Synthesis and Biological Evaluation of Novel 6-Hydroxy-benzo[d][1,3]oxathiol-2-one Schiff Bases as Potential Anticancer Agents

被引：19

作者：

Chazin, Eliza de Lucas ^{[1
]}

Sanches, Paola de Souza ^{[1
]}

Lindgren, Eric Brazil ^{[1
,2
]}

Vellasco Junior, Walcimar Trindade ^{[1
,3
]}

Pinto, Laine Celestino ^{[4
]}

Rodriguez Burbano, Rommel Mario ^{[4
]}

Yoneda, Julliane Diniz ^{[5
]}

Leal, Katia Zaccur ^{[1
]}

Brandao Gomes, Claudia Regina ^{[3
]}

Wardell, James Lewis ^{[3
,6
]}

Silva Veloso Wardell, Solange Maria ^{[7
]}

Montenegro, Raquel Carvalho ^{[4
]}

Alves Vasconcelos, Thatyana Rocha ^{[1
]}

机构：

[1] Univ Fed Fluminense, Inst Quim, Programa Posgrad Quim, BR-24020141 Niteroi, RJ, Brazil

[2] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[3] Fundacao Oswaldo Cruz, Inst Tecnol Farmacos Farmanguinhos, BR-21041250 Rio De Janeiro, RJ, Brazil

[4] Fed Univ Para, Inst Ciencias Biol, BR-66075110 Belem, Para, Brazil

[5] Univ Fed Fluminense, Inst Ciencias Exatas, Dept Quim, BR-27213415 Volta Redonda, RJ, Brazil

[6] Univ Aberdeen, Dept Chem, Old Aberdeen AB24 3UE, Scotland

[7] CHEMSOL, Aberdeen AB15 5NY, Scotland

来源：

MOLECULES | 2015年 / 20卷 / 02期

关键词：

OXATHIOLONE FUSED CHALCONES; ANTIMYCOBACTERIAL ACTIVITY; ORAL BIOAVAILABILITY; ANTITUMOR EVALUATION; MICROORGANISMS; DOXORUBICIN; HYDRAZONES; CHEMISTRY; CHLORIDE; ACID;

D O I：

10.3390/molecules20021968

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

With the aim of discovering new anticancer agents, we have designed and synthesized novel 6-hydroxy-benzo[d][1,3]oxathiol-2-one Schiff bases. The synthesis started with the selective nitration at 5-position of 6-hydroxybenzo[d][1,3]oxathiol-2-one (1) leading to the nitro derivative 2. The nitro group of 2 was reduced to give the amino intermediate 3. Schiff bases 4a-r were obtained from coupling reactions between 3 and various benzaldehydes and heteroaromatic aldehydes. All the new compounds were fully identified and characterized by NMR (H-1 and C-13) and specifically for 4q by X-ray crystallography. The in vitro cytotoxicity of the compounds was evaluated against cancer cell lines (ACP-03, SKMEL-19 and HCT-116) by using MTT assay. Schiff bases 4b and 4o exhibited promising cytotoxicity against ACP-03 and SKMEL-19, respectively, with IC50 values lower than 5 mu M. This class of compounds can be considered as a good starting point for the development of new lead molecules in the fight against cancer.

引用

页码：1968 / 1983

页数：16

共 38 条

[1]

Anand P., 2012, INT J DRUG DESIGN DI, V3, P851

[2]

[Anonymous], CRYSTALCLEAR

[3]

[Anonymous], 2020, CA Cancer J Clin, DOI DOI 10.3322/CAAC.21590

[4]

[Anonymous], 2011, SPARTAN10

[5]

SELECTIVE REDUCTION OF AROMATIC NITRO-COMPOUNDS WITH STANNOUS CHLORIDE IN NON-ACIDIC AND NON-AQUEOUS MEDIUM [J].

BELLAMY, FD ;

OU, K .

TETRAHEDRON LETTERS, 1984, 25 (08) :839-842

[6]

Lipomer of doxorubicin hydrochloride for enhanced oral bioavailability [J].

Benival, Derajram M. ;

Devarajan, Padma V. .

INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2012, 423 (02) :554-561

[7]

Novel Cyano- and Amidinobenzothiazole Derivatives: Synthesis, Antitumor Evaluation, and X-ray and Quantitative Structure-Activity Relationship (QSAR) Analysis [J].

Caleta, Irena ;

Kralj, Marijeta ;

Marjanovic, Marko ;

Bertosa, Branimir ;

Tomic, Sanja ;

Pavlovic, Gordana ;

Pavelic, Kresimir ;

Karminski-Zamola, Grace .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (06) :1744-1756

[8]

Cambridge Crystallographic Data Centre, 2013, MERCURY 3 01

[9]

The cytotoxic and embryotoxic effects of kaurenoic acid, a diterpene isolated from Copaifera langsdorffii oleo-resin [J].

Costa-Lotufo, LV ;

Cunha, GMA ;

Farias, PAM ;

Viana, GSB ;

Cunha, KMA ;

Pessoa, C ;

Moraes, MO ;

Silveira, ER ;

Gramosa, NV ;

Rao, VSN .

TOXICON, 2002, 40 (08) :1231-1234

[10]

Schiff bases: A short review of their antimicrobial activities [J].

da Silva, Cleiton M. ;

da Silva, Daniel L. ;

Modolo, Luzia V. ;

Alves, Rosemeire B. ;

de Resende, Maria A. ;

Martins, Cleide V. B. ;

de Fatima, Angelo .

JOURNAL OF ADVANCED RESEARCH, 2011, 2 (01) :1-8

← 1 2 3 4 →