6-butylfuro[2,3-d]pyrimidin-2-one | 473450-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃[2,3-d]嘧啶
• 英文名称: 6-butylfuro[2,3-d]pyrimidin-2-one
• 英文别名: 6-butyl-3H-furo[2,3-d]pyrimidin-2-one；6-butyl-1H-furo[2,3-d]pyrimidin-2-one
• CAS: 473450-34-9
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: ZAESGNQGLBAHBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  >220 °C (decomp)(Solv: ethyl acetate (141-78-6); ethanol (64-17-5))
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-butylfuro[2,3-d]pyrimidin-2-one 、 1-碘戊烷 在 solid 作用下， 生成 6-butyl-3-pentyl-3H-furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Heterocyclic compounds for use in the treatment of viral infections

  摘要：

  6-取代-3-取代-3H-呋喃[2,3-d]嘧啶-2-酮和6-取代-2-取代-呋喃[2,3-d]嘧啶新化合物在治疗病毒感染，特别是巨细胞病毒感染方面具有用途。取代基独立地选自烷基，芳基，烯基和炔基。在6位的首选取代基是烷基。

  公开号：

  US20070191373A1
• 作为产物：
  描述：

  5-碘尿嘧啶 、 1-己炔 在 四(三苯基膦)钯 copper(l) iodide 、 N,N-二异丙基乙胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 6-butylfuro[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  THE JOURNEY TOWARDS ELUCIDATING THE ANTI-HCMV ACTIVITY OF ALKYLATED BICYCLIC FURANO PYRIMIDINES

  摘要：

  Bicyclic furanopyrimidines were recently discovered by us to be potent and selective inhibitors of VZV. Related studies to investigate the role of the sugar in this activity uncovered dideoxy furanopyrimidines as inhibitors of HCMV and this led to the preparation of highly modified long alkyl chain furanopyrimidines from the N- and O-alkylation of their parent bases. Herein we describe their synthesis and subsequent biological evaluation against HCMV. O-alkylated derivatives were almost invariably found to be at least equiactive with their N-alkylated counterparts. At this point, little change in activity has been found with large variation in N- and O-substituent.

  DOI：

  10.1081/ncn-200060122

文献信息

• [EN] HETEROCYCLIC COMPOUNDS FOR USE IN THE TREATMENT OF VIRAL INFECTIONS<br/>[FR] COMPOSES HETEROCYCLIQUES DESTINES A ETRE UTILISES DANS LE TRAITEMENT D'INFECTIONS VIRALES
  申请人：UNIV CARDIFF

  公开号：WO2004096813A1

  公开（公告）日：2004-11-11

  6-substituted-3-substituted-3H-furo[2,3-d]pyrimidin-2-one and 6-substituted-2-substituted-furo[2,3-d]pyrimidine novel compounds are useful in the treatment of viral infection, in particular cytomegalovirus viral infection. The substituents are independently selected from alkyl, aryl, alkenyl and alkynyl. The preferred substituent at the 6 position is alkyl.

  6-取代-3-取代-3H-呋喃[2,3-d]嘧啶-2-酮和6-取代-2-取代-呋喃[2,3-d]嘧啶新化合物在治疗病毒感染，特别是巨细胞病毒感染方面具有用途。 取代基可独立地选择自烷基、芳基、烯基和炔基。 在6位的首选取代基是烷基。
• Synthesis and biological evaluation of 5-(alkyn-1-yl)-1-(<i>p</i>-toluenesulfonyl)uracil derivatives
  作者：Zlatko Janeba、Jan Balzarini、Graciela Andrei、Robert Snoeck、Erik De Clercq、Morris J Robins

  DOI：10.1139/v06-041

  日期：2006.4.1

  Sonogashira coupling of 5-iodouracil (2) and trimethylsilylacetylene gave 5-(trimethylsilylethynyl)uracil (3), which was deprotected to give 5-ethynyluracil (4). Copper(I)-catalyzed cyclization of 4 gave furo[2,3-d]pyrimidin-2(3H)-one (5). Tosylation of 2 and 4 gave the 1-(p-toluenesulfonyl) derivatives 6 and 7, respectively. The tosylated compound 6 and trimethylsilylacetylene did not undergo Sonogashira coupling, and copper(I)-catalyzed cyclization of 7 did not occur. Coupling of 2 with several terminal alkynes gave 5-(alkyn-1-yl)uracil derivatives (9), which underwent tosylation to produce the targeted 5-(alkyn-1-yl)-1-(p-toluenesulfonyl)uracil compounds (11). Copper(I)-catalyzed cyclization of 9 gave the respective furopyrimidines (10) in low yields. Again, cyclization did not occur with the tosyl derivatives (11). Activity against varicella-zoster virus (VZV) was observed with longer-chain analogues of 9 and 11, and compound 7 showed activity against human cytomegalovirus (HCMV) at near cytotoxic levels.Key words: antiviral screening, furo[2,3-d]pyrimidin-2(3H)-one derivatives, Sonogashira coupling, 1-(p-toluenesulfonyl)pyrimidine derivatives.

  5-iodouracil (2) 与三甲基硅基乙炔的 Sonogashira 偶联得到 5-(三甲基硅乙炔基)脲嘧啶 (3)，经脱保护后得到 5-乙炔基脲嘧啶 (4)。在铜（I）催化下，4 环化得到呋喃并[2,3-d]嘧啶-2(3H)-酮（5）。对 2 和 4 进行对甲苯磺酰基化反应，分别得到 1-（对甲苯磺酰基）衍生物 6 和 7。对甲苯磺酰化的化合物 6 和三甲基硅基乙炔没有发生 Sonogashira 偶联反应，也没有发生铜（I）催化的 7 环化反应。2 与几种末端炔烃偶联后得到 5-(炔-1-基)尿嘧啶衍生物 (9)，这些衍生物经过对甲苯磺酰基化反应生成目标 5-(炔-1-基)-1-(对甲苯磺酰基)尿嘧啶化合物 (11)。在铜(I)催化下，9 的环化反应以低产率生成了相应的呋喃嘧啶（10）。同样，甲苯磺酰基衍生物也没有发生环化反应（11）。9 和 11 的长链类似物对水痘-带状疱疹病毒（VZV）具有活性，化合物 7 对人类巨细胞病毒（HCMV）具有接近细胞毒性水平的活性。
• Pyrimidine compounds as anti-ictogenic and/or anti-epileptogenic agents
  申请人：Queen's University

  公开号：US20030153584A1

  公开（公告）日：2003-08-14

  Methods and compounds useful for the inhibition of convulsive disorders, including epilepsy, are disclosed. The methods and compounds of the invention inhibit or prevent ictogenesis and/or epileptogenesis. Methods for preparing the compounds of the invention are also described. Particularly preferred compounds of the invention include: 1

  本发明揭示了用于抑制惊厥性疾病，包括癫痫的方法和化合物。本发明的方法和化合物能够抑制或预防发作和/或癫痫发生。本发明还描述了制备本发明化合物的方法。本发明特别优选的化合物包括：1
• Efficient palladium-mediated or base-induced 5-endo-dig cyclisation of C5-alkynylated pyrimidine derivatives: conventional and microwave-assisted synthesis of novel furo[2,3-d]pyrimidines
  作者：Tatjana Gazivoda Kraljević、Andrea Bistrović、Matea Dedić、Sandra Kraljević Pavelić、Mirela Sedić、Silvana Raić-Malić

  DOI：10.1016/j.tetlet.2012.07.068

  日期：2012.9

  A series of the novel 5-alkynyl- and furo[2,3-d]pyrimidine derivatives in which the sugar moiety is replaced by a methoxymethyl (MOM) group is synthesised using the Sonogashira cross-coupling reaction under both conventional and microwave conditions, in good to excellent yields. The 5-endo-dig cyclisation of 5-alkynylpyrimidine derivatives promoted by a Pd-catalyst or base gives the corresponding furo[2,3-d]pyrimidines in good yields. (C) 2012 Elsevier Ltd. All rights reserved.
• EP1385831A2
  申请人：——

  公开号：EP1385831A2

  公开（公告）日：2004-02-04