- LIPIDIC FURAN, PYRROLE, AND THIOPHENE COMPOUNDS FOR USE IN THE TREATMENT OF ATROPHIC VAGINITIS
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Provided herein are lipidic furan, pyrrole, and thiophene compounds, compositions, and methods using such compounds and compositions for the treatment of atrophic vaginitis. Specifically, the invention includes administering an effective amount of a compound of Formula I, I′, or I″, or a pharmaceutically acceptable composition, salt, isotopic analog, prodrug, or combination thereof, to a subject suffering from atrophic vaginitis.
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Paragraph 0167; 0168; 0169; 0170; 0171
(2017/11/16)
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- LIPIDIC FURAN, PYRROLE, AND THIOPHENE COMPOUNDS FOR TREATMENT OF CANCER, NEUROLOGICAL DISORDERS, AND FIBROTIC DISORDERS
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Compounds, methods, and compositions are provided for the treatment of cancer, neurological disorders, and fibrotic disorders. Specifically, the invention includes administering an effective amount of a compound of Formula I, II, or III, or a pharmaceutically acceptable composition, salt, isotopic analog, prodrug, or combination thereof, to a subject suffering from a cancer, neurological disorder, or fibrotic disorder.
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Page/Page column 41; 45
(2014/10/15)
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- A divergent synthesis of [1-14C]-mono-E isomers of fatty acids
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A convenient synthesis of [1-14C]-mono-trans fatty acid using olefin inversion as a key-step is described. This methodology allows for a facile synthesis of [1-14C]-labelled mono-trans analogues of oleic, linoleic and linolenic acids. As an example, only eleven steps were necessary to obtain the [1-14C]-mono-E isomers of linolenic acid from its commercial all-Z form. In the first step, Barton's decarboxylation procedure yielded a bromo intermediate. Epoxidation of this compound resulted in the formation of three monoepoxides, which could be separated by HPLC. After identification by 1H NMR and MS, the pure monoepoxides were then subjected to inversion consisting of a stereospecific deoxygenation followed by a β-elimination step. Finally, the labelling was introduced by substitution of the bromine by a [14C]-cyano group followed by hydrolysis.
- Georgin,Taran,Mioskowski
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- Large-scale preparation of (9Z,12E)-[1-13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1-13C]-octadeca-9,12,15-trienoic acid and their [1-13C] all-cis isomers
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Several grams of labelled trans linoleic and linolenic acids with high chemical and isomeric purities (>97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z,12E)-[1-13C]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z,15E)-[1-13C]-octadeca-9,12,15-trienoic acid were obtained in, respectively, seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-13C]-octadeca-9,12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-13C]-octadeca-9,12,15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities (>0.5%) of each labelled fatty acid have been characterised. Copyright (C) 2000 Elsevier Science Ireland Ltd.
- Loreau,Maret,Poullain,Chardigny,Sebedio,Beaufrere,Noel
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- Novel antifeedant and insecticidal compounds from avocado idioblast cell oil
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Several insecticidal compounds have been identified by bioassaydriven fractionation of avocado, Persea americana Mill, idioblast cell oil. A flash chromatography fraction of the oil showed substantial toxicity to early instars of the generalist insect herbivore, Spodoptera exigua (Hubner) (100% mortality after seven days). Following further fractionation, five biologically active compounds, 2-(pentadecyl)furan, 2-(heptadecyl)furan, 2-(1E-pentadecenyl)furan, 2-(8Z, 11Z-heptadecadienyl)furan, and the triglyceride triolein, were identified. Several minor components were also tentatively identified, including 2-(1Z-pentadecenyl)furan, 2-(1E-heptadecenyl)furan, and 2-(1E,8Z, 11Z-heptadecatrienyl)furan. Several 2-alkylfurans of this type have been reported previously from avocado (Persea spp.) and have received the common name of avocadofurans. The major compounds were tested individually for toxic and growth inhibitory effects. Individually, the compounds had low to moderate toxicity. Of these, 2-(pentadecyl)furan had the greatest effects, with an LC50 value of 1031 μg/g. At concentrations of 600 μg/g or higher in diets, larval growth was inhibited by >70% compared to controls. The analogous 2-(heptadecyl)furan had an LC50 value of 1206 μg/g, and also significantly reduced larval growth (>75% versus controls) at concentrations of > 600 μg/g. The unsaturated analogs 2-(1E-pentadecenyl)furan and 2-(8Z, 11Z-heptadecadienyl)furan were less toxic. Triolein was only weakly toxic, with an LC50 value of 10,364 μg/g diet. Larval growth was inhibited only at concentrations of 7000 μg/g or higher. The potential of avocadofurans in insect control is discussed.
- Rodriguez-Saona, Cesar,Millar, Jocelyn G.,Maynard, David F.,Trumble, John T.
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p. 867 - 889
(2007/10/03)
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- Synthesis of (9Z,12E)- and (9E,12Z)-[1-14C]linoleic acid and (5Z,8Z,11Z,14E)-[1-14C]arachidonic acid
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(3Z,6E)-1-Bromododeca-3,6-diene, a common intermediate in the synthesis of labelled 12t linoleic acid and 14t arachidonic acid, was obtained from (E)-3-nonyl-1-ol: in four steps, via conventional functional manipulations. Cross-coupling of this bromododecadiene with the Grignard reagent of 1-chloro-5-(tetrahydropyranyloxy)pentane gave a C17 dienic ether which was further transformed in three steps to 12t-[l-14C]linoleic acid in 22% overall yield from 3-nonyl-1-ol (eight steps). The synthesis of 14t arachidonic acid involves a Wittig reaction between (Z)-7-(t-butyldiphenylsilyloxy)hept-3-enal and the ylide of (3Z,6E)-dodeca-3,6-dienyl-triphenylphosphonium bromide. The resulting C19 tetraenic ether was transformed in three steps to 14t [l-14C]arachidonic acid (isomeric and radiochemical purities > 99%). 9t Linoleic acid was obtained by a stepwise six-carbon elongation chain of both ends of(E)-6-(2-tetrahydropyranyloxy)-hex-3-enyltriphenylphosphonium salt in 20% overall yield.
- Berdeaux,Vatele,Eynard,Nour,Poullain,Noel,Sebedio
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- Synthesis of the Avocado Antifungal, (Z,Z)-2-Hydroxy-4-oxohenicosa-12,15-dien-1-yl Acetate
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A synthesis of the avocado antifungal, (Z,Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl acetate (la), confirms the structure of the compound as isolated from both avocado fruit and leaves, and provides the absolute configuration of the natural lipid.
- Bull, Steven D.,Carman, Raymond M.
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p. 1661 - 1672
(2007/10/02)
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