Synthesis, Molecular Docking and Antiproliferative Activity Studies of a Thiazole-Based Compound Linked to Hydrazone Moiety

被引：24

作者：

Kekecmuhammed, Huseyin ^{[1
]}

Tapera, Michael ^{[1
]}

Tuzun, Burak ^{[2
]}

Akkoc, Senem ^{[3
,4
]}

Zorlu, Yunus ^{[5
]}

Saripinar, Emin ^{[1
]}

机构：

[1] Erciyes Univ, Dept Chem, TR-38039 Kayseri, Turkey

[2] Sivas Cumhuriyet Univ, Dept Plant & Anim Prod, TR-58140 Merkez Merkez, Sivas, Turkey

[3] Suleyman Demirel Univ, Dept Basic Pharmaceut Sci, TR-32260 Merkez Isparta, Turkey

[4] Bahcesehir Univ, Dept Pharm, TR-34349 Istanbul, Turkey

[5] Gebze Tech Univ, Dept Chem, Cumhuriyet 2254,Sk 2, TR-41400 Gebze, Turkey

来源：

CHEMISTRYSELECT | 2022年 / 7卷 / 26期

关键词：

antiproliferative activity; crystal X-ray analysis; hydrazone; molecular docking; 4-oxothiazolidin-2-ylidene; ANTITUMOR-ACTIVITY; DOMAIN;

D O I：

10.1002/slct.202201502

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(A new 4-oxothiazolidin-2-ylidene derivative bearing hydrazone moiety was synthesized via Michael addition between the reaction of 4-(4-nitrophenyl)-3-thiosemicarbazide and dimethyl acetylenedicarboxylate (DMAD). The structure of synthesized compound was elucidated using various spectral techniques such as FTIR, UV-spec, H-1 NMR and C-13 NMR. The structure of the related compound was confirmed by single-crystal X-ray analysis. Antiproliferative activity of the synthesized compound was evaluated in two human cancer cell lines, HepG2 (liver hepatocellular carcinoma cell line) and DLD-1 (human colon cancer cell line). In addition, molecular docking of synthesized compound was investigated to give an insight of its activity against Epidermal Growth Factor Receptor tyrosine kinase domain proteins (EGFR) (lung cancer) (PDB ID: 1 M17), deleted in Liver Cancer 2 proteins (DLC2) (liver cancer) (PDB ID: 2H80), and MLK4 kinase proteins (colon cancer) (PDB ID: 4UYA) were investigated. Furthermore, the ability of the molecule to be a drug was examined by ADME/T analysis.)

引用

页数：10

共 37 条

[1] Colon Cancer: A Clinician's Perspective in 2019 [J].

Ahmed, Monjur .

GASTROENTEROLOGY RESEARCH, 2020, 13 (01) :1-10

[2] Design, synthesis, characterization, and in vitro cytotoxic activity evaluation of 1,2-disubstituted benzimidazole compounds [J].

Akkoc, Senem .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2021, 34 (01)

[3] Crystal structure of methyl (2Z)-2-[(2Z)-2-(2-cyclopentylidenehydrazin-1-yl-idene)-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene]ethanoate [J].

Akkurt, Mehmet ;

Smolenski, Victoria A. ;

Mohamed, Shaaban K. ;

Jasinski, Jerry P. ;

Hassan, Alaa A. ;

Albayati, Mustafa R. .

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 :O776-U515

[4] Antiproliferative activity and molecular docking studies of new 4-oxothiazolidin-5-ylidene acetate derivatives containing guanylhydrazone moiety [J].

Al-Janabi, Ihab Adnan Salman ;

Yavuz, Sevtap Caglar ;

Kopru, Semiha ;

Tapera, Michael ;

Kekecmuhammed, Huseyin ;

Akkoc, Senem ;

Tuzun, Burak ;

Patat, Aban ;

Saripinar, Emin .

JOURNAL OF MOLECULAR STRUCTURE, 2022, 1258

[5] Heterocyclic Scaffolds: Centrality in Anticancer Drug Development [J].

Ali, Imran ;

Lone, Mohammad Nadeem ;

Al-Othman, Zeid A. ;

Al-Warthan, Abdulrahman ;

Sanagi, Mohd Marsin .

CURRENT DRUG TARGETS, 2015, 16 (07) :711-734

[6] Alkyl chain modified metalophthalocyanines with enhanced antioxidant-antimicrobial properties by doping Ag+ and Pd2+ ions [J].

Alici, Esma Hande ;

Bilgicli, Ahmet T. ;

Tuzun, Burak ;

Gunsel, Armagan ;

Arabaci, Gulnur ;

Yarasir, M. Nilufer .

JOURNAL OF MOLECULAR STRUCTURE, 2022, 1257

[7] Design, Synthesis, and Evaluation of a New Series of Thiazole-Based Anticancer Agents as Potent Akt Inhibitors [J].

Altintop, Mehlika Dilek ;

Sever, Belgin ;

Ciftci, Gulsen Akalin ;

Ozdemir, Ahmet .

MOLECULES, 2018, 23 (06)

[8] HYDRAZINE DERIVATIVES OF THE CARBONIC AND THIOCARBONIC ACIDS .1. THE PREPARATION AND PROPERTIES OF THIOCARBOHYDRAZIDE [J].

AUDRIETH, LF ;

SCOTT, ES ;

KIPPUR, PS .

JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (05) :733-741

[9] Synthesis, characterization, molecular modeling against EGFR target and ADME/T analysis of novel purine derivatives of sulfonamides [J].

Bhat, Mashooq A. A. ;

Tuzun, Burak ;

Alsaif, Nawaf A. A. ;

Khan, Azmat Ali M. ;

Naglah, Ahmed M. .

JOURNAL OF MOLECULAR STRUCTURE, 2022, 1257

[10] Octa-substituted Zinc(II), Cu(II), and Co(II) phthalocyanines with 1-(4-hydroxyphenyl)propane-1-one: Synthesis, sensitive protonation behaviors, Ag(I) induced H-type aggregation properties, antibacterial-antioxidant activity, and molecular docking studies [J].

Bilgicli, Ahmet T. ;

Kandemir, Tugberk ;

Tuzun, Burak ;

Ariduru, Rana ;

Gunsel, Armagan ;

Abak, Cagla ;

Yarasir, M. Nilufer ;

Arabaci, Gulnur .

APPLIED ORGANOMETALLIC CHEMISTRY, 2021, 35 (10)

← 1 2 3 4 →