106757-57-7Relevant articles and documents
Stereoselective synthesis and antiproliferative activity of the isomeric sphinganine analogues
?onková, Miroslava,Martinková, Miroslava,Gonda, Jozef,Jacková, Dominika,Pilátová, Martina Bago,Kupka, Daniel,Jáger, Dávid
, p. 76 - 85 (2018/12/11)
A flexible synthetic approach to biologically active sphingoid base-like compounds with a 3-amino-1,2-diol framework was achieved through a [3,3]-sigmatropic rearrangement and late stage olefin cross-metathesis as the key transformations. The stereochemistry of the newly created stereogenic centre was assigned via a single crystal X-ray analysis of the (4S,5R)-5-(hydroxymethyl)-4-vinyloxazolidine-2-thione. In order to rationalise the observed stereoselectivity of the aza-Claisen rearrangement, DFT calculations were carried out. The targeted isomeric sphingoid bases were screened in vitro for anticancer activity on a panel of seven human malignant cell lines. Cell viability experiments revealed that C17-homologues are more active than their C12 congeners.
Synthesis and evaluation of eight- and four-membered iminosugar analogues as inhibitors of testicular ceramide-specific glucosyltransferase, testicular β-glucosidase 2, and other glycosidases
Lee, Jae Chul,Francis, Subhashree,Dutta, Dinah,Gupta, Vijayalaxmi,Yang, Yan,Zhu, Jin-Yi,Tash, Joseph S.,Schoenbrunn, Ernst,Georg, Gunda I.
experimental part, p. 3082 - 3098 (2012/05/31)
Eight- and four-membered analogues of N-butyldeoxynojirimycin (NB-DNJ), a reversible male contraceptive in mice, were prepared and tested. A chiral pool approach was used for the synthesis of the target compounds. Key steps for the synthesis of the eight-membered analogues involve ring-closing metathesis and Sharpless asymmetric dihydroxylation and for the four-membered analogues Sharpless epoxidation, epoxide ring-opening (azide), and Mitsunobu reaction to form the four-membered ring. (3S,4R,5S,6R,7R)-1-Nonylazocane-3,4,5,6,7-pentaol (6) was moderately active against rat-derived ceramide-specific glucosyltransferase, and four of the other eight-membered analogues were weakly active against rat-derived β-glucosidase 2. Among the four-membered analogues, ((2R,3S,4S)-3-hydroxy-1-nonylazetidine-2,4-diyl)dimethanol (25) displayed selective inhibitory activity against mouse-derived ceramide-specific glucosyltransferase and was about half as potent as NB-DNJ against the rat-derived enzyme. ((2S,4S)-3-Hydroxy-1-nonylazetidine-2,4-diyl)dimethanol (27) was found to be a selective inhibitor of β-glucosidase 2, with potency similar to NB-DNJ. Additional glycosidase assays were performed to identify potential other therapeutic applications. The eight-membered iminosugars exhibited specificity for almond-derived β-glucosidase, and the 1-nonylazetidine 25 inhibited α-glucosidase (Saccharomyces cerevisiae) with an IC50 of 600 nM and β-glucosidase (almond) with an IC50 of 20 μM. Only N-nonyl derivatives were active, emphasizing the importance of a long lipophilic side chain for inhibitory activity of the analogues studied.
STEREOCONTROLLED SYNTHESIS OF A C14-C20 BUILDING BLOCK FOR AMPHOTERICIN B USING A NOVEL WITTIG REARRANGEMENT
Bruecker, Reinhard
, p. 5747 - 5750 (2007/10/02)
The C14-C20 unit 11 of the polyene macrolide antibiotic amphotericin B (1) was synthesized from L-arabinose in 13 steps.The key step 7 -> 10 features diastereocontrol through asymmetric induction in a novel Wittig rearrangement.
General Method for the Preparation of α-Methylene-γ-butyrolactones from (R)- and (S)-1,2-Isopropylideneglyceraldehydes
Suzuki, Toshio,Sato, Etsuko,Kamada, Shinko,Tada, Hitoshi,Unno, Katsuo,Kametani, Tetsuii
, p. 387 - 392 (2007/10/02)
Both (R) - and (S)-1,2-isopropylideneglyceraldehydes (1) and (18) are shown to be useful, inexspensive chiral starting materials for syntheses of α-methylene-γ-butyrolactones (15) and (28) which are potential intermediates for biologically important sesquiterpene lactones.
