Pd-N-heterocyclic carbene catalyzed synthesis of piperidine alkene-alkaloids and their anti-cancer evaluation.
A facile synthesis of piperidine alkene-alkaloids including natural (+)-Caulophyllumine B in high yields has been developed by Heck cross-coupling reaction catalyzed by simple in situ formed palladium-N-heterocyclic carbenes (Pd-NHCs). Formation of Pd(0) nanoparticles has been noticed during the reaction course. The synthesized piperidine alkene-alkaloids were evaluated for in vitro anti-cancer activity against a panel of human tumor cell lines of lung, breast and ovarian. Several of these piperidine alkene-alkaloids were found to possess highest growth inhibition activity than the standard drug cisplatin and support the concept to modulate drug receptor interaction.
Department of Chemistry, Kakatiya University, Warangal, India. Electronic address: shravankankala@yahoo.com.
Shravankumar
S
Kankala
Institute of Biotechnology, National Dong-Hwa University, Shou-Feng, Hualien 974, Taiwan, ROC.
Ranjith Kumar
RK
Kankala
Department of Chemistry, Satavahana University, Karimnagar, India.
Ramesh
R
Balaboina
Department of Chemistry, Kakatiya University, Warangal, India.
Narasimha Swamy
NS
Thirukovela
Department of Chemistry, Kakatiya University, Warangal, India.
Ravinder
R
Vadde
Department of Chemistry, Satavahana University, Karimnagar, India.
Chandra Sekhar
CS
Vasam
D000470:Alkaloids / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006571:Heterocyclic Compounds / Q000737:chemistry; D006801:Humans; D061986:MCF-7 Cells; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000470:Alkaloids; D000475:Alkenes; D000970:Antineoplastic Agents; D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D010880:Piperidines; C030011:carbene; D010165:Palladium; C032727:piperidine; D008697:Methane
Anti-cancer activity; Heck coupling; N-Heterocyclic carbene; Natural products; Piperidine alkene–alkaloids