Design, Synthesis and Anticancer Activity Studies of Novel Indole-Pyrimidine Biaryl Derivatives

Zhang, Danqing; Liu, Xu; Pang, Xiaowu; Liu, Hong‐Min; Zhang, Qiurong

doi:10.6023/cjo202006054

Cited by 6 publications

(3 citation statements)

References 5 publications

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“…15.81 µM) against MCF-7 cells. [82] The introduction of the second substituents into the pyrimidine motif was also tolerated, and hybrid 45 (IC 50 : 26.78 µM) was as effective as 5-fluorouracil (IC 50 : 24.36 µM) against MCF-7 cells. [83] Additionally, the activity was significantly influenced by the linker between indole and pyrimidine, and hybrids 46a,b (IC 50 : 5.85 and 5.94 µM) were approximately two times more active than sorafenib (IC 50 : 11.84 µM) against MDA-MB-231 cells.…”

Section: Indole-pyrimidine/pyridine Hybridsmentioning

confidence: 99%

The anti‐breast cancer potential of indole/isatin hybrids

Wang,

Huang,

Yuan

et al. 2023

Archiv der Pharmazie

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Breast cancer (BC) is one of the most prevalent malignancies and the major contributor to cancer mortality in women globally, with a high degree of heterogeneity and a dismal prognosis. As drug resistance is responsible for most BC fatalities and advanced BC is currently considered incurable, finding innovative anti‐BC chemotherapeutics is urgently required. Indole and its analog isatin (indole‐1H‐2,3‐dione) are prominent pharmacophores in the development of novel medications, and their derivatives exhibit strong anticancer activities, also against BC. In particular, indole/isatin hybrids exhibit significant potency against BC including multidrug‐resistant forms and excellent selectivity by influencing a variety of biological targets associated with the disease, supplying helpful building blocks for the identification of potential new BC treatment options. This review includes articles from 2020 to the present and provides insights into the in vitro and in vivo anti‐BC potential, molecular mechanisms, and structure–activity relationships (SARs) of indole/isatin hybrids that may be helpful in the development of innovative anti‐BC chemotherapeutics.

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Section: Indole-pyrimidine/pyridine Hybridsmentioning

confidence: 99%

The anti‐breast cancer potential of indole/isatin hybrids

Wang,

Huang,

Yuan

et al. 2023

Archiv der Pharmazie

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“…There are many drugs containing indoles that have been approved by the FDA for the treatment of different human diseases, such as the anticancer drugs Panobinostat (HDAC inhibitor) [ 25 ] and Osimertinib (3rd EGFR tyrosine kinase inhibitor) [ 26 ], and the anti-inflammatory drug Indomethacin [ 27 ]. Therefore, indoles are widely considered as one class of dominant skeletons for the development of novel drugs [ 18 , 22 , 28 , 29 , 30 ]. In addition, indole biaryl structures have been widely used in the discovery of antitumor drugs.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of [1,2,4]Triazolo[1,5-a]pyrimidine Indole Derivatives against Gastric Cancer Cells MGC-803 via the Suppression of ERK Signaling Pathway

Zhang

et al. 2022

Molecules

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[1,2,4]Triazolo[1,5-a]pyrimidine and indole skeletons are widely used to design anticancer agents. Therefore, in this work, a series of [1,2,4]triazolo[1,5-a]pyrimidine indole derivatives were designed and synthesized by the molecular hybridization strategy. The antiproliferative activities of the target compounds H1–H18 against three human cancer cell lines, MGC-803, HCT-116 and MCF-7, were tested. Among them, compound H12 exhibited the most active antiproliferative activities against MGC-803, HCT-116 and MCF-7 cells, with IC50 values of 9.47, 9.58 and 13.1 μM, respectively, which were more potent than that of the positive drug 5-Fu. In addition, compound H12 could dose-dependently inhibit the growth and colony formation of MGC-803 cells. Compound H12 exhibited significant inhibitory effects on the ERK signaling pathway, resulting in the decreased phosphorylation levels of ERK1/2, c-Raf, MEK1/2 and AKT. Furthermore, compound 12 induced cell apoptosis and G2/M phase arrest, and regulated cell cycle-related and apoptosis-related proteins in MGC-803 cells. Taken together, we report here that [1,2,4]triazolo[1,5-a]pyrimidine indole derivatives, used as anticancer agents via the suppression of ERK signaling pathway and the most active compound, H12, might be a valuable hit compound for the development of anticancer agents.

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“…At present, a large number of studies have reported that the photochemical response recognition technique can promote rapid and efficient selectivity between the guest and receptor, promoting the realization of qualitative and quantitative detection of specific ions [ 14 ]. Generally, in the anionic recognition system, amides [ 15 , 16 ], thioureas [ 17 , 18 ], pyridines [ 19 , 20 ], and indoles [ 21 , 22 ] are considered desirable ligands with high sensitivity and selectivity. In addition, cholesteric compounds are of great interest to researchers due to their simple preparation method and mild reaction process, as well as flexible and multifunctional recognition sites in their structures.…”

Section: Introductionmentioning

confidence: 99%

Cholesteric Chiral Molecular Tweezer for Rapid Detection of F− in Food Samples

et al. 2022

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Chiral cholesteric molecular tweezer 7d was synthesized and its influences on changes in the ultraviolet (UV) and fluorescence spectra of various anions were investigated. The results displayed that molecular tweezer 7d selectively recognized F− ions in dimethyl sulfoxide with a detection limit of 5.14 μmol/L, while other anions had little interference. On this basis, a method for the rapid detection of F− ions by host molecular tweezer 7d was established, and the naked-eye detection of F− was realized through the unique yellow color of the complex solution. According to the determination of F− ions in real food samples, it was proved that the established method had good application prospects in F− ion detection.

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Design, Synthesis and Anticancer Activity Studies of Novel Indole-Pyrimidine Biaryl Derivatives

Cited by 6 publications

References 5 publications

The anti‐breast cancer potential of indole/isatin hybrids

The anti‐breast cancer potential of indole/isatin hybrids

Design, Synthesis and Biological Evaluation of [1,2,4]Triazolo[1,5-a]pyrimidine Indole Derivatives against Gastric Cancer Cells MGC-803 via the Suppression of ERK Signaling Pathway

Cholesteric Chiral Molecular Tweezer for Rapid Detection of F− in Food Samples

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