Synthesis and biological evaluation of phenyl-amino-pyrimidine and indole/oxindole conjugates as potential BCR-ABL inhibitors

Rahim, Afidah Abdul; Syed, Rabbani; Poornachandra, Y.; Malik, M. Shaheer; Reddy, Ch. Venkata Ramana; Alvala, Mallika; Boppana, Kiran; Sridhar, B.; Amanchy, Ramars; Kamal, Ähmed

doi:10.1007/s00044-019-02318-4

Cited by 6 publications

(1 citation statement)

References 63 publications

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“…Incorporation of amide into N‐1 position of isatin moiety was also tolerated and hybrids 10 (GI 50 : <0.02–0.21 μM, SRB assay) exhibited promising activity against MCF‐7 cancer cells and molecular docking studies showed that these hybrids could inhibit EGFR effectively. [ 44–47 ] The SAR demonstrated that chloro at R 1 position and methyl at R 2 position could boost up the activity. Particularly, the activity of hybrids 10a–d (GI 50 : <0.02 μM, total growth inhibition [TGI]: 0.07–0.09 μM) was on the same level with that of doxorubicin (GI 50 : <0.02 μM, TGI: 0.02 μM) against MCF‐7 cancer cells.…”

Section: Isatin–coumarin Hybridsmentioning

confidence: 99%

Recent advances in isatin hybrids as potential anticancer agents

Ding

Zhou

Zeng

2020

Archiv der Pharmazie

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The isatin framework is a useful template for the development of novel anticancer agents. This is exemplified by the fact that several isatin‐based anticancer agents, such as semaxanib, sunitinib, nintedanib, and hesperadin, are already in use or under clinical trials for the treatment of diverse kinds of cancers. Isatin‐based hybrids could be obtained by incorporating other anticancer pharmacophores into the isatin skeleton and they have the potential to overcome drug resistance with reduced side effects. Thus, isatin‐based hybrids may provide attractive scaffolds for the development of novel anticancer agents. This review covers the recent advances of isatin‐based hybrids with anticancer activity, covering articles published between 2001 and 2019. The anticancer activities of these molecules and the structure–activity relationships are also discussed. The purpose of this review article is to set up the direction for the design and development of isatin‐based hybrids with high efficacy and low toxicity.

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Section: Isatin–coumarin Hybridsmentioning

confidence: 99%

Recent advances in isatin hybrids as potential anticancer agents

Ding

Zhou

Zeng

2020

Archiv der Pharmazie

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Palladium‐Catalyzed Regioselective C4 Functionalization of Indoles with Quinones

et al. 2022

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A synthetic strategy for the installation of diversely functionalized quinones at the C4 position of indoles is developed via palladium-catalyzed CÀ H and double CÀ H functionalization. This synthetic protocol provides a rapid route to a variety of 4-quinonylindoles via the direct coupling of 3-formylindoles with quinones. Furthermore, this synthetic methodology also efficiently affords biologically interesting bis(indol-4yl)quinones in good yields by direct one-pot double CÀ H activation of 3-formylindoles with the corresponding quinones.

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Synthesis and Characterization of Telmisartan‐Derived Cell Death Modulators to Circumvent Imatinib Resistance in Chronic Myeloid Leukemia

et al. 2020

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New strategies to eradicate cancer stem cells in chronic myeloid leukemia (CML) include a combination of imatinib with peroxisome proliferator‐activated receptor gamma (PPARγ) ligands. Recently, we identified the partial PPARγ agonist telmisartan as effective sensitizer of resistant K562 CML cells to imatinib treatment. Here, the importance of the heterocyclic core on the cell death‐modulating effects of the telmisartan‐derived lead 4′‐((2‐propyl‐1H‐benzo[d]imidazol‐1‐yl)methyl)‐[1,1′‐biphenyl]‐2‐carboxylic acid (3 b) was investigated. Inspired by the pharmacodynamics of HYL‐6d and the selective PPARγ ligand VSP‐51, the benzimidazole was replaced by a carbazole or an indole core. The results indicate no correlation between PPARγ activation and sensitization of resistant CML cells to imatinib. The 2‐COOH derivatives of the carbazoles or indoles achieved low activity at PPARγ, while the benzimidazoles showed 60‐100 % activation. Among the 2‐CO2CH3 derivatives, only the ester of the lead (2 b) slightly activated PPARγ. Sensitizing effects were further observed for this non‐cytotoxic 2 b (80 % cell death), and to a lesser extent for the lead 3 b or the 5‐Br‐substituted ester of the benzimidazoles (5 b).

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Synthesis and biological evaluation of phenyl-amino-pyrimidine and indole/oxindole conjugates as potential BCR-ABL inhibitors

Cited by 6 publications

References 63 publications

Recent advances in isatin hybrids as potential anticancer agents

Recent advances in isatin hybrids as potential anticancer agents

Palladium‐Catalyzed Regioselective C4 Functionalization of Indoles with Quinones

Synthesis and Characterization of Telmisartan‐Derived Cell Death Modulators to Circumvent Imatinib Resistance in Chronic Myeloid Leukemia

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