Quinazoline alkaloids, solid-phase

Eguchi S (2006) Quinazoline Alkaloids and Related Chemistry. 6 113-156 Erd lyi M (2006) Solid-Phase Methods for the Microwave-Assisted Synthesis of Heterocycles. 1 79-128... 

The same approach was readily adaptable to solid-phase synthesis. A small library of unnatural derivatives of 140 was prepared with variation of the configuration and nature of R1 and R4 and with substitution on the benzene ring <2000JC0186>. Three natural alkaloids, Verrucine A, B, and Anacine, were synthesized by a similar pathway and the pyrazino[2,l- ]quinazoline as opposed to the benzodiazepine structure of Anacine was proved <2001JNP1497>. Fiscalin B and other derivatives were prepared by solid-phase synthesis using polyethylene glycol (PEG) resin <2002USP6376667>. 

Fused pyrimidine-2,4-diones are important heterocyclic pharmacophores examples include natural purine bases, alkaloids, and pteridines. Benzo derivatives in this series (quinazoline-2,4-diones) bear ample precedence as potent ligands and inhibitors of receptors and enzymes of pharmaceutical interest. Based on these precedents, Gordeev et al. reported a solid-phase protocol for the synthesis of fused pyrimidine-2,4-diones. 

Keywords Aza-Wittig reaction Quinazolinone annelation Quinazoline alkaloids -Microwave-assisted synthesis Solid-phase synthesis... 

The fourth chapter Quinazoline Alkaloids and Related Chemistry by Shoji Eguchi provides a perspective review focusing on developements of the synthetic methodologies and their synthetic applications. A brief historical background, aza-Wittig methodology, microwave-assisted synthesis, solid-phase... 

Related quinazoline alkaloids have also been prepared using SPOS. For example, in 2001, Wang and Sim reported on the solid-phase synthesis of verrucine A 18 and its... 

Wang H, Sim MM. Total solid phase syntheses of the quinazoline alkaloids verrucines A and B and anacine. J. Nat. Prod. 2001 64 1497-1501. 

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