Synthesis, antibacterial and potential anti-HIV activity of some novel imidazole analogs

R. C. Gallo, S. Z. Salahuddin, M. Popovic, G. M. Shearer, M. Kaplan, B. F. Haynes, T. J. Palker, R. Redfield, J. Oleske and B. Safai, Frequent detection and isolation of cytopathic retroviruses (HTLV-III) from patients with AIDS and at risk for AIDS, Science 224 (1984) 500-503; DOI: 10.1126/science.6200936.10.1126/science.62009366200936Search in Google Scholar

F. S. Barre, J. C. Chermann, F. Rey, M. T. Nugeyre, S. Chamaret, J. Gruest, C. Dauguet, C. Axler-Blin, F. Vezinet-Brun, C. Rouzioux, W. Rozenbaum and L. Montagnier, Isolation of a T-lymphotropic retrovirus from a patient at risk for acquired immune deficiency syndrome (AIDS), Science 220 (1983) 868-871; DOI: 10.1126/science.6189183.10.1126/science.61891836189183Search in Google Scholar

E. De Clercq, Toward improved anti-HIV chemotherapy: Therapeutic strategies for intervention with HIV infections, J. Med. Chem. 38 (1995) 2491-2517; DOI: 10.1021/jm00014a001.10.1021/jm00014a0017543152Search in Google Scholar

E. De Clercq, New developments in anti-HIV chemotherapy, Biochem. Biophys. Acta 1587 (2002) 258-275; DOI: 10.1016/S0014-827X (01)01007-2.Search in Google Scholar

D. Sriram, R. B. Tanushree and P. Yogeeswari, Design, synthesis and biological evaluation of novel non-nucleoside HIV-1 reverse transcriptase inhibitors with broad-spectrum chemotherapeutic properties, Bioorg. Med. Chem. 12 (2004) 5865-5873; DOI: 10.1016/j.bmc.2004.08.028.10.1016/j.bmc.2004.08.02815498662Search in Google Scholar

J. J. Ren, C. Nicolas, L. E. Bird, T. Fujiwara, H. Sugimoto and D. Stuart, Binding of the second generation non-nucleoside inhibitor S-1153 to HIV-1 reverse transcriptase involves extensive main chain hydrogen bonding, J. Biol. Chem. 275 (2000) 14316-14320; DOI: 10.1074/jbc.275.19. 14316.Search in Google Scholar

R. Silvestri, M. Artico, S. Massa, T. Marceddu, F. De Montis and P. La Colla, 1-[2-(Diphenylmethoxy) ethyl]-2-methyl-5-nitroimidazole: a potent lead for the design of novel NNRTIs, Bioorg. Med. Chem. Lett. 10 (2000) 253-256; DOI: 10.1016/S0960-894X (99)00664-2.Search in Google Scholar

R. Silvestri, M. Artico, G. De Martino, R. Ragno, S. Massa, R. Lodda, C. Mugioni, A. Giulia Loi, P. La Colla and A. Pani, Synthesis, biological evaluation and binding mode of novel 1-[2-(diarylmethoxy) ethyl]-2-methyl-5-nitroimidazoles targeted at the HIV-1 reverse transcriptase, J. Med. Chem. 45 (2002) 1567-1576; DOI: 10.1021/jm010904a.10.1021/jm010904a11931611Search in Google Scholar

G. De Martino, G. Regina, A. D. Pasquali, A. Bergamini, C. Ciaprini, A. Sinistro, G. Maga, E. Crespan, M. Artico and R. Silvestri, Novel 1-[2-(diarylmethoxy) ethyl]-2-methyl-5-nitroimidazoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. A structure-activity relationship investigation, J. Med. Chem. 48 (2005) 4378-4388; DOI: 10.1021/jm050273a.10.1021/jm050273a15974590Search in Google Scholar

I. M. Lagoja, C. Pannecouque, Z. Debyser, J. Balzarini, A. V. Aerschot, M. Witvtouw and P. Herdewijn, N-Aminoimidazole derivatives inhibiting retroviral replication via a yet unidentified mode of action, J. Med. Chem. 46 (2003) 1546-1553; DOI: 10.1021/jm0211117.10.1021/jm021111712672256Search in Google Scholar

S. Ganguly, M. Sankaran, N. Prasanthi, O. Alptürk, B. Herman and N. S. Cremer, Synthesis and anti-HIV-1 activity of a novel series of aminoimidazole analogs, Lett. Drug Des. Discov. 7 (2010) 318-323; DOI: 10.2174/157018010791163424.10.2174/157018010791163424288230820535242Search in Google Scholar

S. Ganguly, V. Gopalakrishnan and R. Chandra, Synthesis and antibacterial activity of some new 1-substituted 2-methyl-4-nitroimidazoles, Int. J. Chem. Sci. 7 (2009) 204-210.Search in Google Scholar

M. Hoffer and E. Grunberg, Synthesis and antiprotozoal activity of 1-(3-chloro-2-hydroxypropyl)-substituted nitroimidazoles, J. Med. Chem. 17 (1974) 1019-1020; DOI: 10.1021/jm00255a026.10.1021/jm00255a0264370421Search in Google Scholar

Z. Soyer, F. S. Kilic, K. Erol and V. Pabuccuoglu, Synthesis and anticonvulsant activity of some ω-(1H-imidazol-1-yl)-N-phenylacetamide and propionamide derivatives, Farmaco 59 (2003) 595-600; DOI: 10.1016/j.farmac.2003.07.011.10.1016/j.farmac.2003.07.01115262528Search in Google Scholar

S. T. Selvi, V. Nadaraj, S. Mohan, R. Sasi and M. Hema, Solvent free microwave synthesis and evaluation of antimicrobial activity of pyrimido [4,5-b] and pyrazolo [3,4-b] quinolines, Bioorg. Med. Chem. 14 (2006) 3896-3903; DOI: 10.1016/j.bmc.2006.01.048.10.1016/j.bmc.2006.01.04816464602Search in Google Scholar

D. V. Nissley, J. Radzio, Z. Ambrose, C. W. Sheen, N. Hamamouch, K. L. Moore, G. Tachedjian and N. S. Cremer, Characterization of novel non-nucleoside reverse transcriptase (RT) inhibitor resistance mutations at residues 132 and 135 in the 51 kDa subunit of HIV-1 RT, Biochem. J. 404 (2007) 151-157; DOI: 10.1042/BJ20061814.10.1042/BJ20061814186883417286555Search in Google Scholar

A. L. Hopkins, J. Ren, R. M. Esnouf, B. E. Wilcox, E. Y. Jones, C. Ross, T. Miyasaka, R. T. Walker, H. Tanaka, D. K. Stammers and D. I. Stuart, Complexes of HIV-1 reverse transcriptase with inhibitors of the HEPT series reveal conformational changes relevant to the design of potent non-nucleoside inhibitors, J. Med. Chem. 39 (1996) 1589-1600; DOI: 10.1021/jm960056x.10.1021/jm960056x8648598Search in Google Scholar

W. L. Jorgensen, D. S. Maxwell and J. Tirado-Rives, Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids, J. Am. Chem. Soc. 118 (1996) 11225-11236; DOI: 10.1021/ja9621760.10.1021/ja9621760Search in Google Scholar