title: Synthesis and biological evaluation of novel biaryl type α-noscapine congeners.
abstract: Natural α-noscapine, a known antitussive drug, is also now known to possess weak anticancer efficacy with relatively safe toxicity profile. In this study, we report synthesis and evaluation of novel biaryl type α-noscapine congeners designed by adding aryl unit to the tetrahydroisoquinoline part of natural α-noscapine core. Palladium catalyzed Suzuki cross coupling of 9-bromo α-noscapine with aryl boronic acids was employed using mild and inexpensive reagents to attain desired noscapinoids 5a-g in excellent yields. Screening anti-proliferative activity for new noscapinoids 5b-g, on human cancer cell lines resulted three compounds 5b, 5d and 5f as potent analogues, active against human breast epithelial (MCF-7), human cervix cancer (HeLa) and human lung adenocarcinoma epithelial (A549) cell lines.
authors.affiliation: Organic Chemistry Division-II (CPC Division), CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India.
authors.forename: Naresh K
authors.initials: NK
authors.lastname: Manchukonda
authors.affiliation: Department of Biotechnology, Guru Ghasidas Vishwavidyalaya, A Central University, Koni, Bilaspur 495 009, Chhattisgarh, India. Electronic address: pknaik1973@gmail.com.
authors.forename: Pradeep K
authors.initials: PK
authors.lastname: Naik
authors.affiliation: Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India.
authors.forename: Balasubramanian
authors.initials: B
authors.lastname: Sridhar
authors.affiliation: Organic Chemistry Division-II (CPC Division), CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India; Academy of Scientific and Innovative Research, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India. Electronic address: kantevari@yahoo.com.
authors.forename: Srinivas
authors.initials: S
authors.lastname: Kantevari
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D006367:HeLa Cells; D006801:Humans; D061986:MCF-7 Cells; D008968:Molecular Conformation; D009665:Noscapine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D010165:Palladium / Q000737:chemistry; D044005:Tetrahydroisoquinolines / Q000737:chemistry
chemical_list: C000622044:9-(3-pyridyl)noscapine; D000970:Antineoplastic Agents; D001897:Boronic Acids; D044005:Tetrahydroisoquinolines; D010165:Palladium; D009665:Noscapine
keywords: Alkaloid; Isoquinoline; Noscapine; Suzuki reaction; Tubulin