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Literature DB >> 23976798

Condensation reactions of guanidines with bis-electrophiles: Formation of highly nitrogenous heterocycles.

David M Arnold¹, Matthew G Laporte, Shelby M Anderson, Peter Wipf.

Abstract

2-Amino-1,4-dihydropyrimidines were reacted with bis-electrophiles to produce novel fused bi-pyrimidine, pyrimido-aminotriazine, and pyrimido-sulfonamide scaffolds. In addition, a quinazoline library was constructed using a guanidine Atwal-Biginelli reaction with 1-(quinazolin-2-yl)guanidines. The product heterocycles have novel constitutions with high nitrogen atom counts and represent valuable additions to screening libraries for the discovery of new modulators of biological targets.

Entities: CellLine Chemical Disease Species

Keywords: Atwal-Biginelli reaction; Guanidines; Pyrimidines; Quinazolines; Screening library

Year: 2013 PMID： 23976798 PMCID： PMC3746774 DOI： 10.1016/j.tet.2013.04.127

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

30 in total

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2. Skeletal diversity construction via a branching synthetic strategy.

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Review 3. Impact of high-throughput screening in biomedical research.

Authors: Ricardo Macarron; Martyn N Banks; Dejan Bojanic; David J Burns; Dragan A Cirovic; Tina Garyantes; Darren V S Green; Robert P Hertzberg; William P Janzen; Jeff W Paslay; Ulrich Schopfer; G Sitta Sittampalam
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4. Evolution of anti-HIV drug candidates. Part 2: Diaryltriazine (DATA) analogues.

Authors: D W Ludovici; R W Kavash; M J Kukla; C Y Ho; H Ye; B L De Corte; K Andries; M P de Béthune; H Azijn; R Pauwels; H E Moereels; J Heeres; L M Koymans; M R de Jonge; K J Van Aken; F F Daeyaert; P J Lewi; K Das; E Arnold; P A Janssen
Journal: Bioorg Med Chem Lett Date: 2001-09-03 Impact factor: 2.823

5. Efficient Synthesis of 1,4-Dihydro-2H-isoquinoline-3,5,8-triones via Cyclobutene Ring Expansion.

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6. Diversity-oriented synthesis of azaspirocycles.

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7. Synthesis and stereochemical determination of batzelladine C methyl ester.

Authors: Michael Butters; Christopher D Davies; Mark C Elliott; Joseph Hill-Cousins; Benson M Kariuki; Li-ling Ooi; John L Wood; Stuart V Wordingham
Journal: Org Biomol Chem Date: 2009-10-13 Impact factor: 3.876

8. Regiospecific synthesis of 3-substituted imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[1,2-c]pyrimidine.

Authors: Alan R Katritzky; Yong-Jiang Xu; Hongbin Tu
Journal: J Org Chem Date: 2003-06-13 Impact factor: 4.354

Condensation reactions of guanidines with bis-electrophiles: Formation of highly nitrogenous heterocycles.

Review 1. Exploring new chemical space by stereocontrolled diversity-oriented synthesis.

2. Skeletal diversity construction via a branching synthetic strategy.

Review 3. Impact of high-throughput screening in biomedical research.

4. Evolution of anti-HIV drug candidates. Part 2: Diaryltriazine (DATA) analogues.

5. Efficient Synthesis of 1,4-Dihydro-2H-isoquinoline-3,5,8-triones via Cyclobutene Ring Expansion.

6. Diversity-oriented synthesis of azaspirocycles.

7. Synthesis and stereochemical determination of batzelladine C methyl ester.

8. Regiospecific synthesis of 3-substituted imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[1,2-c]pyrimidine.

9. Quinazolines as adenosine receptor antagonists: SAR and selectivity for A2B receptors.

Review 10. Towards the optimal screening collection: a synthesis strategy.

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