caa a22 4500 467919690 CHVBK 20180406152913.0 cr unu---uuuuu 170328e20061201xx s 000 0 eng 10.1007/s00706-006-0548-3 doi (NATIONALLICENCE)springer-10.1007/s00706-006-0548-3 Synthesis and Anti-HIV-1 Activity of Novel MKC-442 Analogues Containing Alkenyl Chains or Reactive Functionalities in the 6-Benzyl Group [Elektronische Daten] [Youssef L. Aly, Erik B. Pedersen, Paolo La Colla, Roberta Loddo] Summary.: In an effort to obtain more insight into the anti-HIV efficacy of MKC-442 analogues (1-(alkoxymethyl)-6-benzyluracils), a new series of compounds was synthesized and evaluated for inhibition of HIV-1 replication. The modifications include a reactive center such as an aldehyde or an epoxide substituted at the benzyl group. It was believed that such reactive groups could improve the activity against HIV for the Y181C mutant by forming a covalent bond to the mercapto group in cysteine in the hydrophobic pocket. Unfortunately, only moderate activities were found in cell-based assays for such compounds against wild-type HIV and no activity against the Y181C mutant. However, higher activities were found for a corresponding oxime and the precursor molecules with butenyl and allyloxy substituents in the benzyl group. A few amino-DABO and S-DABO analogues were also synthesized, but they were found inactive against HIV. Springer-Verlag, 2006 Keywords. Bioorganic chemistry nationallicence Drug research nationallicence HIV-1 nationallicence MKC-442 nationallicence Non-nucleoside nationallicence Aly Youssef L. Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, Odense M, Denmark aut Pedersen Erik B. Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, Odense M, Denmark aut La Colla Paolo Dipartimento di Scienze e Tecnologie Biomediche, Sezione di Microbiologia e Virologia Generale e Biotecnologie Microbiche, Universita di Cagliari, Monserrato, Italy aut Loddo Roberta Dipartimento di Scienze e Tecnologie Biomediche, Sezione di Microbiologia e Virologia Generale e Biotecnologie Microbiche, Universita di Cagliari, Monserrato, Italy aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/12(2006-12-01), 1557-1570 0026-9247 137:12<1557 2006 137 706 https://doi.org/10.1007/s00706-006-0548-3 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s00706-006-0548-3 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Aly Youssef L. Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, Odense M, Denmark aut NATIONALLICENCE 700 1- Pedersen Erik B. Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, Odense M, Denmark aut NATIONALLICENCE 700 1- La Colla Paolo Dipartimento di Scienze e Tecnologie Biomediche, Sezione di Microbiologia e Virologia Generale e Biotecnologie Microbiche, Universita di Cagliari, Monserrato, Italy aut NATIONALLICENCE 700 1- Loddo Roberta Dipartimento di Scienze e Tecnologie Biomediche, Sezione di Microbiologia e Virologia Generale e Biotecnologie Microbiche, Universita di Cagliari, Monserrato, Italy aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/12(2006-12-01), 1557-1570 0026-9247 137:12<1557 2006 137 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer