title: A novel piperazine linked β-amino alcohols bearing a benzosuberone scaffolds as anti-proliferative agents.
abstract: A new series of 1-((9-chloro-2,3-dimethyl-6,7-dihydro-5H-benzo[7]annulen-8-yl)methoxy)-3-(4-phenylpiperzin-1-yl) propan-2-ols (6a-k) have been designed, synthesized and their structures were established by spectroscopic data (FT-IR,1H NMR,13C NMR, HRMS) and further confirmed by X-ray analysis. The newly synthesized compounds 6a-k were evaluated for their in vitro anti-proliferative activity against four cancer cell lines such as HeLa (cervical), MDA-MB-231 (breast), A549 (lung) and MIAPACA (pancreatic). Among the compounds tested, the compound 6e displayed most potent activity against four cancer cell lines with GI50values ranging from 0.010 to 0.097μM. The structure and anti-proliferative activity relationship was further supported by in silico molecular docking study of the active compounds against Colchicine binding site of β-tubulin.
authors.affiliation: Organic Chemistry Division II (CPC), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: Sowmya
authors.initials: S
authors.lastname: Vanguru
authors.affiliation: Organic Chemistry Division II (CPC), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: Lavanya
authors.initials: L
authors.lastname: Jilla
authors.affiliation: Organic Chemistry Division II (CPC), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: Yasodakrishna
authors.initials: Y
authors.lastname: Sajja
authors.affiliation: Organic Chemistry Division II (CPC), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: Rajashaker
authors.initials: R
authors.lastname: Bantu
authors.affiliation: Organic Chemistry Division II (CPC), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India. Electronic address: lnagarapuiict@yahoo.com.
authors.forename: Lingaiah
authors.initials: L
authors.lastname: Nagarapu
authors.affiliation: Center for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: Jagadeesh Babu
authors.initials: JB
authors.lastname: Nanubolu
authors.affiliation: Center for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: Bala
authors.initials: B
authors.lastname: Bhaskar
authors.affiliation: Center for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: Nishant
authors.initials: N
authors.lastname: Jain
authors.affiliation: Molecular Modeling and Medicinal Chemistry Group, Department of Chemistry, Osmania University, Tarnaka, Hyderabad 500007, India.
authors.forename: Sreekanth
authors.initials: S
authors.lastname: Sivan
authors.affiliation: Molecular Modeling and Medicinal Chemistry Group, Department of Chemistry, Osmania University, Tarnaka, Hyderabad 500007, India.
authors.forename: Vijjulatha
authors.initials: V
authors.lastname: Manga
mesh_terms: D000072283:A549 Cells; D000605:Amino Alcohols / Q000737:chemistry* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D001665:Binding Sites; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003078:Colchicine / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D003374:Coumarins / Q000737:chemistry* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D015195:Drug Design; D006367:HeLa Cells; D006801:Humans; D008968:Molecular Conformation; D062105:Molecular Docking Simulation; D010879:Piperazines / Q000737:chemistry* / Q000494:pharmacology*; D017434:Protein Structure, Tertiary; D014404:Tubulin / Q000737:chemistry / Q000378:metabolism
chemical_list: D000605:Amino Alcohols; D000970:Antineoplastic Agents; D003374:Coumarins; D010879:Piperazines; D014404:Tubulin; C000594239:benzosuberone; D003078:Colchicine
keywords: Anti-proliferative; Benzosuberone; Cell lines; Molecular modeling; Piperazine; β-Amino alcohol