Discovery of N-(1,3,4-thiadiazol-2-yl)benzamide derivatives containing a 6,7-methoxyquinoline structure as novel EGFR/HER-2 dual-target inhibitors against cancer growth and angiogenesis

Li, Xinyang; Wang, De-pu; Li, Shuai; Xue, Wen-han; Qian, Xin-hua; Liu, Kai-li; Lin, Qi-qi; Dong, Gang; Meng, Fan‐hao; Jian, Lingyan

doi:10.1016/j.bioorg.2021.105469

Cited by 11 publications

(3 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Additional research revealed that 70 a could increase the expression of ROS in SK-BR-3 cells and inhibited proliferation by inducing the release of cytochrome c. Moreover, compounds 70 a could reduce the secretion of VEGF and EFGF factors from SK-BR-3 cells (IC 50 : 0.77 μM), which inhibited angiogenesis and tube formation. [142] 12.9 Quinoxaline Benzopyrazine is commonly termed quinoxaline. It is a complex heterocyclic ring consisting of a benzene ring fused with a pyrazine scaffold.…”

Section: Pyrazolinementioning

confidence: 99%

Nitrogen‐Containing Heterocyclic Scaffolds as EGFR Inhibitors: Design Approaches, Molecular Docking, and Structure‐Activity Relationships

Pal¹,

Teli²,

Matada³

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

proved to be the magical weapon in designed and discovery of synthetic molecules as they acquired comprehensive range of pharmacological properties. In recent year (2018-2022) Nheterocyclic derivatives were uncovered as the potential EGFR TKIs. The present review summarised the research progress of EGFR TKIs to dazed the limitations of currently accessible drugs by consecrating, anatomy, mutation of EGFR, and its role in different types of cancer. The review highlights the medicinal chemistry prospective emphasising about the designing strategies, docking studies, biological evaluation, selectivity and structural activity relationship of N-heterocyclic compounds. Our review will support the medicinal chemists in direction for the development of novel N-heterocyclic based EGFR TKIs.

show abstract

Section: Pyrazolinementioning

confidence: 99%

Nitrogen‐Containing Heterocyclic Scaffolds as EGFR Inhibitors: Design Approaches, Molecular Docking, and Structure‐Activity Relationships

Pal¹,

Teli²,

Matada³

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…Kardile et al reported the in vitro screening, molecular docking, and absorption, distribution, metabolism, and excretion (ADME) predictions of quinolone derivatives . The derivatives with a quinoline core are also known as potent tubulin assembly inhibitors, mutant epidermal growth factor receptor (EGFR) inhibitors targeting resistance in lung cancer cells, anti-tubulin agents targeting the colchicine binding site, potential anti-hepatoma agents, and various other anticancer activities; − hence, we intend to synthesize new quinoline derivatives and screen them for their activity against the breast cancer 3ERT protein. The synthesis of biaryls involving carbon–carbon bond formation through palladium-mediated Suzuki–Miyaura cross-coupling plays a key role in the synthetic chemistry to build complex molecules from simple precursors since the formation of biaryls using Suzuki–Miyaura coupling is the most reliable and efficient method .…”

Section: Introductionmentioning

confidence: 99%

Palladium-Mediated Synthesis of 2-([Biphenyl]-4-yloxy)quinolin-3-carbaldehydes through Suzuki–Miyaura Cross-Coupling and Their in Silico Breast Cancer Studies on the 3ERT Protein

et al. 2023

View full text Add to dashboard Cite

A series of novel quinoline appended biaryls have been synthesized (5a−5o) by reacting various substituted boronic acids (4e−4h) with various substituted 2-(4-bromophenoxy)quinolin-3-carbaldehydes (3a−3d) through carbon−carbon bond formation. Effects of various quinoline appended biaryls (5a−5o) on the breast cancer protein 3ERT are moderate to high, as found by in silico molecular docking studies. Comparatively, all quinoline appended biaryls (5a−5o) 5h show better efficacy with a binding energy of −9.39 kcal/mol, and hydrogen bonds are Thr347, Glu353, and Arg394 in the binding pocket. Conclusively, the final novel quinoline appended biaryls (5a−5o) have been confirmed with all the spectral studies, and their efficacy has been validated with in silico studies.

show abstract

“…A series of amide derivatives of 5-aryl substituted 1,3,4-thiadiazole-2-amine were developed as micromolar inhibitors of the focal adhesion kinase (FAK) by targeting the ATP-binding pocket [17]. The antitumor capacity of 1,3,4-thiadiazole-2-amine derivatives is also related to their potential to inhibit topoisomerase II [18], glutaminase [19], histone deacetylase [20], Abl kinase [21] or the human epidermal growth factor receptor [22]. A series of representative 1,3,4-thiadiazole-2-amine derivatives are presented in Figure 2.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,3,4-Thiadiazole Derivatives and Their Anticancer Evaluation

Stecoza,

Nitulescu,

Draghici

et al. 2023

IJMS

View full text Add to dashboard Cite

Thiadiazole derivatives have garnered significant attention in the field of medicinal chemistry due to their diverse pharmacological activities, including anticancer properties. This article presents the synthesis of a series of thiadiazole derivatives and investigates their chemical characterization and potential anticancer effects on various cell lines. The results of the nuclear magnetic resonance (NMR) analyses confirmed the successful formation of the target compounds. The anticancer potential was evaluated through in silico and in vitro cell-based assays using LoVo and MCF-7 cancer lines. The assays included cell viability, proliferation, apoptosis, and cell cycle analysis to assess the compounds’ effects on cancer cell growth and survival. Daphnia magna was used as an invertebrate model for the toxicity evaluation of the compounds. The results revealed promising anticancer activity for several of the synthesized derivatives, suggesting their potential as lead compounds for further drug development. The novel compound 2g, 5-[2-(benzenesulfonylmethyl)phenyl]-1,3,4-thiadiazol-2-amine, demonstrated good anti-proliferative effects, exhibiting an IC50 value of 2.44 µM against LoVo and 23.29 µM against MCF-7 after a 48-h incubation and little toxic effects in the Daphnia test.

show abstract

Discovery of N-(1,3,4-thiadiazol-2-yl)benzamide derivatives containing a 6,7-methoxyquinoline structure as novel EGFR/HER-2 dual-target inhibitors against cancer growth and angiogenesis

Cited by 11 publications

References 30 publications

Nitrogen‐Containing Heterocyclic Scaffolds as EGFR Inhibitors: Design Approaches, Molecular Docking, and Structure‐Activity Relationships

Nitrogen‐Containing Heterocyclic Scaffolds as EGFR Inhibitors: Design Approaches, Molecular Docking, and Structure‐Activity Relationships

Palladium-Mediated Synthesis of 2-([Biphenyl]-4-yloxy)quinolin-3-carbaldehydes through Suzuki–Miyaura Cross-Coupling and Their in Silico Breast Cancer Studies on the 3ERT Protein

Synthesis of 1,3,4-Thiadiazole Derivatives and Their Anticancer Evaluation

Contact Info

Product

Resources

About