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Literature DB >> 22622388

Synthesis of peptidomimetics, δ- and ε-lactam tetrazoles.

Steven Gunawan¹, Kristen Keck, Alex Laetsch, Christopher Hulme.

Abstract

A concise two-step procedure for the synthesis of novel δ-lactam tetrazoles has been established via the Ugi-azide reaction using 5-oxohexanoic acid along with primary amines, isocyanides, and azidotrimethylsilane followed by 1,1'-carbonyldiimidazole-mediated intramolecular amide formation. Expansion to ε-lactam tetrazole scaffolds was accomplished using methyl 6-oxoheptanoate via the same Ugi-azide reaction followed by basic hydrolysis and SOCl(2) activation to enable lactam formation.

Entities: Chemical

Mesh：

Substances：

Year: 2012 PMID： 22622388 DOI： 10.1007/s11030-012-9373-2

Source DB: PubMed Journal: Mol Divers ISSN： 1381-1991 Impact factor: 2.943

14 in total

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5. Tetrazole thioacetanilides: potent non-nucleoside inhibitors of WT HIV reverse transcriptase and its K103N mutant.

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6. Synthesis and evaluation of 1,5-diaryl-substituted tetrazoles as novel selective cyclooxygenase-2 (COX-2) inhibitors.

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7. Concise one-pot preparation of unique bis-pyrrolidinone tetrazoles.

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8. Design, synthesis, and conformational analysis of eight-membered cyclic peptidomimetics prepared using ring closing metathesis.

Authors: Christopher J Creighton; Gregory C Leo; Yanming Du; Allen B Reitz
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9. Tetrazole-biarylpyrazole derivatives as cannabinoid CB1 receptor antagonists.

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10. One-step assembly of carbamoyl-substituted heteroannelated [1,4]thiazepines.

Authors: Alexey P Ilyn; Marina V Loseva; Vladimir Y Vvedensky; Elena B Putsykina; Sergey E Tkachenko; Dmitri V Kravchenko; Alexandr V Khvat; Mikhail Y Krasavin; Alexandre V Ivachtchenko
Journal: J Org Chem Date: 2006-03-31 Impact factor: 4.354

4 in total

1. Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity.

Authors: Steven Gunawan; Christopher Hulme
Journal: Org Biomol Chem Date: 2013-09-28 Impact factor: 3.876