Novel thiosemicarbazide derivatives with 4-nitrophenyl group as multi-target drugs: α-glucosidase inhibitors with antibacterial and antiproliferative activity

被引：32

作者：

Wos, Maciej ^{[1
]}

Miazga-Karska, Malgorzata ^{[2
]}

Kaczor, Agnieszka A. ^{[3
,4
]}

Klimek, Katarzyna ^{[2
]}

Karczmarzyk, Zbigniew ^{[5
]}

Kowalczuk, Dorota ^{[6
]}

Wysocki, Waldemar ^{[5
]}

Ginalska, Grazyna ^{[2
]}

Urbanczyk-Lipkowska, Zofia ^{[7
]}

Morawiak, Maja ^{[7
]}

Pitucha, Monika ^{[1
]}

机构：

[1] Med Univ, Dept Organ Chem, 4A Chodzki St, PL-20093 Lublin, Poland

[2] Med Univ, Dept Biochem & Biotechnol, 1 Chodzki St, PL-20093 Lublin, Poland

[3] Med Univ, Comp Modeling Lab, Dept Synth & Chem Technol Pharmaceut Subst, 1 Chodzki St, PL-20093 Lublin, Poland

[4] Univ Eastern Finland, Sch Pharm, Dept Pharmaceut Chem, Yliopistonranta 1,POB 1627, FI-70211 Kuopio, Finland

[5] Siedlce Univ Nat Sci & Humanities, Dept Chem, 3 Maja 54 St, PL-08110 Siedlce, Poland

[6] Med Univ Lublin, Dept Med Chem, Jaczewskiego 4 St, PL-20090 Lublin, Poland

[7] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52 St, PL-01224 Warsaw, Poland

来源：

BIOMEDICINE & PHARMACOTHERAPY | 2017年 / 93卷

关键词：

Antibacterial activity; Antiproliferative activity; alpha-glucosidase inhibitor; Molecular docking; Thiosemicarbazide; BIOLOGICAL EVALUATION; DESIGN; 1,3,4-OXADIAZOLE; SEMICARBAZIDE; HYDRAZONE; APOPTOSIS;

D O I：

10.1016/j.biopha.2017.07.049

中图分类号：

R-3 [医学研究方法]; R3 [基础医学];

学科分类号：

1001 ;

摘要：

A series of thiosemicarbazides with 4-nitrophenyl group was obtained in the reaction of carboxylic acid hydrazides with isothiocyanates. All compounds were checked for their antibacterial and antiproliferative activity. Our results have shown that derivatives 6-8 possessed antibacterial activity against S. aureus, S. epidermidis, S. mutans and S. sanguinis, moderate cytotoxicity and good therapeutic safety in vitro. Additionally, compounds 1 and 4 significantly inhibited A549, HepG2 and MCF-7 cell division. Moreover, PASS software indicated that newly obtained compounds are potential a-glucosidase inhibitors. This was confirmed by in vitro studies. To investigate the mode of interaction with the molecular target compounds were docked to glucose binding site of the enzyme and exhibited a similar binding mode as glucose. (C) 2017 Elsevier Masson SAS. All rights reserved.

引用

页码：1269 / 1276

页数：8

共 62 条

[11] [Anonymous], J CHIN MED
[12] Synthesis of some novel heterocylic compounds derived from 2-[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol-4-yl]acetohydrazide and investigation of their lipase and α-glucosidase inhibition
Bekircan, Olcay
Ulker, Serdar
Mentese, Emre
[J]. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2015, 30 (06) : 1002 - 1009
[13] BHAT AK, 1967, INDIAN J CHEM, V5, P397
[14] Synthesis and anti-Candidal activity of N-(4-aryl/cyclohexyl)-2-(pyridine-4-yl carbonyl) hydrazinecarbothioamide
Bhat, Mashooq Ahmad
Khan, Abdul Arif
Khan, Shahanavaj
Al-Omar, Mohamed A.
Parvez, Mohammad Khalid
Al-Dosari, Mohammed Salem
Al-Dhfyan, Abdullah
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (05) : 1299 - 1302
[15] Synthesis and Promising in Vitro Antiproliferative Activity of Sulfones of a 5-Nitrothiazole Series
Cohen, Anita
Crozet, Maxime D.
Rathelot, Pascal
Azas, Nadine
Vanelle, Patrice
[J]. MOLECULES, 2013, 18 (01) : 97 - 113
[16] GENERAL DEFINITION OF RING PUCKERING COORDINATES
CREMER, D
POPLE, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) : 1354 - 1358
[17] Cisplatin in cancer therapy: Molecular mechanisms of action
Dasari, Shaloam
Tchounwou, Paul Bernard
[J]. EUROPEAN JOURNAL OF PHARMACOLOGY, 2014, 740 : 364 - 378
[18] Deep A, 2010, ACTA POL PHARM, V67, P255
[19] MUSCLE: multiple sequence alignment with high accuracy and high throughput
Edgar, RC
[J]. NUCLEIC ACIDS RESEARCH, 2004, 32 (05) : 1792 - 1797
[20] Screening of α-Glucosidase Inhibitory Activity from Some Plants of Apocynaceae, Clusiaceae, Euphorbiaceae, and Rubiaceae
Elya, Berna
Basah, Katrin
Mun'im, Abdul
Yuliastuti, Wulan
Bangun, Anastasia
Septiana, Eva Kurnia
[J]. JOURNAL OF BIOMEDICINE AND BIOTECHNOLOGY, 2012,

← 1 2 3 4 5 6 7 →