109760-77-2Relevant academic research and scientific papers
Stereoselective synthesis of enantiomerically pure D-threo-PDMP; manipulation of a core 2,3-diamino alcohol unit
Shin, Seong-Ho,Han, Eun Young,Park, Chan Sun,Lee, Won Koo,Ha, Hyun-Joon
, p. 3293 - 3301 (2000)
The C(3)-N bond of various non-activated enantiomerically pure aziridine-2-methanols was regioselectively cleaved by nitrogen nucleophiles to provide a variety of β-aminoalanine derivatives in high yields. Copyright (C) 2000 Elsevier Science Ltd.
New highly efficient stereoselective synthesis of d-threo-PDMP
Righi, Giuliana,Bovicelli, Paolo,Montini, Francesca,Meloni, Federica,Mandic, Emanuela,Pelagalli, Romina
, p. 3318 - 3322 (2011/11/30)
Starting from a suitably functionalized aziridine, a highly efficient stereoselective synthesis of (1R,2R)-phenyl-2-decanoyl-amino-3-morpholinopropan- 1-ol (d-threo-PDMP) is described. The approach, based on the ring expansion of the aziridine ring to oxa
Methods for treating conditions modulated by lactosylceramide
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, (2008/06/13)
The present invention includes methods for treatment and prophylaxis of conditions associated with lactosylceramide. The methods generally provide for administration to a mammal, particularly a human, of a therapeutically effective amount of a compound that increases enzymatic activity of UDPGal:GlcCerβ1→4 galactosylceramide (GalT-2). In vitro and in vivo assays for detecting compounds with therapeutic capacity to modulate GalT-2 are also provided.
Amino alcohol derivative and method for preparing the same
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Example 7, (2010/01/30)
A process for preparing a 2-acylamino alcohol derivative which comprises (A) reacting an aminopropanol derivative represented by the following formula (1): Y—CH2—C*H (NHP1)—C*H(OH)—R1??(1) with an amine represented by R2H to synthesize an amino alcohol derivative represented by the following formula (2): R2—CH2—C*H(NHP1)—C*H(OH)—R1??(2) (B) leaving P1from said amino alcohol derivative represented by formula (2) to synthesize an amino alcohol derivative represented by the following formula (3): R2—CH2—C*H(NH2)—C*H(OH)—R1??(3) (C) reacting said amino alcohol derivative represented by formula (3) with a carboxylic acid represented by R11COOH or a reactive derivative thereof to prepare a 2-acylamino alcohol derivative represented by the following formula (4): R2—CH2—C*H(NHCOR11)—C*H(OH)—R1??(4 ) wherein * represents an asymmetric carbon atom, and P1, R1, R2and R11are defined in the specification. A process for preparing alcohol derivatives having an acylamino group through several steps from amino group-protected 2-aminopropanol derivatives, and novel amino alcohols useful as intermediates in the process for preparing the alcohol derivative.
Methods for treatment of conditions associated with lactosylceramide
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, (2008/06/13)
The present invention includes methods for treatment and prophylaxis of diseases, post-surgical disorders and bacterial infections associated with lactosylceramide. The methods generally provide for administration for a mammal, particularly a human, of a therapeutically effective amount of a compound that inhibits UDPGal:GlcCerβ1->4 galactosylceramide (GalT-2). In vitro and in vivo assays for detecting compounds with therapeutic capacity to modulate GalT-2 are also provided.
Amino alcohol derivative and method for preparing the same
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, (2008/06/13)
Amino alcohol derivatives with a primary amino group or a substituted amino group influence the synthesis of glycolipids and have antiviral, antitumor, metastasis inhibiting and neural cell growth enhancing functions. The amino alcohol derivatives are useful in preparing 2-acylamino alcohol derivatives.
Synthesis and evaluation of morpholino- and pyrrolidinosphingolipids as inhibitors of glucosylceramide synthase
Miura, Tsuyoshi,Kajimoto, Tetsuya,Jimbo, Masayuki,Yamagishi, Kiwamu,Inokuchi, Jin-Chi,Wong, Chi-Huey
, p. 1481 - 1489 (2007/10/03)
This paper describes the new synthesis and evaluation of some morpholino- and pyrrolidinosphingolipids and mimics as inhibitors of glucosylceramide synthase. It was found that the pyrrolidino derivatives are generally more active than the morpholino derivatives and the best one was shown to be a nanomolar inhibitor. Copyright (C) 1998 Elsevier Science Ltd.
Glycosyltransferase inhibitors: Synthesis of D-threo-PDMP, L-threo- PDMP, and other brain glucosylceramide synthase inhibitors from D- or L- serine
Mitchell, Scott A.,Oates, Bryan D.,Razavi, Hossein,Polt, Robin
, p. 8837 - 8842 (2007/10/03)
The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2- decanoylamino-3-N-morpholino-1-propanol (L-threo-PDMP) (1a) from L-serine, and the enantiomer (LR,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (1b) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the β-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure 1b in high yield after six steps. Three other D- threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D- threo-PDPP (1e). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.
