Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 1995 Mar;8(1):89-96.
doi: 10.1007/BF00806547.

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

A Janecka  1 , T Janecki, C Bowers, K Folkers
Affiliations

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

A Janecka et al. Amino Acids. 1995 Mar.

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.

PubMed Disclaimer

References

    1. J Med Chem. 1992 Nov 13;35(23):4270-8 - PubMed
    1. Biochem Biophys Res Commun. 1987 Oct 29;148(2):849-56 - PubMed
    1. Endocr Res Commun. 1975;2(1):1-23 - PubMed
    1. J Med Chem. 1988 Sep;31(9):1820-4 - PubMed
    1. Proc Natl Acad Sci U S A. 1988 Nov;85(21):8236-40 - PubMed