Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

METABOLISM OF POLYCYCLIC COMPOUNDS. THE METABOLISM OF 1,4-EPOXY-1,4-DIHYDRONAPHTHALENE IN RATS.

ABSTRACT: 1. 1,4-Epoxy-1,4-dihydronaphthalene is converted by rats into 1,4:2,3-diepoxy-1,2,3,4-tetrahydronaphthalene, which was isolated from the urine. The synthesis of the diepoxide is described. 2. The monoepoxide also yielded a compound that is believed to be 1,4-dihydro-1,4-dihydroxynaphthalene, but no corresponding mercapturic acid was detected. A number of unidentified metabolites of the monoepoxide were detected that appear to arise by the hydroxylation of the diepoxide. 3. The monoepoxide is converted into the diepoxide by a rat-liver microsomal system. 4. 1,4-Epoxy-1,4-dihydronaphthalene does not appear to be an intermediate in naphthalene metabolism.

SUBMITTER: SIMS P

PROVIDER: S-EPMC1206784 | biostudies-other | 1965 Jun

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Similar Datasets

METABOLISM OF POLYCYCLIC COMPOUNDS. THE METABOLISM OF 9,10-EPOXY-9,10-DIHYDROPHENANTHRENE IN RATS.

Project description:1. 9,10-Epoxy-9,10-dihydrophenanthrene is converted by rats into trans-9,10-dihydro-9,10-dihydroxyphenanthrene and its conjugates and into N-acetyl-S-(9,10-dihydro-9-hydroxy-10-phenanthryl)-l- cysteine. Small amounts of 9-phenanthryl sulphate and glucosiduronate are also formed, together with 9-hydroxy-10-phenanthryl sulphate. 2. The epoxide readily rearranges to 9-hydroxyphenanthrene and reacts with water to give the dihydrodihydroxy compound and with N-acetylcysteine to give the mercapturic acid. One of the diastereoisomeric forms of the methyl ester of the mercapturic acid is identical with the ester of the mercapturic acid excreted by rats dosed with the epoxide or by rats and rabbits dosed with phenanthrene. 3. A rat-liver homogenate converts the epoxide into trans-9,10-dihydrodihydroxyphenanthrene and S-(9,10-dihydro-9-hydroxy-10-phenanthryl)glutathione. The latter compound was not formed when boiled rat-liver homogenate was used, but was formed chemically from the epoxide and glutathione under more vigorous conditions. 4. The results provide further indications that the metabolism of aromatic hydrocarbons involves the intermediary formation of epoxides.

| S-EPMC1206807 | biostudies-other

METABOLISM OF POLYCYCLIC COMPOUNDS. THE METABOLISM OF 7,12-DIMETHYLBENZ(ALPHA)ANTHRACENE BY RAT-LIVER HOMOGENATES.

Project description:1. The main products of the metabolism of 7,12-dimethylbenz[a]anthracene by rat-liver homogenates are the isomeric monohydroxymethyl derivatives. The syntheses of these compounds are described. 2. Two phenolic products and two dihydrodihydroxy compounds were formed, but none of these appeared to have been formed by hydroxylation at the ;K region'. There was little evidence for the formation of a glutathione conjugate of the hydrocarbon. 3. The monohydroxymethyl derivatives are products of the hydroxylation of the hydrocarbon in the ascorbic acid-Fe(2+)-oxygen model hydroxylating system.

| S-EPMC1206806 | biostudies-other

Epoxy derivatives of aromatic polycyclic hydrocarbons. The preparation and metabolism of epoxides related to 7,12-dimethylbenz(a)anthracene.

Project description:The syntheses of 7,12-dimethylbenz[a]anthracene 5,6-oxide, 7-acetoxymethyl-12-methylbenz[a]anthracene 5,6-oxide and a product that appears to be mainly 7-hydroxymethyl-12-methylbenz[a]anthracene 5,6-oxide are described. The compounds readily rearranged to phenols in the presence of mineral acid, and 7,12-dimethylbenz[a]anthracene 5,6-oxide and its 7-hydroxymethyl derivative reacted slowly with water to yield trans-5,6-dihydro-5,6-dihydroxy-7,12-dimethylbenz[a] anthracene and trans-5,6-dihydro-5,6-dihydroxy-7-hydroxymethyl-12-methylbenz [a]anthracene respectively. Both epoxides were converted enzymically by rat liver microsomal fractions and homogenates into the related trans-dihydrodiols. The epoxides reacted chemically with GSH to form conjugates that were identical with the conjugates formed when the epoxides were incubated with rat liver homogenates. The GSH conjugates were more stable to acid than conjugates derived from other arene oxides. In the alkylation of 4-(p-nitrobenzyl)pyridine, 7,12-dimethyl-benz[a]anthracene 5,6-oxide was more active than the 5,6-oxides of 7-methylbenz[a]-anthracene and benz[a]anthracene.

| S-EPMC1177481 | biostudies-other

Polycyclic compounds by Ugi-Pictet-Spengler sequence.

Project description:A general approach to architecturally stimulating polycyclic structures is described by a concise, two-step procedure including a Ugi MCR (multicomponent reaction) and a subsequent Pictet-Spengler reaction starting from phenylethylamine-derived isocyanides. Ten compounds are described in full experimental detail, and yields range from medium to very good. Some of the reactions run with a high degree of stereoselectivity. The compound structures resemble steroid hormones and alkaloid classes of natural products. Exemplary products have been fully reduced to their tertiary amines. As such they could potentially become interesting biological probes.

| S-EPMC3101332 | biostudies-literature

Epoxy derivatives of aromatic polycyclic hydrocarbons. The synthesis of dibenz[a,c]anthracene 10,11-oxide and its metabolism by rat liver preparations.

Project description:The synthesis of dibenz[a,c]anthracene 10,11-oxide is described. The oxide was unstable and was rapidly decomposed with cold mineral acid into a mixture of 10- and 11- hydroxydibenz[a,c]anthracene. The oxide was converted by rat liver microsomal preparations and homogenates into a product that is probably 10,11-dihydro-10,11-dihydroxydibenz[a,c]anthracene and which was identical with the metabolite formed when dibenz[a,c]anthracene was metabolized by rat liver homogenates. The oxide did not react either chemically or enzymically with GSH. 10,11-Dihydrodibenz[a,c]anthracene and 10,11-dihydrodibenz[a,c]anthracene 12,13-oxide were both metabolized by rat liver preparations into trans-10,11,12,13-tetrahydro-10,11-dihydroxydibenz[a,c] anthracene and the oxide was converted chemically into this dihydroxy compound, and it reacted chemically but not enzymically with GSH. In the alkylation of 4-(p-nitrobenzyl)pyridine, the ;K-region' epoxide, dibenz[a,h]anthracene 5,6-oxide, was more active than either dibenz[a,c]anthracene 10,11-oxide or 10,11-dihydrobenz[a,c]anthracene 12,13-oxide.

| S-EPMC1174297 | biostudies-other

1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles.

Project description:We have devised a novel 1,3-benzdiyne equivalent, capable of quadruple functionalization by sequential benzyne generation and reaction with arynophiles. The key features of this method include the chemoselective generation of two triple bonds in a single benzene ring under fluoride-mediated mild conditions, and the regiocontrol of each benzyne reaction by the substituent next to the triple bond. This method produced various benzo-fused heteroaromatic compounds via reactions with arynophiles, such as furans, azides, and diazo compounds. A validation of the method is given in the convergent synthesis of the antipsychotic drug risperidone. A similar strategy has also been applied to a 1,4-benzdiyne equivalent to construct linearly benzo-fused heteroaromatics.

| S-EPMC6020534 | biostudies-literature

UV aged epoxy coatings - Ecotoxicological effects and released compounds.

Project description:Organic coatings can guarantee long-term protection of steel structures due to causing a physical barrier against water and oxygen. Because of their mechanical properties and resistances to heat and chemicals, epoxy resin-based coatings are widely used for corrosion protection. Despite of the aromatic backbone and the resulting susceptibility to UV degradation, epoxy resins are frequently used as binding agent in top layers of anti-corrosion coating systems. Consequently, these organic polymers are directly exposed to sunlight and thus UV radiation. The present study was designed to investigate if toxic effects of epoxy resin-based-coatings are changed by UV-A irradiation. For this purpose, two epoxide-based top coatings were examined with and without UV aging for their bacterial toxicity and estrogenicity. In addition, chemical analyses were performed to identify released compounds as well as photolytic degradation products and to assign toxic effects to individual substances. UV-A irradiation of epoxy resin based top coatings resulted in an overall decrease of acute and specific ecotoxicological effects but as well to the formation of toxic transformation products. Both, in leachates of untreated and UV-A irradiated coatings, 4tBP was identified as the main driver of estrogenicity and toxicity to luminescent bacteria. BPA and structural analogs contributing to estrogenic effects in leachates were formed by UV-A irradiation. The combination of HPTLC coupled bioassays and LC-MS analyses supported the identification of bioactive compounds in terms of an effect-directed analysis. The present findings indicate that epoxide-based coatings are less suitable for the application as top coatings and more UV stable coatings like aliphatic polyurethanes should be preferred.

| S-EPMC8219897 | biostudies-literature

Asymmetric dearomative cyclopropanation of naphthalenes to construct polycyclic compounds.

Project description:Catalytic asymmetric dearomatization (CADA) reactions is an important synthetic method for constructing enantioenriched complex cyclic systems from simple aromatic feedstocks. However, the CADA reactions of nonactivated arenes, such as naphthalenes and benzenes, have been far less explored than those of electronically activated arenes, such as phenols, naphthols and indoles. Herein, we disclose an asymmetric dearomative cyclopropanation of naphthalenes for the rapid construction of polycyclic compounds. With chiral dirhodium carboxylate as a catalyst, the dearomative cyclopropanation proceeded smoothly under mild conditions and afforded benzonorcaradiene-containing tetracycles in good yield and high enantioselectivity (up to 99% ee). Three stereogenic centers, including two all-carbon quaternary centers, were created in the dearomatization reaction. Moreover, a variety of functional groups are well-tolerated in the reaction. The products could be readily converted into other complex polycycles while maintaining the high ee value.

| S-EPMC9669881 | biostudies-literature

Catalytic condensation for the formation of polycyclic heteroaromatic compounds.

Project description:The conservation of our global element resources is a challenge of the utmost urgency. Since aliphatic and aromatic alcohols are accessible from abundant indigestible kinds of biomass, first and foremost lignocellulose, the development of novel chemical reactions converting alcohols into important classes of compounds is a particularly attractive carbon conservation and CO2-emission reduction strategy. Herein, we report the catalytic condensation of phenols and aminophenols or aminoalcohols. The overall reaction of this synthesis concept proceeds via three steps: hydrogenation, dehydrogenative condensation and dehydrogenation. Reusable catalysts recently developed in our laboratory mediate these reactions highly efficient. The scope of the concept is exemplarily demonstrated by the synthesis of carbazoles, quinolines and acridines, the structural motifs of which figure prominently in many important natural products, drugs and materials.

| S-EPMC5931520 | biostudies-literature

Different hydrogen-bonded structures in three 2-thienyl-substituted tetrahydro-1,4-epoxy-1-benzazepines.

Project description:The molecules of (2RS,4SR)-2-exo-(5-bromo-2-thienyl)-7-chloro-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(14)H(11)BrClNOS, (I), are linked into cyclic centrosymmetric dimers by C-H...pi(thienyl) hydrogen bonds. Each such dimer makes rather short Br...Br contacts with two other dimers. In (2RS,4SR)-2-exo-(5-methyl-2-thienyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(15)H(15)NOS, (II), a combination of C-H...O and C-H...pi(thienyl) hydrogen bonds links the molecules into chains of rings. A more complex chain of rings is formed in (2RS,4SR)-7-chloro-2-exo-(5-methyl-2-thienyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(15)H(14)ClNOS, (III), built from a combination of two independent C-H...O hydrogen bonds, one C-H...pi(arene) hydrogen bond and one C-H...pi(thienyl) hydrogen bond.

| S-EPMC2737428 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data