Di(p-methylbenzyl) phosphates of omega-hydroxyalkyl esters of 11-deoxyprostaglandin E1 were synthesized from disubstituted 1,10-decane and 1,22-docosane derivatives for studying permeability of bilayer membranes. The English version of the paper.
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http://dx.doi.org/10.1023/a:1013910404606 | DOI Listing |
Steroids
November 2016
Département de Chimie, Biochimie et Physique, Université du Québec à Trois-Rivières, C.P. 500, Trois-Rivières, Québec G9A 5H7, Canada. Electronic address:
A series of 7α-linked testosterone dimers were made and tested for biological activity on both androgen-dependent (LNCaP) and androgen-independent (DU-145 and PC3) prostate cancer cell lines. The synthesis proceeds through the formation of a trans-4-(17β-acetoxy-4-androsten-3-one-7α-yl)-but-2-enoic acid 4-hydroxy-alkyl ester intermediate of various length (7a-d) followed by the final dimerization step. The dimers showed interesting biological activity in comparison to the ω-hydroxyalkyl ester intermediates 7a-d.
View Article and Find Full Text PDFJ Enzyme Inhib Med Chem
December 2016
a Department of Organic Chemistry , Gdansk University of Technology, Gdansk , Poland and.
Improved derivatives of mycophenolic acid (MPA) are necessary to reduce the frequency of adverse effects, this drug exerts in treated patients. In this study, MPA was coupled with N-(ω-hydroxyalkyl)-9-acridone-4-carboxamides or N-(ω-hydroxyalkyl)acridine-4-carboxamides to give respective ester conjugates upon Yamaguchi protocol. This esterification required protection of phenol group in MPA.
View Article and Find Full Text PDFJ Agric Food Chem
September 2012
College of Life and Environment Sciences, Shanghai Normal University, Shanghai 200234, China.
On the basis of the research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a new series of nitenpyram analogues with an ω-hydroxyalkyl ester arm anchored on the tetrahydropyrimidine ring was designed and synthesized to further enhance the strength of the hydrogen-bonding action they display in binding with the nAChR. The structures of the target compounds were characterized by (1)H NMR, IR, and elemental analysis, and the cis configuration was confirmed by X-ray diffraction. Preliminary bioassays indicated that all of the nitenpyram analogues exhibited good insecticidal activity against Nilaparvata lugens and Myzus persicae at 100 mg/L, whereas analogues 4d and 6a afforded the best in vitro activity that had ≥ 95% mortality at 4 mg/L; the LC(50) values of the analogues 4d and 6a were 0.
View Article and Find Full Text PDFJ Am Chem Soc
November 2003
Department of Chemistry, University of Calgary, Calgary, Alberta, Canada, T2N 1N4.
A series of aliphatic diselenides and selenides containing coordinating substituents was tested for glutathione peroxidase (GPx)-like catalytic activity in a model system in which the reduction of tert-butyl hydroperoxide with benzyl thiol to afford dibenzyl disulfide and tert-butyl alcohol was performed under standard conditions and monitored by HPLC. Although the diselenides showed generally poor catalytic activity, allyl selenides proved more effective. In particular, allyl 3-hydroxypropyl selenide (25) rapidly generated 1,2-oxaselenolane Se-oxide (31) in situ by a series of oxidation and [2,3]sigmatropic rearrangement steps.
View Article and Find Full Text PDFBioorg Khim
July 2002
Latvian Institute of Organic Synthesis, ul. Aizkraukles 21, Riga, LV-1006 Latvia.
Di(p-methylbenzyl) phosphates of omega-hydroxyalkyl esters of 11-deoxyprostaglandin E1 were synthesized from disubstituted 1,10-decane and 1,22-docosane derivatives for studying permeability of bilayer membranes. The English version of the paper.
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