Literature DB >> 24186219

Antide B, an antagonist of LHRH with cis-3-(4-pyrazinylcarbonylaminocyclohexyl)alanine in position 5.

A Janecka1, T Janecki, C Bowers, K Folkers.   

Abstract

Several LHRH antagonists with trans-3-(4-pyrazinylcarbonylaminocyclohexyl)alanine (trans-PzACAla) in the position 5 were synthesized and their antiovulatory activity was compared with the activity of the analogs containing cis-PzACAla in this position. In all cases cis-isomer produced more potent analogs. Introduction of cis-PzACAla in the position 5 of Antide gave Antide B which completely inhibits ovulation at a dose of 0.5µg/rat. Antide B releases negligible histamine (ED50 = 104µg/mL), and has excellent solubility in water. Also, an improved synthesis of cis-PzACAla is reported, involving the hydrogenation of 4-aminophenylalanine on a rhodium catalyst to give the desired cis-isomer with a 53% yield.

Entities:  

Year:  1995        PMID： 24186219     DOI： 10.1007/BF00806547

Source DB:  PubMed          Journal:  Amino Acids        ISSN： 0939-4451            Impact factor:   3.520


  15 in total

1.  Potent gonadotropin releasing hormone antagonists with low histamine-releasing activity.

Authors:  J J Nestor; R Tahilramani; T L Ho; J C Goodpasture; B H Vickery; P Ferrandon
Journal:  J Med Chem       Date:  1992-10-16       Impact factor: 7.446

Review 2.  Gonadotropin-releasing hormone analog design. Structure-function studies toward the development of agonists and antagonists: rationale and perspective.

Authors:  M J Karten; J E Rivier
Journal:  Endocr Rev       Date:  1986-02       Impact factor: 19.871

3.  New effective gonadotropin releasing hormone antagonists with minimal potency for histamine release in vitro.

Authors:  J E Rivier; J Porter; C L Rivier; M Perrin; A Corrigan; W A Hook; R P Siraganian; W W Vale
Journal:  J Med Chem       Date:  1986-10       Impact factor: 7.446

4.  Design, synthesis and bioassays of antagonists of LHRH which have high antiovulatory activity and release negligible histamine.

Authors:  A Ljungqvist; D M Feng; P F Tang; M Kubota; T Okamoto; Y W Zhang; C Y Bowers; W A Hook; K Folkers
Journal:  Biochem Biophys Res Commun       Date:  1987-10-29       Impact factor: 3.575

5.  Antide and related antagonists of luteinizing hormone release with long action and oral activity.

Authors:  A Ljungqvist; D M Feng; W Hook; Z X Shen; C Bowers; K Folkers
Journal:  Proc Natl Acad Sci U S A       Date:  1988-11       Impact factor: 11.205

6.  The reaction of pyridinecarboxylic acids with dicyclohexylcarbodiimide and p-nitrophenol.

Authors:  A Ljungqvist; K Folkers
Journal:  Acta Chem Scand B       Date:  1988-07

7.  Ihibition of the pre-ovulatory proestrous gonadotropin surge, ovulation and pregnancy with a peptide analogue of luteinizing hormone releasing hormone.

Authors:  A Corbin; C W Beattie
Journal:  Endocr Res Commun       Date:  1975

8.  Novel gonadotropin-releasing hormone antagonists: peptides incorporating modified N omega-cyanoguanidino moieties.

Authors:  P Theobald; J Porter; C Rivier; A Corrigan; W Hook; R Siraganian; M Perrin; W Vale; J Rivier
Journal:  J Med Chem       Date:  1991-08       Impact factor: 7.446

9.  Gonadotropin-releasing hormone antagonists with N omega-triazolylornithine, -lysine, or -p-aminophenylalanine residues at positions 5 and 6.

Authors:  J Rivier; J Porter; C Hoeger; P Theobald; A G Craig; J Dykert; A Corrigan; M Perrin; W A Hook; R P Siraganian
Journal:  J Med Chem       Date:  1992-11-13       Impact factor: 7.446

10.  Inhibitory analogues of the luteinizing hormone-releasing hormone having D-aromatic residues in positions 2 and 6 and variation in position 3.

Authors:  J Humphries; Y P Wan; K Folkers; C Y Bowers
Journal:  J Med Chem       Date:  1978-01       Impact factor: 7.446
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