Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2015; 47(19): 3067-3078
DOI: 10.1055/s-0034-1378845
DOI: 10.1055/s-0034-1378845
paper
An Efficient Route to N-Monosubstituted Guanidino-Lactams
Further Information
Publication History
Received: 15 February 2015
Accepted after revision: 05 June 2015
Publication Date:
25 June 2015 (online)
Abstract
A small library of guanidino-lactams were synthesized in four steps and good overall yields by following the routes: preparation of guanylating agents, synthesis of protected guanidino-acids, cyclization to fully protected guanidino-lactams, and deprotection to the target compounds. The guanidino-lactams were assayed as antimicrobials on E. coli showing no significant antibiotic activity.
-
References
- 1 Lednicer D, Mitscher LA. The Organic Chemistry of Drug Synthesis. Vol. 1. Wiley; New York: 1977
- 2 Ghuysen JM. Trends Microbiol. 1994; 372
- 3 Imming P, Klar B, Dix D. J. Med. Chem. 2000; 43: 4328
- 4a StLaurent DR, Balasubramanian N, Han WT, Trehan A, Federici ME, Meanwell NA, Wright JJ, Seiler SM. Bioorg. Med. Chem. 1995; 3: 1145
- 4b Tamura SY, Goldman EA, Brunck TK, Ripka WC, Semple JE. Bioorg. Med. Chem. Lett. 1997; 7: 331
- 4c Salimbeni A, Paleari F, Canevotti R, Criscuoli M, Lippi A, Angiolini M, Belvisi L, Scolastico C, Colombo L. Bioorg. Med. Chem. Lett. 1997; 7: 2205
- 4d Harmat NJ. S, Di Bugno C, Criscuoli M, Giorgi R, Lippi A, Martinelli A, Monti S, Subissi A. Bioorg. Med. Chem. Lett. 1998; 8: 1249
- 4e Bachand B, DiMaio J, Siddiqui MA. Bioorg. Med. Chem. Lett. 1999; 9: 913
- 4f Seo J, Silverman RB. Tetrahedron Lett. 2006; 47: 4069
- 4g Zervas L, Winitz M, Greenstein JP. J. Am. Chem. Soc. 1961; 83: 3300
- 4h Shuman RT, Rothenberger RB, Campbell CS, Smith GF, Gifford-Moore DS, Paschal JW, Gesellchen PD. J. Med. Chem. 1995; 38: 4446
- 4i Balasubramanian N, StLaurent DR, Federici ME, Meanwell NA, Wright JJ, Schumacher WA, Seiler SM. J. Med. Chem. 1993; 36: 300
- 4j Bajusz S, Szell E, Bagdy D, Barabas E, Horvath G, Dioszegi M, Fittler Z, Szabo G, Juhasz A, Tomori E, Szilagyi G. J. Med. Chem. 1990; 33: 1729
- 5 Van Ameijde J, Poot AJ, Van Wandelen LT. M, Wammes AE. M, Ruijtenbeek R, Rijkers DT. S, Liskamp RM. J. Org. Biomol. Chem. 2010; 8: 1629
- 6 Bauaer AW, Kirby WM, Sherris JC, Turck M. Am. J. Clin. Pathol. 1966; 45: 493
- 7 Andrus A, Partridge B, Heck J, Christensen BG. Tetrahedron Lett. 1984; 25: 911