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• W2037100519 abstract "We have previously shown that the substitution of 8-ornithine and 2-O-methyltyrosine alone and in combination in [1-deaminopenicillamine] oxytocin (dPOT) brought about enhancements in antagonistic potencies to responses to oxytocin in vivo. To explore the effects of these subtitutions in analogs of dPOT containing larger alkyl substitutents on the β carbon at position 1 and on the tyrosine residue at position two, the following six analogs were synthesized: [1-(β-mercapto-β, β-diethylpropionic acid), 8-ornithine] vasotocin (1, dEt2OVT); [1-β-mercapto-β, β-cyclopentamethylenepropionic acid), 8-ornithine] vasotocin [2, d(CH2)5OVT); [1-β-mercapto-β, β-diethylpropionic acid), 2-O-methyltyrosine, 8-ornithine]vasotocin [3, dEt2 Tyr(Me)OVT]; [1-(β-mercapto-β, β-diethylpropionic acid), 2-O-ethyltyrosine, 8-ornithine] vasotocin [4, dEt2 Tyr(Et)OVT]; [1-β-mercapto-β', β-cyclopentamethylenepropionic acid), 2-O-methyltyrosine, 8-ornithine] vasotocin [5, d(CH2)5 Tyr(Me)OVT]; [1-β-mercapto-β, β-cyclopentamethylenepropionic acid), 2-O-methyltyrosine, 8-ornithine] vasotocin [6, d(CH2)5 Tyr(Et)OVT]. The required protected intermediates were synthesized by a combination of solid-phase synthesis and by individual 8 + 1 couplings in solution. All six analogs antagonize the actions of oxytocin on the rat uterus in the absence of Mg2+, in the presence of 0.5 mM Mg2+ and in situ. They also antagonize milk ejection responses to oxytocin, and the vasopressor responses to arginine vasopressin, and all have very low antidiuretic activities. With pA2 values of 7.35 ± 0.08 and 7.37 ± 0.17, respectively, compounds 3 and 5 are the two most potent in vivo antagonists of oxytocin reported to date." @default.
• W2037100519 created "2016-06-24" @default.
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• W2037100519 date "2009-01-12" @default.
• W2037100519 modified "2023-10-04" @default.
• W2037100519 title "DESIGN AND SYNTHESIS OF POTENT IN VIVO ANTAGONISTS OF OXYTOCIN" @default.
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• W2037100519 doi "https://doi.org/10.1111/j.1399-3011.1980.tb02962.x" @default.
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