64418-77-5Relevant academic research and scientific papers
The synthesis of some naphtho[2,3-b]pyran-5,10-quinones as preliminary models for biological evaluations
Giles, Robin G.F.,Green, Ivan R.,Hugo, Victor I.,Ireland, Joanne L.
, p. 4589 - 4604 (1998)
Naphtho[2,3-b]pyran-5,10-quinones related to the known antibiotic, erythrostominone 5, have been synthesized and demonstrate that biological activity is a function of the pyran ring as well as substituents at C-2 and C-4.
Trypanosoma cruzi: Activities of lapachol and α- and β-lapachone derivatives against epimastigote and trypomastigote forms
Salas, Cristian,Tapia, Ricardo A.,Ciudad, Karina,Armstrong, Veronica,Orellana, Myriam,Kemmerling, Ulrike,Ferreira, Jorge,Maya, Juan Diego,Morello, Antonio
, p. 668 - 674 (2008/09/17)
Derivatives of natural quinones with biological activities, such as lapachol, α- and β-lapachones, have been synthesized and their trypanocidal activity evaluated in vitro in Trypanosoma cruzi cells. All tested compounds inhibited epimastigote growth and trypomastigote viability. Several compounds showed similar or higher activity as compared with current trypanocidal drugs, nifurtimox and benznidazole. The results presented here show that the anti-T. cruzi activity of the α-lapachone derivatives can be increased by the replacement of the benzene ring by a pyridine moiety. Free radical production and consequently oxidative stress through redox cycling or production of electrophilic metabolites are the potential biological mechanism of action for these synthetic quinones.
Cycloadditions in Syntheses. XXVI. 1,2-Dihydrocyclobuta-naphthalene-3,8-diones: Synthesis by Photochemical Means and Their Reactions via 2,3-Dimethylene-1,4-dioxo-1,2,3,4-tetrahydronaphthalenes
Naito, Toshihiko,Makita, Yoshihiko,Yazaki, Shiomi,Kaneko, Chikara
, p. 1505 - 1517 (2007/10/02)
2-Chloro-1,4-naphthoquinone undergoes photochemical 2+2 addition to alkenes.Elimination of hydrogen chloride from the adducts provides a facile and general synthetic method for 1,2-dihydrocyclobutanaphthalene-3,8-diones.Heating of the latter compounds affords 2,3-dimethylene-1,2,3,4-tetrahydronaphthalene-1,4-diones, which react in situ with alkenes to give the 4+2 adducts. 1-Formyl-1,2-dihydrocyclobutanaphthalene-3,8-dione obtained by the use of the above two-step procedure using acrolein dimethylacetal as the alkene in the first step affords upon heating 1H-naphthopyran-5,10-dione via electrocyclization of the corresponding dimethylene compound.If an enone is used as the alkene in the first step, the addition occurs in a 4+2 manner to give directly 4H-naphthopyran-5,10-diones.Keywords - 1,2-dihydrocyclobutanaphthalene-3,8-dione; 1H-naphthopyran-5,10-dione; 4H-naphthopyran-5,10-dione; Benzocyclobutene method; cyclobutane annelation; phtochemical synthesis; naphthopyrandione; pyran annelation;
