2-amino-5-(hex-1-yn-1-yl)pyrimidine | 948560-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-amino-5-(hex-1-yn-1-yl)pyrimidine
• 英文别名: 5-(hex-1-ynyl)pyrimidin-2-amine；5-Hex-1-ynylpyrimidin-2-amine
• CAS: 948560-21-2
• 化学式: C₁₀H₁₃N₃
• 分子量: 175.233
• InChiKey: YOLLECPVOQCDPK-UHFFFAOYSA-N

物化性质

• 沸点：
  364.1±34.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-5-(hex-1-yn-1-yl)pyrimidine 在 palladium on activated charcoal 、 copper(l) iodide 、 四(三苯基膦)钯 三甲基氯硅烷 、 亚硝酸苄基三乙基铵 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0~50.0 ℃ 、413.7 kPa 条件下， 反应 3.0h， 生成 1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-[2-(5-hexylpyrimid-2-yl)ethynyl]uracil
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of 6-(Alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one Nucleosides and Analogues with Ethynyl, Ethenyl, and Ethyl Spacers at C6 of the Furopyrimidine Core

  摘要：

  Sonogashira coupling strategies were employed to synthesize new furo[2,3-d]pyrimidin-2(3H)-one (FuPyrm) 2'-deoxynucleoside analogues. Partial or complete reduction of ethyne-linked compounds afforded ethenyl-and ethyl-linked derivatives. Levels of inhibition of varicella-zoster virus (VZV), human cytomegalovirus (HCMV), a broad range of other DNA and RNA viruses, and several cancer cell lines were evaluated in cell cultures. The anti-VZV potency decreased with increasing rigidity of the side chain at C6 of the FuPyrm ring in the order dec-1-yn-1-yl < dec-1-en-1-yl < decan-1-yl. In contrast, compounds with a rigid ethynyl spacer between C6 of the FuPyrm ring and a 4-alkylphenyl moiety were more potent inhibitors of VZV than the corresponding derivatives with an ethyl spacer. Replacement of the phenyl moiety in 6-(4-alkylphenyl) derivatives with a pyridine ring (in either regioisomeric orientation) gave analogues with increased solubility in methanol but reduced anti-VZV potency, and replacement with a pyrimidine ring reduced the anti-VZV activity even further. The pyridine-ring-containing analogues were similar to 20-fold more potent inhibitors of VZV than acyclovir but were similar to 6-fold less potent than BVDU and similar to 60-fold weaker than the most active 6-(4-pentylphenyl) -substituted prototype.

  DOI：

  10.1021/jm070210n
• 作为产物：
  描述：

  2-氨基-5-溴嘧啶 、 1-己炔 在 copper(l) iodide 、 四(三苯基膦)钯 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-amino-5-(hex-1-yn-1-yl)pyrimidine
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of 6-(Alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one Nucleosides and Analogues with Ethynyl, Ethenyl, and Ethyl Spacers at C6 of the Furopyrimidine Core

  摘要：

  Sonogashira coupling strategies were employed to synthesize new furo[2,3-d]pyrimidin-2(3H)-one (FuPyrm) 2'-deoxynucleoside analogues. Partial or complete reduction of ethyne-linked compounds afforded ethenyl-and ethyl-linked derivatives. Levels of inhibition of varicella-zoster virus (VZV), human cytomegalovirus (HCMV), a broad range of other DNA and RNA viruses, and several cancer cell lines were evaluated in cell cultures. The anti-VZV potency decreased with increasing rigidity of the side chain at C6 of the FuPyrm ring in the order dec-1-yn-1-yl < dec-1-en-1-yl < decan-1-yl. In contrast, compounds with a rigid ethynyl spacer between C6 of the FuPyrm ring and a 4-alkylphenyl moiety were more potent inhibitors of VZV than the corresponding derivatives with an ethyl spacer. Replacement of the phenyl moiety in 6-(4-alkylphenyl) derivatives with a pyridine ring (in either regioisomeric orientation) gave analogues with increased solubility in methanol but reduced anti-VZV potency, and replacement with a pyrimidine ring reduced the anti-VZV activity even further. The pyridine-ring-containing analogues were similar to 20-fold more potent inhibitors of VZV than acyclovir but were similar to 6-fold less potent than BVDU and similar to 60-fold weaker than the most active 6-(4-pentylphenyl) -substituted prototype.

  DOI：

  10.1021/jm070210n

文献信息

• 2-Aminopyrimidine as a novel scaffold for biofilm modulation
  作者：Erick A. Lindsey、Roberta J. Worthington、Cristina Alcaraz、Christian Melander

  DOI：10.1039/c2ob06871k

  日期：——

  An efficient synthetic route to a series of substituted 2-aminopyrimidine (2-AP) derivatives has been developed. Subsequent biofilm screening has allowed comparison between the biological activity of these new derivatives and that of the 2-aminoimidazole class of anti-biofilm compounds. Several derivatives displayed the ability to modulate bacterial biofilm formation, exhibiting greater activity against Gram-positive strains than Gram-negative strains. Additionally some 2-aminopyrmidines were able to suppress MRSA resistance to conventional antibiotics.

  我们开发出了一系列取代的 2-氨基嘧啶（2-AP）衍生物的高效合成路线。随后的生物膜筛选将这些新衍生物的生物活性与 2-氨基咪唑类抗生物膜化合物的生物活性进行了比较。一些衍生物显示出调节细菌生物膜形成的能力，对革兰氏阳性菌株的活性高于对革兰氏阴性菌株的活性。此外，一些 2-aminopyrmidines 还能抑制 MRSA 对传统抗生素的耐药性。