Cell cycle arrest and induction of apoptosis of newly synthesized pyranoquinoline derivatives under microwave irradiation

Journal Article · Wed May 01 04:00:00 EDT 2019 · Medicinal Chemistry Research (Print)

DOI:https://doi.org/10.1007/S00044-019-02325-5· OSTI ID:22936196

Youssef, Ayman M. S. ^[1]; Afifi, Tarek H. ^[2]; Mora, Ahmed; El-Agrody, Ahmed M. ^[3]

---

1. King Khalid University, Chemistry Department, Faculty of Science (Saudi Arabia)
2. Taibah University, Chemistry Department, Faculty of Science (Saudi Arabia)
3. Al-Azhar University, Chemistry Department, Faculty of Science (Egypt)

A set of 2-amino-4-aryl-4H-pyrano[3,2-h]quinoline-3-carbonitrile derivatives were prepared via a one-pot, three-component condensation reaction between the substituted hydroxyquinoline derivatives, some aryl and/or hetaryl aldehydes, and malononitrile in an ethanol/piperidine solution in a microwave irradiation environment. The structure of the prepared compounds was instituted on the foundations of their spectral data: IR, {sup 1}H NMR, {sup 13}C NMR, and MS. Four human cancer cell lines, MCF-7, HCT-116, HepG-2, and A549 were utilized to evaluate the antiproliferative properties of the target compounds in comparison to the positive controls, Vinblastine and Colchicine using the MTT viability assay. The cell cycle arrest behavior, detected by propidium iodide as well as the apoptosis induction, which was monitored by the flow cytometer, using the Annexin V-FITC kits, was investigated. The results illustrated that the potent cytotoxic compounds induce cell cycle arrest at the G2/M phases and trigger apoptosis in the different tested cancer cells. Finally, the structure−activity relationship (SAR) study showcases the substitution of some specific groups at the 4-, 6-, and 9-positions in the prepared 2-amino-4H-pyrano[3,2-h]quinoline derivatives, which indicates that the lipophilicity manipulates the ability of these moieties against the diverse cell lines.

• OSTI ID: 22936196
• Journal Information: Medicinal Chemistry Research (Print), Journal Name: Medicinal Chemistry Research (Print) Journal Issue: 5 Vol. 28; ISSN 1054-2523
• Country of Publication: United States
• Language: English

Related Subjects

60 APPLIED LIFE SCIENCES
ALDEHYDES
APOPTOSIS
CARBON 13
CELL CYCLE
CELL FLOW SYSTEMS
COLCHICINE
ETHANOL
HYDROGEN 1
NEOPLASMS
NUCLEAR MAGNETIC RESONANCE
PIPERIDINES
QUINOLINES
VINBLASTINE