Related Experiment Video
Updated: Mar 18, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Synthesis and biological evaluation of N(9)-substituted harmine derivatives as potential anticancer agents
Hongtao Du1, Shan Tian2, Juncheng Chen2
1Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, Shaanxi Province, PR China; College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, PR China.
Abstract:
A series of N(9)-substituted harmine derivatives were synthesized and evaluated for their anticancer activity on a panel of cancer cell lines, their apoptosis induction and their cell cycle effects. The results showed that N(9)-substituted harmine derivatives had anticancer effects. In particular, N(9)-haloalkyl derivatives 9a-9c and N(9)-acyl harmine derivatives 11c and 11d, with IC50 values less than 1μM, were more potent than doxorubicin against A-549 and/or MCF-7 cell lines. Moreover, structure-activity relationships (SARs) indicated that introducing a haloalkyl or benzenesulfonyl group in the N(9)-position of harmine could significantly increase the anticancer activity. The most active compound (11d) caused cell cycle arrest in the G2/M phase, and induced cell apoptosis in a dose-dependent manner.
More Related Videos
Related Concept Videos
Physical Properties of Amines
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Nomenclature of Aryl and Heterocyclic Amines
2° Amines to N-Nitrosamines: Reaction with NaNO2
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
Mutagenicity and Carcinogenicity

