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Synthesis, Optical and Antibacterial, Antifungal Studies on Functionalized Triazolophanes: A New Class of Cyclophane
Author(s) -
Selvarani Sivasamy,
Rajakumar Perumal
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800560
Subject(s) - chemistry , density functional theory , antibacterial activity , homo/lumo , stereochemistry , medicinal chemistry , computational chemistry , organic chemistry , molecule , bacteria , biology , genetics
A new class of cyclophanes called triazolophanes has been synthesized by copper (I) catalyzed 1, 3‐dipolar cycloaddition of various aromatic azides to bis‐alkynes under mild conditions at room temperature and characterized by spectral, analytical methods. All the newly synthesized triazolophanes show two strong absorption bands between 243–315 nm. The HOMO‐LUMO energy gap (Eg) was found to lie between 2.56 to 5.06 eV from density functional theory (DFT) calculations and the λmax calculated from the DFT theory was found to lie between 239 to 312 nm which coincides with the observed UV‐vis spectral absorption. All the synthesized triazolophanes show comparable antibacterial and antifungal activity against Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus, Streptococcus pyogens and Candida glabrata, Candida albicans when tested by resazurin reduction method with streptomycin and Amphotericin‐B as standards, which is supported by molecular docking studies with glide energy of −81.40 and −93.52 Kcal/mol for the triazolophanes 8 derived from 2‐aminothiophenol and orthoxylenyl group and the triazolophane 9 derived from 3‐aminophenol and 2, 6‐diphenyl oxadiazole, respectively.