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
  • [41] Access to 6-arylpyrrolo[2,3-d]pyrimidines via a palladium-catalyzed direct C-H arylation reaction
    Dodonova, Jelena
    Tumkevicius, Sigitas
    [J]. RSC ADVANCES, 2014, 4 (68): : 35966 - 35974
  • [42] Ubiquitin-proteasome system, a new anti-tumor target
    Du, Wei
    Mei, Qi-bing
    [J]. ACTA PHARMACOLOGICA SINICA, 2013, 34 (02) : 187 - 188
  • [43] Altered Enthalpy-Entropy Compensation in Picomolar Transition State Analogues of Human Purine Nucleoside Phosphorylase
    Edwards, Achelle A.
    Mason, Jennifer M.
    Clinch, Keith
    Tyler, Peter C.
    Evans, Gary B.
    Schramm, Vern L.
    [J]. BIOCHEMISTRY, 2009, 48 (23) : 5226 - 5238
  • [44] Pyrrolo[2,3-d]pyrimidine synthesis through activation of N-benzyl groups by distal amides
    El Kaim, Laurent
    Grimaud, Laurence
    Wagschal, Simon
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (40) : 6883 - 6885
  • [45] Toward Pyrrolo[2,3-d]pyrimidine Scaffolds
    El Kaim, Laurent
    Grimaud, Laurence
    Wagschal, Simon
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) : 5343 - 5346
  • [46] Structure-activity relationship of heterobase-modified 2′-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication
    Eldrup, AB
    Prhavc, M
    Brooks, J
    Bhat, B
    Prakash, TP
    Song, QL
    Bera, S
    Bhat, N
    Dande, P
    Cook, PD
    Bennett, CF
    Carroll, SS
    Ball, RG
    Bosserman, M
    Burlein, C
    Colwell, LF
    Fay, JF
    Flores, OA
    Getty, K
    LaFemina, RL
    Leone, J
    MacCoss, M
    McMasters, DR
    Tomassini, JE
    Von Langen, D
    Wolanski, B
    Olsen, DB
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (21) : 5284 - 5297
  • [47] Design, synthesis, and enzymatic evaluation of multisubstrate analogue inhibitors of Escherichia coli thymidine phosphorylase
    Esteban-Gamboa, A
    Balzarini, J
    Esnouf, R
    De Clercq, E
    Camarasa, MJ
    Pérez-Pérez, MJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) : 971 - 983
  • [48] New pyrrolopyrimidin-6-yl benzenesulfonamides:: Potent A2B adenosine receptor antagonists
    Esteve, Cristina
    Nueda, Arsenio
    Diaz, Jose Luis
    Beleta, Jorge
    Cardenas, Alvaro
    Lozoya, Estrella
    Cadavid, Maria Isabel
    Loza, Maria Isabel
    Ryder, Hamish
    Vidal, Bernat
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (14) : 3642 - 3645
  • [49] Azetidine based transition state analogue inhibitors of N-ribosyl hydrolases and phosphorylases
    Evans, Gary B.
    Fumeaux, Richard H.
    Greatrex, Ben
    Murkin, Andrew S.
    Schramm, Vern L.
    Tyler, Peter C.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (04) : 948 - 956
  • [50] Exploring structure-activity relationships of transition state analogues of human purine nucleoside phosphorylase
    Evans, GB
    Furneaux, RH
    Lewandowicz, A
    Schramm, VL
    Tyler, PC
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (15) : 3412 - 3423