Synthesis of novel phthalimido oxime esters and evaluation of their cytotoxicity

Asma Mehrez, Ibtisem Chakroun, Dalila Mtat, Hedi Ben Mansour, Ridha Toauti

Abstract


A series of novel optically pure oxime esters derivatives were synthesized by the reaction of substitute keto oximes with various N-substituted α-amino acids chlorides in the presence of triethylamine and dichloromethane at 0°C, and their structures were characterized by IR, and 1D-NMR methods. The synthesized compounds were tested for their ability to inhibit the proliferation of human colon cancer cells and human epithelial cells. Some of them have been revealed a significant cytotoxic effect.


Keywords


oxime esters; α-amino acids; stereoselective; cytotoxic; biological activity; enantiomer.

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References


S. P. Gupta, Chem. Rev., 94 (1994) 1507 (https://doi.org/10.1021/cr00030a003)

(a) N. A. Zhukovskaya, E. A. Dikusar, V. I. Potkin, O. G. Vyglazov, Chem. Nat. Compd. 45 (2009) 148 (http://dx.doi.org/10.1007/s10600-009-9264-7); (b) E. A. Dikusar, N. A. Zhukovskya, Russ. J. Org. Chem. 44 (2008) 1389 (http://dx.doi.org/10.1134/S1070428008090248)

G. V. Crichlow, K. F. Cheng, D. Dabideen, M. Ochani, B. Aljabari, V. A. Pavlov, E. J. Miller, E. Lolis, Y. Al-Abed, J. Biol. Chem. 282 (2007) 3089 (http://dx.doi.org/10.1074/jbc.M701825200)

I. Hayashi, K. Shimizu, Bull. Chem. Soc. Jpn. 56 (1983) 3197 (http://dx.doi.org/10.1248/cpb.17.1937)

D. A. Bachovchin, M. R. Wolfe, K. Masuda, S. J. Brown, T. P. Spicer, V. Fernandez-Vega, P. Chase, P. S. Hodder, H. Rosen, B. F. Cravatt, Med. Chem. Lett. 20 (2010) 2254 (http://dx.doi.org/10.1016/j.bmcl.2010.02.011)

(a) J. R. Hwu, S. Tsay, S. C. Hong, M. Hsu, C. Liu, S. P. Chou, Bioconjugate Chem. 24 (2013) 1778 (http://dx.doi.org/10.1021/bc400060h); (b) P. J. Bindu, K. M. Mahadevan, N. D. Satyanarayan, T. R. RavikumarNaik, Bioorg. Med. Chem. Lett. 22 (2012) 898 (http://dx.doi.org/10.1016/j.bmcl.2011.12.037)

X. H. Liu, L. P. Zhi, B. A. Song, H. L. Xu, Chem. Res. Chin. Univ. 24 (2008) 454 (http://dx.doi.org/10.1016/S1005-9040(08)60095-1)

T. G. Li, J. P. Liu, J. T.Han, B. Fu, D. Q. Wang, M. G. Wang, Chin. J. Org. Chem. 29 (2009) 898 (http://dx.doi.org/10.18596/jotcsa.290589)

B. A. Song, X. H. Liu, S. Yang, D. Y. Hu, L. H. Jin, Y. T. Zhang, Chin. J. Org. Chem. 25 (2005) 507 (http://dx.doi.org/10.1584/jpestics.D13-001)

Y. Gao, J. Song, S. Shang, D. Wang, J. Li, BioResources. 7 (2012) 4150 (http://dx.doi.org/10.2174/157018013804725071)

B. B. Wylie, E. I. Isaacson, G. N. Delgado, J. Pharm. Sci. 54 (1965) 1373 (http://dx.doi.org/10.1002/jps.2600540932)

S. T. Harini, H. Vijay Kumar, J. Rangaswamy, N. Naik, Bioorg. Med. Chem. Lett. 22 (2012) 7588 (http://dx.doi.org/10.1016/j.bmcl.2012.10.019)

A. Karakurt, M. A. Alagöz, B. Sayoğlu, Ü. Çaliş, S. Dalkara, Eur. J. Med. Chem. 57 (2012) 275 (http://dx.doi.org/10.1016/j.ejmech.2012.08.037)

D. Enders, A. Grossmann, D. V. Craen, Org. Biomol. Chem. 11 (2013) 138 (http://dx.doi.org/10.1039/c2ob26974k)

S. C. Santosh Kumar, N. V. Kumar, P. Srinivas, B. K. Bettadaiah, Synthesis 46 (2014) 1847 (http://dx.doi.org/10.1055/s-0034-1378350)

R. Q. Huang, H. Y. Li, J. A. Ma, D.W. Qiu, Chem. J. Chin. Univ. 17 (1996) 571 (http://dx.doi.org/10.1002/jhet.5570430409)

a) C. Mordant, C. Cano de Andrade, R. Touati, V. Ratovelomanana-Vidal, B. Ben Hassine, J. P Genêt, Synthesis 15 (2003) 2405 (http://dx.doi.org/10.1055/s-2003-42397); b) R. Touati, V. Ratovelomanana-Vidal, B. Ben Hassine, J. P. Genêt, Tetrahedron: Asymmetry, 17 (2006) 3400 (http://dx.doi.org/10.1016/j.tetasy.2006.11.048); c) C. Mordant, S. Reymond, H. Tone, D. Lavergne, R. Touati, B. Ben Hassine, V. Ratovelomanana-Vidal, J. P. Genêt, Tetrahedron 63 (2007) 6115 (http://dx.doi.org/10.1016/j.tet.2007.03.036); d) S. Prévost, S. Gauthier, M. C. de Andrade, C. Mordant, R. Touati, P. Lesot, P. Savignac, T. Ayad, P. Phansavath, V. Vidal, J. P. Genêt, Tetrahedron: Asymmetry 21 (2010) 1436 (http://dx.doi.org/10.1016/j.tetast.2010.05.017); e) M. Perez, P. G. Echeverria, E. Martinez-Arripe, M. Ez Zoubir, R. Touati, Z. Zhang, J. P. Genêt, P. Phansavath, T. Ayad, V. Ratovelomanana-Vidal, Eur. J. Org. Chem. 27 (2015) 5949 (http://dx.doi.org/10.1002/ejoc.201500661)

a) A. Essersi, R. Touati, B. Ben Hassine, Letters in Organic Chemistry 7 (2010) 69 (http://dx.doi.org/10.2174/157017810790533869); b) A. Ould Aliyenne, J. Kraiıem, Y. Kacem, B. Ben Hassine, C. R. Chimie 10 (2007) 251 (http://dx.doi.org/10.13140/RG.2.1.1067.0247); c) Y. Kacem, A. Bouraoui, V. Ratovelomanana-Vidal, J. P. Genêt, B. Ben Hassine, C. R. Chimie 5 (2002) 611 (http://dx.doi.org/S1631-0748(02)01418-2)

M. Krifa, A. Della, I. Bouhlel, J. Robert, A. Cherif, D. Barillier, R. Mosrati, L. Chekir-Ghedira, H. Ben Mansour, Environ Sci. Pollut. Res. 20 (2013) 3842 (http://dx.doi.org/10.1007/s11356-012-1322-1)

a) P.J. Bindu, K.M. Mahadevan, N.D. Satyanarayan, T.R. RavikumarNaik, Bioorganic &Medicinal Chemistry Letters 22 (2012) 898 (http://dx.doi.org/10.1016/j.bmcl.2011.12.037); b) W. W. Tan, B. Wu, Y. Wei, N. Yoshikai, Org. Synth. 95 (2018) 1 (https://doi.org/10.15227/orgsyn.95.0001).




DOI: https://doi.org/10.2298/JSC180302082M

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