31560-20-0Relevant articles and documents
PYRROLO PYRIMIDINONE COMPOUND
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, (2021/09/01)
PROBLEM TO BE SOLVED: To provide a novel compound that has inhibitory action on prolyl hydroxylases (PHDs) and is useful as a treatment agent for inflammatory bowel diseases such as ulcerative colitis. SOLUTION: This invention relates to a pyrrolo pyrimidinone compound represented by the formula (I) or a pharmacologically acceptable salt thereof. The compound or a pharmacologically acceptable salt thereof has inhibitory action on prolyl hydroxylases and is useful as a treatment agent for inflammatory bowel diseases such as ulcerative colitis. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands
Zanato, Chiara,Watson, Sonia,Bewick, Guy S.,Harrison, William T. A.,Zanda, Matteo
supporting information, p. 9638 - 9643 (2015/02/19)
(-)-Kainic acid potently increases stretch-induced afferent firing in muscle spindles, probably acting through a hitherto uncloned phospholipase D (PLD)-coupled mGlu receptor. Structural modification of (-)-kainic acid was undertaken to explore the C-4 substituent effect on the pharmacology related to muscle spindle firing. Three analogues 1a-c were synthesised by highly stereoselective additions of a CF3, a hydride and an alkynyl group to the Re face of the key pyrrolidin-4-one intermediate 5a followed by further structural modifications. Only the 4-(1,2,3-triazolyl)-kainate derivative 1c retained the kainate-like agonism, increasing firing in a dose-dependent manner. Further modification of 1c by introduction of a PEG-biotin chain on the 1,2,3-triazole fragment afforded compound 14 which retained robust agonism at 1 μM and appears to be suitable for future use in pull-down assays and far western blotting for PLD-mGluR isolation. This journal is
Cyclopropenone catalyzed substitution of alcohols with mesylate ion
Nacsa, Eric D.,Lambert, Tristan H.
supporting information, p. 38 - 41 (2013/03/28)
The cyclopropenone catalyzed nucleophilic substitution of alcohols by methanesulfonate ion with inversion of configuration is described. This work provides an alternative to the Mitsunobu reaction that avoids the use of azodicarboxylates and generation of hydrazine and phosphine oxide byproducts. This transformation is shown to be compatible with a range of functionality. A cyclopropenone scavenge strategy is demonstrated to aid purification.
Synthetic study of optically active 3-azabicyclo[3.3.0]octane-2,6,8- tricarboxylic acid
Arakawa, Yasushi,Ohnishi, Masafumi,Yoshimura, Norikazu,Yoshifuji, Shigeyuki
, p. 1015 - 1020 (2007/10/03)
Synthesis of (1R,2S,5S,6R,8S)-3-azabicyclo[3.3.0]octane-2,6,8-tricarboxylic acid (2) from trans-4-hydroxy-L-proline (5) was attempted. A Diels-Alder reaction of 3,4-dehydroproline derivative 9 and cyclopentadiene afforded a single stereoisomer 11. The Diels-Alder adduct was smoothly converted to the hydrochloride of 2 (24) via RuO4 oxidation. Although some racemization of the material or product was observed during the synthetic processes, the amino acid 24 proved to be optically pure.
Asymmetric synthesis of α-branched primary amines on solid support via novel hydrazine resins
Enders, Dieter,Kirchhoff, Jan H.,Koebberling, Johannes,Peiffer, Thomas H.
, p. 1241 - 1244 (2007/10/03)
Matrix presented Two novel chiral hydrazine resins for asymmetric solid-phase synthesis have been developed. The enantiopure β-methoxyamino auxiliaries, derived from frans-4-hydroxy-(S) -proline and (R) -leucine, were attached to Merrifield resin and transformed into their corresponding hydrazines. Immobilization of various aldehydes, followed by 1,2-addition of organolithium reagents to the resulting enantiopure hydrazones and reductive cleavage from the solid support, furnished α-branched amines, which were isolated as their corresponding amides in good overall yields and enantiomeric excesses of up to 86%.
Towards a versatile synthesis of kainoids I: Introduction of the C-3 and C-4 substituents
Baldwin, Jack E.,Bamford, Samantha J.,Fryer, Andrew M.,Rudolph, Martin P. W.,Wood, Mark E.
, p. 5233 - 5254 (2007/10/03)
The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated.
N-α-benzoyl-cis-4-amino-L-proline: A γ-turn mimetic
Curran, Timothy P.,Chandler, Nicole M.,Kennedy, Robert J.,Keaney, Meghan T.
, p. 1933 - 1936 (2007/10/03)
Peptides containing N-α-benzoyl-cis-4-amino-L-proline are shown to adopt γ-turn conformations in chloroform solutions.
Stereospecific synthesis of (R)- and (S)-Baclofen and (R)- and (S)- PCPGABA [4-amino-2-(4-chlorophenyl)butyric acid] via (R)- and (S)-3-(4- chlorophenyl)pyrrolidines
Yoshifuji,Kaname
, p. 1302 - 1306 (2007/10/02)
(R)- and (S)-baclofen and (R)- and (S)-PCPGABA [4-amino-2-(4- chlorophenyl)butyric acid] were stereospecifically synthesized via (R)- and (S)-3-(4-chlorophenyl)pyrrolidines, starting from trans-4-hydroxy-L-proline. The syntheses involve two key operations