Literature DB >> 16497007

Short stereoselective synthesis of alpha-substituted gamma-lactams.

Bhooma Raghavan1, Rodney L Johnson.   

Abstract

A concise, stereoselective synthesis of alpha-substituted gamma-lactams is reported. gamma-Lactam scaffolds 2 and 3, possessing an Evans' chiral auxiliary and two types of N substituents, were successfully alkylated with different electrophiles to give alpha-substituted gamma-lactams with reasonable diastereoselectivities. The use of a masked carboxymethyl function off the lactam nitrogen provided a convergent means to alpha-substituted gamma-lactam dipeptide isosteres.

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Year:  2006        PMID： 16497007      PMCID： PMC2562328          DOI： 10.1021/jo052212q

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  Synthesis and dopamine receptor modulating activity of lactam conformationally constrained analogues of Pro-Leu-Gly-NH2.

Authors:  U Sreenivasan; R K Mishra; R L Johnson
Journal:  J Med Chem       Date:  1993-01-22       Impact factor: 7.446

2.  Synthesis and antiinflammatory activities of 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-ones.

Authors:  H Ikuta; H Shirota; S Kobayashi; Y Yamagishi; K Yamada; I Yamatsu; K Katayama
Journal:  J Med Chem       Date:  1987-11       Impact factor: 7.446

3.  Synthesis and dopamine receptor modulating activity of 3-substituted gamma-lactam peptidomimetics of L-prolyl-L-leucyl-glycinamide.

Authors:  Kristine Dolbeare; Giuseppe F Pontoriero; Suresh K Gupta; Ram K Mishra; Rodney L Johnson
Journal:  J Med Chem       Date:  2003-02-27       Impact factor: 7.446

4.  Conformationally constrained renin inhibitory peptides: gamma-lactam-bridged dipeptide isostere as conformational restriction.

Authors:  S Thaisrivongs; D T Pals; S R Turner; L T Kroll
Journal:  J Med Chem       Date:  1988-07       Impact factor: 7.446

5.  Structure-based design, synthesis and evaluation of conformationally constrained cysteine protease inhibitors.

Authors:  K A Scheidt; W R Roush; J H McKerrow; P M Selzer; E Hansell; P J Rosenthal
Journal:  Bioorg Med Chem       Date:  1998-12       Impact factor: 3.641

6.  Dopamine receptor modulation by conformationally constrained analogues of Pro-Leu-Gly-NH2.

Authors:  K L Yu; G Rajakumar; L K Srivastava; R K Mishra; R L Johnson
Journal:  J Med Chem       Date:  1988-07       Impact factor: 7.446
  6 in total

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