4617-33-8Relevant articles and documents
ONE-STEP SYNTHESIS OF ω-HYDROXYCARBOXYLIC ACIDS BY THE REACTION OF ω-METALOXYLATED GRIGNARD REAGENTS WITH β-PROPIOLACTONES
Fujisawa, Tamotsu,Mori, Toshiki,Kawara, Tatsou,Sato, Toshio
, p. 569 - 570 (1982)
ω-Metaloxylated Grignard reagents reacted with β-propiolactones chemo- and regioselectively in the presence of Li2CuCI4 to afford ω-hydroxycarboxylic acids in high yields.
SIMPLE SYNTHESIS OF 15-HYDROXYPENTADECANOIC ACID FROM 10-UNDECENOIC ACID
Zakharkin, L. L.,Pryanishnikov, A. P.
, p. 2300 - 2301 (1982)
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Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors
Shibuya, Kimiyuki,Kawamine, Katsumi,Miura, Toru,Ozaki, Chiyoka,Edano, Toshiyuki,Mizuno, Ken,Yoshinaka, Yasunobu,Tsunenari, Yoshihiko
, p. 4001 - 4013 (2018/06/26)
We describe our molecular design of aortic-selective acyl-coenzyme A:cholesterol O-acyltransferase (ACAT, also abbreviated as SOAT) inhibitors, their structure–activity relationships (SARs) and their pharmacokinetic (PK) and pharmacological profiles. The connection of two weak ligands—N-(2,6-diisopropylphenyl)acetamide (50% inhibitory concentration [IC50] = 8.6 μM) and 2-(methylthio)benzo[d]oxazole (IC50 = 31 μM)—via a linker comprising a 6 methylene group chains yielded a highly potent molecule, 9-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)nonanamide (3h) that exhibited high potency (IC50 = 0.004 μM) toward aortic ACAT. This head-to-tail design made it possible to markedly enhance the activity to 2150- to 7750-fold and to discriminate the isoform-selectivity based on the double-induced fit mechanism. At doses of 1 and 3 mg/kg, 3h significantly decreased the lipid-accumulation areas in the aortic arch to 74 and 69%, respectively without reducing the plasma total cholesterol level in high fat- and cholesterol-fed F1B hamsters. Here, we demonstrate the antiatherosclerotic effect of 3h in vivo via its direct action on aortic ACAT and its powerful modulator of cholesterol level. This molecule is a potential therapeutic agent for the treatment of diseases involving ACAT-1 overexpression.
A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues
Cochrane, James R.,Yoon, Dong Hee,McErlean, Christopher S.P.,Jolliffe, Katrina A.
supporting information, p. 1344 - 1351 (2012/11/07)
The cyclic peptide core of the antifungal and antibiotic cyclic depsipeptide LI-F04a was synthesised by using a modified Yamaguchi macrolactonization approach. Alternative methods of macrolactonization (e.g., Corey-Nicolaou) resulted in significant epimerization of the C-terminal amino acid during the cyclization reaction. The D-stereochemistry of the alanine residue in the naturally occurring cyclic peptide may be required for the antifungal activity of this natural product.
