98793-02-3Relevant academic research and scientific papers
Convenient synthesis and efficient resolution of 3,3′-bis(benzyloxy)-1,1′-binaphthalene-2,2′-diol
Tsubaki, Kazunori,Morikawa, Hiroshi,Tanaka, Hiroyuki,Fuji, Kaoru
, p. 1393 - 1396 (2003)
The synthesis and resolution of 3,3′-bis(benzyloxy)-1,1′-binaphthalene-2,2′-diol 1 is described. A diastereomeric mixture of 7 (derived from (±)-1 and Boc-Ala-OH) was separated using crystallization and column chromatography.
Structure-affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101
Bolchi, Cristiano,Catalano, Paolo,Fumagalli, Laura,Gobbi, Marco,Pallavicini, Marco,Pedretti, Alessandro,Villa, Luigi,Vistoli, Giulio,Valoti, Ermanno
, p. 4937 - 4951 (2007/10/03)
A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the α1a-AR with respect to the other two α1 subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the α1a-AR, α1b-AR, α1d-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific α1a affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high α1a affinity of (S)-1 and its α1a versus α1b selectivity slightly increasing the α1a/α1d and α1a/5HT 1A affinity ratios. The SAR data were evaluated in the light of known α1 subtype pharmacophores and of the α1a-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models.
SULFURIC ACID ESTERS OF SUGAR ALCOHOLS
-
, (2008/06/13)
Compounds of the formula STR1 wherein n 1-n 9 are each independently 0 or 1;m 1-m 9 are each independently 0 or 1, but with the proviso that at least one of m 1, m 2 and m. sup.3, at least one of m 4, m 5 and m 6 and, when present, at least one of m 7, m 8 and m 9 is 1; and whereinX. sup.1-X 18 each independently is--O--,--CONR 1,--NR 1 CO--or--NR 1--;R 1 is hydrogen or lower alkyl;W is a benzene or s-triazine; Y. sup.1-Y 9 each independently is an aromatic ring systems;A 1-A 3 each independently is a residue of a sugar alcohol devoid of the 1-hydroxy group or a derivative thereof, a residue of a sugar acid devoid of the 1-carboxy group or a derivative thereof or tris-(hydroxymethyl)-methyl;D is the di-residue of a sugar alcohol devoid of 2 hydroxy groups or a derivative thereof or the di-residue of a sugar dicarboxylic acid devoid of 2 carboxy group or a derivative thereof;Q 1-Q. sup.3 and Z 1-Z3 each independently are the di-residue of a sugar alcohol devoid of 2 hydroxy groups or a derivative thereof or the di-residue of a sugar dicarboxylic acid devoid of 2 carboxy groups or a derivative thereof or didesoxyglycopyranoside or a derivative thereof, wherein at least one hydroxy group of residues A 1-A 3, D, Q 1-Q 3 and Z. sup.1-Z 3 is esterified with sulfuric acid, and pharmaceutically usable salts thereof are useful for the treatment of disorders which are characterized by excessive or destructive proliferation of smooth muscle cells.
Synthesis and Molecular Inclusion of Naphtho- and Benzonaphtho-Fused Pyridino Crowns - Crystal Structure of a Dioxane Clathrate
Weber, Edwin,Koehler, Hans-Juergen,Reuter, Hans
, p. 959 - 968 (2007/10/02)
New naphtho- and benzonaphtho-fused pyridino crown compounds 5-7 are synthesized.The new crown ethers form numerous stoichiometric crystalline inclusion complexes with typical dipolar-aprotic and apolar compounds including dimethylformamide and ureas, dimethyl sulfoxide, nitro compounds, and nitriles or dioxane, benzene, and toluene.On the other hand, 5-7 do not include alcohols and other protic compounds.As expected, the monobenzopyridino crown 4, synthesized as a reference compound, is unable to form inclusions.During the synthesis of 4 the 42-membered dimer macro ring 10 is also obtained.The structure of the crystalline dioxane inclusion compound of the trinaphthopyridino crown 7 is determined by X-ray structure analysis.It shows a specific crystal packing of the host molecules providing free lattice interspace which is occupied by the guest molecules.Based on the conformation of the host molecule and by comparison with the crystal structure of the benzo-analogous parent compound 2, conclusions for future design of host molecules for the crystal phase are drawn. - Key Words: Crown ethers / Pyridino crown ethers / Clathrates
