Diphenylacetic Acid Research Articles

ChemInform Abstract: Novel Hydrolytic Cleavage of 4‐(Pyrrol‐2‐yl)azetidin‐2‐ones

Alkaline hydrolysis of 1-aryl-3,3-diphenyl-4-(pyrrol-2-yl)azetidin-2-ones results in an unusual dualpath fragmentation of the β-lactam ring to give diphenylacetic acid, 2-iminomethylpyrroles, arylamines, and 1,1-diphenyl-2-(pyrrol-2-yl)ethylene. The product distribution is shown to be dependent on temperature.

ChemInform Abstract: Diphenylacetic Acid from Benzilic Acid: An Ecologically and Economically Improved Procedure.

AbstractBenzilic acid (I) is dimerized in the presence of p‐toluenesulfonic acid under azeotropic removal of water, yielding the cyclic diester (II).

Novel hydrolytic cleavage of 4-(pyrrol-2-yl)azetidin-2-ones

Alkaline hydrolysis of 1-aryl-3,3-diphenyl-4-(pyrrol-2-yl)azetidin-2-ones results in an unusual dualpath fragmentation of the β-lactam ring to give diphenylacetic acid, 2-iminomethylpyrroles, arylamines, and 1,1-diphenyl-2-(pyrrol-2-yl)ethylene. The product distribution is shown to be dependent on temperature.

Diphenylacetic Acid from Benzilic Acid: An Ecologically and Economically Improved Procedure

Abstract Overall yields better than 90% of pure diphenylacetic acid may be obtained by the route benzilic acid — benzilic acid dimeric ester — diphenylacetic acid.

Synthesis, reactivity and x-ray crystal structures of mixed thiazolato- or carboxylato- carbonyl(phosphine) rhenium(I) complexes

The compound [Re(CO)3(PPh3)2Cl] reacts with the lithium salt of thiazole derivatives (L1H = 2-amino-benzothiazole, L2H = 2−N-methyl-aminothiazole, L3H = 2−N-phenylaminothiazole, L4H = 2−N-(4-methoxyphenyl)aminothiazole, L5H = 2−N(4-nitrophenyl)aminothiazole) to give [Re(CO)2-(PPh3)2(L)]. The compounds have been characterized by elemental analysis, i.r. and1H n.m.r. spectra. At room temperature [Re(CO)2(PPh3)(L2)] reacts with L6H (L6H = diphenylacetic acid), to give the carboxylato complex [Re(CO)2 .

Metabolism of diphenylacetylglycine in higher plants

Studies were conducted on the biotransformation of the growth-regulating diphenylacetylglycine. For this purpose this substance was radio-labelled prepared from (14COOH)diphenylacetic acid and glycine. In plants of wheat of the sort "Remo", barley of the sort "Certina", and tomatoes of the sort "Harzfeuer" the agent undergoes only a low metabolism. Diphenylacetic acid is not formed, therefore, the peptide linkages are rather stable. Only little quantities of more polar metabolites have been found, one of them being chromatographically indicated as diphenylacetylglycine glucose ester.

Studies on benzhydryl derivatives. IV. Synthesis and anti-inflammatory activity of 2-O-(diphenylacetyl)salicylic acids.

A synthetic route to 2-O-(diphenylacetyl)salicylic acid derivatives was developed and the effects of the products on the heat-denaturation of albumin and on heat-induced erythrocytolysis were examined (in vitro anti-inflammation test). Trichloroethyl salicylate was acylated with diphenylacetic acid and its derivatives in the presence of methanesulfonyl chloride and pyridine, and the products were deprotected with zinc-acetic acid to give 2-O-(diphenylacetyl)salicylic acid derivatives. Their biological effects resembled those of ibuprofen.

Determination of adiphenine, diphenylacetic acid and diethylaminoethanol by high-performance liquid chromatography

Determination of adiphenine, diphenylacetic acid and diethylaminoethanol by high-performance liquid chromatography

Metabolism of adiphenine. II. Identification of major excretion metabolites in rats

1. Major metabolites isolated from rat urine after administration of a single dose of [14C]adiphenine or [3H]adiphenine were identified by chromatography and n.m.r. spectrometry, and by comparison with authentic reference compounds chemically synthesized. 2. Adiphenine was extensively metabolized by hydrolysis of the ester bond into diethylaminoethanol, diphenylacetic acid, diphenylacetic acid glucuronide and, in small quantities, the corresponding glycine and glutamine conjugates.

Diphenylacetic Acid: Synthesis, Paper‐ and Thinlayer Chromatographic and Mass Spectroscopic Properties of Amino Acid Derivatives

Diphenylacetic Acid: Synthesis, Paper‐ and Thinlayer Chromatographic and Mass Spectroscopic Properties of Amino Acid Derivatives

Zur Protonenkatalysierten Decarbonylierung der Diphenyl‐ und Triphenylessigsäure

Decarbonylation of Diphenylacetic and Triphenylacetic Acids Catalysed by ProtonsIn acetic acid solutions which contain less than 4 M H2SO4 the logarithm of the pseudo‐first order rate constant increases in a straight line with the Hammett acidity function −H0. At the same acidity and temperature the rate constant for triphenylacetic acid is higher by two orders of magnitude than for diphenylacetic acid.

Determination of adiphenine hydrochloride and diphenylacetic acid by ion-pair high-performance liquid chromatography

Determination of adiphenine hydrochloride and diphenylacetic acid by ion-pair high-performance liquid chromatography

The effect of treatment with some phase II substrates on hepatic xenobiotic metabolism and the urinary excretion of metabolites of the d-glucuronic acid pathway in the rat

Investigations have been conducted to study the relationship between the activities of certain enzymes of Phase I and Phase II hepatic xenobiotic metabolism and the urinary excretion of some metabolites of the d-glucuronic acid pathway. Male Sprague-Dawley rats were treated for 7 days with daily ip injections of either diphenylacetic acid, guaiacol, 4-hydroxybiphenyl, 2-naphthol, 1-naphthylacetic acid, paracetamol (acetaminophen), 2-phenylpropionic acid, n-propyl gallate, or phenylacetic acid. None of the compounds administered had any effect on a number of parameters of hepatic Phase I xenobiotic metabolism, namely mixed function oxidase enzyme activities, cytochrome P-450 and the microsomal content of protein. However, some of the compounds did stimulate hepatic microsomal UDP-glucuronyltransferase activity. While none of the compounds stimulated the urinary excretion of either d-glucaric acid, l-gulonic acid, or xylitol, all of the compounds except phenylacetic acid increased the urinary excretion of total (free and conjugated) d-glucuronic acid. The results indicate that when hepatic xenobiotic conjugative activity is increased without the stimulation of mixed function oxidases and cytochrome P-450, the urinary excretion of certain metabolites of the d-glucuronic acid pathway, other than d-glucuronic acid, remains unchanged.

Enterohepatic recycling of phenolphthalein, morphine, lysergic acid diethylamide (LSD) and diphenylacetic acid in the rat. Hydrolysis of glucuronic acid conjugates in the gut lumen.

1. Biliary elimination in female Wistar albino rats 3 h after i.p. injection of [3H]phenolphthalein, [3H]morphine, 14C-LSD and [14C]diphenylacetic acid was 90%, 45%, 75% and 57% respectively, predominantly as glucuronides. 2. Infusion of 3 h bile from the previous experiments into the duodena of bile-duct-cannulated animals demonstrated enterohepatic circulation, amounting in 24 h to 85%, 41%, 28% and 66% of the infused doses of the conjugates of phenolphthalein, morphine, LSD and diphenylacetic acid respectively. 3. Pretreatment with antibiotics to suppress intestinal microflora decreased this enterohepatic recirculation to 22%, 8.6% and 21% in 24 h for phenolphthalein, morphine and diphenylacetic acid glucuronides respectively. Antibiotic pretreatment did not influence the absorption and re-excretion of infused doses of the free aglycones, thus demonstrating the importance of bacterial beta-glucuronidase hydrolysis of the biliary conjugates. 4. The extent of intestinal absorption of the aglycones after bacterial beta-glucuronidase hydrolysis of the conjugates is related to their lipid-solubility as estimated by octan-1-ol:0.1 M phosphate buffer partition ratios (P-values). 5. The persistence of compounds in the enterohepatic circulation is determined by the faecal and urinary elimination of the circulating compounds. Faecal elimination is governed by the extent of intestinal absorption of the circulating compounds, which is influenced by the efficacy of intestinal hydrolysis of the conjugates and the relative lipophilicity of the aglycones released.

Routes for the improvement of methods for the identification of spasmolytics in a series of diphenylacetic acid esters

Routes for the improvement of methods for the identification of spasmolytics in a series of diphenylacetic acid esters

ChemInform Abstract: SYNTHETIC APPLICATIONS OF 2‐CHLOROTETRAHYDROFURAN: PROTECTION OF ALCOHOLS AS TETRAHYDRO‐2‐FURANYL (THF) ETHERS

AbstractDie durch Chlorierung von THF (im Überschuß eingesetzt) mit SO2Cl2 leicht zugängliche Titelverbindung (II) reagiert (im Gegensatz zu III) in Gegenwart von Triethylamin mit Alkoholen, Phenolen, Mercaptanen und Carbonsäuren glatt unter Bildung von Tetrahydrofuryl‐(2)‐ethern, ‐thioethern bzw. ‐estern; Azole, Amide und Imide lassen sich mit (II)/Triethylamin analog zu N‐Tetrahydrofuryl‐(2)‐Derivaten umsetzen.

ChemInform Abstract: THERMAL REACTIONS OF AZULENES WITH MALONIC, DIPHENYLACETIC, AND HALOACETIC ACIDS

Chemischer InformationsdienstVolume 10, Issue 30 Isocyclic Compounds ChemInform Abstract: THERMAL REACTIONS OF AZULENES WITH MALONIC, DIPHENYLACETIC, AND HALOACETIC ACIDS YU. N. PORSHNEV, YU. N. PORSHNEVSearch for more papers by this authorV. I. ERIKHOV, V. I. ERIKHOVSearch for more papers by this authorM. I. CHERKASHIN, M. I. CHERKASHINSearch for more papers by this authorV. M. MISIN, V. M. MISINSearch for more papers by this author YU. N. PORSHNEV, YU. N. PORSHNEVSearch for more papers by this authorV. I. ERIKHOV, V. I. ERIKHOVSearch for more papers by this authorM. I. CHERKASHIN, M. I. CHERKASHINSearch for more papers by this authorV. M. MISIN, V. M. MISINSearch for more papers by this author First published: July 24, 1979 https://doi.org/10.1002/chin.197930185AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume10, Issue30July 24, 1979 RelatedInformation

Thermal reactions of azulenes. with malonic, diphenylacetic, and haloacetic acids

1. The thermal acylation of azulene with diphenylacetic and malonic acids is structurally directed to the 1 and 3 positions. In 4,6,8-trimethylazulene the acylation is predominantly in the 2 position. 2. The thermal alkylation of 4,6,8-trimethylazulene with bromo(chloro) acetic acid leads to 4,6,8-trimethylazulenyl-1-acetic acid. The radical mechanism is postulated for the reaction. 3. The thermal reaction of the 1-acetyl-, 1-benzoyl-, and 1-phenylsulfonyl-4,6,8-tri-methylazulenes with monohaloacetic acids is accompanied by cleavage, and also by the partial 1–2 migration of the substituents. 1-Nitro- and 1-trifluoroacetyl-4,6,8-trimethylazulene do not react under similar conditions. 4. Ferrocene, pyrene, anthracene, 6,6-diphenylfulvene, and 2-phenylbenzo[b]cyclopenta-[e]pyran when heated with malonic acid give monoacetyl derivatives.

Synthetic applications of 2‐chlorotetrahydrofuran: Protection of alcohols as tetrahydro‐2‐furanyl (THF) ethers

Abstract2‐Chlorotetrahydrofuran (2‐Cl‐THF) is formed in 85% yield by reaction of sulfuryl chloride with excess THF. 2‐Cl‐THF reacts with alcohols, phenols, acids, thiols, azoles, amides and imides to give the corresponding tetrahydro‐2‐furanyl derivatives. Reaction with uracil derivatives provides N1‐ and N3‐monosubstituted and N1,N3‐disubstituted compounds. The reaction with alcohols provides a convenient general procedure for protecting the hydroxyl function. The THF group can be readily removed by acid catalyzed hydrolysis or reaction with methanol. The THF derivative of diphenylacetic acid can also be utilised for introducing the tetrahydro‐2‐furanyl moiety. THF ethers are converted into alkyl bromides by treatment with triphenylphosphine dibromide.

Crown ether catalysis of decarboxylation: a general survey of reactivity and detailed analysis of the triphenylacetate anion

The effect of 18-crown-6 ether 3 on the decarboxylation rate in THF of sodium salts of carboxylic acids formally derived from hydrocarbons has been investigated and these acids include 9-phenylfluorene-9-carboxylic acid, fluorene-9-carboxylic acid, phenylacetylene carboxylic acid, triphenylacetic acid, and diphenylacetic acid. Addition of equimolar 3 resulted in an increase in decarboxylation rate of 13- to 500-fold and there was a correlation between the decarboxylation rate and the pKa value of the product hydrocarbon.The decarboxylation of triphenylacetate was investigated in detail. The effect on reaction rate of cation (Li+, Na+, K+), crown ether concentration, water concentration, and solvent polarity has provided information as to optimum reaction conditions and has helped to clarify the reaction mechanism.