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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 8
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PEG-400 promoted a simple, efficient and eco-friendly synthesis of functionalized novel isoxazolyl pyrido[2,3-d]pyrimidines and their antimicrobial and anti-inflammatory activity

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Pages 1171-1183 | Received 27 Oct 2020, Published online: 01 Feb 2021

References

  • (a) Anastas, P. T.; Warner, J. C. Green Chemistry, Theory and Practice; Oxford University Press: Oxford, 1998; (b) Dunn, P. J. Chem. Soc. Rev. 2012, 41, 1452–1461. DOI: 10.1039/C1CS15041C.
  • Toda, F.; Tanaka, K. Chem. Rev. 2000, 100, 1025–1074.
  • (a) Harvath, I. T. Acc. Chem. Res. 1998, 31, 641; DOI: 10.1021/ar970342i.; (b) Luo, Z.; Zhang, Q.; Oderaotoshi, Y.; Curran, D. P. Science. 2001, 291, 1766–1769. DOI: 10.1126/science.1057567.
  • Oakes, R. S.; Clifford, A. A.; Rayner, C. M. J. Chem. Soc. Perkin Trans. 1. 2001, 917–941. DOI: 10.1039/b101219n.
  • (a) Wasserscheid, P.; Keim, W. Angew. Chem. Int. Ed. 2000, 39, 3772–3789. DOI: 10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5.; (b) Welton, T. Chem. Rev. 1999, 99, 2071–2084. DOI: 10.1021/cr980032t.; (c) Gordon, C. M. Appl. Catal. A. 2001, 222, 101–117. DOI: 10.1016/S0926-860X(01)00834-1.; (d) Earle, M. J.; Seddon, K. R. Pure Appl. Chem. 2000, 72, 1391–1398. DOI: 10.1351/pac200072071391.
  • Breslow, R. Acc. Chem. Res. 1991, 24, 159–164. DOI: 10.1021/ar00006a001.
  • (a) Suman, L. J.; Sweety, S.; Bir, S. Green Chem. 2007, 9, 740.; (b) Ballini, R.; Barboni, L.; Palmieri, A. Green Chem. 2008, 10, 1004. DOI: 10.1039/b805985c.; (c) Kumar, R.; Chaudhary, P.; Nimesh, S.; Chandra, R. Green Chem. 2006, 8, 356. DOI: 10.1039/b517397c.; (d) Zhang, Z. H.; Yin, L.; Wang, Y. M.; Liu, J. Y.; Li, Y. Green Chem. 2004, 6, 563. DOI: 10.1039/b410583d.; (e) Vasudevan, V. N.; Rajender, S. V. Green Chem. 2001, 3, 146; (f) Haimov, A.; Neumann, R. Chem. Commun. 2002, 876–877. DOI: 10.1039/b200559j.; (g) Kamal, A.; Reddy, D. R.; Rajendar, S. Tetrahedron Lett. 2005, 46, 7951. DOI: 10.1016/j.tetlet.2005.09.082.
  • (a) Supriya, D.; Bajaj, S. O. Synth. Commun. 2018, 48, 1; (b) Estévez, V.; Villacampa, M.; Menéndez, J. C. Chem. Soc. Rev. 2010, 39, 4402–4421. DOI: 10.1039/b917644f.; (c) In Handbook of Heterocyclic Chemistry, 3rd ed.; Katritzky, A. R.; Ramsden, C. A.; Joule, J. A.; Zhdankin, V. V., Eds.; Elsevier: Oxford, 2010; pp 29.
  • (a) Gong, H.; Qi, H.; Sun, W.; Zhang, Y.; Jiang, D.; Xiao, J.; Yang, X.; Wang, Y.; Li, S. Molecules. 2012, 17, 9961–9970. DOI: 10.3390/molecules17089961.; (b) Matulenko, M. A.; Lee, C.-H.; Jiang, M.; Frey, R. R.; Cowart, M. D.; Bayburt, E. K.; Didomenico, S.; Gfesser, G. A.; Gomtsyan, A.; Zheng, G. Z.; et al. Bioorg. Med. Chem. 2005, 13, 3705–3720. DOI: 10.1016/j.bmc.2005.03.023.; (c) Wendt, J. A.; Deeter, S. D.; Bove, S. E.; Knauer, C. S.; Brooker, R. M.; Augelli-Szafran, C. E.; Schwarz, R. D.; Kinsora, J. J.; Kilgore, K. S. Bioorg. Med. Chem. Lett. 2007, 17, 5396–5399. DOI: 10.1016/j.bmcl.2007.07.047.; (d) Kolla, V. E.; Deyanov, A. B.; Nazmetdinov, F. Y.; Kashina, Z. N.; Drovosekova L. P., Khim-Farm Zh, 1993, 27, 29.
  • (a) Rao, C. B.; Almeida, A. K.; Katkar, K. V.; Khanna, S.; Ghosh, U.; Keche, A.; Shah, P.; Srivastava, A.; Korde, V.; Nemmani, K. V. S.; et al. Bioorg. Med. Chem. 2012, 20, 2930–2939. DOI: 10.1016/j.bmc.2012.03.019.; (b) Teixidó, J.; Borrell, J. I.; Colominas, C.; Deupí, X.; Matallana, J. L.; Falcó, J. L.; Martinez-Teipel, B. J. Org. Chem. 2001, 66, 192–199. DOI: 10.1021/jo0056390.; (c) Beauchamp, L. M.; Serling, B. L.; Kelsey, J. E.; Biron, K. K.; Collins, P.; Selway, J.; Lin, J.-C.; Schaeffer, H. J. J. Med. Chem. 1988, 31, 144–149. DOI: 10.1021/jm00396a021.; (d) Saxena, A. K.; Saxena, M. Prog. Drug. Res. 1986, 30, 248.
  • (a) Cody, V.; Pace, J.; Queener, S. F.; Adair, O. O.; Gangjee, A. Antimicrob. Agents Chemother. 2013, 57, 2669–2677. DOI: 10.1128/AAC.00172-13.; (b) DeGoey, D. A.; Betebenner, D. A.; Grampovnik, D. J.; Liu, D.; Pratt, J. K.; Tufano, M. D.; He, W.; Krishnan, P.; Pilot-Matias, T. J.; Marsh, K. C.; et al. Bioorg. Med. Chem. Lett. 2013, 23, 3627–3630. DOI: 10.1016/j.bmcl.2013.04.009.; (c) Suresh, M.; Lavanya, P.; Vasu, K.; Sudhakar, D.; Venkata Rao, C. J. Chem. Pharm. Res. 2010, 2, 82; (d) Chan, D. C. M.; Fu, H.; Forsch, R. A.; Queener, S. F.; Rosowsky, A. J. Med. Chem. 2005, 48, 4420–4431. DOI: 10.1021/jm0581718.
  • (a) Gangjee, A.; Vasudevan, A.; Queener, S. F.; Kisliuk, R. L. J. Med. Chem. 1996, 39, 1438–1446. DOI: 10.1021/jm950786p.; (b) Gangjee, A.; Adair, O. O.; Pagley, M.; Queener, S. F. J. Med. Chem. 2008, 51, 6195–6200. DOI: 10.1021/jm800694g.
  • (a) Song, Y.; Hou, Y.; Gupta, S.; Reed, A. D. U.S. Pat 0082920, 2007; (b) Bourrie, M.; Casellas, P.; Jegham, S.; Muneaux, C.; Perreaut, P. FR. Pat 2887882, 2007
  • Deyanov, A. B.; Niyazov, R. K.; Nazmetdinov, F. Y.; Syropyatov, B. Y.; Kolla, V. E.; Konshin, M. E. Khim-Farm. Zh. 1991, 25, 26.
  • Schroeder, M. C.; Hamby, J. M.; Connolly, C. J.; Grohar, P. J.; Winters, R. T.; Barvian, M. R.; Moore, C. W.; Boushelle, S. L.; Crean, S. M.; Kraker, A. J.; et al. J. Med. Chem. 2001, 44, 1915–1926. DOI: 10.1021/jm0004291.
  • (a) Pike, K. G.; Malagu, K.; Hummersone, M. G.; Menear, K. A.; Duggan, H. M. E.; Gomez, S.; Martin, N. M. B.; Ruston, L.; Pass, S. L.; Pass, M. Bioorg. Med. Chem. Lett. 2013, 23, 1212–1216. DOI: 10.1016/j.bmcl.2013.01.019.; (b) Ibrahim, D. A.; Ismail, N. S. M. Eur. J. Med. Chem. 2011, 46, 5825–5832. DOI: 10.1016/j.ejmech.2011.09.041.; (c) Lippa, B.; Kauffman, G. S.; Arcari, J.; Kwan, T.; Chen, J.; Hungerford, W.; Bhattacharya, S.; Zhao, X.; Williams, C.; Xiao, J.; et al. Bioorg. Med. Chem. Lett. 2007, 17, 3081–3086., DOI: 10.1016/j.bmcl.2007.03.046.; (d) Cordeu, L.; Cubedo, E.; Bandrés, E.; Rebollo, A.; Sáenz, X.; Chozas, H.; Victoria Domínguez, M.; Echeverría, M.; Mendivil, B.; Sanmartin, C.; et al. Bioorg. Med. Chem. 2007, 15, 1659–1669. DOI: 10.1016/j.bmc.2006.12.010.
  • (a) Li, W.-T.; Hwang, D.-R.; Chen, C.-P.; Shen, C.-W.; Huang, C.-L.; Chen, T.-W.; Lin, C.-H.; Chang, Y.-L.; Chang, Y.-Y.; Lo, Y.-K.; et al. J. Med. Chem. 2003, 46, 1706–1715., DOI: 10.1021/jm020471r.; (b) Daidone, G.; Raffa, D.; Maggio, B.; Plescia, F.; Cutuli, V. M. C.; Mangano, N. G.; Caruso, A. Arch. Pharm. Pharm. Med. Chem. 1999, 332, 50–54. DOI: 10.1002/(SICI)1521-4184(19993)332:2<50::AID-ARDP50>3.0.CO;2-S.; (c) Tomita, K.; Takahi, Y.; Ishizuka, R.; Kamamura, S.; Nakagawa, M.; Ando, M.; Nakanishi, T.; Nakamura, T.; Udaira, H. Ann. Sankyo Res. Lab 1973, 1, 25; Chem. Abstr. 1974, 80, 120808; (d) Talley, J. J. Prog. Med. Chem. 1999, 13, 201. (e) Talley, J. J.; Brown, D. L.; Carter, J. S.; Graneto, M. J.; Koboldt, C. M.; Masferrer, J. L.; Perkins, W. E.; Rogers, R. S.; Shaffer, A. F.; Zhang, Y. Y.; et al. J. Med. Chem. 2000, 43, 775–777. DOI: 10.1021/jm990577v.; (f) Haripara, K.; Patel, S.; Joshi, A.; Parekh, H. Indian J. Heterocycl. Chem. 2004, 13, 221.
  • (a) Ragab, H. M.; Teleb, M.; Haidar, H. R.; Gouda, N. Bioorg. Chem. 2019, 86, 557–568. DOI: 10.1016/j.bioorg.2019.02.033.; (b) Andrews, L. D.; Kane, T. R.; Dozzo, P.; Haglund, C. M.; Hilderbrandt, D. J.; Linsell, M. S.; Machajewski, T.; McEnroe, G.; Serio, A. W.; Wlasichuk, K. B.; et al. J. Med. Chem. 2019, 62, 7489–7505. DOI: 10.1021/acs.jmedchem.9b00625.; (c) Fayed, E. A.; Sabour, R.; Harras, M. F.; Mehany, A. B. M. Med. Chem. Res. 2019, 28, 1284–1297. DOI: 10.1007/s00044-019-02373-x.; (d) Hussein, B. R. M.; Moustafa, A. H. Synth. Commun. 2019, 49, 2401–2410. DOI: 10.1080/00397911.2019.1626892.; (e) Zhang, F.; Li, C.; Liang, X. Green Chem. 2018, 20, 2057–2063. DOI: 10.1039/C7GC03812G.; (f) Reddy, M. V. R.; Akula, B.; Cosenza, S. C.; Athuluridivakar, S.; Mallireddigari, M. R.; Pallela, V. R.; Billa, V. K.; Subbaiah, D. R. C. V.; Bharathi, E. V.; Vasquez-Del Carpio, R.; et al. J. Med. Chem. 2014, 57, 578–599. DOI: 10.1021/jm401073p.; (g) Estévez, V.; Van Baelen, G.; Lentferink, B. H.; Vlaar, T.; Janssen, E.; Maes, B. U. W.; Orru, R. V. A.; Ruijter, E. ACS Catal. 2014, 4, 40–43. DOI: 10.1021/cs400926z.; (h) Hemdan, M. M.; Abd El-Mawgoude, H. K. Chem. Pharm. Bull. 2015, 63, 450–456. DOI: 10.1248/cpb.c15-00047.
  • (a) Vanaja Rani, N.; Ravindhranath, K. Synth. Commun. 2020. DOI: 10.1080/00397911.2020.1825743.; (b) Nagi Reddy, M.; Praveen Kumar, P. Tetrahedron Lett. 2017, 58, 4790–4795. DOI: 10.1016/j.tetlet.2017.11.027.; (c) Rayudu, S. V.; Dipankar, K.; Kumar, P. Tetrahedron Lett. 2019, 60, 151025. DOI: 10.1016/j.tetlet.2019.151025.; (d) Nagaraju, D.; Rajanarendar, E.; Praveen Kumar, P.; Nagi Reddy, M. New J. Chem. 2017, 41, 4783–4787. DOI: 10.1039/C7NJ01165B.; (e) Nagi Reddy, M.; Praveen Kumar, P. New J. Chem. 2017, 41, 14062; (f) Nagaraju, D.; Rajanarendar, E.; Praveen Kumar, P.; Nagi Reddy, M. ChemistrySelect. 2017, 2, 5110; (g) Nagi Reddy, M.; Rajanarendar, E.; Praveen Kumar, P. Green Chem. Lett. Rev. 2017, 10, 48. DOI: 10.1080/17518253.2017.1285966. (h) Rajanarendar, E.; Nagi Reddy, M.; Rama Krishna, S.; Rama Murthy, K.; Reddy, Y. N.; Rajam, M. V. Eur. J. Med. Chem. 2012, 55, 273–283. DOI: 10.1016/j.ejmech.2012.07.029.; (i) Rajanarendar, E.; Nagi Reddy, M.; Shaik, F. P. Indian J. Chem. Chem. 2011, 50B, 245; (j) Rajanarendar, E.; Nagi Reddy, M.; Rama Krishna, S.; Reddy, K. G.; Reddy, Y. N.; Rajam, M. V. Eur. J. Med. Chem. 2012, 50, 344–349. DOI: 10.1016/j.ejmech.2012.02.013.; (k) Rajanarendar, E.; Nagi Reddy, M.; Rama Krishna, S.; Rama Murthy, K.; Surendar, P.; Reddy, R. N.; Reddy, Y. N. Bioorg. Med. Chem. Lett. 2012, 22, 149–153. DOI: 10.1016/j.bmcl.2011.11.044.
  • Rajanarendar, E.; Rama Murthy, K.; Nagi Reddy, M.; Reddy, K. G. Indian. J. Chem. 2011, 50B, 721.
  • National Committee for Clinical Laboratory Standards (NCCLS). National Committee for Clinical Laboratory Standards Ltd., Villanova. 1982, 242.
  • Margery Linday, E. Practical Introduction to Microbiology; E. & F.N. Spon Ltd., 1962; pp. 177.
  • Winter, C. A.; Risley, E. A.; Nuss, G. W.; Proc. Soc. Exp. Biol. Med. 1962, 111, 544–547. DOI: 10.3181/00379727-111-27849.

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