Synthetic Entries to and Biological Activity of Pyrrolopyrimidines

被引:139
作者
De Coen, Laurens M. [1 ]
Heugebaert, Thomas S. A. [1 ]
Garcia, Daniel [1 ]
Stevens, Christian V. [1 ]
机构
[1] Univ Ghent, Dept Sustainable Organ Chem & Technol, B-9000 Ghent, Belgium
关键词
PURINE NUCLEOSIDE PHOSPHORYLASE; ADENOSINE-KINASE-INHIBITORS; TRANSITION-STATE ANALOGS; SELECTIVE ALPHA(1)-ADRENOCEPTOR LIGANDS; COUPLED FOLATE TRANSPORTER; STRUCTURE-BASED DESIGN; VIRUS-RNA REPLICATION; DIELS-ALDER REACTION; ONE-POT SYNTHESIS; GYRASE B GYRB;
D O I
10.1021/acs.chemrev.5b00483
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review summarizes recent literature (2000-2015) on the synthesis and pharmaceutical properties of pyrrolopyrimidines. These modified pyrimidine bases, fused to a pyrrole ring, and their corresponding nucleosides display a broad applicability in medicinal chemistry. This overview is divided into three main sections, according to the respective isomers: pyrrolo[2,3-d]pyrimidines, pyrrolo[3,2-d]pyrimidines, and pyrrolo[3,4-d]pyrimidines. Each section contains a description of common retro-synthetic strategies, with particular attention for newly reported synthetic entries to the scaffold. Next, the synthetic strategies and the ways in which the scaffolds can be further modified are exemplified according to the biological properties of the obtained products.
引用
收藏
页码:80 / 139
页数:60
相关论文
共 186 条
  • [1] A convenient synthesis of pyrrolo[2,3-b]pyridines and pyrido[2′,3′:5,4]pyrrolo[2,3-d]pyrimidines
    Abdel-Mohsen, Shawkat A.
    Geies, Ahmed A.
    [J]. MONATSHEFTE FUR CHEMIE, 2008, 139 (10): : 1233 - 1240
  • [2] Synthesis and antiviral activity of novel acyclic nucleosides in the 5-alkynyl- and 6-alkylfuro[2,3-d]pyrimidine series
    Amblard, F
    Aucagne, V
    Guenot, P
    Schinazi, RF
    Agrofoglio, LA
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (04) : 1239 - 1248
  • [3] Tasocitinib
    不详
    [J]. Drugs in R & D, 2010, 10 (4) : 271 - 284
  • [4] Novel Compounds with a Viologen Skeleton and N-Heterocycles on the Peripheries: Electrochemical and Spectroscopic Properties
    Asaftei, Simona
    Lepadatu, Ana Maria
    Ciobanu, Marius
    [J]. HELVETICA CHIMICA ACTA, 2011, 94 (06) : 1091 - 1101
  • [5] Discovery of pyrrolo[2,3-d]pyrimidin-4-ones as corticotropin-releasing factor 1 receptor antagonists with a carbonyl-based hydrogen bonding acceptor
    Aso, Kazuyoshi
    Kobayashi, Katsumi
    Mochizuki, Michiyo
    Kanzaki, Naoyuki
    Sako, Yuu
    Yano, Takahiko
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (08) : 2365 - 2371
  • [6] Highly efficient AgNO3-catalyzed preparation of substituted furanopyrimidine nucleosides
    Aucagne, V
    Amblard, F
    Agrofoglio, LA
    [J]. SYNLETT, 2004, (13) : 2406 - 2408
  • [7] The Methylation Effect in Medicinal Chemistry
    Barreiro, Eliezer J.
    Kuemmerle, Arthur E.
    Fraga, Carlos A. M.
    [J]. CHEMICAL REVIEWS, 2011, 111 (09) : 5215 - 5246
  • [8] Batcho A.D., 1985, Org. Synth, V63, P214, DOI DOI 10.15227/orgsyn.063.0214
  • [9] Practical synthesis of a potent hepatitis C virus RNA replication inhibitor
    Bio, MM
    Xu, F
    Waters, M
    Williams, JM
    Savary, KA
    Cowden, CJ
    Yang, CH
    Buck, E
    Song, ZGJ
    Tschaen, DM
    Volante, RP
    Reamer, RA
    Grabowski, EJJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (19) : 6257 - 6266
  • [10] Adenosine kinase inhibitors.: 6.: Synthesis, water solubility, and antinociceptive activity of 5-phenyl-7-(5-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidines substituted at C4 with glycinamides and related compounds
    Bookser, BC
    Ugarkar, BG
    Matelich, MC
    Lemus, RH
    Allan, M
    Tsuchiya, M
    Nakane, M
    Nagahisa, A
    Wiesner, JB
    Erion, MD
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (24) : 7808 - 7820