Thieno[3,2-c]pyran-4-one based novel small molecules: their synthesis, crystal structure analysis and in vitro evaluation as potential anticancer agents.
Novel thieno[3,2-c]pyran-4-one based small molecules were designed as potential anticancer agents. Expeditious synthesis of these compounds was carried out via a multi-step sequence consisting of few steps such as Gewald reaction, Sandmeyer type iodination, Sonogashira type coupling followed by iodocyclization and then Pd-mediated various C-C bond forming reactions. The overall strategy involved the construction of thiophene ring followed by the fused pyranone moiety and then functionalization at C-7 position of the resultant thieno[3,2-c]pyran-4-one framework. Some of the compounds synthesized showed selective growth inhibition of cancer cells in vitro among which two compounds for example, 5d and 6c showed IC(50) values in the range of 2.0-2.5 μM. The crystal structure analysis of an active compound along with hydrogen bonding patterns and molecular arrangement present within the molecule is described.
Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, AP, India.
Ali
A
Nakhi
Raju
R
Adepu
D
D
Rambabu
Ravada
R
Kishore
G R
GR
Vanaja
Arunasree M
AM
Kalle
Manojit
M
Pal
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D017209:Apoptosis / Q000187:drug effects; D002460:Cell Line; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D057809:HEK293 Cells; D056945:Hep G2 Cells; D006801:Humans; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D011714:Pyrans / Q000737:chemistry*; D054852:Small Molecule Libraries / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D013876:Thiophenes / Q000737:chemistry
D000970:Antineoplastic Agents; D011714:Pyrans; D054852:Small Molecule Libraries; D013876:Thiophenes