Design and synthesis of opioidmimetics containing 2',6'-dimethyl-L-tyrosine and a pyrazinone-ring platform.

Design and synthesis of opioidmimetics containing 2',6'-dimethyl-L-tyrosine and a pyrazinone-ring platform. Research Abstract Details 

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Design and synthesis of opioidmimetics containing 2',6'-dimethyl-L-tyrosine and a pyrazinone-ring platform. Abstract Text:

Kimitaka Shiotani,Tingyou Li,Anna Miyazaki,Yuko Tsuda,Toshio Yokoi,Akihiro Ambo,Yusuke Sasaki,Sharon D Bryant,Lawrence H Lazarus,Yoshio Okada,Kimitaka Shiotani,Tingyou Li,Anna Miyazaki,Yuko Tsuda,Toshio Yokoi,Akihiro Ambo,Yusuke Sasaki,Sharon D Bryant,Lawrence H Lazarus,Yoshio Okada,

Twelve 2',6'-dimethyl-L-tyrosine (Dmt) analogues linked to a pyrazinone platform were synthesized as 3- or 6-[H-Dmt-NH(CH(2))(n)],3- or 6-R-2(1H)-pyrazinone (n=1-4). 3-[H-Dmt-NH-(CH(2))(4)]-6-beta-phenethyl-5-methyl-2(1H)-pyrazinone 11 bound to mu-opioid receptors with high affinity (K(i)mu=0.13 nM; K(i)delta/K(i)mu=447) with mu-agonism (GPI IC(50)=15.9 nM) and weak delta-antagonism (MVD pA(2)=6.35). Key factors affecting opioid affinity and functional bioactivity are the length of the aminoalkyl chain linked to Dmt and the nature of the R residue. These data present a simplified method for the formation of pyrazinone opioidmimetics and new lead compounds.

Design and synthesis of opioidmimetics containing 2',6'-dimethyl-L-tyrosine and a pyrazinone-ring platform. Publishing Authors By Initials

K Shiotani,T Li,A Miyazaki,Y Tsuda,T Yokoi,A Ambo,Y Sasaki,SD Bryant,LH Lazarus,Y Okada,K Shiotani,T Li,A Miyazaki,Y Tsuda,T Yokoi,A Ambo,Y Sasaki,SD Bryant,LH Lazarus,Y Okada,

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Design and synthesis of opioidmimetics containing 2',6'-dimethyl-L-tyrosine and a pyrazinone-ring platform. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Bioorganic & medicinal chemistry letters

VOLUME: 17

Page Numbers: 5768-71

Journal Abbreviation: Bioorg. Med. Chem. Lett.

ISSN: 0960-894X

DAY: 28

MONTH: 08

YEAR: 2007

Design and synthesis of opioidmimetics containing 2',6'-dimethyl-L-tyrosine and a pyrazinone-ring platform. Information

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LANGUAGE: eng

NlmUniqueID: 9107377

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Grant and Affiliation Information for Design and synthesis of opioidmimetics containing 2',6'-dimethyl-L-tyrosine and a pyrazinone-ring platform.

AFFILIATION: The Graduate School of Food and Medicinal Sciences, Kobe Gakuin University, Nishi-ku, Kobe 651-2180, Japan.

Country: England

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MEDLINETA: Bioorg Med Chem Lett

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