Synthesis and antimicrobial evaluation of some novel dithiolane, thiophene, coumarin, and 2-pyridone derivatives

References

• Crowther, A. F.; Smith, L. H. β-Adrenergic blocking agents. II. Propranolol and related 3-amino-1-naphthoxy-2-propanols. J. Med. Chem. 1968, 11, 1009–1013.
   PubMed Web of Science ®Google Scholar
• Oxley, P.; Short, W. F. Amidines. Part VI. Preparation of 2-substituted 4: 5-Dihydroglyoxalines and ring homologues from cyanides and alkylenediamines. J. Chem. Soc. 1947, 69(3), 497–505.
   Web of Science ®Google Scholar
• Harrison, I. T.; Lewis, B.; Nelson, P.; Rooks, W.; Roszkowski, A.; Tomolony, A.; Fried, J. H. Nonsteroidal antiinflammatory agents. I. 6-Substituted 2-naphthylacetic acids. J. Med. Chem. 1970, 13, 203–205.
   PubMed Web of Science ®Google Scholar
• Goudie, A. C.; Gaster, L. M.; Lake, A. W.; Rose, C. J.; Freeman, P. C.; Hughes, B. O.; Miller, D. 4-(6-Methoxy-2-naphthyl)butan-2-one and related analogs, a novel structural class of antiinflammatory compounds. J. Med. Chem. 1978, 21, 1260–1264.
   PubMed Web of Science ®Google Scholar
• Lee, K. H.; Huang, B. R. Synthesis and cytotoxic evaluation of alpha-methylene-gamma-butyrolactone bearing naphthalene and naphtho[2,1-b]furan derivatives. Eur. J. Med. Chem. 2002, 37, 333–338.
   PubMed Web of Science ®Google Scholar
• Yuan, J. W.; Wang, S. F.; Luo, Z. L.; Qiu, H. Y.; Wang, P. F.; Zhang, X.; Yang, Y. A.; Yin, Y.; Zhang, F.; Zhu, H. L. Synthesis and biological evaluation of compounds which contain pyrazole, thiazole and naphthalene ring as antitumor agents. Bioorg. Med. Chem. Lett. 2014, 24, 2324–2328.
   PubMed Web of Science ®Google Scholar
• Imramovsky, A.; Polanc, S.; Vin_sova, J.; Kocevar, M.; Jampitek, J.; Reckova, Z.; Kaustova, J. A. A new modification of anti-tubercular active molecules. Bioorg. Med. Chem. 2007, 15, 2551.
   PubMed Web of Science ®Google Scholar
• Janin, Y. Antituberculosis drugs: Ten years of research. Bioorg. Med. Chem. 2007, 15, 2479.
   PubMed Web of Science ®Google Scholar
• Dimmock, J. R.; Vasishtha, S. C.; Stables, J. P. Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds. Eur. J. Med. Chem. 2000, 35, 241.
   PubMed Web of Science ®Google Scholar
• Lima, P. C.; Lima, L. M.; Silva, K. C.; Leda, P. H.; Miranda, A. L. P.; Fraga, C. A. M.; Barreiro, J. E. Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole#. Eur. J. Med. Chem. 2000, 35, 187.
   PubMed Web of Science ®Google Scholar
• Salgin-Goksen, U.; Gokham-Keleci, N.; Gostal, O.; Koysal, Y.; Kilici, E.; Isik, S.; Aktay, G.; Ozalp, M. 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: Synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorg. Med. Chem. 2007, 15, 5738.
   PubMed Web of Science ®Google Scholar
• Silva, G. A.; Costa, L. M. M.; Brito, F. C. F.; Miranda, A. L. P.; Barreiro, E. J.; Fraga, C. A. M. New class of potent antinociceptive and antiplatelet 10H-phenothiazine-1-acylhydrazone derivatives. Bioorg. Med. Chem. 2004, 12, 3149.
   PubMed Web of Science ®Google Scholar
• Savini, L.; Chiasserini, L.; Travagli, V.; Pellerano, C.; Novellino, E.; Consentino, S.; Pisano, M. B. New α-(N)-heterocyclichydrazones: Evaluation of anticancer, anti-HIV and antimicrobial activity. Eur. J. Med. Chem. 2004, 39, 113.
   PubMed Web of Science ®Google Scholar
• Bijev, A. New heterocyclic hydrazones in the search for antitubercular agents: Synthesis and in vitro evaluations. Lett. Drug. Des. Discov. 2006, 3, 506.
   Web of Science ®Google Scholar
• Loncle, C.; Brunel, J. M.; Vidal, N.; Dherbomez, M.; Letourneux, Y. Synthesis and antifungal activity of cholesterol-hydrazone derivatives. Eur. J. Med. Chem. 2004, 39, 1067.
   PubMed Web of Science ®Google Scholar
• Abdel-Aal, M. T.; El-Sayed, W. A.; El-Ashry, E. H. Synthesis and antiviral evaluation of some sugar arylglycinoylhydrazones and their oxadiazoline derivatives. Arch. Pharm. Chem. Life Sci. 2006, 339, 656.
   PubMed Web of Science ®Google Scholar
• Capilla, J.; Serena, C.; Javier, F.; Ortoneda, T.; Guarro, J. Efficacy of voriconazole in treatment of systemic scedosporiosis in neutropenic mice. Antimicrob. Agents Chemother. 2003, 47, 3976.
   PubMed Web of Science ®Google Scholar
• Walcourt, A.; Loyevsky, M.; Lovejoy, D. B.; Gordeuk, V. R.; Richardson, D. R. Novel aroylhydrazone and thiosemicarbazone iron chelators with anti-malarial activity against chloroquine resistant and sensitive parasites. Int. J. Biochem. Cell. Biol. 2004, 36, 401.
   PubMed Web of Science ®Google Scholar
• Jund, L.; Corse, J.; King, A. S.; Bayne, H.; Mihrag, K. Antimicrobial properties of 6,7-dihydroxy-, 7,8-dihydroxy-, 6-hydroxy- and 8-hydroxycoumarins. Phytochemistry 1971, 10, 2971.
   Web of Science ®Google Scholar
• El-Ansary, S. L.; Aly, E. I.; Halem, M. A. New coumarin derivatives as antibacterial agents. Egypt. J. Pharm. Sci. 1992, 33, 379.
   Google Scholar
• Reddy, Y. D.; Somayojulu, V. V. Synthesis, spectra and physiological activity of 7H-pyrano [3,2-c]benzoxazole-7-one. J. Indian Chem. Soc. 1981, 58, 599.
   Web of Science ®Google Scholar
• Weber, U. S.; Steffen, B.; Siegers, C. Antitumor activities of coumarin, 7-hydroxycoumarin and its glucuronide in several human tumor cell lines. Res. Commun. Mol. Pathol. Pharmacol. 1998, 99, 93.
   PubMed Web of Science ®Google Scholar
• Anderson, W. K.; Dean, D. C.; Endo, T. Synthesis, chemistry, and antineoplastic activity of α-halopyridinium salts: Potential pyridone prodrugs of acylated vinylogous carbinolamine tumor inhibitors. J. Med. Chem. 1990, 33, 1667–1675.
   PubMed Web of Science ®Google Scholar
• Li, Q.; Mitscher, L. A.; Shen, L. L. The 2-pyridone antibacterial agents: Bacterial topoisomerase inhibitors. Med. Res. Rev. 2000, 20, 231–293.
   PubMed Web of Science ®Google Scholar
• Dragovich, P. S.; Prins, T. J.; Zhou, R.; Brown, E. L.; Maldonado, F. C.; Fuhrman, S. A.; Zalman, L. S.; Tuntland, T.; Lee, C. A.; Patick, A. K.; Matthews, D. A.; Hendrickson, T. F.; Kosa, M. B.; Liu, B.; Batugo, M. R.; Gleeson, J.-P. R.; Sakata, S. K.; Chen, L.; Guzman, M. C.; Meador, J. W.; Ferre, R. A.; Worland, S. T. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 6: Structure–activity studies of orally bioavailable, 2-pyridone-containing peptidomimetics. J. Med. Chem. 2002, 45, 1607–1623.
   PubMed Web of Science ®Google Scholar
• Dragovich, P. S.; Prins, T. J.; Zhou, R.; Johnson, T. O.; Brown, E. L.; Maldonado, F. C.; Fuhrman, S. A.; Zalman, L. S.; Patick, A. K.; Matthews, D. A.; Hou, X.; Meador III, J. W.; Ferre, R. A.; Worland S. T. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. Part 7: Structure–activity studies of bicyclic 2-pyridone-containing peptidomimetics. Bioorg. Med. Chem. Lett. 2002, 12, 733–738.
   PubMed Web of Science ®Google Scholar
• Mahmoud, M. R.; El-Ziaty, A. K.; Abu El-Azm, F. S. M.; Ismail, M. F.; Shiba, S. A. Utility of cyano-N-(2-oxo-1,2-dihydroindol-3-ylidene) acetohydrazide in the synthesis of novel heterocycles. J. Chem. Res. 2013, 37, 80–85.
   Web of Science ®Google Scholar
• Mahmoud, M. R.; Abu El-Azm, F. S. M. Synthesis and spectral studies of novel heterocycles from 2-cyano-N/(9H-fluoren-9-ylidene)acetohydrazide. Eur. Chem. Bull. 2013, 2(6), 335–340.
   Google Scholar
• Mahmoud, M. R.; Abu El-Azm, F. S. M. Synthesis and spectral study of novel benzopyrone and quinolinone derivatives. J. Chem. Res. 2013, 37, 535–541.
   Web of Science ®Google Scholar
• Mahmoud, M. R.; El-Ziaty, A. K.; Abu El-Azm, F. S. M.; Ismail, M. F.; Shiba, S. A. Synthesis and reactions of novel 2,5-disubstituted 1,3,4-thiadiazoles. Synth. Commun. 2014, 44, 1094–1102.
   Web of Science ®Google Scholar
• Mahmoud, M. R.; Abu El-Azm, F. S. M.; Ali, A. T.; Ali, Y. M. Design, synthesis and antimicrobial evaluation of novel thienopyrimidines and triazolopyrimidines. Synth. Commun. 2015, 45, 982–992.
   Web of Science ®Google Scholar
• Zhang, Y. Y.; Meng, X. M.; Wang, X. L.; Xu, L. X. Studies on the synthesis and spectra characteristics of stilbenylcoumarin organic materials. Dyes Pigm. 2003, 56, 189.
   Web of Science ®Google Scholar
• Rahman, A. U.; Choudhary, M. I.; Thomsen, W. J. Bioassay Techniques for Drug Development; Harwood Academic Publishers: The Netherlands, 2001.
   Google Scholar
• Fadda, A. A.; El-Mekawy, R. E.; El-Shafei, A. I.; Freeman, H. Synthesis and pharmacological screening of novel meso substituted porphyrin analogs. Arch. Pharm. Chem. Life Sci. 2013, 346, 53.
   PubMed Web of Science ®Google Scholar
• Ehsan, U. M.; Muhammad, A.; Zakir, H.; Aurangzeb, H.; Amina, S.; Muhammad, R.; Iqbal, C. Synthesis and antibacterial activity of substituted flavones, 4-thioflvones and 4-iminoflavones. Bioorg. Med. Chem. 2006, 14, 4704–4711.
   PubMed Web of Science ®Google Scholar
• Lee, J. I. An efficient synthesis of 2-phenyl-4H-1-benzothiopyran-4-ones from thiosalicylic acid. Bull. Korean Chem. Soc. 2009, 30, 710–712.
   Web of Science ®Google Scholar