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Synthesis and Analgesic Activities of Endomorphin‐2 and Its Analogues
Author(s) -
Shi ZhiHao,
Wei YunYang,
Wang ChuanJin,
Yu Li
Publication year - 2007
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200790038
Subject(s) - chemistry , analgesic , stereochemistry , asparagine , nociception , pharmacology , medicinal chemistry , amino acid , biochemistry , receptor , medicine
Endomorphin‐2 ( 1 ; H‐Tyr‐Pro‐Phe‐Phe‐NH 2 ; EM2) and its novel cyclic asparagine ( cyclo Asn) analogues, H‐Tyr‐ c Asn(CHPh)‐Phe‐Phe‐NH 2 ( 2 ) and H‐Tyr‐ c Asn(CHMe 2 )‐Phe‐Phe‐NH 2 ( 3 ), were synthesized via liquid‐phase synthesis. The structures of the products and intermediates were characterized by IR, 1 H‐NMR, MS, and HR‐MS analyses. The antinociceptive activity of EM2 and its cyclic asparagine analogues were assessed in AcOH‐induced abdominal constriction tests in mice with i.p. injection. The results show that the antinociceptive activities of EM2 and its cyclic asparagine analogue 2 were higher than those of aspirine and meperidine. Analogue 2 was observed to be a stronger analgesic with dose‐dependence than EM2. The test mice did not show any tendency to be addicted while administrated of analogue 2 repeatedly and regularly.