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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Docking Investigation on Bis (Nitro Indazolyl) Methanes; Synthesis and Antimicrobial Activity Towards Breast Cancer Applications

Author(s): S. Jagadeesan and S. Karpagam*

Volume 19, Issue 5, 2022

Published on: 04 February, 2021

Page: [388 - 399] Pages: 12

DOI: 10.2174/1570178618666210204110358

Price: $65

Abstract

Bismuth (III) nitrate pentahydrate (BN) was found to be a mild and efficient catalyst for the electrophilic condensation of 5-nitroindazole with a wide range of aldehydes to obtain Bis (5-nitro indazolyl) methanes 3 (a-h) at ambient temperature. This was structurally confirmed through FTIR, NMR, and HR-MS technique. Molecular docking studies of all compounds were carried out using breast cancer-causing human estrogen receptor (ER) from Molegro Virtual Docker software. Hydroxy Bis (nitro indazolyl) methanes (3b) were shown better binding affinities and the score obtained was - 150.146 Kcal/mol compared with Tamoxifen drug. The major H-bond interactions were observed with the compound 3f and the value was -5.679. The antimicrobial activity results revealed that compounds 3b and 3d showed promising activity against bacteria Escherichia coli, Klebsiella pneumonia, Staphylococcus aureus, and Pseudomonas aeruginosa and maximum inhibition against Aspergillus niger and Aspergillus flavus. Methoxy derivatives of Bis (nitro indazolyl methanes) (3e) have shown better antioxidant activity and low MIC (6.25 μg/ml) observed for the compounds 3a and 3b. The synthesized compounds have a very promising starting point for the development and improvement of anti-breast cancer drugs.

Keywords: Anti breast cancer, bis (5-nitroindazolyl) methanes, docking studies, human estrogen receptor, antimicrobial activity, bismuth (III) nitrate pentahydrate.

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[1]
Dong, J.; Zhang, Q.; Wang, Z.; Huang, G.; Li, S. ChemMedChem, 2018, 13(15), 1490-1507.
[http://dx.doi.org/10.1002/cmdc.201800253] [PMID: 29863292]
[2]
Ikeda, Y.; Takano, N.; Matsushita, H.; Shiraki, Y.; Koide, T.; Nagashima, R.; Fujimura, Y.; Shindo, M.; Suzuki, S.; Iwasaki, T. Arzneimittelforschung, 1979, 29(3), 511-520.
[PMID: 114190]
[3]
Picciola, G.; Ravenna, F.; Carenini, G.; Gentili, P.; Riva, M. Farmaco Ed. Sci, 1981, 36, 1037.
[4]
Mosti, L.; Menozzi, G.; Fossa, P.; Schenone, P.; Lampa, E.; Parrillo, C.; D’Amisco, M.; Rossi, F. Farmaco, 1992, 47(5), 567-584.
[PMID: 1388602]
[5]
Andronati, S.; Sava, V.; Makan, S.; Kolodeev, G. Pharmazie, 1999, 54(2), 99-101.
[http://dx.doi.org/10.1002/chin.199921121] [PMID: 10084155]
[6]
Kharitonov, V.G.; Sharma, V.S.; Magde, D.; Koesling, D. Biochemistry, 1999, 38(33), 10699-10706.
[http://dx.doi.org/10.1021/bi990277f] [PMID: 10451364]
[7]
Rodgers, J.D.; Johnson, B.L.; Wang, H.; Greenberg, R.A.; Erickson-Viitanen, S.; Klabe, R.M.; Cordova, B.C.; Rayner, M.M.; Lam, G.N.; Chang, C.H. Bioorg. Med. Chem. Lett., 1996, 6, 2919.
[http://dx.doi.org/10.1016/S0960-894X(96)00531-8]
[8]
Morie, T.; Harada, H.; Kato, S. Synth. Commun., 1997, 27, 559.
[http://dx.doi.org/10.1080/00397919708003326]
[9]
Olea-Azar, C.; Cerecetto, H.; Gerpe, A.; Gonzalez, M.; Aran, V.J.; Rigol, C.; Opazo, L. Spec. Acta A Mol. Biomol. Spec., 2006, 63, 36.
[10]
Koch, W.; Garcia-Sanchez, R.N.; Nogel-Ruiz, J.J.; Escario, J.A.; Gomez-Barrio, A.; Martinez-Fernandez, A.R.; Aran, V. ChemMedChem, 2009, 4(1), 6.
[http://dx.doi.org/10.1002/cmdc.200800385] [PMID: 19130451]
[11]
Arán, V.J.; Ochoa, C.; Boiani, L.; Buccino, P.; Cerecetto, H.; Gerpe, A.; González, M.; Montero, D.; Nogal, J.J.; Gómez-Barrio, A.; Azqueta, A.; López de Ceráin, A.; Piro, O.E.; Castellano, E.E. Bioorg. Med. Chem., 2005, 13(9), 3197-3207.
[http://dx.doi.org/10.1016/j.bmc.2005.02.043] [PMID: 15809155]
[12]
Esmaielpour, M.; Akhlaghinia, B.; Jahanshani, R. J. Chem. Sci., 2017, 129, 313.
[http://dx.doi.org/10.1007/s12039-017-1246-x]
[13]
Yadav, J.S.; Subba, R.B.V.; Murthy, Ch.V.S.R.; Mahesh, K.G.; Madan, Ch. Synthesis, 2001, 5, 783.
[14]
Nagarajan, R.; Perumal, P.T. Tetrahedron, 2002, 58, 1229.
[http://dx.doi.org/10.1016/S0040-4020(01)01227-3]
[15]
Mi, X.; Luo, S.; He, J.; Cheng, J.P. Tetrahedron Lett., 2004, 45, 4567.
[http://dx.doi.org/10.1016/j.tetlet.2004.04.039]
[16]
Leonard, N.M.; Wieland, L.C.; Mohan, R.S. Tetrahedron, 2002, 58, 8373.
[http://dx.doi.org/10.1016/S0040-4020(02)01000-1]
[17]
Mohammadpoor-Baltork, I.; Aliyan, H.; Khosropour, A.R. Tetrahedron, 2001, 57, 5851.
[http://dx.doi.org/10.1016/S0040-4020(01)00521-X]
[18]
Vijay, J.T.; Babu, K.V.; Uma, A. Bioinformation, 2019, 15, 321.
[http://dx.doi.org/10.6026/97320630015321] [PMID: 31249434]
[19]
Dandawate, P.; Khan, E.; Padhye, S.; Gaba, H.; Sinha, S.; Deshpande, J.; Venkateswara Swamy, K.; Khetmalas, M.; Ahmad, A.; Sarkar, F.H. Bioorg. Med. Chem. Lett., 2012, 22(9), 3104-3108.
[http://dx.doi.org/10.1016/j.bmcl.2012.03.060] [PMID: 22483392]
[20]
Naveen Tittal, R.K.; Pinki, Y.; Lal, K.; Vikas, G.; Kumar, A. New J. Chem., 2019, 43, 8052.
[http://dx.doi.org/10.1039/C9NJ00473D]
[21]
Jordan, V.C. Br. J. Pharmacol., 2006, 147, 269.
[http://dx.doi.org/10.1038/sj.bjp.0706399] [PMID: 16299547]
[22]
Saundane, A.R.; Katkar, V.T.; Vaijinath, A.V. J. Chem., 2013, 1.
[23]
Perez, C.; Paul, M.; Bazerque, P. Acta Biol. Med. Exp., 1990, 15, 113.
[24]
Drews. J. Sci., 1960, 17, 287.
[25]
Ilhami, G.; Ekrem, K.; Elmastas, M.; Hassan, Y.A. Res. J. Biol. Sci., 2007, 2, 372.
[26]
Thongson, C.; Davidson, P.M.; Mahakarnchanakul, W. Weiss, J. Lett. Appl. Microbiol. 2004. 39(5), 401-406.
[http://dx.doi.org/10.1111/j.1472-765X.2004.01605.x] [PMID: 15482429 ]

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