Hybrid probes of aromatic amine and barbituric acid: highly promising leads for anti-bacterial, anti-fungal and anti-cancer activities

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• 作者：Bhaveshkumar D. Dhorajiya (1)
  Bharatkumar Z. Dholakiya (1)
  Rafat M. Mohareb (2)
  
• 关键词：Green chemistry ; N ; formylation ; Knoevenagel condensation ; Anti ; bacterial ; Anti ; fungal ; Cytotoxicity
• 刊名：Medicinal Chemistry Research
• 出版年：2014
• 出版时间：September 2014
• 年：2014
• 卷：23
• 期：9
• 页码：3941-3952
• 全文大小：386 KB
• 参考文献：1. Boyd MR, Paull KD (1995) Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Dev Res 34:91鈥?09 CrossRef
  2. Dhorajiya BD, Dholakiya BZ (2013) Green chemistry multi-component approach for / N-formylation and Knoevenagel condensation for synthesis of thiobarbiturates in aqueous system. Res Chem Intermed. doi:10.1007/s11164-013-1190-4
  3. Dhorajiya BD, Ibrahim AS, Badria FA, Dholakiya BZ (2014) Design and synthesis of novel nucleobasebased barbiturate derivatives as potential anticancer agents. Med Chem Res 23:839鈥?47. doi:10.1007/s00044-013-0683-4 CrossRef
  4. Gillespie SH (1994) Medical microbiology鈥攊llustrated. Butterworth Heinemann Ltd., United Kingdom, pp 234鈥?47
  5. Goodman LS, Gilman A (1991) In the pharmacological basis of therapeutics. Mc Graw-Hill, New Delhi, pp 358鈥?60
  6. Hawkey PM, Lewis DA (1994) Medical bacteriology鈥攁 practical approach. Oxford University Press, United Kingdom, pp 181鈥?94
  7. Huang LYM, Barker JL (1980) Pentobarbital stereospecific actions of (+) and (鈥? isomers revealed on cultured mammalian neurons. Science 207:195鈥?97 CrossRef
  8. Jacobson (1937) U. S. Patent 2,090, 594, [C. A. 31, 7068]
  9. Jain S, Bhimireddy NR, Kolisetty SR (2011) l -Proline catalyzed Knoevenagel condensation: synthesis of some new indole derivatives and biological activities. Int J ChemTech Res 3:817鈥?24
  10. Kisfaludy L, Laszlo O (1987) Rapid and selective formylation with pentafluorophenyl formate. Synthesis 5:510 CrossRef
  11. Meunier B (2008) Hybrid molecules with a dual mode of action: dream or reality? Acc Chem Res 41:69鈥?7 CrossRef
  12. Nerveux M, Bruneaum C, Dixneuf PH (1991) Enol formates: ruthenium catalysed formation and formylating reagents. J Chem Soc Perkin Trans 5:1197鈥?199 CrossRef
  13. Nicoll RA, Wojtowicz JM (1980) The effects of pentobarbital and related compounds on frog motoneurons. Brain Res 191:225鈥?37
  14. Siddiqui ZN, Musthafa TN, Ahmad A, Khan AU (2011) Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents. Bioorg Med Chem Lett 15:2860鈥?865 CrossRef
  15. Silverstein RM, Webster FX (1997) Spectrometric identification of organic compounds, 6th edn. Wiley, New York, pp 79鈥?23
  16. Singh P, Kaur M, Verma P (2009) Design, synthesis and anticancer activities of hybrids of indole and barbituric acids鈥攊dentification of highly promising leads. Bioorg Med Chem Lett 19:3054鈥?058 CrossRef
  17. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82:1107鈥?112 CrossRef
  18. Sundberg RJ (1996) Indoles. Academic Press, San Diego
  
• 作者单位：Bhaveshkumar D. Dhorajiya (1)
  Bharatkumar Z. Dholakiya (1)
  Rafat M. Mohareb (2)
  
  1. Department of Applied Chemistry, S.V. National Institute of Technology, Ichchhanath, Surat, 395007, Gujarat, India
  2. Department of Chemistry, Faculty of Science, Cairo University, Giza, Arab Republic of Egypt
  
• ISSN：1554-8120

文摘

Today, cancer and resistant microbes remain one of the most deadly diseases in the world. In search of novel anti-cancer and anti-microbial probes, a series of newly hybrid molecules is synthesized by combining the structural features of aromatic amines and barbituric acid, using the concept of green chemistry. This approach was accomplished efficiently using water as the greener solvent and in the absence of catalyst to give the corresponding adducts. All newly synthesized compounds were characterized by spectral analysis FT-IR, 1H NMR, 13C NMR, HMBC and Elemental Analysis. Evaluations of these probes over four human cancer cell lines (Breast adenocarcinoma cancer cell line MCF-7, Non-small cell lung cancer cell line NCI-H460, CNS cancer cell line SF-268 and fibroblast cancer cell line WI-38), anti-microbial activity against five bacterial strains (S. pyogenes MTCC 442 and S. aureus MTCC 96 as the gram positive, E. coli MTCC 443, P. aeruginosa MTCC 424 and K. pneumoniae MTCC 109 as the gram negative) and four fungal strains (C. albicans MTCC 227, A. clavatus MTCC 1323, T. rubrum MTCC 296 and Penicillium wild strain). Out of set of nineteen probes, three probes show significant anti-cancer activities against MCF-7, NCI-H460 and SF-268, whereas sixteen probes exhibit potent anti-tumour activity against WI-38 cell lines. Within anti-microbial bioassay, three molecules exhibited significant activity against both the gram-positive as well as gram-negative bacteria, whereas two compounds showed highly potent activity against T. rubrum fungi, while three molecules were found to be equipotent against T. rubrum as a fungal strain.