Synthesis, molecular modeling of N-acyl benzoazetinones and their docking simulation on fungal modeled target

References

• (a) Ceric, H.; Sindler-Kulyk, M.; Kovacevic, M.; Peric, M.; Zivkovic, A. Bioorg. Med. Chem. 2010, 18, 3053; (b) Webber, J. A.; Wheeler, W. J. In Chemistry and Biology of Beta-Lactam Antibiotics; R. B. Morin, M. Gorman (Eds.); Academic Press: New York, 1982, pp. 372–436; (c) Long, T. E.; Turos, E. Curr. Med. Chem. 2002, 1, 251; (d) Cromwell, N. H.; Philips, B. Chem. Rev. 1979, 79, 331; (e) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; A. Padwa (Ed.); Elsevier Science, 1996; vol. 1B, pp. 507–589; (f) Bruggink, A. Synthesis of β-Lactam Antibiotics; Springer Science & Business Media: Dordrecht, 2001; (g) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; A. R. Katritzky, C. W. Rees, E. F. V. Scriven (Eds.); Pergamon Press: Oxford, 1996, p. 149; (h) Georg, G. I.; Ravikumar, V. T. The Organic Chemistry of β-Lactams; G. I. Georg (Ed.); VCH: New York, 1993, pp. 295–368.
   PubMed Web of Science ®Google Scholar
• (a) Suffness, M. Taxol Science and Applications; CRC Press: Boca Raton, FL, USA, 1995, pp. 379–415; (b) Bose, A. K.; Mathur, C.; Wagle, D. R.; Manhas, M. S. Tetrahedron Symp. Print 2000, 56, 5603; (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437.
   Google Scholar
• Buynak, J. Curr. Med. Chem. 2004, 11, 1951.
   PubMed Web of Science ®Google Scholar
• (a) Burnett, D. A. Curr. Med. Chem. 2004, 11, 1873; (b) Clader, J. W. J. Med. Chem. 2004, 47, 1.
   PubMed Web of Science ®Google Scholar
• Finke, P. E.; Shah, S. K.; Fletcher, D. S.; Ashe, B. M.; Brause, K. A.; Chandler, G. O.; Dellea, P. S.; Hand, K. M.; Maycock, A. L.; Osinga, D. G.; Underwood, D. J.; Weston, H.; Davies, P.; Doherty, J. B. J. Med. Chem. 1995, 38, 2449.
   PubMed Web of Science ®Google Scholar
• O’Driscoll, M.; Greenhalgh, K.; Young, A.; Turos, E.; Dickey, S.; Lim, D. V. Bioorg. Med. Chem. 2008, 16, 7832.
   PubMed Web of Science ®Google Scholar
• Kanafani, Z. A.; Perfect, J. R. Clinic. Infect. Dis. 2008, 46, 120.
   PubMed Web of Science ®Google Scholar
• Limper, A. H.; Knox, K. S.; Sarosi, G. A.; Ampel, N. M.; Bennett, J. E.; Catanzaro, A.; Davies, S. F.; Dismukes, W. E.; Hage, C. A.; Marr, K. A.; Mody, C. H.; Perfect, J. R.; Stevens, D. A. Am. J. Respir. Crit. Care Med. 2011, 183, 96.
   PubMed Web of Science ®Google Scholar
• Andriole, V. T. Int. J. Antimicrob. Agents 2000, 16, 317.
   PubMed Web of Science ®Google Scholar
• Giraud, F.; Guillon, R.; Logé, C.; Pagniez, F.; Picot, C.; Le Borgne, M.; Le Pape, P. Med. Chem. Lett. 2009, 19, 301.
   PubMed Web of Science ®Google Scholar
• Vanden, B. H.; Dromer, F.; Improvisi, I.; Lozano-Chiu, M.; Rex, J. H.; Sanglard, D. Med. Mycol. 1997, 36, 119.
   Google Scholar
• Perfect, J. R. Med. Myco. 2009, 47, S324.
   PubMed Web of Science ®Google Scholar
• Masubuchi, M.; Ebiike, H.; Kawasaki, K. I.; Sogabe, S.; Morikami, K.; Shiratori, Y.; Tsujii, S.; Fujii, T.; Sakata, K.; Hayase, M.; Shindoh, H.; Aoki, Y.; Ohtsuka, T.; Shimma, N. Bioorg. Med. Chem. 2003, 11, 4463.
   PubMed Web of Science ®Google Scholar
• Saha, S.; Priyadharshini, A.; Dhanasekaran, D.; Thajuddin, N.; Chandraleka, S.; Chandramohan, G.; Panneerselvam, A. Comput. Boil. Med. 2012, 42, 542.
   PubMed Web of Science ®Google Scholar
• Crešnar, B.; Petric, S. Biochim. Biophys. Acta 2011, 1814, 29.
   PubMed Web of Science ®Google Scholar
• Kelly, S. L.; Kelly, D. E. Phil. Trans. R. Soc. 2013, 368, 1612.
   Web of Science ®Google Scholar
• Podobnik, B.; Stojan, J.; Lah, L.; Kraševec, N.; Seliškar, M.; Rižner, T. L.; Rozman, D.; Komel, R. J. Med. Chem. 2008, 51, 3480.
   PubMed Web of Science ®Google Scholar
• Sandanayaka, V. P.; Prashad, A. S.; Yang, Y.; Williamson, T.; Lin, Y. I.; Mansour, T. S. J. Med. Chem. 2003, 46, 2569.
   PubMed Web of Science ®Google Scholar
• Buynak, J. D.; Rao, A. S.; Fod, G. P.; Carver, C.; Adam, G.; Geng, B.; Bachmann, B.; Shobassy, S.; Lackey, S. J. Med. Chem. 1997, 40, 3423.
   PubMed Web of Science ®Google Scholar
• Bonneau, P. R.; Hasani, F.; Plouffe, C.; Malenfant, E.; Laplante, S. R.; Guse, I.; Ogilvie, W. W.; Plante, R.; Davidson, W. C.; Hopkins, J. L.; Morelock, M. M.; Cordingley, M. G. Deziel, R. J. Am. Chem. Soc. 1999, 121, 2965.
   Web of Science ®Google Scholar
• (a) Pitts, C. R.; Lectka, T. Chem. Rev. 2014, 114, 7930; and references there in (b) Banik, B. K.; Ghatak, A.; Becker, F. F. J. Chem. Soc. Perkin Trans. 2000, 1, 2179; (c) Banik, B. K.; Becker, F. F. Tetrahedron Lett. 2000, 41, 6551; (d) Ng, S.; Banik, I.; Okawa, A.; Becker, F. F.; Banik, B. K. J. Chem. Res. (S) 2001, 3, 118; (e) Banik, B. K.; Samajdar, S.; Banik, I. Tetrahedron Lett. 2003, 44, 1699; (f) Banik, B. K.; Adler, D.; Nguyen, P.; Srivastava, N. Heterocycles 2003, 61, 101; (g) Banik, B. K.; Lecea, B.; Arrieta, A.; Cozar, A.; Cossio, F. P. Angew. Chem. Int. Ed. 2007, 46, 3028; (h) Banik, B. K.; Aguilar, H.; Cordova, D. Heterocycles 2008, 11, 2321.
   PubMed Web of Science ®Google Scholar
• (a) Fodor, L.; Csomos, P.; Holczbauer, T.; Kalman, A.; Csampai, A.; Sohar, P. Tetrahedron Lett. 2011, 52, 224; (b) Janikowska, K.; Pawelska, N.; Makowiec, S. Synthesis 2011, 1, 69; (c) Dubey, A.; Srivastava, S. K.; Srivastava, S. D. Bioorg. Med. Chem. Lett. 2011, 21, 569; (d) Feroci, M.; Chiarotto, I.; Orsinib, M.; Inesi, A. Chem. Commun. 2010, 46, 4121; (e) Keri, R. S.; Hosamani, K. M.; Shingalapur, R. V.; Reddy, H. R. S. Eur. J. Med. Chem. 2009, 44, 5123; (f) Dekeukeleire, S.; D’hooghe, M.; Muller, C.; Vogt, D.; De Kimpe, N. New J. Chem. 2010, 34, 1079; (g) Jarrahpour, A.; Zarei, M. Molecules 2006, 11, 49; (h) Jarrahpour, A.; Khalili, D. Tetrahedron Lett. 2007, 48, 7140; (i) Jarrahpour, A.; Ebrahimi, E. Molecules 2010, 15, 515.
   Web of Science ®Google Scholar
• Burgess, E. M.; Milne, G. Tetrahedron Lett. 1966, 7, 93.
   Google Scholar
• Smalley, R. K.; Suschitzky, H.; Tanner, E. M. Tetrahedron Lett. 1966, 7, 3465.
   Google Scholar
• Chiu, S.-J.; Chou, C.-H. Tetrahedron Lett. 1999, 40, 9271.
   Web of Science ®Google Scholar
• Olofson, R. A.; Vander Meer, R. K.; Stournas, S. J. Am. Chem. Soc. 1971, 93, 1543.
   Web of Science ®Google Scholar
• Dai, W-M.; Cheung, Y. K.; Tang, K. W.; Choi, P. Y.; Chung, S. L. Tetrahedron 1995, 51, 12263.
   Web of Science ®Google Scholar
• Nowak, M.; Malinowski, Z.; Jozwiak, A.; Fornal, E.; Blaszczyk, A.; Kontek, R. Tetrahedron 2014, 70, 5153.
   Web of Science ®Google Scholar
• Kayarmar, R.; Nagaraja, G. K.; Bhat, M.; Naik, P.; Rajesh, K. P.; Shetty, S.; Arulmoli, T. Med. Chem. Res. 2014, 23, 2964.
   Web of Science ®Google Scholar
• Cioffi, C. L.; Dobri, N.; Freeman, E. E.; Conlon, M. P.; Chen, P.; Stafford, D. G.; Schwarz, D. M. C.; Golden, K. C.; Zhu, L.; Kitchen, D. B.; Barnes, K. D.; Racz, B.; Qin, Q.; Michelotti, E.; Cywin, C. L.; Martin, W. H.; Pearson, P. G.; Johnson, G.; Petrukhin, K. J. Med. Chem. 2014, 57, 7731.
   PubMed Web of Science ®Google Scholar
• Emenike, B. U.; Liu, A. T.; Naveo, E. P.; Roberts, J. D. J. Org. Chem. 2013, 78, 11765.
   PubMed Web of Science ®Google Scholar
• Alam, A.; Pal, C.; Goyal, M.; Kundu, M. K.; Kumar, R.; Iqbal, M. S.; Dey, S.; Bindu, S.; Sarkar, S.; Pal, U.; Maiti, N. C. Bioorg. Med. Chem. 2011, 19, 7365.
   PubMed Web of Science ®Google Scholar
• Mondal, S.; Mondal, B.; Bandyopadhyay, A. K. Int. J. Eng. Sci. Technol. 2013, 5, 992.
   Google Scholar
• Mondal, B.; Sen Gupta, P. S.; Roy, C.; Islam, R. N. U.; Hazra, N.; Bandyopadhyay, A. K. Int. J. Pharm. Bio Sci. 2016, 7, 406.
   Google Scholar
• Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graphs 1996, 29, 33.
   Google Scholar
• Webb, B.; Sali, A. Curr. Protoc. Bioinf. 2014, 8, 5.
   Google Scholar
• Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. J. Comp. Chem. 2009, 16, 2785.
   Web of Science ®Google Scholar
• Wang, H. C.; Yan, X. Q.; Yan, T. L.; Li, H. X.; Wang, Z. C.; Zhu, H. L. Molecules 2016, 21, 1012.
   PubMed Web of Science ®Google Scholar
• Trott, O.; Olson, A. J. Comp. Chem. 2010, 31, 455.
   PubMed Web of Science ®Google Scholar