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Synthesis and anti-HIV-1 activity of 1,3-phenylene bis-uracil analogues of MKC-442

✍ Scribed by Youssef L. Aly; Erik B. Pedersen; Paolo La Colla; Roberta Loddo

Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
447 KB
Volume
44
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Reaction of 1,3‐phenylenediacetonitrile with the zinc organometallic reagent of ethyl 2‐bromobutyrate afforded the 1,3‐phenylene‐bis(acetoacetate) 2 which was used as the starting material for the synthesis of 1,3‐phenylene‐bis[6‐(2‐thiouracil)] 4. Desulphurization of 4 gave the corresponding bis‐uracil 6, which after silylation was N‐1 alkylated with bis(allyoxy)methane using TMS‐triflate as the catalyst or with chloromethyl ethyl ether to give the MKC‐442 analogues 7 and 9. The amino‐DABO and S‐DABO derivatives 11, 12a,b and 14 were also synthesized. The anti‐HIV‐1 activity test showed that when MKC‐442 analogues were constructed with 1,3‐phenylene in all cases they were detrimental to have activity against HIV‐1.

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