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Chemical Compound Review

Thiophen     thiophene

Synonyms: THIOPHENE, Thiaphene, Thiofen, Thiofuram, Thiofuran, ...
 
 
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Disease relevance of thiophene

 

Psychiatry related information on thiophene

  • Based on femtosecond time-resolved spectroscopy and single photon timing experiments, intramolecular photoinduced charge transfer has been investigated in two systems containing a peryleneimide chromophore (P) and thiophene (T) groups [6].
 

High impact information on thiophene

  • We have identified a novel thiophene diketo acid, 4-[5-(benzoylamino)thien-2-yl]-2,4-dioxobutanoic acid, that selectively inhibits polymerase-independent RNase H cleavage (IC(50) = 3.2 microm) but has no effect on DNA polymerization (IC(50) > 50 microm) [7].
  • This sensor is based on the different conformations adopted by a cationic polythiophene when electrostatically bound to ss-DNA or ds-DNA, and on the efficient and fast energy transfer between the resulting fluorescent polythiophene/ds-DNA complex and neighboring fluorophores attached to ss-DNA probes [8].
  • A combination of van der Waals and electrostatic interactions was used to integrate SWNT and a suitably functionalized polythiophene into nanostructured ITO electrodes [9].
  • In this work we examine with MP2 and Car-Parrinello ab initio calculations the actuation properties of a novel class of thiophene-based materials introduced by Swager et al [10].
  • We report the specific detection of a few hundred molecules of genetic material using a fluorescent polythiophene biosensor [11].
 

Chemical compound and disease context of thiophene

 

Biological context of thiophene

  • In an effort to develop an orthogonal third base pair for the storage of genetic information, thiophene and furan heterocycles have been examined as nucleobase analogues [17].
  • Molecular structure and hepatotoxicity: compared data about two closely related thiophene compounds [18].
  • Inspection of the structure-activity relationships revealed that the thiophene ring and the carbonyl group are the structural components which to a large extent contribute to the positive biological profile in terms of both wideness of spectrum and low cytotoxicity [19].
  • In both series, an acyl group at the 2-position of the anilide of these thiophene sulfonamides improved oral bioavailability [20].
  • A second region in the allosteric binding site interacts constructively with alkyl substituents at thiophene C-4 and/or C-5 [21].
 

Anatomical context of thiophene

 

Associations of thiophene with other chemical compounds

  • The highly reactive cyclooctyne 2b serves as sulfur acceptor for both sulfur donors, namely the sultene 1A and thiophene endoperoxide 1B to afford sulfur-transfer products [27].
  • Unusual sulfur chemistry in the thermal reaction of sultene and thiophene endoperoxide sulfur donors with cyclic alkynes: reversible formation of a persistent thiirenium ion and trapping of a thiirene by [4 + 2] cycloaddition [27].
  • X-ray results indicate a small bond angle difference between the C-S-C angle of thiophene and the C-O-C angle of furan that, when amplified out to the terminal amidines of the benzimidazole compounds, yields a very significant difference in the positions of the amidines and their DNA interaction strength [28].
  • Bioisosteric replacement of one of the phenyl rings of the diphenylmethoxy moiety by a thiophene ring was tolerated well and produced the most potent compound 13b (IC50 = 13.8 nM) in the series [29].
  • The thiophene analogue was found to be equal in activity to 5-DACTHF in the MCF-7 cell growth inhibition assay while the thiazole analogue was 9-fold more active [30].
 

Gene context of thiophene

  • It involves the intermediate formation of an electrophilic thiophene sulfoxide, which may react at position 5 of its thiophene ring either with H2O to give 5-OHTA or with a nucleophilic group of an amino acid residue of the P450 active site, which results in its covalent binding to P450 protein [31].
  • In addition, constitutively at both of the previously characterized fadR and atoC loci was required for efficient thiophene breakdown [32].
  • Carbonic anhydrase inhibitors: sulfonamides incorporating furan-, thiophene- and pyrrole-carboxamido groups possess strong topical intraocular pressure lowering properties as aqueous suspensions [33].
  • Among the compounds tested, only the 3-(p-methylsulfonylphenyl) substituted thiophene derivatives 17 and 22, showed a certain COX-2 inhibitory activity, accompanied by an appreciable COX-2 versus COX-1 selectivity [34].
  • Among the three series of macrocycles, the oxygen atom and thiophene containing linkers yielded molecules with higher inhibitory potency at GSK-3 beta (K(i)=0.011-0.079 microM) while the nitrogen atom containing linkers yielded molecules with lower potency (K(i)=0.150->1 microM) [35].
 

Analytical, diagnostic and therapeutic context of thiophene

  • The thiophene analogue was efficacious against human xenograft PANC-1, a pancreatic carcinoma which was completely resistant to 5,10- dideazatetrahydrofolate [2].
  • A chiral regioregular polythiophene (PT), poly[3-[4-((R)-4-ethyl-2-oxazolin-2-yl)phenyl]thiophene] (poly-1), forms chiral aggregates which exhibit a unique induced circular dichroism (ICD) in the pi-pi transition region derived from the supramolecular chirality in the presence of various poor solvents or metal salts in chloroform [36].
  • Two label-free electrochemical methods for the detection of human alpha-thrombin using a water-soluble, ferrocene-functionalized polythiophene transducer and a single-stranded oligonucleotide aptamer probe are described [37].
  • Molecular cloning and sequence of the thdF gene, which is involved in thiophene and furan oxidation by Escherichia coli [38].
  • Two series of push-pull chromophores built around thiophene-based pi-conjugating spacers rigidified either by covalent bonds or by noncovalent intramolecular interactions have been synthesized and characterized by UV-vis spectroscopy, electric field induced second harmonic generation (EFISH) and differential scanning calorimetry [39].

References

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