NDLI: Diversity oriented syntheses of fused pyrimidines designed as potential antifolates

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Diversity oriented syntheses of fused pyrimidines designed as potential antifolates

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Organic & Biomolecular Chemistry Vol - 7 Issue - 8

Organic & Biomolecular Chemistry Vol - 7 Issue - 7

Organic & Biomolecular Chemistry Vol - 7 Issue - 6

Organic & Biomolecular Chemistry Vol - 7 Issue - 5

Organic & Biomolecular Chemistry Vol - 7 Issue - 4

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Organic & Biomolecular Chemistry Vol -6

Organic & Biomolecular Chemistry Vol -5

Organic & Biomolecular Chemistry Vol -4

Organic & Biomolecular Chemistry Vol -3

Organic & Biomolecular Chemistry Vol -2

Diversity oriented syntheses of fused pyrimidines designed as potential antifolates

Content Provider	Royal Society of Chemistry (RSC)
Author	Gibson, Colin L. Kiefer, Lionel Clements, Carol Kennedy, Alan Lee, Jeong Hwan Harvey, Alan L. Hunter, William N. Suckling, Colin J. Huggan, Judith K. Tulloch, Lindsay B.
Copyright Year	2009
Abstract	Diversity oriented syntheses of some furo[2,3-d]pyrimidines and pyrrolo[2,3-d]pyrimidines related to folate, guanine, and diaminopyrimidine-containing drugs have been developed for the preparation of potential anti-infective and anticancer compounds. Amide couplings and Suzuki couplings on the basic heterocyclic templates were used, in the latter case yields being especially high using aromatic trifluoroborates as the coupling partner. A new ring synthesis of 6-aryl-substituted deazaguanines bearing 2-alkylthio groups has been developed using Michael addition of substituted nitrostyrenes. Diversity at C-2 has been introduced by oxidation and substitution with a range of amino nucleophiles. The chemical reactivity of these pyrrolopyrimidines with respect to both electrophilic substitution in ring synthesis and nucleophilic substitution for diversity is discussed. Several compounds were found to inhibit pteridine reductases from the protozoan parasites Trypanosoma brucei and Leishmania major at the micromolar level and to inhibit the growth of Trypanosma brucei brucei in cell culture at higher concentrations. From these results, significant structural features required for inhibition of this important drug target enzyme have been identified.
Starting Page	1829
Ending Page	1842
Page Count	14
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	7
Issue Number	9
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b818339b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Cell culture Electrophilic aromatic substitution Enzyme Pteridine Folic acid Guanine Leishmania Suzuki Michael Trypanosma Amide Nucleophilic substitution Trypanosoma brucei Heterocyclic compound Michael reaction Suzuki reaction Leishmania major
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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