- Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists
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To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified γ-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the γ-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented.
- Kambe, Tohru,Maruyama, Toru,Nagase, Toshihiko,Ogawa, Seiji,Minamoto, Chiaki,Sakata, Kiyoto,Maruyama, Takayuki,Nakai, Hisao,Toda, Masaaki
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experimental part
p. 702 - 713
(2012/03/11)
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- Rearrangements and racemisation during the synthesis of L-serine derived oxazolidin-2-ones
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The propensity for N-Boc-4-hydroxymethyl-oxazolidin-2-ones to undergo rapid O-O and N-O carbonyl transfer makes these L-serine derived chiral auxiliaries unsuitable for attachment to polymers.
- Bew, Sean P,Bull, Steven D,Davies, Stephen G,Savory, Edward D,Watkin, David J
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p. 9387 - 9401
(2007/10/03)
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- Polymer supported oxazolidin-2-ones derived from L-serine - A cautionary tale
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The capacity of N-Boc-4-hydroxymethyl-oxazolidin-2-ones to undergo rapid O-O and N-O acyl transfer makes these serine derived chiral auxiliaries unsuitable for attachment to polymers. (C) 2000 Elsevier Science Ltd.
- Bew,Bull,Davies
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p. 7577 - 7581
(2007/10/03)
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- Synthesis of the (α,α-difluoroalkyl)phosphonate analogue of phosphoserine
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The synthesis of the (α,α-difluoroalkyl)phosphonate analogue of L- phosphoserine, 5, in a form appropriate for solid phase peptide synthesis, is reported. Two independent routes are described, starting from L-serine or (R)-isopropylideneglycerol. In each case, PCF2-C bond formation is achieved by triflate displacement with diethyl lithiodifluoromethylphosphonate.
- Berkowitz, David B.,Shen, Quanrong,Maeng, Jun-Ho
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p. 6445 - 6448
(2007/10/02)
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