4613-58-5Relevant academic research and scientific papers
Synthesis and biological evaluation of benzo[f]indole-4,9-diones n-linked to carbohydrate chains as new type of antitumor agents
Dias, Flaviana R.F.,Guerra, Fabiana S.,Lima, Fernanda A.,de Castro, Yasmin K.C.,Ferreira, Vitor F.,Campos, Vinícius R.,Fernandes, Patrícia D.,Cunha, Anna C.
, p. 476 - 489 (2021/02/12)
In this work, we report the synthesis of three series of carbohydrate-based benzo[f]indole-4,9-diones and amino-1,4-naphthoquinone derivatives and evaluated their cytotoxic activity against eight human cancer cell lines. Several compounds showed a promising cytotoxic activity toward the tumor cell lines (half maximal inhibitory concentration (IC50) 10.0 μM). The importance of the substitution pattern of the quinone derivatives on the antitumor activity was also discussed. 3-Carboethoxy-2-methyl-benzo[f]indole-4,9-dione derivatives were more cytotoxic than their parent compounds and amino-1,4-naphthoquinones. Unlike clinically useful anticancer agent doxorubicin, the majority of synthesized compounds did not exhibit any lytic effects against erythrocytes or normal human leukocytes.
Synthesis and antimicrobial evaluation of amino sugar-based naphthoquinones and isoquinoline-5,8-diones and their halogenated compounds
Dias, Flaviana R.F.,Novais, Juliana S.,Devillart, Talita A. do Nascimento Santos,da Silva, Wanderson Amaral,Ferreira, Matheus O.,Loureiro, Raquel de S.,Campos, Vinícius R.,Ferreira, Vitor F.,de Souza, Maria C.B.V.,Castro, Helena C.,Cunha, Anna C.
, p. 1 - 12 (2018/07/06)
Antibiotic resistance has emerged as a serious global public health problem and lately very few antibiotics have been discovered and introduced into clinical practice. Therefore, there is an urgent need for the development of antibacterial compounds with new mechanism of action, especially those capable of evading known resistance mechanisms. In this work two series of glycoconjugate and non-glycoconjugate amino compounds derived from of isoquinoline-5,8-dione and 1,4-naphthoquinone and their halogenated derivatives were synthesized and evaluated for antimicrobial activity against Gram-positive (Enterococcus faecalis ATCC 29212, Staphylococcus aureus ATCC 25923, S. epidermidis ATCC 12228, S. simulans ATCC 27851) and Gram-negative bacteria (E. coli ATCC 25922, Proteus mirabilis ATCC 15290, K. pneumoniae ATCC 4352 and P. aeruginosa ATCC 27853) strains of clinical importance. This study revealed that glycoconjugate compounds derived from halogeno-substituted naphthoquinones were more active against Gram-negative strains, which cause infections whose treatment is even more difficult, according to the literature. These molecules were also more active than isoquinoline-5,8-dione analogues with minimum inhibitory concentration (MIC = 4–32 μg/mL) within Clinical and Laboratory Standard Institute MIC values (CLSI 0.08–256 μg/mL). Interestingly the minimal bactericidal concentration (MBC) values of the most active compounds were equal to MIC classifying them as bactericidal agents against Gram-negative bacteria. Sixteen compounds among eighteen carbohydrate-based naphthoquinones tested showed no hemolytic effects on health human erythrocytes whereas more susceptibility to hemolytic cleavage was observed when using non-glycoconjugate amino compounds. In silico Absorption, Distribution, Metabolism, Excretion and Toxicity (ADMET) evaluation also pointed out that these compounds are potential for oral administration with low side effects. In general, this study indicated that these compounds should be exploited in the search for a leading substance in a project aimed at obtaining new antimicrobials more effective against Gram-negative bacteria.
Synthesis of a new class of naphthoquinone glycoconjugates and evaluation of their potential as antitumoral agents
Campos, Vinicius R.,Cunha, Anna C.,Silva, Wanderson A.,Ferreira, Vitor F.,Santos De Sousa, Carla,Fernandes, Patrícia D.,Moreira, Vinícius N.,Da Rocha, David R.,Dias, Flaviana R. F.,Montenegro, Raquel C.,De Souza, Maria C. B. V.,Boechat, Fernanda Da C. S.,Franco, Caroline F. J.,Resende, Jackson A. L. C.
, p. 96222 - 96229 (2015/11/24)
A novel series of carbohydrate-based naphthoquinones was synthesized and evaluated for cytotoxicity against different cancer cell lines. The compounds derived from 5-hydroxy-1,4-naphthoquinone (juglone) showed better cytotoxicity profiles against HCT-116, A-549 and MDA-MB 435 human cancer cells than the parent compound. The results suggest that the hydroxyl group on the aromatic ring increased the pro-oxidant activity of these new naphthoquinone derivatives. Furthermore, two derivatives were found to be more active against melanoma cells (MDA-MB435) than the clinically useful anticancer agent doxorubicin, and none of the compounds caused mouse erythrocyte lysis.
Modular furanoside phosphite-phosphoroamidites, a readily available ligand library for asymmetric palladium-catalyzed allylic substitution reactions. Origin of enantioselectivity
Raluy, Eva,Pamies, Oscar,Dieguez, Montserrat
scheme or table, p. 1648 - 1670 (2011/03/18)
A library of furanoside phosphite-phosphoroamidite ligands has been synthesized and screened in the palladium-catalyzed allylic substitution reactions of several substrate types. These series of ligands can be prepared efficiently from easily accessible D
NOVEL DERIVATIVES OF ACYL CYANOPYRROLIDINES
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, (2009/10/22)
A compound of formula (I) or a tautomeric form, regioisomer, stereoisomer, solvate, N-oxide or pharmaceutically acceptable salts thereof; wherein 'a' - is selected from the group consisting of substituted or unsubstituted heterocycloalkyl ring and substituted or unsubstituted carbohydrate moiety y is a member selected from -O-, -CO-, -S02-, aminoalkyl or formula (II) wherein, Rw is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl; x is a member selected from -0-, -S-, -SO-, -S02-, CONR10, NR10CO and -NRd-, or x and y together represent a chemical bond; Z is selected from -CH-, -N-. t is an integer selected from O to 4; with the provisos that when 'a' is substituted or unsubstituted heterocycloalkyl ring then 't' is not O and when y = -CO-, x is not NRd.
1-Aza-sugars from D-Glucose. Preparation of 1-Deoxy-5-dehydroxymethyl-Nojirimycin, its analogues and evaluation of glycosidase inhibitory activity
Patil, Nitin T.,John, Sheeja,Sabharwal, Sushma G.,Dhavale, Dilip D.
, p. 2155 - 2160 (2007/10/03)
D-Glucose derived pentodialdoses 11a-c on reduction followed by tosylation, azide displacement, hydrogenation and protection with -Cbz group gave N-Cbz protected compounds 14a-c, respectively, which on removal of 1,2-acetonide functionality and hydrogenat
Entry to the 2,5-epoxyimidazo[1,5-a][1,3]diazocine and 5,8-epoxy[1,2,3]triazolo[1,5-a][1,3]diazocine systems : Novel reversed cyclonucleoside analogues
Ewing,Goethals,Mackenzie,Martin,Ronco,Vanbaelinghem,Villa
, p. 441 - 450 (2007/10/03)
5-Azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose was used to obtain two reversed nucleoside analogues with either the 5-aminoimidazol-4-carboxamide or 5-amino-1,2,3-triazol-4-carboxamide groups attached, through the N1 site, to the C5′ site of the sugar. When deprotected these two compounds cyclised spontaneously and regiospecifically to form a bond between the exocyclic nitrogen and the anomeric carbon of the sugar. These reversed cyclonucleoside analogues are respectively members of the 2,5-epoxyimidazo[1,5-a][1,3]diazocine and 5,8-epoxy[1,2,3]triazolo[1,5-a][1,3]diazocine systems, novel ring systems with therapeutic potential. The shape of the cyclised imidazole compound and its immediate precursor has been studied by molecular modelling.
Preparation of Novel Cyclophosphamide Derivatives of Sugars
Yamashita, Mitsuji,Takahashi, Chihiro,Seo, Kuniaki
, p. 651 - 654 (2007/10/02)
Novel cyclophosphamide derivatives bearing a sugar structure were prepared by the treatment of the amino sugars from D-glucose and D-xylose with bis-(2-chloroethyl)aminophosphoric dichloride as well as with phosphoryl chloride and nucleophiles.
