title: C-N bond formation under Cu-catalysis: synthesis and in vitro evaluation of N-aryl substituted thieno[2,3-d]pyrimidin-4(3H)-ones against chorismate mutase.
abstract: A series of novel N-aryl substituted thieno[2,3-d]pyrimidin-4(3H)-ones were designed and synthesized as potential inhibitors of chorismate mutase. Synthesis of this class of compounds was carried out by using Cu-mediated C-N bond forming reaction between thieno[2,3-d]pyrimidin-4(3H)-ones and aryl boronic acids. The reaction can be performed in an open flask as the conversion was found to be not sensitive to the presence of air or atmospheric moisture. A range of compounds were prepared by using this method and single crystal X-ray diffraction study was performed using a representative compound. In vitro pharmacological data of some of the compounds synthesized along with dose response studies using active molecules are presented. In silico interactions of these molecules with chorismate mutase are also presented.
authors.affiliation: Institute of Life Sciences, University of Hyderabad Campus, Hyderabad 500046, India.
authors.forename: Raju
authors.initials: R
authors.lastname: Adepu
authors.forename: K
authors.initials: K
authors.lastname: Shiva Kumar
authors.forename: Sandhya
authors.initials: S
authors.lastname: Sandra
authors.forename: D
authors.initials: D
authors.lastname: Rambabu
authors.forename: G
authors.initials: G
authors.lastname: Rama Krishna
authors.forename: C
authors.initials: C
authors.lastname: Malla Reddy
authors.forename: Ajit
authors.initials: A
authors.lastname: Kandale
authors.forename: Parimal
authors.initials: P
authors.lastname: Misra
authors.forename: Manojit
authors.initials: M
authors.lastname: Pal
mesh_terms: D002384:Catalysis; D002826:Chorismate Mutase / Q000037:antagonists & inhibitors* / Q000235:genetics / Q000378:metabolism; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000201:enzymology; D009942:Organometallic Compounds / Q000737:chemistry*; D011744:Pyrimidinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D009942:Organometallic Compounds; D011744:Pyrimidinones; C542082:thieno(2,3-d)pyrimidin-4-one; D003300:Copper; D002826:Chorismate Mutase