Journal: International Journal of Molecular Sciences
Article Title: Naphthoquinone-Quinolone Hybrids with Antitumor Effects on Breast Cancer Cell Lines—From the Synthesis to 3D-Cell Culture Effects
doi: 10.3390/ijms25126490
Figure Lengend Snippet: Synthetic route towards 1,4-naphthoquinone/4-quinolone conjugates. a: (1) EMME, EtOH; (2) Diphenylether, 250 °C; b: (1) K 2 CO 3 , DMF, r. t., 15 min. (2) R1-X, DMF, 80 °C, 24 h.; c: H 2 (20 bar), Pd/C (10%), EtOH, 50 °C, 3 h. (for R1 = ethyl and pentyl); d: NH 4 Cl 0,05 M, Fe, reflux (for R1 = benzyl); e: (1) NaOH, EtOH, r. t. (2) H 2 O, HCl; f: t-butyl nitrite, DMSO, H 2 O, 1,4-naphthoquinone, ultrasound, 25 °C. ( 15a/11a : R 1 = Et, R 2 = Et; 15b/11b : R 1 = Bn, R 2 = Et; 15c / 11c : R 1 = Pentyl, R 2 = Et; 16a / 11d : R 1 = Et, R 2 = H; 16b / 11e : R 1 = CH 2 C 6 H 5 , R 2 = H; 16c / 11f : R 1 = C 5 H 11 , R 2 = H).
Article Snippet: Additionally, compounds 11a , 11b , 11d , 11e , and 11f exhibited zero violations of the drug-likeness rules of Lipinski, Ghose, Veber, Egan, and Muegge.
Techniques: Reflux