Edward J. Parish’s research while affiliated with Auburn University and other places

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Publications (140)


Regulation of 3-Hydroxy-3-Methylglutaryl Coenzyme A Reductase Activity by Side-Chain Oxysterols and Their Derivatives
  • Chapter

November 2020

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9 Reads

Edward J. Parish

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Sarawanee C. Parish

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Shengrong Li


The Synthesis of Novel 7, 19-Bifunctional Androstenediones as Aromatase Inhibitors
  • Article
  • Full-text available

January 2017

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41 Reads

Journal of Chemistry and Biochemistry

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Alyssa M. Parish

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Ashley B. S. Curtiss

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[...]

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Angela M. H. Brodie
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Allylic oxidation of steroidal olefins by vanadyl acetylacetonate and tert-butyl hydroperoxide

June 2015

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31 Reads

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11 Citations

Steroids

Readily available vanadyl acetylacetonate was found to oxidize the allylic sites of Δ(5) steroidal alcohols without protection of hydroxyl groups. Cholesterol, dehydroepandrosterone, cholesterol benzoate, cholesterol acetate, pregnenolone, and 5-pregnen-3,20-diene were oxidized to 7-keto products using vanadyl acetylacetonate in one pot reactions at room temperature in the presence of oxygen and water. Copyright © 2015. Published by Elsevier Inc.


Chemical Synthesis of Ring C oxygenated Derivatives of Cholesterol and their Inhibition of Sterol Biosynthesis

January 2015

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9 Reads

Journal of Chemistry and Biochemistry

Chemical Synthesis of Ring C oxygenated Derivatives of Cholesterol and their Inhibition of Sterol Biosynthesis Nida A McKee, Chi Luo, Don E Parish, Frederick R Taylor, Edward J Parish Abstract Chemical synthesis of oxygenated derivatives of cholesterol and lanosterol, have been shown to produce oxysterols with significant activity as inhibitors of 3-hydroxy-3- methylglutaryl (HMG) CoA reductase, a key regulatory enzyme in sterol biosynthesis. We now reports the detailed chemical synthesis of new ring C oxysterols which have been evaluated as inhibitors of HMG-CoA reductase. The starting material was 3- benzoyloxy-9,11-epoxy-5-cholest-7-ene (1), whose structure has been confirmed by X-ray crystallographic analysis. Chemical modification of 1 produced 9,11- epoxy-5-cholest-7-en-3-ol (2), the 9-H (natural) isomers 5,9-cholest-7-en- 3,11-diol (3) and 5,9-cholest-7-en-3,11-diol (5), and the 9-H (unnatural) isomers 5,9-cholest-7-en-3,11-diol (7) and 5,9-cholest-7-en-3,11-diol (8). The ring C oxysterols 3, 5, 7, and 8 have been found to be potent inhibitors of HMG-CoA reductase activity in cultured mouse L cells. The similar levels of inhibitory activity indicated that the difference in stereochemistry at C-8 was not a crucial factor for the activity of these oxysterols. Full Text: PDF DOI: 10.15640/jcb.v3n2a1 Chemical Synthesis of Ring C oxygenated Derivatives of Cholesterol and their Inhibition of Sterol Biosynthesis Nida A McKee, Chi Luo, Don E Parish, Frederick R Taylor, Edward J Parish Abstract Chemical synthesis of oxygenated derivatives of cholesterol and lanosterol, have been shown to produce oxysterols with significant activity as inhibitors of 3-hydroxy-3- methylglutaryl (HMG) CoA reductase, a key regulatory enzyme in sterol biosynthesis. We now reports the detailed chemical synthesis of new ring C oxysterols which have been evaluated as inhibitors of HMG-CoA reductase. The starting material was 3- benzoyloxy-9,11-epoxy-5-cholest-7-ene (1), whose structure has been confirmed by X-ray crystallographic analysis. Chemical modification of 1 produced 9,11- epoxy-5-cholest-7-en-3-ol (2), the 9-H (natural) isomers 5,9-cholest-7-en- 3,11-diol (3) and 5,9-cholest-7-en-3,11-diol (5), and the 9-H (unnatural) isomers 5,9-cholest-7-en-3,11-diol (7) and 5,9-cholest-7-en-3,11-diol (8). The ring C oxysterols 3, 5, 7, and 8 have been found to be potent inhibitors of HMG-CoA reductase activity in cultured mouse L cells. The similar levels of inhibitory activity indicated that the difference in stereochemistry at C-8 was not a crucial factor for the activity of these oxysterols. Full Text: PDF DOI: 10.15640/jcb.v3n2a1


The Remote Functionalization of Steroid side Chains by Chromic Anhydrides

January 2015

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23 Reads

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2 Citations

Journal of Chemistry and Biochemistry

The Remote Functionalization of Steroid side Chains by Chromic Anhydrides Nida A McKee, Alyssa M Parish, Edward J Parish Abstract The chemical modification of saturated steroid side chains usually requires a multistep synthesis to construct new side chains to be added to the steroid nucleus. We have found that chromal acetates can be used to directly introduce functionality onto the steroid side chain to produce useful products. These initial products may also provide an entry towards the further modification of the side chain to provide steroids which could previously be obtained only with great difficulty. Full Text: PDF DOI: 10.15640/jcb.v3n2a1


ChemInform Abstract: A One-Step Synthesis of 6β-Hydroxy-δ4-3-ketones. Novel Oxidation of Homoallylic Sterols with Permanganate Ion

December 2010

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6 Reads

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2 Citations

ChemInform

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.


ChemInform Abstract: Selective Oxidation of Steroidal Homoallylic Alcohols Using Pyridinium Chlorochromate (PPC).

August 2010

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11 Reads

ChemInform

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.




Citations (51)


... The use of plant-based lipid sources to replace FO in aquaculture feeds results in reduced dietary cholesterol content, because they contain high levels of phytosterols and very little cholesterol compared to fish oils (Norambuena et al., 2013). Cholesterol is an integral component of cell membranes and serves as a precursor to important metabolites, such as sterol hormones and bile acids (Thomas et al., 2012; Parish et al., 2008; Norambuena et al., 2013). Most of the significant correlations among cholesterol-related genes with dietary and muscle tissue sterol and FA content were related to cholesterol catabolism or reduced cholesterol synthesis. ...

Reference:

Growth performance, tissue composition, and gene expression responses in Atlantic salmon (Salmo salar) fed varying levels of different lipid sources
4 Chemistry of Waxes and Sterols: Chemistry, Nutrition, and Biotechnology, Fourth Edition
  • Citing Chapter
  • March 2017

... Further work on the synthesis of steroid 5,6-epoxides from olefins using KMnO 4 /metal sulphate and nitrate systems has been published [40] and two mechanistic approaches have been proposed for this reaction. Parish and Li suggested that there was coordination of the copper ion on the less hindered -face of the double bond, forming a -complex that weakened it and provided for the subsequent permanganate attack on the -face [41,42]. Another study, however, suggested that the mechanism involved the kinetically controlled attack of the MnO 4 − ion in the omega phase on the alkene, in a Markovnikoff manner and in an axial sense. ...

The Study of Epoxidation of Steroidal Alkenes with Potassium Permanganate-Inorganic Salts
  • Citing Article
  • June 1996

... It was significant that under the solvent-free conditions 3-acetoxy cholesterol (11) was typically oxidized by PFC to 3-acetoxy-7-ketocholesterol (11a) in 64% isolated yield in about 2 hr at 658C. Incidentally, although oxidation of D 5 -steroids in refluxing benzene with PFC was quite effective, [20] a similar oxidation in CH 2 Cl 2 or CH 3 CN under prolonged reflux did not afford any promising results. [9] The efficacy of the protocol is demonstrated also by the alacrity with which the deoximation of 12 to the corresponding ketone (12a) occurred. ...

Allylic Oxidation of Δ5-Steroids with Pyridinium Fluorochromate
  • Citing Article
  • December 1996

... They usually contain very long-chain fatty acids, primary and secondary alcohols, hydrocarbons, sterol esters, aliphatic aldehydes, ketones, b-diketones, triacylglycerols, triterpenes, and sterols. Genetic and environmental factors influence the quality of waxes and the structure (chain length, degree of unsaturation, and branching) of the substances in their composition (Parish et al. 2002;Tinto et al. 2017). Animal sources of waxes include insects (bees, Apis mellifera), whales (Physeter macrocephalus), and sheep (Ovis aries) (Tinto et al. 2017). ...

The Chemistry of Waxes and Sterols
  • Citing Chapter
  • April 2002

... Labile tetrakis-acetonitrile complexes of the [Cu(CH 3 CN) 4 ]X type, where X ¼ BF 4 À , PF 6 À , ClO 4 À (ref. 1 and 2) are widely used in research laboratories and industrial processes as catalysts in cycloaddition 3,4 and Ullmann 5 reactions, intramolecular aromatic annulations, 6,7 oxidation of primary alcohols 8 and many other popular reactions of organic synthesis. [9][10][11][12][13] At the same time they serve as important precursors for the synthesis of overwhelming majority of mononuclear [14][15][16] and homo-17 and hetero-polynuclear 18,19 copper(I) complexes, which also have numerous practical applications, [20][21][22] one of which is large-scale production of emitting materials for OLED fabrication. ...

e-EROS Encyclopedia of Reagents for Organic Synthesis
  • Citing Chapter
  • March 2007

... The response is reversible when cycled at 1-min exposure to Cl 2 followed by the 1-min N 2 cleaning. The EuPc 2 -based amperometric sensor may be considered to be selective to Cl 2 in light of the observation that there is no change in conductivity on exposure to ammonia (NH 3 ), nitric oxide (NO) and NO 2 [35]. The 5-100 ppm NO 2 sensing response of evaporated cobalt phthalocyanine films (35-80 nm thick) on Au-interdigitated electrodes has been investigated by recording current at a constant bias of 1 V. Like the LB phthalocyanine films, the kinetic responses over 100 min are characterised by initially rapid surface adsorption, and subsequently, slow diffusion into the bulk and the complete recovery is, therefore, not achieved [36]. ...

Europium bisphthalocyanine LB films for gas sensibility and selectivity
  • Citing Article
  • October 1998

Supramolecular Science

... Authentic samples of 3P-hydroxy-5a-cholest-8(14)-en- 15-one (1) (l), 3a-hydroxy-5a-cholest-8(14)-en-15-one (13), 5a-cholest-8(14)-en-15-one (14), 5a-cholest-8(14)-ene-3,15dione (15), 3fl-hydroxy-5a-cholesta-6,8(14)-dien-l5-one (16), 5a-cholesta-6,8(14)-diene-3,15-dione (16), and [ 2,2,3a,4,4-*HI-1 (15) were prepared as described previously. [4-14C]-1, a gift from Lederle Laboratories (Pearl River, NY), was purified as described previously (lo). ...

Chemical syntheses of 5α-cholesta-6,8(14)-dien-3β-ol-15-one and related 15-oxygenated sterols
  • Citing Article
  • December 1979

Chemistry and Physics of Lipids

... Gas-liquid chromatography (GLC) was performed with flame ionization detection using a 15-30 m DB-5 capillary column (0.25 mm ID, 0.10 pm film thickness, 5 psi N,). High performance liquid chromatography (HPLC) was performed on a Spherisorb ODS-I1 column (C,,, 5 Houston, TX) using a Waters instrument (Model 6000 pump, U6K injector, and either a Model R401 refractive index detector or Model 490 UV detector; Milford, MA). Elemental analyses were performed by Galbraith Laboratories (Knoxville, TN). ...

Inhibition of sterol biosynthesis by 9α-fluoro and 9α-hydroxy derivatives of 5α-cholest-8(14)-en-3β-ol-15-one
  • Citing Article
  • November 1979

Biochemical and Biophysical Research Communications