title: Synthesis, bioassay, crystal structure and ab initio studies of Erlenmeyer azlactones.
abstract: Several 4-arylidene-2-phenyl-5(4H)-azlactones have been synthesized via Erlenmeyer method. The synthesized compounds have been characterized on the basis of systematic spectral studies (IR, (1)H NMR, (13)C NMR, and MS). The compound (4Z)-4-(3,5-dimethoxybenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one, C(18)H(15)NO(4), (5), crystallizes in the orthorhombic system, space group P2(1)2(1)2(1), with a=5.6793(3) Å, b=15.2038(7) Å, c=17.6919(10) Å, Mr=309.31, V=1527.64(14) Å(3), Z=4 and R=0.0547. The compound (4Z)-2-phenyl-4-(3,4,5-trimethoxybenzylidene)-1,3-oxazol-5(4H)-one, C(19)H(17)NO(5), (6) crystallizes in triclinic geometry with space group P-1, having unit cell parameters a=7.3814(3) Å, b=8.1446(3) Å, c=13.9845(5) Å, α=86.918(3), β=83.314(2), γ=82.462(3), Mr=339.34, V=827.16(5) Å(3), Z=2 and R=0.0433. The DFT calculations of compounds (5) and (6) have been carried out to ascertain the stability of Z-conformer. The in vitro antimicrobial activity of all the compounds (1-6) was evaluated by the disk diffusion method against gram +ve and gram -ve microorganism and fungal strains. The MIC of the synthesized compounds was determined by agar well diffusion method in 96-well microtiter plate. All the synthesized compounds were also screened for their free radical scavenging activity by DPPH method.
authors: Department of Chemistry, Aligarh Muslim University, Aligarh 202-002, India. mehtab.organic2009@gmail.com
authors: Mehtab
authors: M
authors: Parveen
authors: Akhtar
authors: A
authors: Ali
authors: Sarfaraz
authors: S
authors: Ahmed
authors: Ali Mohammed
authors: AM
authors: Malla
authors: Mahboob
authors: M
authors: Alam
authors: P S
authors: PS
authors: Pereira Silva
authors: Manuela Ramos
authors: MR
authors: Silva
authors: Dong-Ung
authors: DU
authors: Lee
mesh_terms: D000900:Anti-Bacterial Agents / Q000494:pharmacology; D000935:Antifungal Agents / Q000494:pharmacology; D000975:Antioxidants / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001681:Biological Assay; D001713:Biphenyl Compounds / Q000737:chemistry; D002939:Ciprofloxacin / Q000494:pharmacology; D018360:Crystallography, X-Ray; D005658:Fungi / Q000187:drug effects; D006860:Hydrogen Bonding; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D010851:Picrates / Q000737:chemistry; D011789:Quantum Theory
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000975:Antioxidants; D001713:Biphenyl Compounds; D007783:Lactones; D010851:Picrates; D002939:Ciprofloxacin; C004931:1,1-diphenyl-2-picrylhydrazyl