Substitution of phenyl oxazolidinones with carbon-linked azoles resulted in the discovery of a new class of potent oxazolidinones that have excellent Gram-positive activity. In addition, replacement of the C-5 acetamide side chains with a 4-methyl triazole diminished monoamine oxidase activity. The synthesis and biological evaluation of these compounds are reported.
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http://dx.doi.org/10.1016/j.bmcl.2006.10.063 | DOI Listing |
Mol Divers
December 2023
Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, 75169, Iran.
A one-pot, efficient oxidative-condensation process for constructing both 4-alkyl and 4-aryl-5-(arylthio) thiazol-2-amines using DMSO/I is introduced. In this procedure, methyl ketones, thiourea, DMSO, and thiols are reacted together in the presence of molecular I at 80 °C simply to produce 4-alkyl or aryl-5-(arylthio)thiazol-2-amines due to formation of a C-S bond between thiourea and methyl carbon linked to carbonyl group and the another C-S bond formation between thiol and thiazol ring. Under reaction conditions, both aryl and alkyl methyl ketones including acetophenone and substituted acetophenones also, 2-alkanones such as acetone, 2-butanone, 2-pentanone, and 2-heptanone yield those products successfully.
View Article and Find Full Text PDFAcc Chem Res
June 2022
Department of Chemistry, The University of Texas at Austin, 105 East 24th Street Stop A 5300, Austin, Texas 78712-1224, United States.
"Functional molecular systems", discrete and self-assembled constructs where control over molecular recognition, structure, bonding, transport, release, catalytic activity, etc., is readily achieved, are a topic of current interest. Within this broad paradigm, oligopyrrolic cages have garnered attention due to their responsive recognition features.
View Article and Find Full Text PDFEur J Med Chem
February 2019
Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Herestraat 49, bus 1041, 3000, Leuven, Belgium. Electronic address:
Cyclin G-associated kinase (GAK) is a cellular regulator of the clathrin-associated host adaptor proteins AP-1 and AP-2, which regulates intracellular trafficking of dengue virus during early and late stages of the viral lifecycle. Previously, the discovery of isothiazolo[4,3-b]pyridines as potent and selective GAK inhibitors with promising antiviral activity was reported. In this manuscript, the synthesis of isothiazolo[4,3-b]pyridines with a carbon-linked substituent at position 3 is described by the application of regioselective Suzuki and Sonogashira coupling reactions.
View Article and Find Full Text PDFBioorg Med Chem Lett
June 2012
Amgen Inc., 360 Binney St., Cambridge, MA 02142, USA.
Deregulation of the receptor tyrosine kinase c-Met has been implicated in several human cancers and is an attractive target for small molecule drug discovery. Herein, we report the discovery of a structurally diverse series of carbon-linked quinoline triazolopyridinones, which demonstrates nanomolar inhibition of c-Met kinase activity. This novel series of inhibitors exhibits favorable pharmacokinetics as well as potent inhibition of HGF-mediated c-Met phosphorylation in a mouse liver pharmacodynamic model.
View Article and Find Full Text PDFJ Am Chem Soc
May 2007
Department of Chemistry, Georgia State University, P.O. Box 4098, Atlanta, Georgia 30302-4098, USA.
To better understand the molecular basis for recognition of the DNA minor groove by heterocyclic cations, a series of "reversed amidine" substituted heterocycles has been prepared. Amidine derivatives for targeting the minor groove have the amidine carbon linked to a central heterocyclic system, whereas in the reverse orientation, an amidine nitrogen provides the link. The reverse system has a larger dihedral angle as well as a modified spatial relationship with the groove relative to amidines.
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