Synthesis and evaluation of pyrazolidine derivatives as dipeptidyl peptidase IV (DP-IV) inhibitors

Ahn, Jin Hee; Kim, Jin Ah; Kim, Hye-Min; Kwon, Hyuk-Man; Huh, Sun-Chul; Rhee, Sang Dal; Kim, Kwang-Rok; Yang, Sung-Don; Park, Sung-Dae; Lee, Jae Mok; Kim, Sung Soo; Cheon, Hyae Gyeong

doi:10.1016/j.bmcl.2005.01.020

Cited by 36 publications

(5 citation statements)

References 26 publications

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“…Since pyrazolidines show significant activity in the field of antitumor medicine, 20 we investigated the potential bioactivities of the products. Their cytotoxicities were tested using A549 lung cancer cells, HepG2 liver cancer cells, MCF-7 breast cancer cells, and CFPAC-1 human pancreatic cancer cells.…”

Section: Resultsmentioning

confidence: 99%

Copper(i)-catalyzed asymmetric [3 + 2] cycloaddition of N-ester acylhydrazones and β-trifluoromethyl-α,β-unsaturated ketones

et al. 2022

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Section: Resultsmentioning

confidence: 99%

Copper(i)-catalyzed asymmetric [3 + 2] cycloaddition of N-ester acylhydrazones and β-trifluoromethyl-α,β-unsaturated ketones

et al. 2022

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“…Pyrazolidines have been widely studied as fungicides, herbicides, antiinflammatories, antibacterials, anesthetics, and anticonvulsants [115,116]. N- …”

Section: Pyrazolidinementioning

confidence: 99%

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

Beagle

2015

Topics in Heterocyclic Chemistry

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Application of benzotriazole methodology for the preparation of nitrogen-containing heterocyclic compounds is summarized in this review. The characteristic advantages of benzotriazole are first briefly considered followed by an overview of its use in the synthesis of heterocycles organized by the ring size. Finally, the use of benzotriazole in the synthesis of bicyclic systems is showcased in only selected examples.

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“…Then, pyrazolidines are N-heterocyclic compounds with an N-N single bond. The research on the cytotoxic activity of pyrazolidine has become a hot topic [15][16][17]. Interestingly, two important scaffold combination may show good biological activity.…”

Section: Introductionmentioning

confidence: 99%

LFZ-4-46, a tetrahydroisoquinoline derivative, induces apoptosis and cell cycle arrest via induction of DNA damage and activation of MAPKs pathway in cancer cells

Huang

Zhu

et al. 2021

Anti-Cancer Drugs

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LFZ-4-46, that is [2-hydroxy-1-phenyl-1,5,6,10b-tetrahydropyrazolo(5,1-a) isoquinolin-3(2 H )-yl](phenyl) methanone, a tetrahydroisoquinoline derivative with a pyrazolidine moiety, was synthetically prepared. The anti-cancer mechanism of the compound has not been clarified yet. In this study, the anticancer effects and potential mechanisms of LFZ-4-46 on human breast and prostate cancer cells were explored. (a) 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazoliumbromide assay was first performed to detect the effects of LFZ-4-46 on the viability of human cancer cells. (b) Comet assay was utilized to evaluate DNA damage. (c) Cell cycle, apoptosis and mitochondrial membrane potential were detected by flow cytometry. (d) The expression of relative proteins was detected by western blotting assay. LFZ-4-46 significantly inhibited the viability of cancer cells in a time- and dose-dependent manner and had no obviously inhibitory effect on the viability of mammary epithelial MCF-10A cells. Mechanistic studies demonstrated that LFZ-4-46-induced cell apoptosis and cycle arrest were mediated by DNA damage. It caused DNA damage through activating γ-H2AX and breaking DNA strands. Further studies showed that mitogen-activated protein kinasess pathway was involved in these activated several key molecular events. Finally, LFZ-4-46 showed a potent antitumor effect in vivo . These results suggest that LFZ-4-46 may be a potential lead compound for the treatment of breast and prostate cancer.

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Synthesis and evaluation of pyrazolidine derivatives as dipeptidyl peptidase IV (DP-IV) inhibitors

Cited by 36 publications

References 26 publications

Copper(i)-catalyzed asymmetric [3 + 2] cycloaddition of N-ester acylhydrazones and β-trifluoromethyl-α,β-unsaturated ketones

Copper(i)-catalyzed asymmetric [3 + 2] cycloaddition of N-ester acylhydrazones and β-trifluoromethyl-α,β-unsaturated ketones

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

LFZ-4-46, a tetrahydroisoquinoline derivative, induces apoptosis and cell cycle arrest via induction of DNA damage and activation of MAPKs pathway in cancer cells

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