Starting from 2-(2-aminoethyl)pyridine, a series of N-diazinyl-N′-[2-(2-pyridyl)ethyl]thioureas was prepared via the (2-pyridyl)ethylisothiocyanate and was screened as non-nucleoside human immunodeficiency virus type 1 reverse transcriptase inhibitors. Derivatives bearing a 3-pyridazinyl or a 4-pyrimidinyl moiety turned out to be the most potent compounds. However, they exhibited less activity than nevirapine or trovirdine.
BellFWCantrellASHögbergMJaskunasSRJohanssonNGJordanCLKinnickMDLindPMorinJMJrNoreenRÖbergBPalkowitzJAParrishCAPrancPSahlbergCTernanskyRJVasileffRTVrangLWestSJZhangH & ZhouX-X (1995) Phenethylthiazolethiourea (PETT) compounds, a new class of HIV-1 reverse transcriptase inhibitors. 1. Synthesis and basic structure–activity relationship studies of PETT analogs. Journal of Medicinal Chemistry38:4929–4936.
2.
De ClercqE (1994a) Non-nucleoside reverse transcriptase inhibitors (NNRTIs). Expert Opinion on Investigational Drugs3:253–271.
3.
De ClercqE (1994b) Resistance of human immunodeficiency virus type 1 (HIV-1) to non-nucleoside HIV-1-specific reverse transcriptase inhibitors. International Journal of Immunotherapy10:145–158.
4.
De ClercqE (1995) Antiviral therapy for human immunodeficiency virus infections. Clinical Microbiology Reviews8:200–239.
5.
HargraveKDProudfootJRGrozingerKGCullenEKapadiaSRPatelURFuchsVUMauldinSCVitousJBehnkeMLlaunderJMPalKSkilesJWMcNeilDWRoseJMChowGCSkoogMTWuJCSchmidtGEngelWWEberleinWGSaboeTDCampbellSJRosenthalAS & AdamsJ (1991) Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. 1. Tricyclic pyrido- and dipyridodiazepinones. Journal of Medicinal Chemistry34:2231–2241.
6.
HeinischGMatuszczakBPürstingerG & RakowitzD (1995) Diazine-substituted tert-butylureas and tert-butylthioureas and a convenient access to the related carbodiimides. Journal of Heterocyclic Chemitstry32:13–16.
7.
HeinischGLukavskyPMatuszczakB & RakowitzD (1997) Complete assignment of the 13C NMR spectra of diazinyl-substituted ureas and thioureas. Magnetic Resonance in Chemistry (in press).
8.
RahmanMF (1980) Synthesis of 4-substituted thiosemicarbazones of 3-methyl-4-phenylpyridine-2-carboxaldehyde as antitumor agents. Indian Journal of Chemistry19:828–830.