Efficient Synthesis of Some Benzochromenone Analogues as Potential Novel Antioxidant and Antimicrobial Agents
[1]
Hala Ahmed Abd El-Aty, Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt.
[2]
El-Sayed Ibrahim El-Desoky, Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt.
[3]
Abdel-Rahman Hassan Abdel-Rahman, Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt.
New benzo[f]chromen-1-one derivatives were prepared by a sequence of reactions starting from appropriate 1-(2,3-dihydroxynaphthalen-1-yl)ethanone. The prepared target compounds were confirmedupon correct elemental analysis and spectroscopic data. Compounds were evaluated as antioxidant agents using DPPH assay and ascorbic acid was used as a reference drug. Compounds 3 (inhibitive concentration (IC50) = 0.0013 mg/mL), 7 (IC50= 0.013 mg/mL) and 10 (IC50= 0.0166 mg/mL) have the best activities higher than ascorbic acid, in which compound 3 is the best antioxidant agent. The prepared compounds were evaluated as antibacterial agents against Gram (+)- and Gram (-)-bacterial strainsusing streptomycin as a reference drug. In general, most the tested compounds are considered as potent antioxidant and antibacterial agents compared to standard substances. Compound 3 exhibited the highest antibacterial activity compared to streptomycin. We hope in future work that compound 3 could be used in drug design for developingnew antioxidant agent with good property.
2,3-Dihydroxynaphthalene, Benzochromenones, Organic Synthesis, Antioxidant and Antimicrobial Activities
[1]
(a) Z. L. Mao, W. B. Sun, L. Y. Fu, H. Y. Luo, D. W. Lai and L. G. Zhou, Molecules, 2014, 19, 5088-5108. (b) H.-N. Lv, P.-F. Tu and Y. Jiang, Mini-Rev. Med. Chem., 2014, 14, 603-622.(c) Y. L. Garazd and M. M. Garazd, Chem. Nat. Compd., 2016, 52, 1-18.
[2]
(a) P. R. Nandaluru and G. J. Bodwell, Org. Lett., 2012, 14, 310-313.(b) W. Sun, L. D. Cama, E. T. Birzin, S. Warrier, L. Locco, R. Mosley, M. L. Hammond and S. P. Rohrer, Bioorg. Med. Chem. Lett., 2006, 16, 1468-1472.(c) K. Koch, J. Podlech, E. Pfeiffer and M. Metzler, J. Org. Chem., 2005, 70, 3275-3276.(d) C. Garino, F. Bihel, N. Pietrancosta, Y. Laras, G. Quéléver, I. Woo, P. Klein, J. Bain, J.-L. Boucher and J.-L. Kraus, Bioorg. Med. Chem. Lett., 2005, 15, 135-138.(e) H. Abe, K. Nishioka, S. Takeda, M. Arai, Y. Takeuchi and T. Harayama, Tetrahedron Lett., 2005, 46, 3197-3200.(f) Y.-Y. Ku, T. Grieme, P. Raje, P. Sharma, S. A. King and H. E. Morton, J. Am. Chem. Soc., 2002, 124, 4282-4286.
[3]
R. R. A. Kitson, A. Millemaggi andR. J. K. Taylor, Angew. Chem., Int. Ed. 2009, 48, 9426.
[4]
S. Zhang, Y.-K. Won, Ch.-N. Ong andH.-M. Shen, Curr. Med. Chem. 2005, 5, 239.
[5]
Y. Zhang, Y. Tian, P. Xiang, N. Huang, J. Wang, J.-H. Xu and M. Zhang, Org. Biomol. Chem., 2016, 14, 9874-9882.
[6]
S. I. El-Desoky, E. M. Keshk, A. A. El-Sawi, and A. H. Abdel-Rahmana, Mansoura J. Chem. 2013, 40(1), 109-123.
[7]
S. I. El-Desoky, M. A. Abozeid, E. A. Kandeel, and A. H. Abdel-Rahmana, J. Heterocycl. Chem. 2014. doi 10.1002/jhet.2117.
[8]
S. I. El-Desoky, F. A. Badria, M. A. Abozeid, E. A. Kandeel and A. H. Abdel-Rahman, Med. Chem. Res., 2013, 22 (5), 2105–2114. doi 10.1007/s00044-012-0201-0
[9]
S. I. El-Desokyand S. S. El-Shihry, J. Heterocycl. Comp. 2008, 45, 1153.
[10]
S. I. El-Desoky, J. Heterocycl. Comp.2007, 44, 1309-1315.
[11]
S. I. El-Desoky, E. M. El-Telbany, M. A. Hammad and A. H. Abdel-Rahman, Zeitschrift fur Naturforschung, 1998, 53b, 909-915.
[12]
S. Rast, M. Stephan, and B. Mohar, Tetrahedron Lett. 2012, 53, 6815-6818.
[13]
P. Ciuffreda, S. Casati and E. Santaniello, Tetrahedron2000, 56, 317-321.
[14]
A. Ueno and S. Fukushima, Chem. Pharm. Bull. 1966, 14, 129-139.
[15]
J.. Ragavendran, D. Sriram, S. K. Patel, I. V. Reddy, N. Bharathwajan, J. Stables and P. Yogeeswari, Eur. J. Med. Chem. 2007, 42, 146-151.
[16]
T. Ito, I. P. Fraser, Yeo Yoon, C. B. Highley, E. Bellas and D. S. Kohane, Biomaterials2007, 28, 1778-1786.
[17]
B. N. Acharya, D. Saraswat and M. P. Kaushik, Eur. J. Med. Chem. 2008, 43, 2840-2852.
[18]
X. Yong, C. D. Fan, B. X. Zhao, J. Zhao, D. S. Shin and J. Y. Miao, Eur. J. Med. Chem. 2008, 43, 2347-2353.
[19]
P. M. Ronad, M. N. Noolvi, S. Sapkal, S. Dharbhamulla and V. S. Maddi, Eur. J. Med. Chem. 2010, 45, 85-89.
[20]
F. Borges, F. Roleira, L. Santana and E. Uriare, Curr. Med. Chem. 2005, 12, 887-916.
[21]
M. A. Metwally, S Bondock, S. I. El-Desouky and M. M. Abdou, Coloration Technol. 2013, 129 (6), 418-424. doi: 10.1111/cote.12052
[22]
M. M. Abdou, S. Bondock, E. I. El-Desouky and M. A. Metwally, Am. J. Chem., 2013, (3), 59-67. doi: 10.5923/j.chemistry.20130303.04
[23]
M. A. Metwally, S. Bondock, E. I. El-Desouky and M. M. Abdou, J. Korean Chem. Soc., 2012, 56(3), 348-356. http://dx.doi.org/10.5012/jkcs.2012.56.3.348
[24]
S. Rallas, N. Gulerman and H. Erdeniz, Farmaco2002, 57, 171-174.
[25]
A. Gursoy, N. Terzioglu and G. Otuk, Eur. J. Med. Chem. 1997, 32, 753-757.
[26]
E. M. El-Telbany, E. I. El-Desouky, M. A. Hammad, A. H. Abdel-Rahman and R. R. Schmidt, Carbohydrate Res. 1998, 306, 463-467.
[27]
H. M. Refat and A. A. Fadda, Eur. J. Med. Chem. 2013, 70, 419-426.
[28]
C. Mallikarjunaswamy, D. G. Bhadregowda and L. Mallesha, J. Saudi Chem. Soc. 2016, 20 (1), S606-S614. https://doi.org/10.1016/j.jscs.2013.04.005
[29]
M. A. Sgariglia, J. R. Soberon, D. A. Sampietro, E. N. Quiroga and M. A. Vattuone, Food Chem. 2011, 126, 395-404.
[30]
R. R. Hafidh, A. S. Abdulamir, L. S. Vern, F. Abu Bakar, F. Abas, F. Jahanshiri and Z. Sekawi, The Open Microbiology J., 2011, 5, 96-106.
[31]
D. B. Adimpong, K. I. Sørensen, L. Thorsen, B. Stuer-Lauridsen, W. S. Abdelgadir, D. S. Nielsen, P. M. F. Derkx and L. Jespersen, Appl. Environ. Microbiol.2012, 78 (22), 7903-7914. doi: 10.1128/AEM.00730-12
[32]
M. A. Ebrahimzadeh, S. M. Nabavi, S. F. Nabavi and B. Eslami, Pharmacologyonline, 2009, 2, 796-802.
[33]
A. A. Fadda and K. M. Elattar, J. Chem., 2013, 2013, 1-10. Article ID 928106. http://dx.doi.org/10.1155/2013/928106
[34]
D. R. Emam, A. M. Alhajoj, K. M. Elattar, N. A. Kheder and A. A. Fadda, Molecules2017, 22(6), 971-980. doi:10.3390/molecules22060971.
