Beta-unsaturated Ketones Research Articles

Computer-assisted quantitative infrared conformational analysis of alpha, beta-unsaturated ketones

Investigates the s-cis s-trans conformational equilibrium of alpha, beta-unsaturated ketones.

Biosynthesis of 18-oxocortisol by aldosterone-producing adrenal tissue.

Aldosterone-biosynthesizing adrenal tissue contains an angular methyl oxidase which converts corticosterone to 18-hydroxycorticosterone and aldosterone. Cortisol, when incubated with an active source of this oxidase, the bullfrog interrenal gland, was converted to 18-hydroxycortisol and a new C-18-oxygenated steroid identified as 11 beta, 17 alpha,21-trihydroxy-3,20-diketo-4-pregnene-18-al, or 18-oxocortisol. Proof of structure was based on the evidence that it was an alpha, beta-unsaturated ketone biosynthesized from cortisol with an empirical formula of C21H28O6. Low resolution gas chromatography-mass spectrometry of its fully derivatized methoxime trimethylsilyl ether confirmed a trioxopregnenetriol structure in which one aldehyde group was partially masked as an internal hemiacetal. That the oxo group had replaced the C-18 angular methyl was shown by oxidative degradation of the side chain with either periodic acid or sodium bismuthate to yield an hydroxy gamma-lactone rather than an etioacid. It is suggested that the corticosterone methyl oxidase system of aldosterone-producing cells has diminished substrate specificity enabling it to accept cortisol as a suboptimal substrate. Angular methyl oxidation of cortisol to its 18-hydroxy and 18-oxoderivative in two hypertensive disorders is attributed to a derangement in adrenocortical functional zonation permitting access of glucocorticoid products into the mineralocorticoid-biosynthesizing system.

Aspects of the metabolism of the peripheral vasodilator mecinarone (14C-6809 MD) in rat, dog and man.

The major proportion of oral doses of 14C-mecinarone was excreted in the faeces by rat, dog and man, and in all species the faecal metabolites were more polar than mecinarone and the O-desmethyl reference compounds. Rat faecal extracts contained two major components each accounting for about 30-40% of the radioactivity. Dog and human faecal extracts contained some mecinarone but also three major, more polar components, two of which corresponded to the rat metabolites. Rat bile contained three major components and dog bile two components. One of the components in both bile samples was shown to be a conjugate of O-desmethyl-mecinarone. Besides mecinarone human urine contained a component corresponding to the phenol resulting from 0-demethylation in the p-methoxycinnamoyl group. The same two compounds were also detected in human plasma. The two major components in rat and dog faecal extracts gave mass spectra identical to mecinarone and the p-hydroxycinnamoyl derivative (O-desmethyl-mecinarone). It is postulated that these thermally-labile metabolites were formed by nucleophilic addition of a substituent to the alpha, beta-unsaturated ketone. It has been demonstrated in vitro that mecinarone forms a glutathione conjugate. The metabolites may be compounds of this type where the glutathione moiety has been degraded in the gastrointestinal tract.

Conjugate Addition of Lithium Dimethylcuprate to an alpha,beta,beta,-Trialkylthio-alpha,beta-unsaturated Ketone.

Conjugate Addition of Lithium Dimethylcuprate to an alpha,beta,beta,-Trialkylthio-alpha,beta-unsaturated Ketone.

Reduction of alpha beta unsaturated ketones with lithium aluminium hydride—aluminium chloride.

Reduction of alpha beta unsaturated ketones with lithium aluminium hydride—aluminium chloride.

Antibiotic A-130, isolation and characterization.

An antibiotic, A-130, was isolated from a strain identified as Streptomyces hygroscopicus, strain A-130. The antibiotic belongs to the nigericin group and like dianemycin, has an alpha, beta-unsaturated ketone chromophore in its molecule. A-130 is active against gram-positive organisms.

Prostaglandins. IV. Total syntheses of dl-11-deoxy PGE 1 and 13,14-dihydro derivatives of 11-deoxy PGE 1 , PGF 1 , and PGF 1 .

A photoannelation reaction between 2 alpha, beta-unsaturated ketones is described. The photoadduct was isolated and characterized by spectral analysis and was transformed into methoxy and acetoxy derivatives. Some mechanistic implications of photoannelation and the finding of a rearrangement product are discussed. Transformations of diketone to other prostanoic acid derivatives are also described. Structural formulas are depicted in a stepwise manner.

Synthesis of alpha, beta-unsaturated ketones and their oximes. 8. Unsaturated oximes

AbstractAromatische Aldehyde außer Furfural kondensieren im Sauren mit Butanon zu 4‐Aryl‐3‐methyl‐3‐buten‐2‐onen (II). Im Alkalischen erhält man eine Mischung aus 4‐Aryl‐3‐methyl‐3‐buten‐2‐on (II) und 1‐Aryl‐1‐penten‐3‐on (III). Diese Mischung wird oximiert und durch präp. DC aufgetrennt.

Ketalisation of α,β-unsaturated ketones. Part I 3-methoxy-N-methylmorphinan derivatives and 14-hydroxycodeinone

Ketalisation of α,β-unsaturated ketones. Part I 3-methoxy-N-methylmorphinan derivatives and 14-hydroxycodeinone

Chemistry of the Sex Hormones.

It may be presumptuous of the clinician to think that it is possible him to comprehend the complicated field of the steroid chemist, but Dr. Bishop makes this possibility come very close to reality. Presented in a clear, concise style it is remarkable how much information is contained in this small book for clinicians by a clinician. Those of us who have struggled with the etios, allos, epis, and alpha, beta unsaturated ketones have it all unfolded before us in a few brief, simple but understandable pages, enlivened with sly humor. Having dealt with the essentials of organic chemistry in six easy pages, the author conveys the three dimensional concept of stereoisomerism, difficult those to appreciate who are not inherently endowed with depth perception, in a manner capable of being understood by a one-eyed practitioner with no more than an average IQ. There follows an excellent detailed description

METHYLENEBUTYRYL PHENOXYACETIC ACID: NOVEL AND POTENT NATRIURETIC AND DIURETIC AGENT.

PHARMACOLOGICAL AGENTS which increase salt and water excretion by the kidney represent one of the most significant therapeutic advances in the past decade. Investigation of the nature of the action of these drugs has helped to clarify the mechanisms involved in renal transport of electrolyte and water and has provided information about the homeostatic processes controlling salt and water balance, upset of which results in edema formation. Four major categories of diuretics which act on renal tubular transport systems are recognized: (1) the organic mercurials, (2) the chloruretic sulfonamides (thiazide derivatives), (3) sulfonamides which inhibit carbonic anhydrase, and (4) aldosterone antagonists, —17 spironolactones. Recently, a chemically different group of agents has been developed, alpha, beta unsaturated ketone derivations of aryloxyacetic acids.1These compounds were found to be highly effective diuretic agents when administered to the dog, but were inactive in the rat. Compounds of the group with a significant

ALPHA, BETA-UNSATURATED KETONE DERIVATIVES OF ARYLOXYACETIC ACIDS, A NEW CLASS OF DIURETICS.

ALPHA, BETA-UNSATURATED KETONE DERIVATIVES OF ARYLOXYACETIC ACIDS, A NEW CLASS OF DIURETICS.

Steroid-Protein Interactions. V. Comparison of Spectrophotometric and Equilibriumdialysis Procedures for Determination of Binding Constants1

Abstract : An attempt was made to establish the validity of the spectrophotometric procedure for the determination of interaction between proteins and delta4-3-ketosteroids, this method was to be compared with the equilibrium-dialysis technique. The binding values obtained by the spectrophotometric method agree with those determined independently by equilibrium dialysis. The reduction of the extinction coefficient of an alpha, beta-unsaturated ketone by interaction with proteins provides an adequate basis for the determination of binding values. (Author)

Copolymerization of Alpha, Beta-Unsaturated Ketones

Copolymerization of Alpha, Beta-Unsaturated Ketones

The Reaction between Alpha, Beta-Unsaturated Ketones and Organic Magnesium Compounds. Unsaturated Mesitylenic Ketones

The Reaction between Alpha, Beta-Unsaturated Ketones and Organic Magnesium Compounds. Unsaturated Mesitylenic Ketones

THE OXIMES OF ALPHA, BETA-UNSATURATED KETONES AND THE BECKMANN REARRANGEMENT. II

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTHE OXIMES OF ALPHA, BETA-UNSATURATED KETONES AND THE BECKMANN REARRANGEMENT. IIA. H. Blatt and Julius F. StoneCite this: J. Am. Chem. Soc. 1931, 53, 11, 4134–4149Publication Date (Print):November 1, 1931Publication History Published online1 May 2002Published inissue 1 November 1931https://doi.org/10.1021/ja01362a032RIGHTS & PERMISSIONSArticle Views189Altmetric-Citations10LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (1 MB) Get e-Alerts Get e-Alerts