Synthesis of novel phthalimido oxime pseudoesters and evaluation of their cytotoxicity

Article Sidebar

PDF (2,045 kB) Supplementary Material (3.41 MB)
Published: Feb 13, 2020
DOI: https://doi.org/10.2298/JSC180302082M
Keywords:
oxime esters α-amino acids stereoselective cytotoxic biological activity enantiomer.

Main Article Content

Asma Mehrez
Laboratory of Asymmetric Organic Synthesis and Homogeneous Catalysis (UR11ES56), Faculty of Sciences of Monastir, Avenue of the Environment, 5019 Monastir
Ibtisem Chakroun
Laboratory for Analysis, Treatment and Recovery of Environmental Pollutants and Products, Faculty of Pharmacy, Avicenne Street, 5000 Monastir
Dalila Mtat
Laboratory of Asymmetric Organic Synthesis and Homogeneous Catalysis (UR11ES56), Faculty of Sciences of Monastir, Avenue of the Environment, 5019 Monastir
Hedi Ben Mansour
Research Unit Analyzes and Processes Applied to the Environment (UR17ES32), Higher Institute of Applied Sciences and Technology of Mahdia, 5111 Mahdia
Ridha Toauti
Laboratory of Asymmetric Organic Synthesis and Homogeneous Catalysis (UR11ES56), Faculty of Sciences of Monastir, Avenue of the Environment, 5019 Monastir

Abstract

A series of novel optically pure oxime pseudoesters 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 were revealed to have a significant cytotoxic effect.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Article Details

How to Cite
[1]
A. Mehrez, I. Chakroun, D. Mtat, H. Ben Mansour, and R. Toauti, “Synthesis of novel phthalimido oxime pseudoesters and evaluation of their cytotoxicity”, J. Serb. Chem. Soc., vol. 85, no. 1, pp. 1–8, Feb. 2020.
Issue
Vol. 85 No. 1 (2020)
Section
Organic Chemistry

Creative Commons лиценца
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

Read more....

Author Biographies

Asma Mehrez, Laboratory of Asymmetric Organic Synthesis and Homogeneous Catalysis (UR11ES56), Faculty of Sciences of Monastir, Avenue of the Environment, 5019 Monastir

Laboratory of Asymmetric Organic Synthesis and Homogeneous Catalysis

Ibtisem Chakroun, Laboratory for Analysis, Treatment and Recovery of Environmental Pollutants and Products, Faculty of Pharmacy, Avicenne Street, 5000 Monastir

Laboratory for analysis, treatment and recovery of environmental pollutants and products

Dalila Mtat, Laboratory of Asymmetric Organic Synthesis and Homogeneous Catalysis (UR11ES56), Faculty of Sciences of Monastir, Avenue of the Environment, 5019 Monastir

Laboratory of Asymmetric Organic Synthesis and Homogeneous Catalysis

Hedi Ben Mansour, Research Unit Analyzes and Processes Applied to the Environment (UR17ES32), Higher Institute of Applied Sciences and Technology of Mahdia, 5111 Mahdia

Research Unit Analyzes and Processes Applied to the Environment 

Ridha Toauti, Laboratory of Asymmetric Organic Synthesis and Homogeneous Catalysis (UR11ES56), Faculty of Sciences of Monastir, Avenue of the Environment, 5019 Monastir

Laboratory of Asymmetric Organic Synthesis and Homogeneous Catalysis
Crossref
Scopus
Google Scholar
Europe PMC

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. Ravikumar Naik, 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, Lett. Org. Chem. 7 (2010) 69 (http://dx.doi.org/10.2174/157017810790533869); b) A. Ould Aliyenne, J. Kraiıem, Y. Kacem, B. Ben Hassine, C. R. Chim. 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. Chim. 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)

W. W. Tan, B. Wu, Y. Wei, N. Yoshikai, Org. Synth. 95 (2018) 1 (https://doi.org/10.15227/orgsyn.95.0001).