Non-nucleoside inhibitors of the measles virus RNA-dependent RNA polymerase: Synthesis, structure-activity relationships, and pharmacokinetics

Journal of Medicinal Chemistry

Volumn 55, Issue 9, 2012, Pages 4220-4230

  Ndungu, J Maina ^a   Krumm, Stefanie A ^b   Yan, Dan ^b   Arrendale, Richard F ^a   Reddy, G Prabhakar ^a   Evers, Taylor ^a   Howard, Randy ^a   Natchus, Michael G ^a   Saindane, Manohar T ^a   Liotta, Dennis C ^a   Plemper, Richard K ^b,c   Snyder, James P ^a   Sun, Aiming ^a  

^a EMORY UNIVERSITY   (United States)

^b EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c CHILDREN'S HEALTHCARE OF ATLANTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE; RNA POLYMERASE; VIRUS RNA;

ANTIVIRAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; HIGH THROUGHPUT SCREENING; IN VITRO STUDY; MAXIMUM PLASMA CONCENTRATION; MEASLES VIRUS; NONHUMAN; RAT; RNA SYNTHESIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIVIRAL AGENTS; ENZYME INHIBITORS; INHIBITORY CONCENTRATION 50; MEASLES; MEASLES VIRUS; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRAZOLES; RATS; RATS, SPRAGUE-DAWLEY; RNA REPLICASE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84861079881     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201699w     Document Type: Article

References (21)

1. Centers for Disease Control and Prevention. Update: Measles-United States, January-July 2008. MMWR Morb. Mortal. Wkly. Rep. 2008, 57, 893-896.
2. Kremer, J. R.; Muller, C. P. Measles in Europe - There is room for improvement Lancet 2009, 373, 356-358
3. http://www.oregonlive.com/opinion/index.ssf/2011/01/vaccines-halting-an- epidemic-o.html.
4. http://www.who.int/csr/don/2011-04-21/en/.
5. Chakrabarti, S.; Collingham, K. E.; Holder, K.; Fegan, C. D.; Osman, H.; Milligan, D. W. Pre-emptive oral ribavirin therapy of paramyxovirus infections after haematopoietic stem cell transplantation: A pilot study Bone Marrow Transplant. 2001, 21, 759-763 (Pubitemid 33085568)
6. Shigeta, S.; Mori, S.; Baba, M.; Ito, M.; Honzumi, K.; Nakamura, K.; Oshitani, H.; Numazaki, Y.; Matsuda, A.; T. Obara, T.; Shuto, S.; De Clercq, E. Antiviral activities of ribavirin, 5-ethynyl-1-D-ribofuranosylimidazole-4- carboxamide, and 6-(R)-6- C -methylneplanocin A against several ortho- and paramyxoviruses Antimicrob. Agents Chemother. 1992, 36, 435-439
7. Plemper, R. K.; Snyder, J. P. Measles control - Can measles virus inhibitors Curr. Opin. Invest. Drugs (BioMed Central) 2009, 10, 811-820
8. White, L. K.; Yoon, J.-J.; Lee, J. K.; Sun, A.; Du, Y.; Fu, H.; Snyder, J. P.; Plemper, R. K. Non nucleoside Inhibitor of Measles Virus RNA Dependent RNA Polymerase Complex Activity Antimicrob. Agents Chemother. 2007, 51, 2293-2303 (Pubitemid 47047303)
9. Yoon, J.; Krumm, S. A.; Ndungu, J. M.; Hoffman, V.; Bankamp, B.; Rota, P. A.; Sun, A.; Snyder, J. P.; Plemper, R. K. Target analysis of the experimental measles therapeutic AS-136A Antimicrob. Agents Chemother. 2009, 53, 3860-3870
10. Sun, A.; Chandrakumar, N.; Yoon, J.-J.; Plemper, R. K.; Snyder, J. P. Non nucleoside inhibitors of the measles virus RNA-dependent RNA polymerase activity: Synthesis and in vitro evaluation Bioorg. Med. Chem. Lett. 2007, 17, 5199-5203 (Pubitemid 47259649)
11. Sun, A.; Yoon, J. J.; Yin, Y.; Prussia, A.; Yang, Y.; Min, J.; Plemper, R. K.; Snyder, J. P. Potent non-nucleoside inhibitors of the measles virus RNA-dependent RNA polymerase complex J. Med. Chem. 2008, 51, 3731-3741 (Pubitemid 351956505)
12. Lahm, G. P.; Selby, T. P.; Freudenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Smith, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Insecticidal anthranilic diamides: A new class of potent ryanodine receptor activators Bioorg. Med. Chem. Lett. 2005, 15, 4898-4906 (Pubitemid 41403276)
13. Tanaka, M.; Nakamura, M.; Ikeda, T.; Ikeda, K.; Ando, H.; Shibutani, Y.; Yajima, S.; Kimura, K. J. Org. Chem. 2001, 66, 7008-7012
14. Paulissen, R.; Reimlinger, H.; Hayez, E.; Hubert, A. J.; Teyssié, P. Transition metal catalysed reaction of diazocompounds - II insertion in the hydroxylic bond Tetrahedron Lett. 1973, 2233-2236
15. Moody, C. J.; Miller, D. J. Synthetic applications of the O-H insertion reactions of carbenes and carbenoids derived from diazocarbonyl and related diazo compounds Tetrahedron 1995, 51, 10811-10843
16. McGeary, R. P. Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium borohydride Tetrahedron Lett. 1998, 39, 3319
17. Szadkowska, A.; Makal, A.; Wozniak, K.; Kadyrov, R.; Grela, K. Organometallics 2009, 28, 2693-2700
18. Sun, H.; Pang, K. S. Permeability, Transport, and Metabolism of Solutes in Caco-2 Cell Monolayers: A Theoretical Study Drug Metab. Dispos. 2008, 36, 102-123
19. Sarkadi, B; Homolya, L.; Szakacs, G.; Varadi, A. Human Multidrug Resistance ABCB and ABCG Transporters: Participation in a Chemoimmunity Defense System Physiol. Rev. 2006, 86, 1179-1236 (Pubitemid 44521651)
20. Krumm, S. A.; Ndungu, J. M.; Dochow, M.; Yoon, J.-J.; Sun, A.; Natchus, M.; Snyder, J. P.; Plemper, R. K. Host-Directed Small-Molecule Inhibitors of Myxovirus RNA-dependent RNA-polymerases PLoS One 2011, 6, e20069
21. Sun, A.; Ndungu, J. M.; Krumm, S. A.; Yoon, J.-J.; Thepchatri, P.; Natchus, M.; Plemper, R. K.; Snyder, J. P. Host-directed Inhibitors of Myxoviruses: Synthesis and in vitro Biochemical Evaluation ACS Med. Chem. Lett. 2011, 2, 798-803