title: Synthesis and antiproliferative activities of quebecol and its analogs.
abstract: Simple and efficient synthesis of quebecol and a number of its analogs was accomplished in five steps. The synthesized compounds were evaluated for antiproliferative activities against human cervix adenocarcinoma (HeLa), human ovarian carcinoma (SK-OV-3), human colon carcinoma (HT-29), and human breast adenocarcinoma (MCF-7) cancer cell lines. Among all the compounds, 7c, 7d, 7f, and 8f exhibited antiproliferative activities against four tested cell lines with inhibition over 80% at 75 μM after 72 h, whereas, compound 7b and 7g were more selective towards MCF-7 cell line. The IC50 values for compounds 7c, 7d, and 7f were 85.1 μM, 78.7 μM, and 80.6 μM against MCF-7 cell line, respectively, showing slightly higher antiproliferative activtiy than the synthesized and isolated quebecol with an IC50 value of 104.2 μM against MCF-7.
authors: Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India.
authors: Kasiviswanadharaju
authors: K
authors: Pericherla
authors: Amir Nasrolahi
authors: AN
authors: Shirazi
authors: V Kameshwara
authors: VK
authors: Rao
authors: Rakesh K
authors: RK
authors: Tiwari
authors: Nicholas
authors: N
authors: DaSilva
authors: Kellen T
authors: KT
authors: McCaffrey
authors: Yousef A
authors: YA
authors: Beni
authors: Antonio
authors: A
authors: González-Sarrías
authors: Navindra P
authors: NP
authors: Seeram
authors: Keykavous
authors: K
authors: Parang
authors: Anil
authors: A
authors: Kumar
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D005260:Female; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D009369:Neoplasms / Q000188:drug therapy; D020005:Propanols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D020005:Propanols; D006139:Guaiacol
keywords: Antiproliferative; Phenolic; Quebecol; Structure–activity relationship; Synthesis
references: J Med Food. 2010 Apr;13(2):460-8
references: 20132041
references: J Agric Food Chem. 2010 Nov 24;58(22):11673-9
references: 21033720
references: Phytother Res. 2012 Jul;26(7):995-1002
references: 22147441
references: J Org Chem. 1996 Jun 14;61(12):3969-3976
references: 11667269
references: Eur J Med Chem. 2009 Mar;44(3):1223-9
references: 18973966