74652-31-6Relevant academic research and scientific papers
Synthetic approaches and: In vitro cytotoxic evaluation of 2-acyl-3-(3,4,5-trimethoxyanilino)-1,4-naphthoquinones
Valderrama, Jaime A.,Cabrera, Mónica,Benites, Julio,Ríos, David,Inostroza-Rivera, Ricardo,Muccioli, Giulio G.,Calderon, Pedro Buc
, p. 24813 - 24821 (2017)
2-Acyl-1,4-naphthoquinones react with 3,4,5-trimethoxyaniline, under aerobic conditions, to give benzophenanthridinequinone, benzocarbazole and 2-acyl-3-(3,4,5-trimethoxyanilino)-1,4-naphthoquinone derivatives. The formation of the heterocyclic compounds is discussed in terms of the ring closure of C-C Michael type adduct intermediates through two alternative N-C-bond formations. The propensity of the substrates to undergo preferential C-C instead of C-N bond formation and the further heterocyclization of the C-C Michael type adduct intermediates is rationalized by using product stability parameters assessed by DFT calculations. Preliminary results are reported on a convenient access towards 2-acyl-3-(3,4,5-trimethoxyanilino)-1,4-naphthoquinones from 2-acylnaphthoquinones and their cytotoxic activities on cancer cells.
Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells
Sunassee, Suthananda N.,Veale, Clinton G.L.,Shunmoogam-Gounden, Nelusha,Osoniyi, Omalaja,Hendricks, Denver T.,Caira, Mino R.,De La Mare, Jo-Anne,Edkins, Adrienne L.,Pinto, Antonio V.,Da Silva Junior, Eufranio N.,Davies-Coleman, Michael T.
, p. 98 - 110 (2013/05/09)
Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, α- and β-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6-11.7 μM) compared to the current drug of choice cisplatin (IC 50 = 16.5 μM). This study also established that the two new synthetic halogenated compounds 12a and 16a (IC50 = 3.0 and 7.3 μM) and the previously reported compound 11a (IC50 = 3.9 μM), were non-toxic to NIH3T3 normal fibroblast cells. Cell death of oesophageal cancer cells by processes involving PARP cleavage caused by 11a was shown to be associated with elevated c-Jun levels, suggesting a role for this pathway in the mechanism of action of this cohort of naphthoquinone compounds.
A novel manganese(iii) acetate mediated reaction between 2-benzoyl-1,4-naphthoquinones and 1,3-dicarbonyl compounds
Lin, Chien-Yu,Cheng, Yu-Chih,Tsai, An.-I.,Chuang, Che-Ping
, p. 1097 - 1103 (2008/02/02)
A manganese(iii)-mediated reaction between 2-benzoyl-1,4-naphthoquinones and 1,3-dicarbonyl compounds is described. This reaction provides an effective method for the synthesis of naphtho[2,3-c]furan-4,9-diones and naphthacene-5,12-diones, and it shows fa
The "photo-Friedel-Crafts acylation" of 1,4-naphthoquinones
Oelgemoeller, Michael,Schiel, Christian,Froehlich, Roland,Mattay, Jochen
, p. 2465 - 2474 (2007/10/03)
The photochemical reaction between 1,4-naphthoquinone (3) and several aliphatic and aromatic aldehydes 5a-f resulted in the formation of acylated naphthohydroquinones 6a-f in moderate to good yields of 42-79%. When benzaldehyde was used, the dibenzoylated product 7 was also isolated, in 14% yield. The regioselectivity was studied with the unsymmetrical substituted naphthoquinone 4 and butyraldehyde 5b and benzaldehyde 5f. With 5f, the corresponding diaroylated compound 12 was again isolated as a minor product. Oxidation of selected photoproducts afforded the corresponding acylated naphthoquinones 8a, 8b, 8f, and 13 in moderate to excellent yields of 53-94%. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
An improved method for the preparation of 4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates from 2-acyl-1,4-benzoquinones and mercaptoacetates
Kobayashi, Kazuhiro,Yoneda, Keiichi,Uchida, Masaharu,Matsuoka, Hideki,Morikawa, Osamu,Konishi, Hisatoshi
, p. 2423 - 2430 (2007/10/03)
4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates (4) have been synthesized in a one-pot procedure from 2-acyl-1,4-benzoquinones (1) and mercaptoacetates (2) by using 1-trimethylsilylimidazole as a protective reagent as well as a base. Thus, reaction of 1 with 2 in THF at room temperature was followed by treatment with excess of 1-trimethylsilylimidazole at 80°C. Then the cooled mixture was hydrolyzed with hydrochloric acid and oxidized with cerium(IV) ammonium nitrate (CAN) to give the expected thiophenequinone derivatives (4). 4,9-Dioxo-4,9-dihydronaphtho[2,3-b]thiophene-2-carboxylates (7) were similarly prepared from 2-acyl-1,4-naphthoquinones (5) and mercaptoacetates, in general, by omitting the CAN oxidation procedure.
