75677-04-2Relevant articles and documents
Synthesis and biological activity of new 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitors: 2-oxetanones with a side chain mimicking the folded structure of 1233A.
Hashizume,Ito,Yamada,Nagashima,Kanao,Tomoda,Sunazuka,Kumagai,Omura
, p. 512 - 520 (2007/10/02)
To mimic the folded side chain conformation of 1233A (1), which is a 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitor, 1233A analogs with aromatic rings in the side chain were synthesized. The 2-oxetanone moiety was kept intact. Among 1233A and its synthetic analogs, trans-3-hydroxymethyl-4-[2-(7-methoxycarbonyl-1-naphthyl)ethyl]-2-oxe tanone (23) showed the highest HMG-CoA synthase inhibitory activity in vitro. The structure-activity relationship at the side chain is discussed.
Synthesis and biological activity of new 3-hydroxy-3-methylglutaryl-CoA synthase inhibitors: 2-Oxetanones with a meta-substituent on the benzene ring in the side chain
Hashizume,Ito,Kanaya,Nagashima,Usui,Oshima,Kanao,Tomoda,Sunazuka,Kumagai,Omura
, p. 1272 - 1278 (2007/10/02)
Isosteric side chain analogs of 3a were synthesized and tested for inhibitory activities towards 3-hydroxy-3-methylglutaryl coenzyme A (HMG- CoA) synthase and upon cholesterol production in Hep G2 cells and in mouse liver. It became clear that the lipophi
Regioselective synthesis of 1,8-dihydroxytetralins through a tandem reduction/intramolecular hydroxyalkylation of 4-(3-hydroxyphenyl)alkanoates
Guanti, Giuseppe,Banfi, Luca,Riva, Renata
, p. 11945 - 11966 (2007/10/02)
A series of 4-(3-hydroxyphenyl)butanoates 3 has been prepared and transformed into 1,8-dihydroxytetralins of general formula 2 by treatment with 2 equivalents of DIBALH followed by quenching with aqueous NH4Cl. A possible mechanism for this novel totally regioselective intramolecular hydroxyalkylation is suggested and the factors affecting the stability of 1,8-dihydroxytetralins 2 are also discussed.
Intramolecular arylation of a soft carbon centre using Mn(III) acetate: Studies towards the spirostructure of fredericamycin-A
Aidhen, Indrapal Singh,Narasimhan, N. S.
, p. 222 - 228 (2007/10/02)
The potential of Mn(III) acetate has been explored for oxidative cyclisation in the indanediones 3, for the synthesis of the core subunit 2 of fredericamycin-A(1).
Tandem Reduction / Intramolecular Hydroxyalkylation of (3-Hydroxyphenyl)alkanoates: a New Regioselective Approach to 1,8-Dihydroxytetralins
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica,Riva, Renata,Thea, Sergio
, p. 3919 - 3922 (2007/10/02)
4-(3-hydroxyphenyl)-butanoates 4, on treatment with DIBALH, followed by hydrolytic work-up, undergo a novel completely regioselective intramolecular hydroxyalkylation reaction to give 1,8-dihydroxytetralins.The yield of the reaction depends heavily on the structure of starting material, best results being achieved with 3,3-disubstituted butanoates.