title: Synthesis and antiproliferative activity of 2-chlorophenyl carboxamide thienopyridines.
abstract: 3-Amino-2-arylcarboxamide-thieno[2,3-b]pyridines are a known class of antiproliferative compounds with activity against the phospholipase C enzyme. To further investigate the structure activity relationships of these derivatives a series of analogues were prepared modifying key functional groups. It was determined that modification of the 3-amino and 2-aryl carboxamide functionalities resulted in complete elimination of activity, whilst modification at C-5 allowed compounds of greater activity to be prepared.
authors.affiliation: School of Chemical Sciences, University of Auckland, New Zealand.
authors.forename: Michelle
authors.initials: M
authors.lastname: van Rensburg
authors.affiliation: Auckland Cancer Society Research Centre and Department of Molecular Medicine and Pathology, University of Auckland, New Zealand.
authors.forename: Euphemia
authors.initials: E
authors.lastname: Leung
authors.affiliation: School of Chemical Sciences, University of Auckland, New Zealand.
authors.forename: Natalie A
authors.initials: NA
authors.lastname: Haverkate
authors.affiliation: School of Chemical Sciences, University of Auckland, New Zealand.
authors.forename: Chatchakorn
authors.initials: C
authors.lastname: Eurtivong
authors.affiliation: School of Chemical Sciences, University of Auckland, New Zealand.
authors.forename: Lisa I
authors.initials: LI
authors.lastname: Pilkington
authors.affiliation: School of Chemical Sciences, University of Auckland, New Zealand.
authors.forename: Jóhannes
authors.initials: J
authors.lastname: Reynisson
authors.affiliation: School of Chemical Sciences, University of Auckland, New Zealand. Electronic address: d.barker@auckland.ac.nz.
authors.forename: David
authors.initials: D
authors.lastname: Barker
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001665:Binding Sites; D045744:Cell Line, Tumor; D006801:Humans; D006860:Hydrogen Bonding; D062105:Molecular Docking Simulation; D054803:Phospholipase C delta / Q000037:antagonists & inhibitors / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis / Q000494:pharmacology*; D011804:Quinolines / Q000138:chemical synthesis / Q000494:pharmacology*; D013876:Thiophenes / Q000138:chemical synthesis / Q000494:pharmacology*
chemical_list: C000622940:3-amino-2-((2'-chlorophenyl)carbamoyl)-5,6,7,8-tetrahydrothieno(2,3-b)quinolin-5-yl acetate; D000970:Antineoplastic Agents; D011725:Pyridines; D011804:Quinolines; D013876:Thiophenes; C518024:PLCD1 protein, human; D054803:Phospholipase C delta
keywords: Antiproliferative; Cancer; Phospholipase C; Thieno[2,3-b]pyridine; Tyrosyl-DNA phosphodiesterase I