Synthesis of β‐Fluorophenethyl Halopyridyl Thiourea Compounds as Non‐nucleoside Inhibitors of HIV‐1 Reverse Transcriptase

References

• Cantrell , A. S. , Engelhardt , P. , Hogberg , M. , Jaskunas , S. R. , Johansson , N. G. , Jordan , C. L. , Kangasmetsa , J. , Kinnick , M. D. , Lind , P. , Morin , J. M. Jr. , Muesing , M. A. , Noreen , R. , Oberg , B. , Pranc , P. , Sahlberg , C. , Ternansky , R. J. , Vasileff , R. T. , Vrang , L. , West , S. J. and Zhang , H. 1996 . Phenethylthiazolylthiourea (PETT) compounds, a new class of HIV‐1 reverse transcriptase inhibitors. 1. Synthesis and further structure–activity relationship studies of PETT analogs . J. Med. Chem. , 39 : 4261 – 4274 .
   PubMed Web of Science ®Google Scholar
• Bell , F. W. , Cantrell , A. S. , Hogberg , M. , Jaskunas , S. R. , Johansson , N. G. , Jordan , C. L. , Kinnick , M. D. , Lind , P. , Morin , J. M. Jr. , Noreen , R. , Oberg , B. , Palkowitz , J. A. , Parrish , C. A. , Pranc , P. , Sahlberg , C. , Ternansky , R. T. , Vasileff , R. T. , Vrang , L. , West , S. J. , Zhang , H. and Zhou , X. X. 1995 . Phenethylthiazolylthiourea (PETT) compounds, a new class of HIV‐1 reverse transcriptase inhibitors. 1. Synthesis and basic structure–activity relationship studies of PETT analogs . J. Med. Chem. , 38 : 4929 – 4936 .
   PubMed Web of Science ®Google Scholar
• Mao , C. , Vig , R. , Venkatachalam , T. K. , Sudbeck , E. A. and Uckun , F. M. 1998 . Structure‐based design of N‐[2‐(1‐piperidinylethyl)]‐N′‐[2‐(5‐bromopyridyl)]‐thiourea and N‐[2‐(1‐piperazinylethyl)]‐N'‐[2‐(5‐bromopyridyl)]‐thiourea as potent non‐nucleoside inhibitors of HIV‐1 reverse transcriptase . Bioorg. Med. Chem. Lett. , 8 : 2213 – 2218 .
   PubMed Web of Science ®Google Scholar
• Mao , C. , Sudbeck , E. A. , Venkatachalam , T. K. and Uckun , F. M. 1999 . Rational design of N‐[2‐(2,5‐dimethoxyphenylethyl)]‐N′‐[2‐(5‐bromopyridyl)]‐thioruea (HI‐236) as a potent non‐nucleoside inhibitor of drug‐resistant human immunodeficiency virus . Bioorg. Med. Chem. Lett. , 9 : 1593 – 1598 .
   PubMed Web of Science ®Google Scholar
• Mao , C. , Sudbeck , E. A. , Venkatachalam , T. K. and Uckun , F. M. 2000 . Structure‐based drug design of non‐nucleoside inhibitors for wild‐type and drug‐resistant HIV reverse transcriptase . Biochem. Pharmacol. , 60 : 1251 – 1265 .
   PubMed Web of Science ®Google Scholar
• Uckun , F. M. , Mao , C. , Pendergrass , S. , Maher , D. , Zhu , D. , Tuel‐Ahlgren , L. and Venkatachalam , T. K. 1999 . N‐[2‐(1‐cyclohexenyl)ethyl]‐N′‐[2‐(5‐bromopyridyl)]‐thiourea and N′‐[2‐(1‐cyclohexenyl)ethyl]‐N′‐[2‐(5‐chloropyridyl)]‐thiourea as potent inhibitors of multidrug‐resistant human immunodeficiency virus‐1 . Bioorg. Med. Chem. Lett. , 9 : 2721 – 2726 .
   PubMed Web of Science ®Google Scholar
• Uckun , F. M. , Mao , C. , Pendergrass , S. , Maher , D. , Zhu , D. , Tuel‐Ahlgren , L. and Venkatachalam , T. K. 2000 . N‐[2‐(4‐Methylphenyl) ethyl]‐N′‐[2‐(5‐bromopyridyl)]‐thiourea as a potent inhibitor of NNRTI‐resistant and multidrug‐resistant human immunodeficiency virus type 1 . Antivir. Chem. Chemother. , 11 : 135 – 140 .
   PubMed Web of Science ®Google Scholar
• Uckun , F. M. , Pendergrass , S. , Maher , D. , Zhu , D. , Tuel‐Ahlgren , L. , Mao , C. and Venkatachalam , T. K. 1999 . N′‐[2‐(2‐Thiophene)ethyl]‐N′‐[2‐(5‐bromopyridyl)] thiourea as a potent inhibitor of NNI‐resistant and multidrug‐resistant human immunodeficiency virus‐1 . Bioorg. Med. Chem. Lett. , 9 : 3411 – 3416 .
   PubMed Web of Science ®Google Scholar
• Vig , R. , Mao , C. , Venkatachalam , T. K. , Tuel‐Ahlgren , L. , Sudbeck , E. A. and Uckun , F. M. 1998 . 5‐Alkyl‐2‐[(methylthiomethyl)thio]‐6‐(benzyl)‐pyrimidin‐4‐(1H)‐ones as potent non‐nucleoside reverse transcriptase inhibitors of S‐DABO series . Bioorg. Med. Chem. Lett. , 8 : 1461 – 1466 .
   PubMed Web of Science ®Google Scholar
• Zarling , J. M. , Moran , P. A. , Haffar , O. , Sias , J. , Richman , D. D. , Spina , C. A. , Myers , D. E. , Kuebelbeck , V. , Ledbetter , J. A. and Uckun , F. M. 1990 . Inhibition of HIV replication by pokeweed antiviral protein targeted to CD4+ cells by monoclonal antibodies . Nature , 347 : 92 – 95 .
   PubMed Web of Science ®Google Scholar
• Uckun , F. M. , Chelstrom , L. M. , Tuel‐Ahlgren , L. , Dirbirdik , I. , Irvin , J. D. , Chandan‐Langlie , M. and Myers , D. E. 1998 . TXU (anti‐CD7)‐pokeweed antiviral protein as a potent inhibitor of human immunodeficiency virus . Antimicrob. Agents Chemother. , 42 : 383 – 388 .
   PubMedGoogle Scholar