6-decyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one | 791782-89-3

• 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-decyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one
• 英文别名: 6-decyl-1H-furo[2,3-d]pyrimidin-2-one
• CAS: 791782-89-3
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: XVRWNQWADQRIJG-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C (decomp)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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-decyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one 、 1-碘戊烷 在 potassium carbonate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 4.0h， 以35%的产率得到6-decyl-2-pentyloxy-2,3-dihydrofuro[2,3-d]pyrimidine
  参考文献：
  名称：

  [EN] HETEROCYCLIC COMPOUNDS FOR USE IN THE TREATMENT OF VIRAL INFECTIONS
  [FR] COMPOSES HETEROCYCLIQUES DESTINES A ETRE UTILISES DANS LE TRAITEMENT D'INFECTIONS VIRALES

  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。

  公开号：

  WO2004096813A1
• 作为产物：
  描述：

  5-(dodecyn-1-yl)uracil 在 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 为溶剂， 以38%的产率得到6-decyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Inhibition of Mycobacterial Replication by Pyrimidines Possessing Various C-5 Functionalities and Related 2′-Deoxynucleoside Analogues Using in Vitro and in Vivo Models

  摘要：

  Tuberculosis (TB) has become an increasing problem since the emergence of human immunodeficiency virus and increasing appearance of drug-resistant strains. There is an urgent need to advance our knowledge and discover a new class of agents that are distinct than current therapies. Antimycobacterial activities of several 5-alkyl, 5-alkynyl, furanopyrimiclines and related 2'-deoxynucleosides were investigated against Mycobacterium tuberculosis. Compounds with 5-arylalkynyl substituents (23-26,33, 35) displayed potent in vitro antitubercular activity against Mycobacterium bovis and Mycobacterium tuberculosis. The in vivo activity of 5-(2-pyridylethyny1)-uracil (26) and its 2'-deoxycytidine analogue, 5-(2-pyridylethynyI)-2'-deoxycytidine (35), was assessed in BA LB/c mice infected with M. tuberculosis (H 37 Ra). Both compounds 26 and 35 given at a dose of 50 mg/kg for 5 weeks showed promising in vivo efficacy in a mouse model, with the 2'-deoxycytidine derivative being more effective than the uracil analogue and a reference drug o-cycloserine. These data indicated that there is a significant potential in this class of compounds.

  DOI：

  10.1021/jm100568q

文献信息

• Heterocyclic compounds for use in the treatment of viral infections
  申请人：McGuigan Christopher

  公开号：US20070191373A1

  公开（公告）日：2007-08-16

  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。
• THE JOURNEY TOWARDS ELUCIDATING THE ANTI-HCMV ACTIVITY OF ALKYLATED BICYCLIC FURANO PYRIMIDINES
  作者：M. R. Kelleher、C. McGuigan、O. Bidet、A. Carangio、H. Weldon、G. Andrei、R. Snoeck、E. De Clercq、J. Balzarini

  DOI：10.1081/ncn-200060122

  日期：2005.4.1

  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.
• SYNTHESIS AND BIOLOGICAL EVALUATION OF N- AND O-ALKYLATED BICYCLIC FURANOPYRIMIDINES AS NON-NUCLEOSIDIC INHIBITORS OF HUMAN CYTOMEGALOVIRUS
  作者：M. R. Kelleher、C. McGuigan、G. Andrei、R. Snoeck、E. De Clercq、J. Balzarini

  DOI：10.1081/ncn-200060118

  日期：2005.4.1

  2',3'-Dideoxy furanopyrimidines were shown to display anti-HCMV activity via a non-nucleaside mechanism. Further studies into highly modified sugar derivatives led to the preparation of N- and O-alkylated C-10 furanopyrimidine analogues, and this work is described herein. These compounds were tested against HCMV strains, and the first case of submicromolar activity was observed.
• Inhibition of Mycobacterial Replication by Pyrimidines Possessing Various C-5 Functionalities and Related 2′-Deoxynucleoside Analogues Using in Vitro and in Vivo Models
  作者：Naveen C. Srivastav、Dinesh Rai、Christopher Tse、B. Agrawal、Dennis Y. Kunimoto、Rakesh Kumar

  DOI：10.1021/jm100568q

  日期：2010.8.26

  Tuberculosis (TB) has become an increasing problem since the emergence of human immunodeficiency virus and increasing appearance of drug-resistant strains. There is an urgent need to advance our knowledge and discover a new class of agents that are distinct than current therapies. Antimycobacterial activities of several 5-alkyl, 5-alkynyl, furanopyrimiclines and related 2'-deoxynucleosides were investigated against Mycobacterium tuberculosis. Compounds with 5-arylalkynyl substituents (23-26,33, 35) displayed potent in vitro antitubercular activity against Mycobacterium bovis and Mycobacterium tuberculosis. The in vivo activity of 5-(2-pyridylethyny1)-uracil (26) and its 2'-deoxycytidine analogue, 5-(2-pyridylethynyI)-2'-deoxycytidine (35), was assessed in BA LB/c mice infected with M. tuberculosis (H 37 Ra). Both compounds 26 and 35 given at a dose of 50 mg/kg for 5 weeks showed promising in vivo efficacy in a mouse model, with the 2'-deoxycytidine derivative being more effective than the uracil analogue and a reference drug o-cycloserine. These data indicated that there is a significant potential in this class of compounds.
• [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。