406216-02-2Relevant academic research and scientific papers
Novel chiral derivatizing agents for 1H NMR determination of enantiomeric purities of carboxylic acids
Wada, Koji,Goto, Mizuko,Yamashita, Hiroshi,Nagasawa, Kazuo
, p. 964 - 978 (2017/06/13)
(S)-4-(3-Aminopyrrolidin-1-yl)coumarin (1), (S)-4-(3-aminopiperidin-1-yl)coumarin (4), and (S)-4-(3-aminoazepan-1-yl)coumarin (7), prepared from 4-chlorocoumarin and (S)-pyrrolidin-3-amine, (S)-piperidin-3-amine, and (S)-azepan-3-amine, respectively, were proven to be versatile and reliable 1H NMR optical purity determination agents for chiral carboxylic acids.
Versatile synthesis of the signaling peptide glorin
Barnett, Robert,Raszkowski, Daniel,Winckler, Thomas,Stallforth, Pierre
supporting information, p. 247 - 250 (2017/03/14)
We present a versatile synthesis of the eukaryotic signaling peptide glorin as well as glorinamide, a synthetic analog. The ability of these compounds to activate glorin-induced genes in the social amoeba Polysphondylium pallidum was evaluated by quantita
Development of a large-scale synthesis of sulphostin, a dipeptidyl peptidase IV inhibitor
Abe, Masatoshi,Nagai, Masashi,Yamamoto, Keiichiro,Yamazaki, Hiroko,Koga, Ichiro,Satoh, Yoshitaka,Muraoka, Yasuhiko,Kurashige, Shuji,Ichikawa, Yuh-Ichiro
, p. 570 - 576 (2012/12/25)
For the progress of the in vivo study on sulphostin, a dipeptidyl peptidase IV inhibitor, its large-scale synthetic method was investigated. The optical resolution of (3S,RSP)-1-amino(sulfoamino)phosphinyl-3- benzyloxycarbonylamino-2-piperidinone, which was the most difficult step in the previous method, was simplified by using fractional crystallization. The use of 2 mol equiv of (1S,2R)-(+)-2-amino-1,2-diphenylethanol for optical resolution gave desired diastereomer 15 in good yield as a less soluble salt. In the present synthetic method, there were no requirements for purification using column chromatography, reaction at cryogenic temperature, and treatment using the haloalkane solvents. The total yield of the new method was 4.6%, which was an improvement of approximately 2-fold compared to the method reported previously.
NEW HETEROCYCLIC AMIDE COMPOUNDS USEFUL FOR THE TREATMENT OF INFLAMMATORY AND ALLERGIC DISORDERS: PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
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Page 85, (2010/11/30)
The present invention relates to novel heterocyclic compounds that inhibit phosphodiesterase type 4 (PDE 4). The compounds are useful for treating inflammatory conditions, diseases of the central nervous systems and insulin resistant diabetes.
Three-step synthesis of (R)- and (S)-Thalidomides from ornithine
Suzuki, Emiko,Shibata, Norio
, p. 275 - 279 (2007/10/03)
Three-step synthesis of enantiomerically pure thalidomide is described. D-Ornithine (2) reacted with thionyl chloride in methanol followed by treatment with triethylamine to give the (R)-3-amino-piperidin-2-one hydrochloride (3) in good yield. Protection of amino moiety by the use of N-carboethoxyphtalimide in DMSO furnished (R)-N-phtaloylpiperidin-2-one (4) as colorless crystals. Finally, the oxidation using a catalytic amount of RuO2 in the presence of excess sodium metaperiodate in a two-phase system gave (R)-thalidomide (1) in good yield without racemization. (S)-Thalidomide (1) was also synthesized from L-ornithine (2) in good overall yield. Since all the intermediates to thalidomide are easily recrystallized, the present method can be performed on a large scale without purification by column chromatography.
Dopamine Receptor Modulation by Conformationally Constrained Analogues of Pro-Leu-Gly-NH2
Yu, Kuo-Long,Rajakumar, G.,Srivastava, Lalit K.,Mishra, Ram K.,Johnson, Rodney L.
, p. 1430 - 1436 (2007/10/02)
Two series of conformationally constrained analogues of Pro-Leu-Gly-NH2 (PLG) have been synthesized.In one series of analogues, the Leu-Gly-NH2 dipeptide segment of PLG was replaced with the γ-lactam residues 3(S)- and 3(R)-amino-2-oxopyrrolidineacetamide
Reactions of Copper(II) Complexes of Optically Active N-Substituted Diamines with Alk-3-en-2-ones or 4-Hydroxyalkan-2-ones: Formation of Optically Active Macrocycles
Miyamura, Kazuo,Hata, Kazuhiko,Makino, Tadashi,Saburi, Masahiko,Yoshikawa, Sadao
, p. 1127 - 1132 (2007/10/02)
The reaction of biscopper(II) with but-3-en-2-one in methanol in the presence of ammonia gives an optically active tetra-azamacrocyclic comlex in ca. 80percent yield.Analogous optically active complexes are also obtained from biscopper(II) or biscopper(II) by the same procedure.The introduction of methyl and/or a hydroxyl group at the C4 position of but-3-en-2-one leads to a decrease in the reactivity of the ketones, and changes the species and distribution of the reaction products.In particular, when the C4 position is fully substituted with methyl groups, C-N bond formation with the secondary amino group no longer proceeds.The change in the reaction mode due to the substituents at C4 is discussed.
NEW CHIRAL AMINOPHOSPHINES PREPARED FROM L-ORNITHINE AND CATALYTIC ASYMMETRIC HYDROGENATION USING THEIR RHODIUM(I) COMPLEXES
Osakada, Kohtaro,Ikariya, Takao,Saburi, Masahiko,Yoshikawa, Sadao
, p. 1691 - 1694 (2007/10/02)
From readily preparable chiral diamines were obtained new aminophosphines, (3S)--3-aminopiperidine, and (3S)--3-(methylamino)piperidine.Asymmetric hydrogenation of α-acylaminoacrylic acids, employing Rh(I) complexes with these aminophosphines as catalyst, gave optically active N-acyl-α-amino acids.
