title: An efficient one-pot synthesis of thiochromeno[3,4-d]pyrimidines derivatives: Inducing ROS dependent antibacterial and anti-biofilm activities.
abstract: An efficient synthesis of thiochromeno[3,4-d]pyrimidine derivatives has been achieved successfully via a one-pot three-component reaction of thiochrome-4-one, aromatic aldehyde and thiourea in the presence of 1-butyl-3-methyl imidazolium hydrogen sulphate [Bmim]HSO4. This new protocol has the advantages of environmental friendliness, high yields, short reaction times, and convenient operation. Furthermore, among all the tested derivatives, compounds 4b and 4c exhibited promising antibacterial, minimum bactericidal concentration and anti-biofilm activities against Staphylococcus aureus MTCC 96, Staphylococcus aureus MLS16 MTCC 2940 and Bacillus subtilis MTCC 121. The compound 4c also showed promising intracellular ROS accumulation in Staphylococcus aureus MLS16 MTCC 2940 comparable to that of ciprofloxacin resulting in apoptotic cell death of the bacterium.
authors: Department of Chemistry, National Institute of Technology, Warangal 506 004, Telangana, India.
authors: Lingala
authors: L
authors: Suresh
authors: Department of Chemistry, National Institute of Technology, Warangal 506 004, Telangana, India.
authors: P
authors: P
authors: Sagar Vijay Kumar
authors: Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500 007, Telangana, India.
authors: Y
authors: Y
authors: Poornachandra
authors: Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500 007, Telangana, India. Electronic address: cgkumar5@gmail.com.
authors: C
authors: C
authors: Ganesh Kumar
authors: Department of Chemistry, National Institute of Technology, Warangal 506 004, Telangana, India. Electronic address: gvpc2000@gmail.com.
authors: G V P
authors: GV
authors: Chandramouli
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001412:Bacillus subtilis / Q000187:drug effects* / Q000378:metabolism; D018441:Biofilms / Q000187:drug effects*; D002839:Chromans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017382:Reactive Oxygen Species / Q000378:metabolism*; D013211:Staphylococcus aureus / Q000187:drug effects* / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D002839:Chromans; D011743:Pyrimidines; D017382:Reactive Oxygen Species; C000620879:thiochromeno(3,4-d)pyrimidine
keywords: Anti-biofilm; Antibacterial activity; Ionic liquid; Reactive Oxygen Species (ROS); Thiochromeno[3,4-d]pyrimidine