A series of new 1,2-substituted 2,3-dihydro-1H-benzo[4,5]imidazo[1,2-c][1,3,2]diazaphosphol-1-oxides (5a – 5j) were synthesized and characterized by IR and NMR (1H, 13C, and 31P) spectral analysis. The resulting compounds were studied for their antibacterial and antiproliferative activity. Compounds 5f, 5c and 5g showed significantly higher antibacterial activity against both E. Coli and B. Subtilis compared to other compounds. Similarly, MTT assay using THP-I cells showed that all these compounds had significant antiproliferative activity compared to the solvent control, with compounds 5i, 5g and 5c showing more potency than others. The obtained results suggest that compounds 5a – 5j can have a wide variety of pharmaceutical applications.
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N. V. Shitole, K. S. Niralwad, B. B. Shingate, and M. S. Shingare, Arab. J. Chem., 9 (1), S858 – S860 (2016).
P. K. Sahu, RSC Adv., 7, 42000 – 42012 (2017).
N. Srestha, J. Banerjee, and S. Srivastava, J. Pharm., 4 (12), 28 – 41 (2014).
K. R. M. Naidu, P. V. Rao, C. N. Raju, and K. Srinivasulu, Arch. Pharm. Chem. Life Sci., 344, 765 – 770 (2011).
F. A. S. Alasmary, A. M. Snelling, M. E. Zain, et al., Molecules, 20, 15206 – 15223 (2015).
M. Shaharyar, M. M. Abdullah, M. A. Bakht, and J. Majeed, Eur. J. Med. Chem., 45, 114 – 119 (2010).
P. Singla, V. Luxami, and P. Paul, RSC Adv., 4, 12422 – 12440 (2014).
E. Vitaku, T. D. Smith, and T. J. Njardarson, J. Med. Chem., 57(24), 10257 – 10274 (2014).
S. Demirayak, U. A. Mohsen, and A. C. Karaburun, Eur. J. Med. Chem., 37, 255 – 260 (2002).
Y. B. Bai, A. L. Zhang, J. J. Tang, and J. M. Gao, J. Agric. Food Chem., 61(11), 2789 – 2795 (2013).
R. Sethi, S. Arora, D. Saini, and S. Jain, Ind. J. Phar. Edu. Res., 50, 424 – 434 (2016).
L. Jiang, M. Y. Wang, F. X. Wan, and Z. Q. Qu, Phosphorus Sulfur Silicon. Relat. Elem., 190(10), 1599 – 1605 (2015).
Y. H. Babu, M. A. Kumar, K. Srinivasulu and C. S. Reddy, et al., Arkivoc, 189 – 197 (2006).
G. C. S. Reddy, M. V. N. Reddy, C. R. Rani, et al., Heteroat. Chem., 23, 247 – 253 (2012).
R. A. Nugent, M. Murphy, S. T. Schlachter and C. J. Dunn, et al., Chin. J. Chem., 24, 1581 – 1588 (2006).
X. Li, D. Zhang, H. Pang, et al., Org. Lett., 7(22), 4919 – 4922 (2005).
Y. Haribabu, K. Srinivasulu, C. S. Reddy, and C. D. Reddy, Arkivoc., 95 – 103 (2006).
T. E. Ali and R. M. Abdel-Rahman, J. Sulfur Chem., 35, 399 – 411 (2014).
S. Liang, M. Neisius, H. Mispreuve, et al., Polym. Degrad. Stabil., 97, 2428 – 2440 (2012).
H. Kojima, S. Takeuchi, N. V. D. Eede, and A. Covachi, Toxicol. Lett., 245, 31 – 39 (2016).
R. R. Chinthaparthi, C. S. R. Gangireddy, V. R. Mudumala, et al., Tetrahedron Lett., 54, 6071 – 6076 (2013).
E. A. Tarik and M. A. K. Somaia, Int. J. Mat. Chem., 2(5), 192 – 196 (2012).
M. V. N. Reddy, A. U. Ravi Sankar, B. Siva Kumar, et al., S. Afr. J. Chem., 61, 43 – 46 (2008).
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One of the authors, Dr. M. R. Ganesh, thanks DBT India for support (BT/PR9930/NDB/39/457/2013).
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Sankar, V., Cheeran, V., Ganesh, M.R. et al. Synthesis, Antibacterial and Anticancer Activity of 1,2-Substituted 2,3-Dihydro-1H-Benzo[4,5]Imidazo[1,2-c][1,3,2]Diazaphosphol-1-Oxides. Pharm Chem J 54, 827–833 (2020). https://doi.org/10.1007/s11094-020-02282-z
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DOI: https://doi.org/10.1007/s11094-020-02282-z