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Synthesis of Novel Thio-Substituted Aminonaphthoquinones

Yıl 2018, Cilt: 6 Sayı: 2, 179 - 184, 03.08.2018
https://doi.org/10.21541/apjes.373934

Öz

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.

Kaynakça

  • [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.

Synthesis of Novel Thio-Substituted Aminonaphthoquinones

Yıl 2018, Cilt: 6 Sayı: 2, 179 - 184, 03.08.2018
https://doi.org/10.21541/apjes.373934

Öz

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.

Kaynakça

  • [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.
Toplam 3 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Mahmut Yıldız

Amaç Fatih Tuyun

Yayımlanma Tarihi 3 Ağustos 2018
Gönderilme Tarihi 3 Ocak 2018
Yayımlandığı Sayı Yıl 2018 Cilt: 6 Sayı: 2

Kaynak Göster

IEEE M. Yıldız ve A. F. Tuyun, “Synthesis of Novel Thio-Substituted Aminonaphthoquinones”, APJES, c. 6, sy. 2, ss. 179–184, 2018, doi: 10.21541/apjes.373934.