62830-53-9Relevant articles and documents
Organocatalytic Enantioselective Michael-Aldol[3+2] Annulation for the Synthesis of Nitro-Methanobenzo[7] annulenes
Zhang, Yang,Liu, Jin-Yu,Zhang, Xiao-Hai
supporting information, p. 5008 - 5011 (2021/09/28)
We report an enantioselective Michael-Aldol[3+2] annulation between 2-alkyl-3-hydroxynaphthalene-1,4-diones and nitroalkenes using a bifunctional thiourea catalyst, and a series of nitro-methanobenzo[7]annulenes with potential biological activities were synthesized in good yields with excellent enantio- and diastereoselectivities. A gram-scale synthesis and further transformation of the product demonstrated the synthetic value of this reaction.
A new method to prepare 3-alkyl-2-hydroxy-1,4-naphthoquinones: Synthesis of lapachol and phthiocol
Ferreira, Sabrina Baptista,Rodriguesdarocha, David,Carneiro, José Walkimar M.,Santos, Wilson Costa,Ferreira, Vitor Francisco
supporting information; experimental part, p. 1551 - 1554 (2011/08/04)
In this article a mild, simple, safe, and chemoselective synthesis and reduction of o-quinone methides to the corresponding 3-alkyl-2-hydroxy-1,4- naphthoquinones, compounds with interesting biological activity, mediated by the formic acid-water system is described. This new one-pot methodology was applied to the synthesis of lapachol and constitutes an efficient and inexpensive alternative for the preparation of this natural bioactive compound Georg Thieme Verlag Stuttgart ? New York.
Synthesis and evaluation of quinonoid compounds against tumor cell lines
Da Silva Jr., Eufranio N.,Cavalcanti, Bruno C.,Guimar?es, Tiago T.,Pinto, Maria Do Carmo F.R.,Cabral, Igor O.,Pessoa, Cláudia,Costa-Lotufo, Letícia V.,De Moraes, Manoel O.,De Andrade, Carlos K.Z.,Dos Santos, Marcelo R.,De Simone, Carlos A.,Goulart, Marilia O.F.,Pinto, Antonio V.
scheme or table, p. 399 - 410 (2011/02/27)
Thirty two compounds were synthesized in moderate to high yields and showed activity against cancer cells HL-60 (leukemia), MDA-MB435 (melanoma), HCT-8 (colon) and SF295 (central nervous system), with IC50 below 2 μM for some compounds. The β-lapachone-based 1,2,3-triazoles showed the best cytoxicity profile and emerge as promising anticancer prototypes. Insights about the reactive oxygen species (ROS) mechanism of anticancer action for some compounds were obtained by addition of 1-bromoheptane that deplete reduced glutathione (GSH) content and by using N-acetylcysteine that protects cells against apoptotic cellular death, as well by analysis of thiobarbituric acid reactive substances (TBARS) formation, and oxidative DNA damage after treatment detected by the comet assay with the bacterial enzymes formamidopyrimidine DNA-glycosylase (FPG) and endonuclease III (ENDOIII).
Quinonoid and phenazine compounds: Synthesis and evaluation against H 37Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis
Carneiro, Paula F.,Pinto, Maria Do Carmo F.R.,Coelho, Tatiane S.,Cavalcanti, Bruno C.,Pessoa, Cláudia,De Simone, Carlos A.,Nunes, Isabelle K.C.,De Oliveira, Nathalia M.,De Almeida, Renata G.,Pinto, Antonio V.,De Moura, Kelly C.G.,Da Silva, Pedro A.,Da Silva Júnior, Eufranio N.
scheme or table, p. 4521 - 4529 (2011/11/06)
Several quinonoid and phenazine compounds were synthesized in moderate to high yields and showed activity against H37Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis. The cytotoxity of the compounds were evaluated against human peripheral blood mononuclear cells (PBMC) and these substances emerge as promising antitubercular prototypes.
