Synthesis and biological evaluation of thiobenzanilides as anticancer agents

Hu, Wan‐Ping; Yu, Hsin‐Su; Chen, Yan-Ren; Tsai, Yi-Min; Chen, Yin-Kai; Liao, Chao-Cheng; Chang, Long‐Sen; Wang, Jhi-Joung

doi:10.1016/j.bmc.2008.03.003

Cited by 41 publications

(17 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The dihedral angle between the substituted Cp ring (C1-C5) and the pyrazole ring (N1/N2/C11/C12/C13) of 12.0(2) in 6f and 13.1 (2) in 6g are in the range of that of the ferrocenyl-substituted pyrazole (8.20 w 45.36 ) [27,31,32]. The C1-C11 distance 1.459(4) Å of 6g is slightly shorter than that of 6f (1.467(4) Å).…”

Section: Single-crystal Structurementioning

confidence: 99%

See 1 more Smart Citation

Synthesis, single-crystal characterization and preliminary biological evaluation of novel ferrocenyl pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives

Xie¹,

Zhao²,

Su³

et al. 2010

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

Section: Single-crystal Structurementioning

confidence: 99%

“…One characteristic of cancer cells is their highly proliferative nature. Consequently, inhibition of proliferative pathways is considered to be an effective strategy to fight cancer and much attention has recently been paid to the discovery and development of new, more selective anti-cancer agents [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, single-crystal characterization and preliminary biological evaluation of novel ferrocenyl pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives

Xie¹,

Zhao²,

Su³

et al. 2010

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

“…Despite significant advances, which have resulted in notable cure rates for various malignancies, cancer is one of the leading causes of death worldwide [1,2]. Since the inhibition of proliferative pathways is considered as an effective strategy to fight cancer, much attention has recently been devoted to the discovery and development of new, more selective anticancer agents [3,4]. In this respect, the incorporation of heterocyclic residues into perspective pharmaceutical lead candidates constitutes an important strategy which provides activity and safety features.…”

Section: Introductionmentioning

confidence: 99%

“…The critical step for their synthesis is the 2,4,6-trichloro [1,3,5] triazine (TCT)/DMF [22] promoted cyclization of the hydrazine substrates which provided the desired pyrazole derivatives backbone. The in vitro anticancer activities of these compounds were evaluated against three characteristic human cancer cell lines, namely DU145 prostate cancer, A2058 melanoma cancer and MCF-7 breast cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In Vitro Biological Evaluation of Novel Pyrazole Derivatives as Potential Antitumor Agents

Christodoulou

Fokialakis²,

Nam³

et al. 2012

med chem

View full text Add to dashboard Cite

The synthesis of twenty seven novel pyrazole derivatives bearing aryl substituted groups at positions 1 and 3 of the pyrazole structural motif and various functional groups at position 4 is presented. The critical step for their synthesis is the TCT/DMF promoted cyclization of the corresponding hydrazine precursors, which provided the desired pyrazole skeleton. The anticancer properties of the novel pyrazole derivatives were evaluated in vitro against human prostate (DU145), melanoma (A2058) and breast cancer (MCF-7) cell lines. Among the compounds tested, pyrazole 5a and its methoxy derivatives 3d,e were assayed as the most potent, displaying selective activity against the MCF-7 cell line with IC(50) values of 14, 10 and 12 µM respectively. Results herein indicate that the reported backbone represents a promising structural lead for further development as antitumor agents.

show abstract

“…A549 is a lung adenocarcinoma cell line that has been well characterized and is frequently used for molecular cancer biology research. Uncontrolled proliferation is a key feature of cancer cells, and therefore, inhibition of proliferative pathways is an effective approach for cancer therapy [2][3][4] .…”

Section: Introductionmentioning

confidence: 99%

Novel ferrocenyl derivatives exert anti-cancer effect in human lung cancer cells in vitro via inducing G1-phase arrest and senescence

Han

et al. 2013

Acta Pharmacol Sin

View full text Add to dashboard Cite

Aim: To investigate the effects of 7 novel 1-ferrocenyl-2-(5-phenyl-1H-1,2,4-triazol-3-ylthio) ethanone derivatives on human lung cancer cells in vitro and to determine the mechanisms of action. Methods: A549 human lung cancer cells were examined. Cell viability was analyzed with MTT assay. Cell apoptosis and senescence were examined using Hoechst 33258 and senescence-associated-β-galactosidase (SA-β-gal) staining, respectively. LDH release was measured using a detection kit. Cell cycle was analyzed using a flow cytometer. Intracellular ROS level was measured with the 2′,7′-dichlorodihydrofluorescein probe. Phosphorylation of p38 was determined using Western blot. Results: Compounds 5b, 5d, and 5e (40 and 80 µmol/L) caused significant decrease of A549 cell viability, while other 4 compounds had no effect on the cells. Compounds 5b, 5d, and 5e (80 µmol/L) induced G 1 -phase arrest (increased the G 1 population by 22.6%, 24.23%, and 26.53%, respectively), and markedly increased SA-β-gal-positive cells. However, the compounds did not cause nuclear DNA frag mentation and chromatin condensation in A549 cells. Nor did they affect the release of LDH from the cells. The compounds significantly elevated the intracellular ROS level, decreased the mitochondrial membrane potential, and increased p38 phosphorylation in the cells. In the presence of the antioxidant and free radical scavenger N-acetyl-L-cysteine (10 mmol/L), above effects of compounds 5b, 5d, and 5e were abolished. Conclusion: The compounds 5b, 5d, and 5e cause neither apoptosis nor necrosis of A549 cells, but exert anti-cancer effect via inducing G 1 -phase arrest and senescence through ROS/p38 MAP-kinase pathway.

show abstract

Synthesis and biological evaluation of thiobenzanilides as anticancer agents

Cited by 41 publications

References 14 publications

Synthesis, single-crystal characterization and preliminary biological evaluation of novel ferrocenyl pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives

Synthesis, single-crystal characterization and preliminary biological evaluation of novel ferrocenyl pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives

Synthesis and In Vitro Biological Evaluation of Novel Pyrazole Derivatives as Potential Antitumor Agents

Novel ferrocenyl derivatives exert anti-cancer effect in human lung cancer cells in vitro via inducing G1-phase arrest and senescence

Contact Info

Product

Resources

About