Synthesis and Biological Activity Research of 4-Substitued-1-(2-methyl-6-(pyridin-3-yl)-nicotinoyl) Semicarbazides

胡鸿雨,; 吴俊,; 袁建锋,; 王珍妮,; 李晨帆,; 严晓阳,; 方美娟,; 赵胜贤,

doi:10.6023/cjoc201902033

Cited by 5 publications

(2 citation statements)

References 3 publications

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“…Interestingly, we found that the introduction of bicyclic aromatic rings, such as naphthalyl and quinoline groups, into the N ’-methylene position of indoles Nur77 modulators can effectively improve the anti-tumor activity of the target compounds [ 19 ]. Over the past few years, we found that some heterocyclic urea/thiourea derivatives have a wide range of anti-tumor activities ( Scheme 1 ) [ 18 , 22 , 23 ]. As part of our ongoing study, here we synthesized a series of naphthalene pyridine urea/thiourea derivatives, which exhibit significant inhibitory effects on a variety of tumor cells, especially in gastric cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of 1-(2-(6-Methoxynaphthalen-2-yl)-6-methylnicotinoyl)-4-Substituted Semicarbazides/Thiosemicarbazides as Anti-Tumor Nur77 Modulators

Huang

Cao

et al. 2022

Molecules

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Nur77 is an orphan nuclear receptor that participates in the occurrence and development of a variety of tumors. Many agonists of Nur77 have been reported to have significant anticancer effects. Our previous studies have found that the introduction of bicyclic aromatic rings, such as naphthalyl and quinoline groups, into the N’-methylene position of indoles’ Nur77 modulators can effectively improve the anti-tumor activity of the target compounds. Following our previous studies, a series of novel 1-(2-(6-methoxynaphthalen-2-yl)-6-methylnicotinoyl)-4-substituted semicarbazide/thiosemicarbazide derivatives 9a–9w were designed and synthesized in four steps from 6-methoxy-2-acetonaphthone and N-dimethylformamide dimethylacetal. All compounds were characterized by 1H-NMR, 13C-NMR and HRMS, and their anti-tumor activity on various cancer cell lines such as A549, HepG2, HGC-27, MCF-7 and HeLa are also evaluated. From the series of compounds, 9h exhibited the most potent anti-proliferative activity against several cancer cells. Colony formation and cell cycle experiments showed that compound 9h inhibited cell growth and arrested the cell cycle. Additionally, 9h leads to the cleavage of PARP. We initially explored the mechanism of 9h-induced apoptosis and found that compound 9h can upregulate Nur77 expression and triggered Nur77 nuclear export, indicating the occurrence of Nur77-mediated apoptosis. These results suggested that 9h may be a promising anti-tumor leading compound for the further research.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of 1-(2-(6-Methoxynaphthalen-2-yl)-6-methylnicotinoyl)-4-Substituted Semicarbazides/Thiosemicarbazides as Anti-Tumor Nur77 Modulators

Huang

Cao

et al. 2022

Molecules

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“…Recently, we investigated various urea/thiourea derivatives as potential antitumor agents [16][17][18][19][20]. It was found in our previous studies that indole-substituted urea derivatives showed good antitumor activity [20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activity of 2-Arylidene-N-(quinolin-6-yl)hydrazine-1-carboxamides

Zhao

Cao

Cui

et al. 2020

Journal of Chemistry

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A series of 2-arylidene-N-(quinolin-6-yl)hydrazine-1-carboxamides 5a–5o were synthesized and characterized. The synthesized compounds (5a–5o) were screened in vitro against three breast cancer cell lines: SKBR3, MDA-MB-231, and MCF-7 cancer cell lines by the MTT assay. According to MTT results, compounds 5k and 5l showed better antiproliferative activities over MCF-7 cell lines with IC50 values of 8.50 and 12.51 μM. Colony formation assay indicated 5k/5l treatment obviously inhibited the growth of MCF-7 cells and 5k/5l-induced cell cycle was arrested in the G2-M phase. Moreover, 5k/5l significantly increased the level of cleaved PARP and induced the apoptosis in MCF-7 cells. In addition, compared to Hela cells, MCF-7 cells were more sensitive to 5k/5l treatment.

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Synthesis of new 1,2,4‐triazole–(thio)semicarbazide hybrid molecules: Their tyrosinase inhibitor activities and molecular docking analysis

Gültekin

Bekircan

Kolcuoğlu

et al. 2021

Archiv der Pharmazie

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Tyrosinase inhibition is very important in controlling melanin synthesis. If melanin synthesis is not controlled in metabolism, an unwanted increase in melanin synthesis occurs. As melanin plays a role in the formation of skin color, its unusual levels cause some skin disorders such as pregnancy scars, age spots, and especially skin cancer (melanoma). However, the tyrosinase activity is also related to Parkinson's disease and some neurodegenerative diseases. For all these reasons, the medicinal as well as the cosmetic industries focus on research on tyrosinase inhibitors for the treatment of skin disorders and some neurodegenerative diseases. In this study, 32 new 1,2,4‐triazole–(thio)semicarbazide hybrid molecules (6a–p and 7a–p) were synthesized, starting from 4‐amino‐1‐pentyl‐3‐phenyl‐1H‐1,2,4‐triazole‐5(4H)‐one. These compounds were evaluated for their inhibitory activity against mushroom tyrosinase. The results indicated that 6h, 6m, 6n, and 6p exhibited the most effective inhibitory activity, with IC50 values of 0.00162 ± 0.0109, 0.00166 ± 0.0217, 0.00165 ± 0.019, and 0.00197 ± 0.0063 μM, respectively, compared with kojic acid as the reference drug (IC50 = 14.09 ± 0.02 μM). Also, molecular docking analyses were performed to suggest possible binding poses for the ligands. As a result, derivatives 6h, 6m, 6n, and 6p can be used as promising tyrosinase inhibitor candidates in the medicinal, cosmetics, or food industries.

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Synthesis and Biological Activity Research of 4-Substitued-1-(2-methyl-6-(pyridin-3-yl)-nicotinoyl) Semicarbazides

Cited by 5 publications

References 3 publications

Synthesis and Biological Evaluation of 1-(2-(6-Methoxynaphthalen-2-yl)-6-methylnicotinoyl)-4-Substituted Semicarbazides/Thiosemicarbazides as Anti-Tumor Nur77 Modulators

Synthesis and Biological Evaluation of 1-(2-(6-Methoxynaphthalen-2-yl)-6-methylnicotinoyl)-4-Substituted Semicarbazides/Thiosemicarbazides as Anti-Tumor Nur77 Modulators

Synthesis and Biological Activity of 2-Arylidene-N-(quinolin-6-yl)hydrazine-1-carboxamides

Synthesis of new 1,2,4‐triazole–(thio)semicarbazide hybrid molecules: Their tyrosinase inhibitor activities and molecular docking analysis

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