Synthesis and Aldose Reductase Inhibitory Effect of Some New Hydrazinecarbothioamides and 4-Thiazolidinones Bearing an Imidazo[2,1-b]Thiazole Moiety

Güzeldemirci, Nuray Ulusoy; Cimok, Selin; Daş-Evcimen, Net; Sarıkaya, Mutlu

doi:10.4274/tjps.05900

Cited by 7 publications

(11 citation statements)

References 51 publications

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“…The IR, 1 H-NMR, 13 C-NMR and MS spectra of the novel compounds were in agreement with the assigned structures [19][20][21]. No unacceptable side reactions were observed.…”

Section: Chemistrysupporting

confidence: 81%

Novel 4-thiazolidinone derivatives bearing imidazo[2,1- b]thiazole moiety: design, synthesis, and antiviral activity evaluation

BAŞOĞLU ÜNAL,

CİMOK,

DİNCEL

et al. 2023

jrp

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This paper aimed to synthesize novel compounds carrying imidazo[2,1-b]thiazole nucleus, characterize them with various spectroscopic methods, moreover evaluate their antiviral activity. All novel derivatives were evaluated for their antiviral activity against Coxsackie B4 virus, Respiratory syncytial virus, Influenza A/H1N1 virus, Influenza A/H3N2, and Influenza B virus. Some of the compounds, particularly the derivatives carrying 4methylphenyl and 4-bromophenyl moiety, exhibited higher and comparable activities against both Coxsackie B4 and Respiratory syncytial viruses, moreover the compounds with N-propyl and N-butyl at thiazolidinone ring showed high antiviral activities against Influenza Influenza A/H3N2 viruses. Consequently, the results obtained from in vitro assay data shed light on improving novel antiviral.

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“…The IR, 1 H-NMR, 13 C-NMR and MS spectra of the novel compounds were in agreement with the assigned structures [19][20][21]. No unacceptable side reactions were observed.…”

Section: Chemistrysupporting

confidence: 81%

Novel 4-thiazolidinone derivatives bearing imidazo[2,1- b]thiazole moiety: design, synthesis, and antiviral activity evaluation

BAŞOĞLU ÜNAL,

CİMOK,

DİNCEL

et al. 2023

jrp

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“…(Basoglu & Ulusoy Guzeldemirci, 2020; Mohamed & Abdel‐wahab, 2012; Shareef et al, 2020). Along with our work (Basoglu et al, 2021; Başoğlu‐ünal et al, 2023; Dincel et al, 2020; Gursoy et al, 2020; Ulusoy Guzeldemirci et al, 2019; Ulusoy Guzeldemirci et al, 2017) regarding both scaffolds, many approved drug molecules by FDA are on the market such as Triapine, thioacetazone, methisazone (Dincel et al, 2021), and levamisole (Basoglu et al, 2021) which carry either thiosemicarbazide or imidazo[2,1‐ b ]thiazole moiety. Levamisole was approved for the first time as an anticancer drug with an imidazo[2,1‐ b ]thiazole structure (Basoglu et al, 2021).…”

Section: Introductionsupporting

confidence: 74%

A newly synthesized thiosemicarbazide derivative trigger apoptosis rather than necroptosis on HEPG2 cell line

Başoğlu‐Ünal,

Becer,

Ensarioğlu

et al. 2023

Chem Biol Drug Des

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Thiosemicarbazide derivatives have been the focus of scientists owing to their broad biological activities such as anticancer, antimicrobial, and anti‐inflammatory. Herein, we designed and synthesized a new thiosemicarbazide derivative (TS‐1) and evaluated its antiproliferative potential against the human hepatocellular carcinoma cell line (HEPG2) and human umbilical vein endothelial cell line (ECV‐304). Also, it was aimed to investigate the necroptotic and apoptotic cell death effects of TS‐1 in HEPG2 cells, and these effects were supported by molecular docking. The new synthesized compound structure was characterized using various spectroscopic methods such as FT‐IR, 1H‐NMR, 13C‐NMR, and elemental analysis. The cytotoxic activity of the tested compound was measured by the MTT assay. Apoptotic and necroptotic properties of the TS‐1 were evaluated by indirect immunoperoxidase method using antibodies against Ki‐67, Bax, Bcl‐2, caspase‐3, caspase‐8, caspase‐9, RIP3, and RIPK1. Apoptotic and necroptotic effects of TS‐1 were supported by molecular docking. Compound TS‐1 was synthesized as a pure compound with a high yield. The effective value of TS‐1 was 10 μM in HEPG2 cells. TS‐1 did not show any cytotoxic effect on ECV‐304. Caspase‐3 and RIPK1 immunoreactivities were significantly increased in HEPG2 cells after being treated with TS‐1. As the results of the molecular docking studies, the molecular docking showed that the TS‐1 exhibits H‐bond interaction with various significant amino acid residues in the active site of both RIPK1. It could be concluded that TS‐1 could be a promising novel therapeutic agent by inducing apoptosis rather than necroptosis in HEPG2 cells.

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“…The IR values belonging to the mentioned carbonyl groups of 5a , c , f and 6a ‐ e were in agreement with the literature. [ 49–52 ]…”

Section: Resultsmentioning

confidence: 99%

“…The IR values belonging to the mentioned carbonyl groups of 5a,c,f and 6a-e were in agreement with the literature. [49][50][51][52] According to the literature, N-H proton belonging the hydrazide group of compound 4 was observed in 9.48 ppm as a broad singlet and also the NH 2 protons were observed in 3.45 ppm as a broad singlet. When the results obtained from compound 5a,c,f were examined, it was determined that the peaks of NH 2 protons were disappeared and totally three diverse N-H proton were observed in the region of 10.30-8.16 ppm.…”

Section: Chemistrymentioning

confidence: 99%

See 1 more Smart Citation

Design, synthesis, characterization and antimicrobial evaluation of some novel hydrazinecarbothioamide, 4‐thiazolidinone and 1,2,4‐triazole‐3‐thione derivatives

Dincel

Ulusoy‐Güzeldemirci

Şatana

et al. 2020

Journal of Heterocyclic Chem

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A series of novel hydrazinecarbothioamide (5a,c,f), 4‐thiazolidinone (6a‐e), and 1,2,4‐triazole‐3‐thione (7a‐d) were designed and synthesized. The structural elucidations of the novel compounds were performed by IR, 1H‐NMR, 13C‐NMR, mass and elemental analysis. All novel derivatives were evaluated for their antibacterial and antifungal activities against nine diverse microorganisms. According to the biological activity studies of the compounds, 6d, 7c and 7d displayed hope promising antibacterial activity. Furthermore, 6d displayed potent antifungal activity. Consequently, the obtained results revealed that 6d, 7c and 7d present a leading structure for future drug development due to its straightforward synthesis and relevant bioactivity.

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Synthesis and Aldose Reductase Inhibitory Effect of Some New Hydrazinecarbothioamides and 4-Thiazolidinones Bearing an Imidazo[2,1-b]Thiazole Moiety

Cited by 7 publications

References 51 publications

Novel 4-thiazolidinone derivatives bearing imidazo[2,1- b]thiazole moiety: design, synthesis, and antiviral activity evaluation

Novel 4-thiazolidinone derivatives bearing imidazo[2,1- b]thiazole moiety: design, synthesis, and antiviral activity evaluation

A newly synthesized thiosemicarbazide derivative trigger apoptosis rather than necroptosis on HEPG2 cell line

Design, synthesis, characterization and antimicrobial evaluation of some novel hydrazinecarbothioamide, 4‐thiazolidinone and 1,2,4‐triazole‐3‐thione derivatives

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