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Ru(II)-Catalyzed C(sp)-H Activation Annulation: Synthesis of Fluorescent Benzoisoquinolonyl Acetate/Peptides from -Arylamides and Ethyne at Room Temperature.
J Org Chem
June 2024
School of Chemical Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar, Jatani, Odisha 752050, India.
Benzoisoquinolones are aryl ring extended isoquinolinone derivatives, which are constituents of alkaloid natural products. This report describes the synthesis of novel benzoisoquinolone amino acid/peptide derivatives from the respective -aryl amino esters/peptides through Ru-catalyzed C(sp)-H annulation at room temperature. The -terminal amide acts as an intrinsic directing group and coordinates with the active Ru(II) catalyst for the C-H bond activation and annulation of the aryl ring to produce benzoisoqunolone derivatives.
View Article and Find Full Text PDFDiscovery of new indomethacin-based analogs with potentially selective cyclooxygenase-2 inhibition and observed diminishing to PGE2 activities.
Eur J Med Chem
December 2017
Research Unit, Saco Pharm. Co., 6th of October City, Giza 68330, Egypt.
New ring-extended analogs of indomethacin were designed based on the structure of active binding site of both COX-1 and COX-2 isoenzymes and the interaction pattern required for selective inhibition of COX-2 to improve its selectivity against COX-2. The strategy adopted for designing the new inhibitors involved i) ring extension of indomethacin to reduce the possibility of analogs to be accommodated into the narrow hydrophobic tunnel of COX-1, ii) deletion of carboxylic acid to reduce the possibility of inhibitor to form salt bridge with Arg120 and eventually prevent COX-1 inhibition, and iii) introduction of methylsulfonyl group to increase the opportunity of the analogs to interact with the polar side pocket that's is crucial for inhibition process of COX-2. The three series of tetrahydrocarbazoles involving 4, 5, 9, 10 and 12 were synthesized in quantitative yields adopting limited number of reaction steps, and applying laboratory friendly reaction conditions.
View Article and Find Full Text PDFDesign and synthesis of 1,2,3-triazole-containing N-acyl zanamivir analogs as potent neuraminidase inhibitors.
Eur J Med Chem
November 2016
Department of Chemistry, National Tsing Hua University, 101, Section 2, Kuang-Fu Road, Hsinchu 30013, Taiwan. Electronic address:
The design of potent metabolically stable neuraminidase (NA) inhibitors represents an attractive approach for treating influenza virus infection. In this study, we describe the exploitation of the 150-cavity in the active site of group 1 NA for the design, synthesis, and in vitro evaluation of new triazole-containing N-acyl derivatives related to Zanamivir. Inhibition studies with influenza virus NAs of group 1 (H1N1) and group 2 (H3N2) revealed that several of them are good inhibitors, with IC50 values in the low nanomolar (2.
View Article and Find Full Text PDFSynthesis and evaluation of strand and turn modified ring-extended gramicidin S derivatives.
Bioorg Med Chem
June 2011
Leiden Institute of Chemistry, Leiden University, RA Leiden, The Netherlands.
In this paper, we describe the crystal structure of previously reported ring-extended gramicidin S (GS) derivative 2 (GS14K4), containing a d-amino acid residue in one of the β-strand regions. This structure is in agreement with a previously reported modeling study of the same molecule. The polar side chain of the additional d-amino acid residue is positioned at the same face of the molecule as the hydrophobic side chains, and we believe that because of this compound 2 is considerably less hydrophobic than extended GS derivatives in which the strand regions are exclusively composed of l-amino acids.
View Article and Find Full Text PDFTuning hydrophobicity of highly cationic tetradecameric Gramicidin S analogues using adamantane amino acids.
Bioorg Med Chem
December 2010
Leiden Institute of Chemistry, Leiden University, The Netherlands.
Ring extended Gramicidin S analogues containing adamantane amino acids and six cationic residues were designed and evaluated. Systematic replacement of the hydrophobic residues with adamantane amino acids resulted in a small set of compounds with varying amphipathic character. It was found that the amphipathicity of these compounds is correlated to their biological activity.
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