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Synthesis of Naamidine A and Selective Access to N(2)-Acyl-2-aminoimidazole Analogues.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2015 Oct 16; Vol. 80 (20), pp. 10076-85. Date of Electronic Publication: 2015 Sep 24. - Publication Year :
- 2015
-
Abstract
- A short and scalable synthesis of naamidine A, a marine alkaloid with a selective ability to inhibit epidermal growth factor receptor (EGFR)-dependent cellular proliferation, has been achieved. A key achievement in this synthesis was the development of a regioselective hydroamination of a monoprotected propargylguanidine to deliver N(3)-protected cyclic ene-guanidines. This permits the extension of this methodology to prepare N(2)-acyl analogues in a fashion that obviates the troublesome acylation of the free 2-aminoimidazoles, which typically yields mixtures of N(2)- and N(2),N(2)-diacylated products.<br />Competing Interests: Notes The authors declare no competing financial interest.
- Subjects :
- Acylation
Alkaloids pharmacology
Amination
Animals
ErbB Receptors metabolism
Alkaloids chemical synthesis
ErbB Receptors antagonists & inhibitors
ErbB Receptors chemistry
Guanidines chemical synthesis
Guanidines chemistry
Imidazoles chemical synthesis
Imidazoles chemistry
Imidazoles pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 80
- Issue :
- 20
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 26360634
- Full Text :
- https://doi.org/10.1021/acs.joc.5b01703