97394-52-0Relevant academic research and scientific papers
Amide isosteres in structure-activity studies of antibacterial minor groove binders
Khalaf, Abedawn I.,Anthony, Nahoum,Breen, David,Donoghue, Gavin,MacKay, Simon P.,Scott, Fraser J.,Suckling, Colin J.
experimental part, p. 5343 - 5355 (2012/01/06)
Antibacterial minor groove binders related to the natural product, distamycin, are development candidates for novel antibiotics. Alkenes have been found to be effective substitutes for the isosteric amide links in some positions and alkyl groups larger th
A new synthesis of alkene-containing minor-groove binders and essential hydrogen bonding in binding to DNA and in antibacterial activity
Anthony, Nahoum G.,Breen, David,Donoghue, Gavin,Khalaf, Abedawn I.,MacKay, Simon P.,Parkinson, John A.,Suckling, Colin J.
experimental part, p. 1843 - 1850 (2009/06/27)
A practical synthesis of alkene-containing minor-groove binders for DNA, related to distamycin, with potential for wide structural diversity is described, based upon the Wittig chemistry of N-alkylpyrrole aldehydes. The compounds prepared have been evalua
Antimicrobial lexitropsins containing amide, amidine, and alkene linking groups
Anthony, Nahoum G.,Breen, David,Clarke, Joanna,Donoghue, Gavin,Drummond, Allan J.,Ellis, Elizabeth M.,Gemmell, Curtis G.,Helesbeux, Jean-Jacques,Hunter, Iain S.,Khalaf, Abedawn I.,Mackay, Simon P.,Parkinson, John A.,Suckling, Colin J.,Waigh, Roger D.
, p. 6116 - 6125 (2008/09/16)
The synthesis and properties of 80 short minor groove binders related to distamycin and the thiazotropsins are described. The design of the compounds was principally predicated upon increased affinity arising from hydrophobic interactions between minor groove binders and DNA. The introduction of hydrophobic aromatic head groups, including quinolyl and benzoyl derivatives, and of alkenes as linkers led to several strongly active antibacterial compounds with MIC for Staphylococcus aureus, both methicillin-sensitive and -resistant strains, in the range of 0.1-5 μg mL-1, which is comparable to many established antibacterial agents. Antifungal activity was also found in the range of 20-50 μg mL-1 MIC against Aspergillus niger and Candida albicans, again comparable with established antifungal drugs. A quinoline derivative was found to protect mice against S. aureus infection for a period of up to six days after a single intraperitoneal dose of 40 mg kg-1.
