1,3-Benzoxathiol-2-one and 1,3-Benzothiazole Compounds as Potential Anticancer and Antimicrobial Agents

被引:2
|
作者
Chazin, Eliza de L. [1 ]
Terra, Luciana [1 ]
Moor, Lucas F. E. [1 ]
Sanches, Paola de S. [1 ]
Pinto, Laine C. [1 ]
Martins, Talita [1 ]
de Souza, Marcus Vinicius N. [1 ]
Gomes, Claudia Regina B. [1 ]
Montenegro, Raquel C. [1 ]
Novais, Juliana S. [1 ]
Carvalho, Mariana F. [1 ]
Martins, Francislene J. [1 ]
Figueiredo, Agnes Marie S. [1 ]
Joffily, Ana [1 ]
Castro, Helena Carla [1 ]
Vasconcelos, Thatyana R. A. [1 ]
机构
[1] Univ Fed Fluminense, Inst Quim, Dept Quim Organ, Campus Valonguinho, BR-24020141 Niteroi, RJ, Brazil
关键词
Anticancer; antifungal; 1,3-benzothiazole; 1; 3-benzoxathiol-2-one; drugs; heterocycles; BIOLOGICAL-ACTIVITIES; CANDIDA-GLABRATA; BENZOTHIAZOLES; HETEROCYCLES; MECHANISMS; CHEMISTRY; TOXICITY; GROWTH; DRUGS;
D O I
10.21577/1984-6835.20200125
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Over the years, cancer and infectious diseases have appeared among the leading causes of death worldwide. The data herein highlights the need for new prototypes to design more potent and selective chemotherapeutics, as well as new, non-traditional antimicrobial agents. The main goal of this study was to evaluate some 1,3-benzoxathiol-2-one and 1,3-benzothiazole derivatives for their anticancer, antibacterial and antifungal activities. The compounds were screened for in vitro anticancer activity against melanoma (SKMEL-19), ascitic fluid (AGP-01) and breast (MCF-7) cancer cell lines using an MTT assay. The toxicity profile against erythrocytes and the normal human fibroblast cell line (MRC-5) was also evaluated. Besides that, in vitro Antimicrobial Screening Test (AST), Minimum Inhibitory Concentration (MIC), Minimum Bactericidal Concentration (MBC) and Minimum Fungicidal Concentration (MFC) assays were performed against Gram-positive and Gram-negative bacteria as well as against Candida species. All tests were performed according to CLSI protocols, using vancomycin, ciprofloxacin and ketoconazole as reference drugs. The derivative 6-methoxy-benzo[d][1,3]oxathiol-2-one (7) exhibited considerable cytotoxic activity (IC50 = 3.3 mu M) against SKMEL-19, and the compound (E)-4-((2-(benzo[d]thiazol-2-yl)hydrazono)methyl)benzene-1,2,3-triol) (16m) showed good activity against all Candida species (MIC 8-32 mu g mL(-1)). The MBC/MIC ratio for 16l and 16m derivatives classified them as bactericidal agents against Gram-positive bacteria. Compound 16m presented a fungistatic profile against Candida albicans and non-albicans species evaluated. Overall, the in vitro results pointed to the potential of derivatives 7 and 16m as new anticancer and antifungal prototypes, respectively, to be further explored, since they also presented low toxicity profiles.
引用
收藏
页码:1586 / 1598
页数:13
相关论文
共 50 条
  • [41] Intramolecular hypervalent C=O•••S interactions in a series of 1,3-benzothiazole derivatives
    Navarrete-Vazquez, Gabriel
    Alaniz-Palacios, Alfredo
    Tlahuextl, Margarita
    Bernal-Uruchurtu, Margarita
    Tlahuext, Hugo
    CRYSTENGCOMM, 2012, 14 (04) : 1256 - 1263
  • [42] X-RAY STUDY OF 2-(3,5-DIMETHYLPYRAZOLYL)-1,3-BENZOTHIAZOLE
    BHATIA, SC
    KUMAR, A
    GAUTAM, P
    JAIN, PC
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 : 1908 - 1911
  • [43] A Review on Domino Condensation/Cyclization Reactions for the Synthesis of 2-Substituted 1,3-Benzothiazole Derivatives
    Liu, Xing
    Dong, Zhi-Bing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (04) : 408 - 419
  • [44] Bis[(E)-2-(2,4-dichloro-5-nitrostyryl)-1,3-benzothiazole] hydrate
    Cox, O
    Cordero, M
    Pineiro, S
    Huang, SPD
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1997, 53 : 310 - 311
  • [45] Development of photofunctional materials using TTF derivatives containing a 1,3-benzothiazole ring
    Fujiwara, H.
    Yokota, S.
    Hayashi, S.
    Takemoto, S.
    Matsuzaka, H.
    PHYSICA B-CONDENSED MATTER, 2010, 405 (11) : S15 - S18
  • [46] 1,3-Benzothiazoles as Antimicrobial Agents
    Defrenza, Ivana
    Catalano, Alessia
    Carocci, Alessia
    Carrieri, Antonio
    Muraglia, Marilena
    Rosato, Antonio
    Corbo, Filomena
    Franchini, Carlo
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) : 1705 - 1712
  • [47] A simple synthesis and antimicrobial activity of sulfur-containing poly-condensed heterocyclic derivatives from 1,3-benzothiazole
    El-Gazzar, Abdel-Rahman B. A.
    Hafez, Hend N.
    ACTA CHIMICA SLOVENICA, 2008, 55 (02) : 359 - 371
  • [48] REACTION OF SUBSTITUTED 1,3-BENZOXATHIOL-2-ONES WITH HYDRAZINES
    MATVEEV, LG
    SHVETSOVSHILOVSKII, NI
    PITINA, MR
    SUPIN, GS
    TRENTOVSKAYA, LK
    ZHURNAL OBSHCHEI KHIMII, 1975, 45 (03): : 675 - 678
  • [49] The apparent dipole moments and molar volumes of 1,3-benzothiazole and some derivatives, in nonpolar solvents
    López, R
    Monzó, I
    Tomás, F
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (10): : 2225 - 2229
  • [50] Chemistry and Biological Activities of 1,3-Benzoxathiol-2-ones
    Vellasco Junior, Walcimar T.
    Gomes, Claudia R. B.
    Vasconcelos, Thatyana R. A.
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2011, 8 (01) : 103 - 109