Gene/Protein Disease Symptom Drug Enzyme Compound
Pivot Concepts:   Target Concepts:
Query: CAS:110-02-1 (thiophene)
 5,783 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

The alpha-thiocarbocation generated from the Pummerer reaction of an o-heteroaroyl-substituted sulfoxide is intercepted by the adjacent keto group to produce an alpha-thio-substituted heteroaromatic isobenzofuran. In the presence of a suitable dienophile, the reactive o-xylylene undergoes a Diels-Alder cycloaddition followed by an acid-catalyzed ring-opening and aromatization to give heteroaromatic naphthalene derivatives. This one-pot procedure occurs smoothly with electron-deficient dienophiles. The tandem Pummerer cyclization-cycloaddition sequence also occurs intramolecularly using unactivated alkenyl tethers of variable length. With acetylenic dienophiles, the primary cycloadducts undergo in situ ring-opening to produce hydroxynaphthalene derivatives. In the absence of a dienophile, it was possible to prepare 4-(ethylthio)-6-phenylthieno[2,3-c]furan and 1-ethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole. Various synthetic approaches were used for the preparation of the requisite thiophene- and indole-derived sulfoxide precursors. The facility of the tandem Pummerer-Diels-Alder reaction was very dependent on the experimental conditions used to promote the reaction. The best results were achieved by employing a mixture of acetic anhydride and toluene which contained a catalytic quantity of p-toluenesulfonic acid. The presence of the acid effectively drives the reaction in the desired direction by preventing formation of the acetoxy sulfide, which corresponds to the normal Pummerer product.
 ...
PMID:A Facile and Efficient Synthesis of Thieno[2,3-c]furans and Furo[3,4-b]indoles via a Pummerer-Induced Cyclization Reaction. 1166 51

Several analogues of thuriferic acid and derivatives, with the 3,4-methylenedioxyphenyl ring replaced by naphthalene, furan, thiophene and carbazole ring systems, have been prepared. The synthetic strategy is based on a conjugate addition-alkylation methodology followed by cationic cyclization in order to obtain the isopodophyllone analogues, which are transformed in the thuriferic acids. Their cytotoxic activities against several tumour cells lines are also described.
 ...
PMID:Synthesis and cytotoxic activities of analogues of thuriferic acid. 1174 79

Conjugate adducts obtained by base-induced 1,4-addition-elimination of various aryl/heteroaryl acetonitriles with 1-(2-arylcyclopropyl)-3,3-(bismethylthio)-2-propen-1-ones have been shown to undergo facile acid-induced domino carbocationic rearrangement yielding a variety of substituted tricyclic aromatic and heteroaromatic frameworks in high yields in a one-pot operation. The methodology provides efficient, high-yield routes for synthesis of novel substituted dihydrophenalenes, dihydrobenzo[d,e]anthracene, cyclopenta[a]naphthalene, and fused heteroaromatics such as substituted 4,5-dihydrobenzo[c,d]indole, dihydronaphtho[1,8-b,c]thiophene, dihydroindeno[5,4-b]- and -[4,5-b]-thiophenes, cyclopenta[a]carbazole, and dihydrocyclopenta[e]indazol-3-one derivatives. The probable mechanism of this interesting domino process appears to involve stepwise or concomitant acid-induced ring opening and intramolecular cyclocondensation of cyclopropyl ketones to give benzo-fused arene (or heteroarene) intermediates bearing a reactive benzylic carbocation that is captured intramolecularly either by a preexisting aromatic (or heteroaromatic) ring or by a newly formed benzene ring to give either peri-fused or angularly fused products, respectively. Thus, the overall domino process entails formation of two C-C bonds, a substituted benzene ring along with a peri-fused cyclohexane or angularly fused cyclopentane ring in a single operation.
 ...
PMID:Domino carbocationic cyclization of functionalized cyclopropyl ketones: facile one-pot access to peri- and angularly fused polycyclic aromatic and heteroaromatic frameworks. 1209 6

The complexes formed by a variety of anions with perfluoro derivatives of benzene, naphthalene, pyridine, thiophene, and furan have been calculated using DFT (B3LYP/6-31++G**) and MP2 (MP2/6-31++G** and MP2/6-311++G**) ab initio methods. The minimum structures show the anion interacting with the pi-cloud of the aromatic compounds. The interaction energies obtained range between -8 and -19 kcal mol(-1). The results obtained at the MP2/6-31++G** and MP2/6-311++G** levels are similar. However, the B3LYP/6-31++G** results provide longer interaction distances and smaller interaction energies than do the MP2 results. The interaction energies have been partitioned using an electrostatic, polarization, and van der Waals scheme. The AIM analysis of the electron density shows a variety of topologies depending on the aromatic system considered.
 ...
PMID:Interaction of anions with perfluoro aromatic compounds. 1212 Nov

Compounds having the form TpMo(NO)(1-methylimidazole)(eta(2)-L(pi)) (Tp = hydridotris(pyrazolyl)borate; L(pi) = cyclohexene, naphthalene, furan, thiophene, and acetone) were synthesized in 31-41% yield by the reduction of TpMo(NO)Br(2) in the presence of 1-methylimidazole and the respective pi-acidic organic ligand. The structure of the naphthalene complex was confirmed by single-crystal X-ray diffraction. Degradation studies showed the bound aromatics to have half-lives of 37-236 h in acetone solution at 20 degrees C. A tandem addition across the bound ring of the naphthalene complex yielded a free 1,2-dihydronaphthalene in 80% yield following decomplexation.
 ...
PMID:Binding and activation of aromatic molecules by a molybdenum pi-base. 1259 May 11

Within an overall ring-opening/ring-forming protocol, the (E,E)-4-methylthio-2-nitro-3-phenylsulfonyl-1-pyrrolidino-1,3-butadiene (7) [derived from the initial opening of 3-nitro-4-(phenylsulfonyl)thiophene (6) with pyrrolidine and silver nitrate in EtOH] is revealed to be an excellent precursor of nitro(phenylsulfonyl) derivatives of ring-fused aromatic (naphthalene, phenanthrene) or heteroaromatic (benzothiophene) compounds whose substitution pattern cannot be easily achieved by conventional methods. The key step is represented by a thermal electrocyclic rearrangement of (E,E)-1-aryl-4-methylsulfonyl-2-nitro-3-phenylsulfonyl-1,3-butadienes (9), which, thanks to proper geometric and electronic factors, occurs in unprecedentedly mild conditions and is followed by an irreversible, concerted syn beta-elimination of methanesulfinic acid to aromatize the newly formed cyclohexadienic ring.
 ...
PMID:Access to ring-fused homo- and heteroaromatic derivatives via an initial ring-opening of 3-nitro-4-(phenylsulfonyl)thiophene. 1281 86

Arthrobacter sp. strain PBA metabolized phenylboronic acid to phenol. The oxygen atom in phenol was shown to be derived from the atmosphere using (18)O(2). 1-Naphthalene-, 2-naphthalene-, 3-cyanophenyl-, 2,5-fluorophenyl-, and 3-thiophene-boronic acids were also transformed to monooxygenated products. The oxygen atom in the product was bonded to the ring carbon atom originally bearing the boronic acid substituent with all the substrates tested.
 ...
PMID:Catabolism of arylboronic acids by Arthrobacter nicotinovorans strain PBA. 1283 10

Recombinant Mycobacterium sp. strain MR65 carrying dszABCD genes was used for desulfurization of 10-methylbenzo[b]naphtho[2,1-d]thiophene (10-methyl BNT) in the hexadecane phase. The specific activity was 25% of that of dibenzothiophene (DBT). One of two major metabolites of 10-methyl BNT produced by strain MR65 was identified as 1-methoxy-2-(3-methylphenyl)naphthalene by 1H and 13C NMR. The other major metabolite and two minor metabolites were determined as 1-hydroxy-2-(3-methylphenyl)naphthalene, 2-(2-methoxy-3-methylphenyl)naphthalene and 2-(2-hydroxy-3-methylphenyl)naphthalene, respectively, by HPLC and GC-MS. The production ratio of the two desulfurization metabolite isomers was 0.99:0.01, calculated on the basis of peak GC areas. These results indicated that the C-S bond adjacent to the naphthalene skeleton was selectively cleaved to form the two major compounds.
 ...
PMID:Selective cleavage of 10-methyl benzo[b]naphtho[2,1-d]thiophene by recombinant Mycobacterium sp. strain. 1288 10

Smiles-type free radical rearrangements of arenesulfonates and arenesulfonamides are exploited for synthetic purposes. 4-Substituted benzenesulfonates cause Smiles-type rearrangement only when substituted by an electron withdrawing group. Therefore, ipso-attack by an alkyl radical on arenesulfonates takes place in an electrophilic manner. Arenesulfonamides rearrange only when the amide nitrogen is substituted by an alkoxycarbonyl group, due to the electron withdrawing nature of this group. Sulfonates and the N-ethoxycarbonylsulfonamide derivatives of naphthalene, quinoline, and thiophene cause more rearrangement and show synthetic utility. Aromatic amino acid analogues were synthesized by Smiles-type rearrangement with moderate yields. The radical Smiles-type rearrangement of sulfonate and sulfonamide derivatives can be a useful synthetic route when we understand the electronic character of these reactions.
 ...
PMID:Smiles-type free radical rearrangement of aromatic sulfonates and sulfonamides: syntheses of arylethanols and arylethylamines. 1295 67

During spills of hydrocarbons in soil, it has been observed that aliphatic and the slightly aromatic hydrocarbons are first to be removed, however, branched aliphatic and aromatic compounds, polycyclic aromatic hydrocarbons (PAHs) and their similar heteroatoms with sulfur (PAS) remain strongly absorbed to soil particles. It is important to point out that studies of biodegradation of alkyl-substituted PAHs and PAS are scarce and most of them have been carried out using only available standard compounds. The aim of this investigation was to identify and to quantify the aliphatic, alkyl polycyclic aromatic, and sulfured recalcitrant fractions present in a contaminated soil with drilling wastes. A modified method of shaking-centrifugation extraction was implemented for the extraction of compounds from contaminated soil. The organic extract obtained was purified and fractionated using aluminum oxide. Gas Chromatograph with flame ionization detector (GC-FID) and Gas Chromatograph with mass spectrometer detector (GC-MS) identified the aliphatic, PAHs and PAS fractions. Hydrocarbon composition in the soil contaminated with 140,000 mg TPHs/Kg soil, consisted in 80% of branched aliphatic compounds of C10 to C22, 15% of alkyl PAHs, and 5% of PAS compounds. Lineal, lineal branched, and cyclic branched aliphatic hydrocarbons, as well as their alkyl naphthalene, anthracene and phenantrene, methyldibenzothiophene, dimethyldibenzothiophene, and dimethylnaphto[2,3-b]thiophene compounds were identified by CG-MS. The identification of compounds in soil P31, allowed us to speculate on the origin of the contamination and the natural attenuation that had occurred at this site.
 ...
PMID:Identification of recalcitrant hydrocarbons present in a drilling waste-polluted soil. 1524 35


<< Previous 1 2 3 4 5 6 7 8 9 10 Next >>