Synthesis of Indole-1,3,4-Oxadiazole Based Sulfonyl 1,2,3-Triazoles as Potent Anticancer and EGFR Inhibitors

Velidandla, Jagan Mohan Reddy; Koppula, Shiva Kumar

doi:10.1134/s1068162023060146

Cited by 4 publications

(1 citation statement)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The issues associated with current medications, such as selectivity, specificity, and multidrug resistance, may be avoided by using molecular hybridization to generate molecular hybrids as anticancer treatments. [29][30][31][32][33] In this study, we designed and synthesized anticancer active imidazo[1,2-a]pyridine-isoquinoline hybrids by using the hybridization technique to link imidazo[1,2-a]pyridine [34][35][36] with isoquinoline [37,38] and then tested them for anticancer and Tyrosine kinase EGFR inhibitory activity in vitro (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Imidazo[1,2‐a]pyridine‐Isoquinoline Derivatives as Potent EGFR Inhibiting Anticancer Agents

Gunuguntla,

Hanumantharayappa,

Kumar Koppula

2024

ChemistrySelect

View full text Add to dashboard Cite

Herein, we synthesized some new imidazo[1,2‐a]pyridine‐isoquinoline hybrids (8 a–8 x) and investigated their anticancer activity on two human breast cancer cell lines, namely MCF‐7 and MDA‐MB231. Generally, most of them displayed higher activity on both breast cell lines than the reference drug. Specifically, compounds (2,6‐difluorophenyl)(6‐methoxy‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐3,4‐dihydroisoquinolin‐2(1H)‐yl)methanone, (6‐methoxy‐1‐(2‐phenyl imidazo[1,2‐a]pyridin‐3‐yl)‐3,4‐dihydroisoquinolin‐2(1H)‐yl)(6‐methoxy pyridin‐3‐yl)methanone, (6‐methoxy‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐3,4‐dihydroisoquinolin‐2(1H)‐yl)(pyrimidin‐5‐yl) methanone, 6‐methoxy‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐2‐(phenylsulfonyl)‐1,2,3,4‐tetrahydro isoquinoline, 6‐methoxy‐1‐(2‐phenyl imidazo[1,2‐a]pyridin‐3‐yl)‐2‐tosyl‐1,2,3,4‐tetrahydroisoquinoline, and 6‐methoxy‐2‐((4‐methoxyphenyl)sulfonyl)‐1‐(2‐phenylimidazo[1,2‐a] pyridin‐3‐yl)‐1,2,3,4‐tetrahydroisoquinoline showed higher activity against tested cancer cell lines as compared to the erlotinib. The ability of potent compounds to inhibit the tyrosine kinase EGFR was then studied and found that compounds (6‐methoxy‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐3,4‐dihydroisoquinolin‐2(1H)‐yl)(pyrimidin‐5‐yl) methanone, 6‐methoxy‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐2‐tosyl‐1,2,3,4‐tetra hydroisoquinoline, and 6‐methoxy‐2‐((4‐methoxyphenyl) sulfonyl)‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐1,2,3,4‐tetrahydro isoquinoline exhibited promising potency in comparison to the erlotinib. In silico investigations of the most effective compounds were also performed to find interactions with the EGFR receptor that robustly bind to the protein, and energy estimates were in good agreement with the corresponding IC50 values.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of Imidazo[1,2‐a]pyridine‐Isoquinoline Derivatives as Potent EGFR Inhibiting Anticancer Agents

Gunuguntla,

Hanumantharayappa,

Kumar Koppula

2024

ChemistrySelect

View full text Add to dashboard Cite

show abstract

Synthesis of novel pyrido[3,4‐d]pyrimidine‐thiazolidione‐1,2,4‐oxadiazoles as potent EGFR targeting anticancer agents

Varaprasadu,

Haridasyam,

Koppula

2024

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

In this study, we designed and synthesized a number of novel pyrido[3,4‐d]pyrimidine‐thiazolidine‐1,2,4‐oxadiazole derivatives and investigated them in vitro for their inhibitory action toward epidermal growth factor receptor (EGFR) kinases and antiproliferative activity against two different cell lines, MCF‐7 and A‐549. When compared to the lead chemicals, 5‐fluorouracil and erlotinib, some of the compounds demonstrated acceptable activity. Among them, the most promising compounds 4d and 4e displayed potent anticancer activity against both MCF‐7 and A‐549 cell lines (IC50 values remaining: 1.97 ± 0.28 μM to 8.14 ± 0.52 μM, respectively); the comparative IC50 values for 5‐fluorouracil and erlotinib in these cell lines were 5.56 ± 0.34 μM, 12.66 ± 0.76 μM, and 3.64 ± 0.49 μM, 9.54 ± 0.75 μM, respectively; as well as excellent kinase inhibitory activities (EGFR: IC50 = 0.34 ± 0.07 μM and 0.42 ± 0.06 μM) were more effective than the conventional drug Erlotinib (IC50 = 0.42 ± 0.02 μM).

show abstract

Design and Synthesis of Some New Quinoxaline-Thiazole-Benzamide Hybrids: In Vitro Anticancer Activity and Their Molecular Docking Studies

Dasari,

Pandiri,

Badithapuram

et al. 2024

Russ J Bioorg Chem

View full text Add to dashboard Cite

Synthesis of Indole-1,3,4-Oxadiazole Based Sulfonyl 1,2,3-Triazoles as Potent Anticancer and EGFR Inhibitors

Cited by 4 publications

References 30 publications

Synthesis of Imidazo[1,2‐a]pyridine‐Isoquinoline Derivatives as Potent EGFR Inhibiting Anticancer Agents

Synthesis of Imidazo[1,2‐a]pyridine‐Isoquinoline Derivatives as Potent EGFR Inhibiting Anticancer Agents

Synthesis of novel pyrido[3,4‐d]pyrimidine‐thiazolidione‐1,2,4‐oxadiazoles as potent EGFR targeting anticancer agents

Design and Synthesis of Some New Quinoxaline-Thiazole-Benzamide Hybrids: In Vitro Anticancer Activity and Their Molecular Docking Studies

Contact Info

Product

Resources

About