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Synthesis, Characterization and Biological Evaluation of Some Novel Regioisomers of Ropivacaine Analogues: An Anaesthetic Drug
Corresponding Author(s) : S. Kabilan
Asian Journal of Chemistry,
Vol. 32 No. 9 (2020): Vol 32 Issue 9, 2020
Abstract
A series of ropivacaine analogues were synthesized by altering the methyl group substituent in the aromatic ring. The synthesized compounds (2a-f and 3a-f) were characterized by using IR, NMR and HRMS analysis and then compounds 3a-3f were screened in vitro anticancer (MTT assay) activity against breast cancer cell line (MCF-7), antibacterial and antioxidant (DPPH scavenging assay) studies. The biological studies revealed that the compounds 3c and 3f have shown a good inhibitory activity against MCF-7 cell line. Compounds 3e, 3b, 3c and 3f showed moderate antioxidant activity. There was no inhibition observed against both Gram-positive and Gram-negative bacteria.
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Y.A. Ruetsch, T. Böni and A. Borgeat, Curr. Top. Med. Chem., 1, 175 (2001); https://doi.org/10.2174/1568026013395335
W. Li, L. Ding, H.-M. Liu and Q. You, Med. Chem. Res., 27, 954 (2018); https://doi.org/10.1007/s00044-017-2118-0
B.F. Tullar, J. Med. Chem., 14, 891 (1971); https://doi.org/10.1021/jm00291a033
M.D. Karkas, Chem. Soc. Rev., 47, 5786 (2018); https://doi.org/10.1039/c7cs00619e
J.H. Mcclure, Br. J. Anaesth., 76, 300 (1996); https://doi.org/10.1093/bja/76.2.300
S.R. Verner, Requesting a quote S-(-)-1-Propyl-2′,6′-pipecoloxylidide Hydrochloride Monohydrate, Process for its Preparation and Pharmaceutical Preparation Containing It, European Patent, EP0239710 A1 (1990).
B. Akerman, I.B. Hellberg and C. Trossvik, Acta Anaesthesiol. Scand., 32, 571 (1988); https://doi.org/10.1111/j.1399-6576.1988.tb02788.x
A. De Iuliis, L. Zanatta, E. Vincenti and L. Galzigna, Il Farmaco, 56, 153 (2001); https://doi.org/10.1016/S0014-827X(01)01043-6
M.B. Dalvi, R.S. Kenny and G.R. Kawle, Process for Preparation of (DL)-Norepinephrine Acid Addition Salt, A Key Intermediate of (R)- (-)-Norepinephrine, World Patent WO 2014/009964 A1 (2014).
E.H. Howard, C.F. Cain, C.W. Kang and J.R. Del Valle, J. Org. Chem., 85, 1680 (2020); https://doi.org/10.1021/acs.joc.9b02382
O. Yosef-Brauner, N. Adi, T. Ben Shahar, E. Yehezkel and E. Carmeli, J. Clin. Diagn. Res., 9, 1 (2015); https://doi.org/10.1111/crj.12091
O.N. Aydin, M. Eyigor and N. Aydin, Eur. J. Anaesthesiol., 18, 687 (2001); https://doi.org/10.1097/00003643-200110000-00008
C. Raedler, C. Lass-Florl, F. Puhringer, C. Kolbitsch, W. Lingnau and A. Benzer, Br. J. Anaesth., 83, 657 (1999); https://doi.org/10.1093/bja/83.4.657
R.M. Schmidt and H.S. Rosenkranz, J. Infect. Dis., 121, 597 (1970); https://doi.org/10.1093/infdis/121.6.597
J.T. Murphy, H.F. Allen and A.B. Mangiaracine, Arch. Ophthal., 53, 63 (1955); https://doi.org/10.1001/archopht.1955.00930010065006
A. Venkanna, B. Siva, B. Poornima, P.R. Rao Vadaparthi, K.R. Prasad, K.A. Reddy, G.B.P. Reddy and K.S. Babu, Fitoterapia, 95, 102 (2014); https://doi.org/10.1016/j.fitote.2014.03.003
Protein Preparation Wizard, Epik version 2.3, 2012; Impact version 5.7, Schrödinger, LLC, New York (2012).
W.L. Jorgensen, D.S. Maxwell and J. Tirado-Rives, J. Am. Chem. Soc., 118, 11225 (1996); https://doi.org/10.1021/ja9621760
W. Brand-Williams, M.E. Cuvelier and C. Berset, LWT-Food Sci. Technol., 28, 25 (1995); https://doi.org/10.1016/S0023-6438(95)80008-5
C.A. Lipinski, F. Lombardo, B.W. Dominy and P.J. Feeney, Adv. Drug Deliv. Rev., 23, 3 (1997); https://doi.org/10.1016/S0169-409X(96)00423-1
F. Ntie-Kang, Springerplus, 2, 353 (2013); https://doi.org/10.1186/2193-1801-2-353
Qikprop 3.5 user manual Schrodinger, LLC, New York, NY (2012).