BIOMAT Database Logo BIOMAT Database Logo

Synthesis and evaluation of C3 substituted chalcone-based derivatives of 7-azaindole as protein kinase inhibitors. 2020

Malikotsi A Qhobosheane, and Lesetja J Legoabe, and Béatrice Josselin, and Stéphane Bach, and Sandrine Ruchaud, and Richard M Beteck
Centre of Excellence for Pharmaceutical Sciences, North-West University, Potchefstroom, South Africa.

Chalcones are a group of naturally occurring or synthetic compounds which possess a wide range of biological activities. In this paper, a series of twenty-three 7-azaindole-chalcone hybrids (5a-w) were synthesized and evaluated as potential protein kinase inhibitors. Analyses of structure-activity relationships revealed that some of these compounds exhibit significant activity against Haspin kinase, with compounds 5f and 5q exhibiting IC50 values of 0.47 and 0.41 µM, respectively. Furthermore, 5f also inhibits cyclin-dependent kinase 9 (CDK9/CyclinT) in a micromolar potency (IC50  = 2.26 µM). This novel dual-target inhibitor is a promising lead for the development of chemopreventive/chemotherapeutic agents.

UI MeSH Term Description Entries
D007211 Indoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D015195 Drug Design The molecular designing of drugs for specific purposes (such as DNA-binding, enzyme inhibition, anti-cancer efficacy, etc.) based on knowledge of molecular properties such as activity of functional groups, molecular geometry, and electronic structure, and also on information cataloged on analogous molecules. Drug design is generally computer-assisted molecular modeling and does not include PHARMACOKINETICS, dosage analysis, or drug administration analysis. Computer-Aided Drug Design,Computerized Drug Design,Drug Modeling,Pharmaceutical Design,Computer Aided Drug Design,Computer-Aided Drug Designs,Computerized Drug Designs,Design, Pharmaceutical,Drug Design, Computer-Aided,Drug Design, Computerized,Drug Designs,Drug Modelings,Pharmaceutical Designs
D045744 Cell Line, Tumor A cell line derived from cultured tumor cells. Tumor Cell Line,Cell Lines, Tumor,Line, Tumor Cell,Lines, Tumor Cell,Tumor Cell Lines
D047188 Chalcones Derivatives of CHALCONE that are important intermediates in the formation of FLAVONOIDS with anti-fungal, anti-bacterial, anti-inflammatory, and anti-tumor properties. 1,3-Diphenyl-propanediones,1,3-Diphenyl-propenones,1,3-Diphenylpropanediones,1,3-Diphenylpropenones,Chalconoids,1,3 Diphenyl propanediones,1,3 Diphenyl propenones,1,3 Diphenylpropanediones,1,3 Diphenylpropenones
D047428 Protein Kinase Inhibitors Agents that inhibit PROTEIN KINASES. Protein Kinase Inhibitor,Inhibitor, Protein Kinase,Inhibitors, Protein Kinase,Kinase Inhibitor, Protein,Kinase Inhibitors, Protein

Related Publications

Malikotsi A Qhobosheane, and Lesetja J Legoabe, and Béatrice Josselin, and Stéphane Bach, and Sandrine Ruchaud, and Richard M Beteck
Rational Design, Synthesis, and Biological Evaluation of 7-Azaindole Derivatives as Potent Focused Multi-Targeted Kinase Inhibitors.
April 2016, Journal of medicinal chemistry,
Malikotsi A Qhobosheane, and Lesetja J Legoabe, and Béatrice Josselin, and Stéphane Bach, and Sandrine Ruchaud, and Richard M Beteck
Discovering novel 7-azaindole-based series as potent AXL kinase inhibitors.
February 2017, Bioorganic & medicinal chemistry letters,
Malikotsi A Qhobosheane, and Lesetja J Legoabe, and Béatrice Josselin, and Stéphane Bach, and Sandrine Ruchaud, and Richard M Beteck
Discovery of novel 7-azaindole derivatives bearing dihydropyridazine moiety as c-Met kinase inhibitors.
June 2017, European journal of medicinal chemistry,
Malikotsi A Qhobosheane, and Lesetja J Legoabe, and Béatrice Josselin, and Stéphane Bach, and Sandrine Ruchaud, and Richard M Beteck
Synthesis and Evaluation of Coumarin-Chalcone Derivatives as α-Glucosidase Inhibitors.
January 2022, Frontiers in chemistry,
Malikotsi A Qhobosheane, and Lesetja J Legoabe, and Béatrice Josselin, and Stéphane Bach, and Sandrine Ruchaud, and Richard M Beteck
Design, synthesis and pharmacological evaluation of chalcone derivatives as acetylcholinesterase inhibitors.
November 2014, Bioorganic & medicinal chemistry,
Malikotsi A Qhobosheane, and Lesetja J Legoabe, and Béatrice Josselin, and Stéphane Bach, and Sandrine Ruchaud, and Richard M Beteck
Azaindole derivatives as potential kinase inhibitors and their SARs elucidation.
October 2023, European journal of medicinal chemistry,
Malikotsi A Qhobosheane, and Lesetja J Legoabe, and Béatrice Josselin, and Stéphane Bach, and Sandrine Ruchaud, and Richard M Beteck
Synthesis and biological evaluation of 7-azaindole derivatives, synthetic cytokinin analogues.
April 2007, Bioorganic & medicinal chemistry letters,
Malikotsi A Qhobosheane, and Lesetja J Legoabe, and Béatrice Josselin, and Stéphane Bach, and Sandrine Ruchaud, and Richard M Beteck
ROCK inhibitors 3: Design, synthesis and structure-activity relationships of 7-azaindole-based Rho kinase (ROCK) inhibitors.
August 2018, Bioorganic & medicinal chemistry letters,
Malikotsi A Qhobosheane, and Lesetja J Legoabe, and Béatrice Josselin, and Stéphane Bach, and Sandrine Ruchaud, and Richard M Beteck
2'-substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis.
May 1993, Journal of medicinal chemistry,
Malikotsi A Qhobosheane, and Lesetja J Legoabe, and Béatrice Josselin, and Stéphane Bach, and Sandrine Ruchaud, and Richard M Beteck
Synthesis and pharmacological activities of 7-azaindole derivatives.
January 2008, Pakistan journal of pharmaceutical sciences,
Copied contents to your clipboard!