Abstract
Novel thio-substituted aminonaphthoquinones were synthesized by the reactions of 2-(4-(trifluoromethyl)phenylamino)-3-chloronaphthalene-1,4-dione (3a) and 2-(3-(trifluoromethyl)phenylamino)-3-chloronaphthalene-1,4-dione (3b) with various thiol compounds such as ethanethiol (4a), methyl 2-mercaptoacetate (4b), ethyl 2-mercaptoacetate (4c). 2,3-dichloro-1,4-naphthoquinone (1) was reacted with aryl amines (2a, 2b) containing trifluoromethyl group to give compounds 3a and 3b by applying a method published in literature. Finally, obtained novel compounds (5a-5f) were characterized via IR, 1H NMR, 13C NMR, and MS techniques. Based on previous studies in the literature, it is expected that some potential biological activities of new compounds could find application in medicinal chemistry.
Keywords
CF3 Aminonaphthoquinone 1 4-naphthoquinone thiol aryl amine trifluoromethyl group electron withdrawing group nucleophilic substitution
References
- [1] G.J. Kapadia, M.A. Azuine, V. Balasubramanian and R. Sridhar, “Aminonaphthoquınones-A Novel Class Of Compounds With Potent Antimalarial Activity Against Plasmodium Falciparum” Pharmacol Res., Vol. 43, No. 4, pp. 363-367, 2001.
- [2] P.J. O’Brien, “Molecular mechanisms of quinone cytotoxicity” Chem Biol Interact., Vol. 80, pp. 1-41, 1991.
- [3] D.W. Lamson and S.M. Plaza, “The anticancer effects of vitamin K” Altern Med Rev., Vol. 8, pp. 303-318, 2003.
Abstract
Novel thio-substituted aminonaphthoquinones were synthesized by the reactions of 2-(4-(trifluoromethyl)phenylamino)-3-chloronaphthalene-1,4-dione (3a) and 2-(3-(trifluoromethyl)phenylamino)-3-chloronaphthalene-1,4-dione (3b) with various thiol compounds such as ethanethiol (4a), methyl 2-mercaptoacetate (4b), ethyl 2-mercaptoacetate (4c). 2,3-dichloro-1,4-naphthoquinone (1) was reacted with aryl amines (2a, 2b) containing trifluoromethyl group to give compounds 3a and 3b by applying a method published in literature. Finally, obtained novel compounds (5a-5f) were characterized via IR, 1H NMR, 13C NMR, and MS techniques. Based on previous studies in the literature, it is expected that some potential biological activities of new compounds could find application in medicinal chemistry.
Keywords
Aminonaphthoquinone thiol aryl amine trifluoromethyl group CF3 electron withdrawing group nucleophilic substitution 1 4-naphthoquinone nucleophilic substitution
References
- [1] G.J. Kapadia, M.A. Azuine, V. Balasubramanian and R. Sridhar, “Aminonaphthoquınones-A Novel Class Of Compounds With Potent Antimalarial Activity Against Plasmodium Falciparum” Pharmacol Res., Vol. 43, No. 4, pp. 363-367, 2001.
- [2] P.J. O’Brien, “Molecular mechanisms of quinone cytotoxicity” Chem Biol Interact., Vol. 80, pp. 1-41, 1991.
- [3] D.W. Lamson and S.M. Plaza, “The anticancer effects of vitamin K” Altern Med Rev., Vol. 8, pp. 303-318, 2003.
Details
| Primary Language | English |
|---|---|
| Subjects | Engineering |
| Journal Section | Articles |
| Authors | |
| Publication Date | August 3, 2018 |
| Submission Date | January 3, 2018 |
| Published in Issue | Year 2018 Volume: 6 Issue: 2 |