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Updated: Jul 7, 2025
Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Design, Synthesis, Characterisation, and Evaluation of Substituted Quinolin-2-one Derivatives as Possible Anti-lung
Riya Swar1, Prachita Gauns Dessai1, Shivalingrao MamleDesai1
1Department of Pharmaceutical Chemistry, PES's Rajaram and Tarabai Bandekar College of Pharmacy, Ponda, Goa 403 401, India.
Background:
According to 2022, the estimated number of cancer cases in India was found to be 1,461,427. Lung cancers are the leading cause of death among Indian males. Research on cancer has been conducted to develop better treatments that are safe and effective and could be used to diagnose cancer at an early stage. It was found that quinolin-2-one possesses anticancer activity, which led us to synthesize substituted quinolin-2-one derivatives that can provide a longer future to cancer patients and decrease the risk of dying from cancer.
Objective:
This study aimed to carry out the design, synthesis, characterisation, and evaluation of novel substituted quinolin-2-one analogues as possible anti-lung cancer agents.
Methods:
Compound III a/III b on reaction with acids, sodium acetate and ethylchloroacetate, substituted benzaldehyde, phthalic anhydride, and 2N sodium hydroxide yielded compounds IV a/ IV b, V a/ V b, VI a/ VI b, VI c/ VI d, VI e/ VI f, VII a/ VII b, and VIII a/ VIII b, respectively.
Result:
Among all the synthesised derivatives, compound VII a was found to be most potent with a MolDock score of -132.78 as compared to standard drug imatinib (-114.37) and active ligand 4- anilinoquinazoline (-126.71). All the synthesized derivatives showed a good ADME profile, but compound VII a showed the best ADME data among all the synthesised derivatives. All the synthesised compounds were tested for their in vitro anticancer activity against the Hop-62 (human lung cancer) cell line, out of which compound VII a was found to be most potent, with a percent control growth of -51.7% at a concentration of 80 μg/ml, which was in comparable to the positive control, Adriamycin (-70.5%) and standard imatinib (-84.0%).
Conclusion:
Compound VII a showed the highest MolDock score and was most potent against human lung cancer cell line Hop-62.
Insights
Researchers developed novel substituted quinolin-2-one compounds to combat lung cancer, a leading cause of death in Indian males. Compound VII a demonstrated significant potential as an anti-lung cancer agent, showing high potency in preliminary evaluations.
Area of Science:
- Medicinal Chemistry
- Organic Synthesis
- Cancer Research
Background:
- Lung cancer is a leading cause of mortality in Indian males, with over 1.4 million cases estimated in India in 2022.
- Quinolin-2-one derivatives have shown promise as anticancer agents, necessitating further research for improved efficacy and safety.
- Developing novel, effective, and safe cancer treatments is crucial for improving patient outcomes and reducing cancer-related deaths.
Purpose of the Study:
- To design, synthesize, and characterize novel substituted quinolin-2-one analogues.
- To evaluate the potential of these analogues as anti-lung cancer agents.
- To identify lead compounds with enhanced anticancer activity and favorable pharmacokinetic properties.
Main Methods:
- Synthesis of various substituted quinolin-2-one derivatives through multi-step chemical reactions.
- Characterization of synthesized compounds using appropriate analytical techniques.
- In silico evaluation using MolDock scoring and in vitro assessment of anticancer activity against the Hop-62 human lung cancer cell line.
Main Results:
- Compound VII a exhibited the highest MolDock score (-132.78), surpassing the standard drug imatinib (-114.37).
- All synthesized derivatives displayed favorable ADME (Absorption, Distribution, Metabolism, and Excretion) profiles, with compound VII a showing the best data.
- Compound VII a demonstrated significant in vitro anticancer activity against the Hop-62 cell line, showing -51.7% growth inhibition at 80 μg/ml, comparable to Adriamycin and imatinib.
Conclusions:
- Compound VII a emerged as the most potent derivative with the highest MolDock score.
- Compound VII a exhibited significant in vitro anticancer activity against the human lung cancer cell line Hop-62.
- The synthesized quinolin-2-one analogues represent promising candidates for further development as anti-lung cancer therapeutics.
