title: Synthesis and anticancer potential of certain novel 2-oxo-N'-(2-oxoindolin-3-ylidene)-2H-chromene-3-carbohydrazides.
abstract: Treatment of ethyl 3-hydrazinyl-3-oxopropanoate (6) with indoline-2,3-dione derivatives 7a-g gave ethyl 3-oxo-3-(2-(2-oxoindolin-3-ylidene)hydrazinyl)propanoates 8a-g which were allowed to react with the appropriate salicyaldehyde 9a and/or 9b to furnish the chromene-based hydrazones 10a-i. Compounds 10a-i displayed a significant activity against HT-29 colon cancer cell line and a moderate activity against leukemia K562 cell line. Compound 10f emerged as the most active congener toward HT-29 colon cancer cell line with IC₅₀ = 7.98 ± 0.05 μM whereas compound 10c exhibited the best antiproliferative activity against leukemia K562 cell line with IC₅₀ = 9.44 ± 0.02 μM. Moreover, compound 1e showed 87.81 ± 7% inhibition of side population (SP) HT-29 colon cancer stem cells.
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia; Department of Applied Organic Chemistry, National Research Center, Dokki, Cairo 12622, Egypt. Electronic address: hatem_741@yahoo.com.
authors.forename: Hatem A
authors.initials: HA
authors.lastname: Abdel-Aziz
authors.forename: Tilal
authors.initials: T
authors.lastname: Elsaman
authors.forename: Abdullah
authors.initials: A
authors.lastname: Al-Dhfyan
authors.forename: Mohamed I
authors.initials: MI
authors.lastname: Attia
authors.forename: Khalid A
authors.initials: KA
authors.lastname: Al-Rashood
authors.forename: Abdul-Rahman M
authors.initials: AR
authors.lastname: Al-Obaid
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D019073:HT29 Cells; D006801:Humans; D006834:Hydrazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D020014:K562 Cells; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001578:Benzopyrans; D006834:Hydrazines
keywords: Chromene-2-ones; Colorectal cancer; Hydrazides/hydrazones; Indoline-2,3-dione; Ring-opening; Side population (SP) cells