Novel fluorine-containing DAPY derivatives as potent HIV-1 NNRTIs: a patent evaluation of WO2014072419

Bibliography

• Zhan P, Chen X, Li D, et al. HIV-1 NNRTIs: structural diversity, pharmacophore similarity, and impliations for drug design. Med Res Rev 2013;33:E1-E72
   PubMed Web of Science ®Google Scholar
• Li D, Zhan P, De Clercq E, et al. Strategies for the design of HIV-1 non-nucleoside reverse transcriptase inhibitors: Lessons from the development of seven representative paradigms. J Med Chem 2012;55:3595-613
   PubMed Web of Science ®Google Scholar
• Li X, Zhang L, Tian Y, et al. Novel HIV-1 non-nucleoside reverse transcriptase inhibitors: a patent review (2011 – 2014). Expert Opin Ther Pat 2014;24:1199-227
   PubMed Web of Science ®Google Scholar
• Song Y, Fang Z, Zhan P, et al. Recent advances in the discovery and development of novel HIV-1 NNRTI platforms (Part II): 2009-2013 Update. Curr Med Chem 2014;21:329-55
   PubMed Web of Science ®Google Scholar
• Zhan P, Liu X. Novel HIV-1 non-nucleoside reverse transcriptase inhibitors: a patent review (2005 – 2010). Expert Opin Ther Pat 2011;21:717-96
   PubMed Web of Science ®Google Scholar
• Reynolds C, de Koning CB, Pelly SC, et al. In search of a treatment for HIV - current therapies and the role of non-nucleoside reverse transcriptase inhibitors (NNRTIs). Chem Soc Rev 2012;41:4657-70
   PubMed Web of Science ®Google Scholar
• Jayaweera D, Dilanchian P. New therapeutic landscape of NNRTIs for treatment of HIV: a look at recent data. Expert Opin Pharmacother 2012;13:2601-12
   PubMed Web of Science ®Google Scholar
• Chen X, Zhan P, Li D, et al. Recent advances in DAPYs and related analogues as HIV-1 NNRTIs. Curr Med Chem 2011;18:359-76
   PubMed Web of Science ®Google Scholar
• LEWI. Paulus J. Novel Anti-HIV Compounds. WO072419, 2014
   Google Scholar
• Frey KM, Bollini M, Mislak AC, et al. Crystal structures of HIV-1 reverse transcriptase with picomolar inhibitors reveal key interactions for drug design. J Am Chem Soc 2012;134:19501-3
   PubMed Web of Science ®Google Scholar
• Müller K, Faeh C, Diederich F. Fluorine in pharmaceuticals: looking beyond intuition. Science 2007;317:1881-6
   PubMed Web of Science ®Google Scholar
• Shah P, Westwell AD. The role of fluorine in medicinal chemistry. J Enzyme Inhib Med Chem 2007;22:527-40
   PubMed Web of Science ®Google Scholar
• Purser S, Moore PR, Swallow S, Gouverneur V. Fluorine in medicinal chemistry. Chem Soc Rev 2008;37:320-30
   PubMed Web of Science ®Google Scholar
• Bassetto M, Ferla S, Pertusati F. Polyfluorinated groups in medicinal chemistry. Future Med Chem 2015;7:527-46
   PubMed Web of Science ®Google Scholar
• Swallow S. Chapter Two - Fluorine in medicinal chemistry. In: Lawton G, Witty DR, editors. Prog Med Chem, Elsevier Science, Burlington; 2015; p. 65-133
   PubMedGoogle Scholar
• Hagmann WK. The many roles for fluorine in medicinal chemistry. J Med Chem 2008;51:4359-69
   PubMed Web of Science ®Google Scholar
• Gakh AA, Kirk KL. Fluorinated Heterocycles. 2009;1003:3-20
   Google Scholar
• Kirk KL. Fluorine in medicinal chemistry: recent therapeutic applications of fluorinated small molecules. ChemInform 2006;37:1013-29
   Google Scholar
• Ojima I. Use of fluorine in the medicinal chemistry and chemical biology of bioactive compounds–a case study on fluorinated taxane anticancer agents. ChemBioChem 2004;5:628-35
   PubMed Web of Science ®Google Scholar
• Biffinger JC, Kim HW, DiMagno SG. The Polar hydrophobicity of fluorinated compounds. ChemBioChem 2004;5:622-7
   PubMed Web of Science ®Google Scholar
• Corbett JW, Pan S, Markwalder JA, et al. 3,3a-Dihydropyrano[4,3,2-de]quinazolin-2(1H)-ones are potent non-nucleoside reverse transcriptase inhibitors. Bioorg Med Chem Lett 2001;11:211-14
   PubMed Web of Science ®Google Scholar
• Buckheit Jr RW, Hollingshead MG, Germany-Decker J, et al. Thiazolobenzimidazole: Biological and biochemical anti-retroviral activity of a new nonnucleoside reverse transcriptase inhibitor. Antiviral Res 1993;21:247-65
   PubMed Web of Science ®Google Scholar
• Barreca ML, Rao A, De Luca L, et al. Computational strategies in discovering novel non-nucleoside inhibitors of HIV-1 RT. J Med Chem 2005;48:3433-7
   PubMed Web of Science ®Google Scholar
• Kroeger Smith MB, Hose BM, Hawkins A, et al. Molecular modeling calculations of HIV-1 reverse transcriptase nonnucleoside Inhibitors: correlation of binding energy with biological activity for novel 2-aryl-substituted benzimidazole analogues. J Med Chem 2003;46:1940-7
   PubMed Web of Science ®Google Scholar
• Morningstar ML, Roth T, Farnsworth DW, et al. Synthesis, biological activity, and crystal structure of potent nonnucleoside Inhibitors of HIV-1 reverse transcriptase that retain activity against mutant forms of the enzyme. J Med Chem 2007;50:4003-15
   PubMed Web of Science ®Google Scholar
• Campiani G, Aiello F, Fabbrini M, et al. Quinoxalinylethylpyridylthioureas (QXPTs) as potent non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors. Further SAR studies and identification of a novel orally bioavailable hydrazine-based antiviral agent. J Med Chem 2001;44:305-15
   PubMed Web of Science ®Google Scholar
• Ren J, Diprose J, Warren J, et al. Phenylethylthiazolylthiourea (PETT) Non-nucleoside Inhibitors of HIV-1 and HIV-2 reverse transcriptases: structural and biochemical analyses. J Biol Chem 2000;275:5633-9
   PubMed Web of Science ®Google Scholar
• Sahlberg C, Noréen R, Engelhardt P, et al. Synthesis and anti-HIV activities of urea-pETT analogs belonging to a new class of potent non-nucleoside HIV-1 Reverse transcriptase inhibitors. Bioorg Med Chem Lett 1998;8:1511-16
   PubMed Web of Science ®Google Scholar
• Högberg M, Sahlberg C, Engelhardt P, et al. Urea-PETT compounds as a new class of HIV-1 reverse transcriptase inhibitors. 3. Synthesis and further structure-activity relationship studies of PETT analogues. J Med Chem 1999;42:4150-60
   PubMed Web of Science ®Google Scholar
• Jones LH, Allan G, Barba O, et al. Novel indazole non-nucleoside reverse transcriptase inhibitors using molecular hybridization based on crystallographic overlays. J Med Chem 2009;52:1219-23
   PubMed Web of Science ®Google Scholar
• Sweeney ZK, Harris SF, Arora N, et al. Design of annulated pyrazoles as inhibitors of HIV-1 reverse transcriptase. J Med Chem 2008;51:7449-58
   PubMed Web of Science ®Google Scholar
• Sweeney ZK, Dunn JP, Li Y, et al. Discovery and optimization of pyridazinone non-nucleoside inhibitors of HIV-1 reverse transcriptase. Bioorg Med Chem Lett 2008;18:4352-4
   PubMed Web of Science ®Google Scholar
• Sweeney ZK, Acharya S, Briggs A, et al. Discovery of triazolinone non-nucleoside inhibitors of HIV reverse transcriptase. Bioorg Med Chem Lett 2008;18:4348-51
   PubMed Web of Science ®Google Scholar
• Sweeney ZK, Kennedy-Smith JJ, Wu J, et al. Diphenyl ether non-nucleoside reverse transcriptase inhibitors with excellent potency against resistant mutant viruses and promising pharmacokinetic properties. ChemMedChem 2009;4:88-99
   PubMed Web of Science ®Google Scholar
• Su D-S, Lim JJ, Tinney E, et al. Biaryl ethers as potent allosteric inhibitors of reverse transcriptase and its key mutant viruses: Aryl substituted pyrazole as a surrogate for the pyrazolopyridine motif. Bioorg Med Chem Lett 2010;20:4328-32
   PubMed Web of Science ®Google Scholar
• Côté B, Burch JD, Asante-Appiah E, et al. Discovery of MK-1439, an orally bioavailable non-nucleoside reverse transcriptase inhibitor potent against a wide range of resistant mutant HIV viruses. Bioorg Med Chem Lett 2014;24:917-22
   PubMed Web of Science ®Google Scholar
• Lai M-T, Feng M, Falgueyret J-P, et al. In vitro characterization of MK-1439, a novel HIV-1 nonnucleoside reverse transcriptase inhibitor. Antimicrob Agents Chemother 2014;58:1652-63
   PubMed Web of Science ®Google Scholar
• Mitchell ML, Son JC, Lee IY, et al. N1-Heterocyclic pyrimidinediones as non-nucleoside inhibitors of HIV-1 reverse transcriptase. Bioorg Med Chem Lett 2010;20:1585-8
   PubMed Web of Science ®Google Scholar
• Boyer J, Arnoult E, Médebielle M, et al. Difluoromethylbenzoxazole pyrimidine thioether derivatives: a novel class of potent non-nucleoside HIV-1 reverse transcriptase inhibitors. J Med Chem 2011;54:7974-85
   PubMed Web of Science ®Google Scholar
• Liu B, Lee Y, Zou J, et al. Discovery and SAR of a series of 4,6-diamino-1,3,5-triazin-2-ol as novel non-nucleoside reverse transcriptase inhibitors of HIV-1. Bioorg Med Chem Lett 2010;20:6592-6
   PubMed Web of Science ®Google Scholar
• Radi M, Pagano M, Franchi L, et al. Synthesis, biological activity, and ADME properties of novel S-DABOs/N-DABOs as HIV reverse transcriptase inhibitors. Chem Med Chem 2012;7:883-96
   Web of Science ®Google Scholar
• Rotili D, Tarantino D, Artico M, et al. Diarylpyrimidine-dihydrobenzyloxopyrimidine hybrids: new, wide-spectrum anti-HIV-1 agents active at (Sub)-nanomolar level. J Med Chem 2011;54:3091-6
   PubMed Web of Science ®Google Scholar
• Rotili D, Samuele A, Tarantino D, et al. 2-(Alkyl/Aryl)amino-6-benzylpyrimidin-4(3H)-ones as inhibitors of wild-type and mutant HIV-1: enantioselectivity studies. J Med Chem 2012;55:3558-62
   PubMed Web of Science ®Google Scholar
• Samuele A, Kataropoulou A, Viola M, et al. Non-nucleoside HIV-1 reverse transcriptase inhibitors di-halo-indolyl aryl sulfones achieve tight binding to drug-resistant mutants by targeting the enzyme-substrate complex. Antiviral Res 2009;81:47-55
   PubMed Web of Science ®Google Scholar
• Xu B, Sun Y, Guo Y, et al. Synthesis and biological evaluation of N4-(hetero)arylsulfonylquinoxalinones as HIV-1 reverse transcriptase inhibitors. Bioorg Med Chem 2009;17:2767-74
   PubMed Web of Science ®Google Scholar
• Ren J, Nichols CE, Chamberlain PP, et al. Relationship of potency and resilience to drug resistant mutations for GW420867X revealed by crystal structures of inhibitor complexes for wild-type, Leu100Ile, Lys101Glu, and Tyr188Cys mutant HIV-1 reverse transcriptases. J Med Chem 2007;50:2301-9
   PubMed Web of Science ®Google Scholar
• Murugesan V, Tiwari VS, Saxena R, et al. Lead optimization at C-2 and N-3 positions of thiazolidin-4-ones as HIV-1 non-nucleoside reverse transcriptase inhibitors. Bioorg Med Chem 2011;19:6919-26
   PubMed Web of Science ®Google Scholar
• Bollini M, Gallardo-Macias R, Spasov KA, et al. Optimization of benzyloxazoles as non-nucleoside inhibitors of HIV-1 reverse transcriptase to enhance Y181C potency. Bioorg Med Chem Lett 2013;23:1110-13
   PubMed Web of Science ®Google Scholar
• Ren J, Chamberlain PP, Stamp A, et al. Structural basis for the improved drug resistance profile of new generation benzophenone non-nucleoside HIV-1 reverse transcriptase inhibitors. J Med Chem 2008;51:5000-8
   PubMed Web of Science ®Google Scholar
• Xing L, Blakemore DC, Narayanan A, et al. Fluorine in drug design: a case study with fluoroanisoles. ChemMedChem 2015;10:715-26
   PubMed Web of Science ®Google Scholar
• Zhan P, Liu X, Cao Y, et al. 1,2,3-Thiadiazole thioacetanilides as a novel class of potent HIV-1 non-nucleoside reverse transcriptase inhibitors. Bioorg Med Chem Lett 2008;18:5368-71
   PubMed Web of Science ®Google Scholar
• Zhan P, Liu X, Li Z, et al. Novel 1,2,3-thiadiazole derivatives as HIV-1 NNRTIs with improved potency: Synthesis and preliminary SAR studies. Bioorg Med Chem 2009;17:5920-7
   PubMed Web of Science ®Google Scholar
• Zhan P, Li X, Li Z, et al. Structure-based bioisosterism design, synthesis and biological evaluation of novel 1,2,4-triazin-6-ylthioacetamides as potent HIV-1 NNRTIs. Bioorg Med Chem Lett 2012;22:7155-62
   PubMed Web of Science ®Google Scholar
• Zhan P, Li Z, Liu X, et al. Sulfanyltriazole/tetrazoles: A promising class of HIV-1 NNRTIs. Mini Rev Med Chem 2009;9:1014-23
   PubMed Web of Science ®Google Scholar
• Song Y, Zhan P, Liu X. Heterocycle-thioacetic acid motif: A privileged molecular scaffold with potent, broad-ranging pharmacological activities. Curr Pharm Des 2013;19:7141-54
   PubMed Web of Science ®Google Scholar
• Fang Z, Song Y, Zhan P, et al. Conformational restriction: an effective tactic in ’follow-on’-based drug discovery. Future Med Chem 2014;6:885-901
   PubMed Web of Science ®Google Scholar
• Kiss L, Nonn M, Sillanpää R, et al. Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates. Beilstein J Org Chem 2013;9:1164-9
   PubMed Web of Science ®Google Scholar
• MykhailiukPK. Three-component synthesis of C(2)F(5)-substituted pyrazoles from C(2)F(5)CH(2)NH(2)·HCl, NaNO(2) and electron-deficient alkynes. Beilstein J Org Chem 2015;11:16-24
   PubMed Web of Science ®Google Scholar