Studies on Prostaglandins. VI. Synthesis of 16 (S)-Methyl-20-methoxy-PGE2 (YPG-209) having Oral Bronchodilator Activity and Its Analogs

HIDENORI IWAMOTO; NORIYOSHI INUKAI; ISAO YANAGISAWA; YOSHIO ISHII; TOSHINARI TAMURA; TETSUYA SHIOZAKI; TOKUICHI TAKAGI; KENICHI TOMIOKA; MASUO MURAKAMI

doi:10.1248/cpb.28.1422

Studies on Prostaglandins. VI. Synthesis of 16 (S)-Methyl-20-methoxy-PGE₂ (YPG-209) having Oral Bronchodilator Activity and Its Analogs

HIDENORI IWAMOTO, NORIYOSHI INUKAI, ISAO YANAGISAWA, YOSHIO ISHII, TOSHINARI TAMURA, TETSUYA SHIOZAKI, TOKUICHI TAKAGI, KENICHI TOMIOKA, MASUO MURAKAMI

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Keywords: oral bronchodilator activity

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Volume 28 (1980) Issue 5 Pages 1422-1431

DOI https://doi.org/10.1248/cpb.28.1422

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Abstract

16 (S)-Methyl-20-methoxy-PGE₂ (YPG-209) (Is), 16 (R)-methyl-20-methoxy-PGE₂ (I_R) and several analogs, such as 16 (S)-methyl-20-methoxy-PGA₂ (XIIIs) and -PGB₂ (XIVs), 16-methyl-20-ethoxy-PGE₂ (XXVIIa), 16-methyl-20-hydroxymethyl-PGE₂ (XXVIa), 16-methyl-17-oxa-ω-dihomo-PGE₂ (XXVIIIa) and 20-hydroxymethyl-PGE₂ (XXX), were synthesized by Corey's procedure and their biological activities were investigated. Among these derivatives, I_S and I_R possessed potent oral bronchodilator activity ; the bronchoselectivity of I_S was higher than that of I_R.

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