Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

• Xiaofeng Zhang,
• Xiaoming Ma and
• Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

• -stabilized azomethine ylide; Introduction The 1,3-dipolar cycloaddition of azomethine ylides (AMYs) [1][2][3][4][5][6] is a powerful method for the synthesis of bioactive pyrrolidine-containing compounds and natural product analogs [7][8][9][10][11][12][13][14][15]. AMYs generated from the reaction of

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones

• Alla I. Vaskevych,
• Nataliia O. Savinchuk,
• Ruslan I. Vaskevych,
• Eduard B. Rusanov,
• Oleksandr O. Grygorenko and
• Mykhailo V. Vovk

Beilstein J. Org. Chem. 2021, 17, 2787–2794, doi:10.3762/bjoc.17.189

• their suitability for the synthesis of compound libraries relevant to medicinal chemistry. While many chemoinformatic tools are available for that purpose, we have turned our attention to Ertl’s natural product likeness (NPL) score since the target compounds were designed as natural product analogs [1

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

• Eric J. N. Helfrich,
• Geng-Min Lin,
• Christopher A. Voigt and
• Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

• . Biosynthetic core enzymes of well-characterized classes of natural products, such as modular thiotemplate assembly lines (NRPSs, PKSs), are usually highly specific and produce only a few closely related natural product analogs. Adenylation domains in NRPSs [26][27][28], acyltransferase (AT) domains in cis-AT

Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

• Catalin V. Maftei,
• Elena Fodor,
• Peter G. Jones,
• M. Heiko Franz,
• Gerhard Kelter,
• Heiner Fiebig and
• Ion Neda

Beilstein J. Org. Chem. 2013, 9, 2202–2215, doi:10.3762/bjoc.9.259

• natural products containing a 1,2,4-oxadiazole ring in their structure (quisqualic acid and phidianidines A and B), the natural product analogs 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4) and 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7) were

• starting from tert-butylamidoxime and 4-aminobenzoic acid or 4-nitrobenzonitrile. The structures of compounds 1, 2, 4, 5 and 6 were confirmed by X-ray crystallography. Keywords: antitumor activity; bioisosteres; maleimide; natural product analogs; 1,2,4-oxadiazoles; Introduction The five-membered

• novel natural product analogs of 1,2,4-oxadiazole derivatives bearing N-phenylmaleimide or N-phenylsuccinimide functionalities in order to improve their biological activity. The new derivatives have been tested for in vitro antitumor activity toward a panel of 11 cell lines. Results and Discussion Clapp