- Organocatalytic syn-aldol reactions of dioxanones with (S)-isoserinal hydrate: Synthesis of L-deoxymannojirimycin and L-deoxyidonojirimycin
-
(Chemical Equation Presented) We report a new protocol for synthesis of L-1-deoxymannojirimycin, L-1-deoxyidonojirimycin, and the N-isopropyl derivative of the latter compound from the readily available precursors (S)-isoserinal hydrate and 2-tert-butyl-2
- Palyam, Nagarjuna,Majewski, Marek
-
supporting information; experimental part
p. 4390 - 4392
(2009/09/06)
-
- Novel glucagon receptor antagonists with improved selectivity over the glucose-dependent insulinotropic polypeptide receptor
-
Optimization of a new series of small molecule human glucagon receptor (hGluR) antagonists is described. In the process of optimizing glucagon receptor antagonists, we counter-screened against the closely related human gastric inhibitory polypeptide receptor (hGIPR), and through structure activity analysis, we obtained compounds with low nanomolar affinities toward the hGluR, which were selective against the hGIPR and the human glucagon-like peptide-1 receptor (hGLP-1R). In the best cases, we obtained a >50 fold selectivity for the hGluR over the hGIPR and a >1000 fold selectivity over the hGLP-1R. A potent and selective glucagon receptor antagonist was demonstrated to inhibit glucagon-induced glycogenolysis in primary rat hepatocytes as well as to lower glucagon-induced hyperglycemia in Sprague - Dawley rats. Furthermore, the compound was shown to lower blood glucose in the ob/ob mouse after oral dosing.
- Kodra, János T.,J?rgensen, Anker Steen,Andersen, Birgitte,Behrens, Carsten,Brand, Christian Lehn,Christensen, Inger Th?ger,Guldbrandt, Mette,Jeppesen, Claus Bekker,Knudsen, Lotte B.,Madsen, Peter,Nishimura, Erica,Sams, Christian,Sidelmann, Ulla G.,Pedersen, Raymon A.,Lynn, Francis C.,Lau, Jesper
-
experimental part
p. 5387 - 5396
(2009/07/01)
-
- New convenient reagents for chemoselective N-alkoxycarbonylation of (S)-isoserine: Application in the isepamicin synthesis
-
A synthesis of a series of N-alkoxycarbonyl mercaptobenzothiazoles (MBTs) and their application as reagents for chemoselective protection of amino group are presented herein. It was shown that all new reagents, Z-MBT, Fmoc-MBT, Phoc-MBT, and Tec-MBT, are highly effective in the selective N-alkoxycarbonylation of (S)-isoserine. The transformation is a simple, fast, and low-cost protocol, which is applicable in scale-up experiments. The starting MBT was fully recovered at the end of the process, which is an additional advantage of the method. The efficiency of the Z-reagent was also demonstrated by the selective protection of both gentamicin B and (S)-isoserine before their peptide-type coupling in the synthesis of the aminoglycoside antibiotic isepamicin. Copyright Taylor & Francis Group, LLC.
- Doktorov, Konstantin,Tarpanov, Velichko,Mechkarova, Pepa
-
p. 3709 - 3718
(2008/02/10)
-
- ENHANCED INDOLINONE BASED PROTEIN KINASE INHIBITORS
-
Alpha-hydroxy- omega-(2-oxo-indolylidenemethyl-pyrrole-3'-carbonyl) amino alkanoic acid and amide derivatives have enhanced and unexpected drug properties as inhibitors of protein kinases and are useful in treating disorders related to abnormal protein ki
- -
-
Page/Page column 19
(2010/11/25)
-
- Efficient synthesis of N-benzyloxycarbonyl- and N-tert-butoxycarbonyl-(S)-isoserine and their derivatives
-
A mild and efficient synthesis of N-protected (S)-isoserine from (S)-malic acid monoester via an oxazolidin-2-one is described.
- Andruszkiewicz, Ryszard,Wyszogrodzka, Monika
-
p. 2101 - 2103
(2007/10/03)
-
- Total synthesis of the biphenomycins; II. Synthesis of protected (2S,4R)-4-hydroxyornithines
-
Improved synthetic methods for the preparation of three differently protected (2S,4R)-4-hydroxyornithine (10, 16, 24) have been developed which obviously can be used for the construction of the other stereoisomers. Formation of the corresponding α,β-dideh
- Schmidt,Meyer,Leitenberger,Stabler,Lieberknecht
-
p. 409 - 413
(2007/10/02)
-