2,6-disubstituted and 2,6,8-trisubstituted purines as adenosine receptor antagonists.

@article{Chang200626disubstitutedA2,
  title={2,6-disubstituted and 2,6,8-trisubstituted purines as adenosine receptor antagonists.},
  author={Lisa C W Chang and Ronald F Spanjersberg and Jacobien K. von Frijtag Drabbe K{\"u}nzel and Thea Mulder-Krieger and Johannes Brussee and Adriaan P. IJzerman},
  journal={Journal of medicinal chemistry},
  year={2006},
  volume={49 10},
  pages={
          2861-7
        }
}
Purines have long been exploited as adenosine receptor antagonists. The substitution pattern about the purine ring has been well investigated, and certain criteria have become almost a prerequisite for good affinity at the adenosine A(1) receptor. The adaptation of the pharmacophore and the initial series of pyrimidines developed in an earlier publication resulted in a series of purines with an entirely new substitution pattern. One compound in particular, 8-cyclopentyl-2,6-diphenylpurine (31… 
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38 Citations

38 Citations

Synthesis of diverse 6-(1,2-disubstituted ethyl)purine bases and nucleosides via 6-(oxiran-2-yl)purines
SYNTHESIS OF (PURIN-6-YL)ACETATES AND THEIR TRANSFORMATIONS TO 6-(2-HYDROXYETHYL)- AND 6-(CARBAMOYLMETHYL)PURINES
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A novel approach to the synthesis of (purin-6-yl)acetates was developed based on Pd-catalyzed cross-coupling reactions of 6-chloropurines with a Reformatsky reagent based on Mesylation of the 6-(2-hydroxyethyl)purines followed by nucleophilic substitutions gave rise to several 6-substituted ethyl)purine compounds.
Purine (N)-Methanocarba Nucleoside Derivatives Lacking an Exocyclic Amine as Selective A3 Adenosine Receptor Agonists
TLDR
The modeling suggests that a suitable combination of stabilizing features can partially compensate for the lack of an exocyclic amine, an otherwise important contributor to recognition in the A3AR binding site.
Microwave‐Assisted Synthesis of Substituted Pyrrolo[2,3‐d]pyrimidines
A new synthetic route to triaryl pyrrolo[2,3-d]pyrimidines from common 4,6-dichloropyrimidine has been developed. The triarylated compounds are synthesized by three cross-coupling reactions using…
Direct C-H arylation of purines: development of methodology and its use in regioselective synthesis of 2,6,8-trisubstituted purines.
TLDR
The methodology is general and efficient and was applied in the consecutive regioselective synthesis of 2,6,8-trisubstituted purines bearing three different C-substituents in combination with two cross-coupling reactions.
Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by cross-coupling reactions or cyclopropanations.
TLDR
6-Cyclopropylpurine ribonucleoside exerted a significant cytostatic effect while all substituted derivatives were inactive, and novel purine bases and nucleosides bearing unsubstituted or substituted cyclopropol rings in position 6 are reported.
Synthesis of C8-alkyl-substituted purine analogues by direct alkylation of 8-H purines with tetrahydrofuran catalyzed by CoCl2·6H2O
A class of novel conjugates of substituted purine and Gly-AA-OBzl: synthesis and evaluation of orally analgesic activity.
[2+2+2]-Cocyclotrimerization of 6-Alkynyl-7-benzylpurines with α,ω-Diynes
TLDR
6-Alkynyl- and 6-aryl-7-benzylpurines were prepared by the Sonogashira reaction from 6-chloro- 7-benZylpurine and terminal alkynes and tested for cytostatic activity.
Chapter 6.3 Triazines, tetrazines and fused ring polyaza systems
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