The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Thiophen     thiophene

Synonyms: THIOPHENE, Thiaphene, Thiofen, Thiofuram, Thiofuran, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

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].


  1. Mutagenicity of nitrofurans, nitrothiophenes, nitropyrroles, nitroimidazole, aminothiophenes, and aminothiazoles in Salmonella typhimurium. Wang, C.Y., Muraoka, K., Bryan, G.T. Cancer Res. (1975) [Pubmed]
  2. A novel class of monoglutamated antifolates exhibits tight-binding inhibition of human glycinamide ribonucleotide formyltransferase and potent activity against solid tumors. Habeck, L.L., Leitner, T.A., Shackelford, K.A., Gossett, L.S., Schultz, R.M., Andis, S.L., Shih, C., Grindey, G.B., Mendelsohn, L.G. Cancer Res. (1994) [Pubmed]
  3. DNA protein cross-links produced by NSC 652287, a novel thiophene derivative active against human renal cancer cells. Nieves-Neira, W., Rivera, M.I., Kohlhagen, G., Hursey, M.L., Pourquier, P., Sausville, E.A., Pommier, Y. Mol. Pharmacol. (1999) [Pubmed]
  4. 4-Hydroxy-5,6-dihydropyrones as inhibitors of HIV protease: the effect of heterocyclic substituents at C-6 on antiviral potency and pharmacokinetic parameters. Hagen, S.E., Domagala, J., Gajda, C., Lovdahl, M., Tait, B.D., Wise, E., Holler, T., Hupe, D., Nouhan, C., Urumov, A., Zeikus, G., Zeikus, E., Lunney, E.A., Pavlovsky, A., Gracheck, S.J., Saunders, J., VanderRoest, S., Brodfuehrer, J. J. Med. Chem. (2001) [Pubmed]
  5. Synthesis, structure, and antiproliferative activity of selenophenfurin, an inosine 5'-monophosphate dehydrogenase inhibitor analogue of selenazofurin. Franchetti, P., Cappellacci, L., Sheikha, G.A., Jayaram, H.N., Gurudutt, V.V., Sint, T., Schneider, B.P., Jones, W.D., Goldstein, B.M., Perra, G., De Montis, A., Loi, A.G., La Colla, P., Grifantini, M. J. Med. Chem. (1997) [Pubmed]
  6. Photophysical study of photoinduced electron transfer in a bis-thiophene substituted peryleneimide. Fron, E., Lor, M., Pilot, R., Schweitzer, G., Dincalp, H., De Feyter, S., Cremer, J., Bauerle, P., Mullen, K., Van der Auweraer, M., De Schryver, F.C. Photochem. Photobiol. Sci. (2005) [Pubmed]
  7. Inhibition of HIV-1 ribonuclease H by a novel diketo acid, 4-[5-(benzoylamino)thien-2-yl]-2,4-dioxobutanoic acid. Shaw-Reid, C.A., Munshi, V., Graham, P., Wolfe, A., Witmer, M., Danzeisen, R., Olsen, D.B., Carroll, S.S., Embrey, M., Wai, J.S., Miller, M.D., Cole, J.L., Hazuda, D.J. J. Biol. Chem. (2003) [Pubmed]
  8. Direct molecular detection of nucleic acids by fluorescence signal amplification. Ho, H.A., Doré, K., Boissinot, M., Bergeron, M.G., Tanguay, R.M., Boudreau, D., Leclerc, M. J. Am. Chem. Soc. (2005) [Pubmed]
  9. Combining single wall carbon nanotubes and photoactive polymers for photoconversion. Rahman, G.M., Guldi, D.M., Cagnoli, R., Mucci, A., Schenetti, L., Vaccari, L., Prato, M. J. Am. Chem. Soc. (2005) [Pubmed]
  10. pi-Stacking in thiophene oligomers as the driving force for electroactive materials and devices. Scherlis, D.A., Marzari, N. J. Am. Chem. Soc. (2005) [Pubmed]
  11. Fluorescent polymeric transducer for the rapid, simple, and specific detection of nucleic acids at the zeptomole level. Doré, K., Dubus, S., Ho, H.A., Lévesque, I., Brunette, M., Corbeil, G., Boissinot, M., Boivin, G., Bergeron, M.G., Boudreau, D., Leclerc, M. J. Am. Chem. Soc. (2004) [Pubmed]
  12. Sulfonylureas: a new class of cancer chemotherapeutic agents. Mohamadi, F., Spees, M.M., Grindey, G.B. J. Med. Chem. (1992) [Pubmed]
  13. PHI-443: a novel noncontraceptive broad-spectrum anti-human immunodeficiency virus microbicide. D'Cruz, O.J., Samuel, P., Uckun, F.M. Biol. Reprod. (2004) [Pubmed]
  14. Desulfurization of diesel oils by a newly isolated dibenzothiophene-degrading Nocardia sp. strain CYKS2. Chang, J.H., Rhee, S.K., Chang, Y.K., Chang, H.N. Biotechnol. Prog. (1998) [Pubmed]
  15. Amino derivatives of phenyl alkyl thiophene as inhibitors of bone resorption. Structure-activity relationship. Wierzbicki, M., Boussard, M.F., Sauveur, F., Kirsch, G., Sabatini, M., Lesur, C., Trodjman, C., Bonnet, J. Arzneimittel-Forschung. (1998) [Pubmed]
  16. Thiophene, a sulfur-containing heterocyclic hydrocarbon, causes widespread neuronal degeneration in rats. Mori, F., Tanji, K., Wakabayashi, K. Neuropathology : official journal of the Japanese Society of Neuropathology. (2000) [Pubmed]
  17. Stability and selectivity of unnatural DNA with five-membered-ring nucleobase analogues. Berger, M., Luzzi, S.D., Henry, A.A., Romesberg, F.E. J. Am. Chem. Soc. (2002) [Pubmed]
  18. Molecular structure and hepatotoxicity: compared data about two closely related thiophene compounds. Mansuy, D. J. Hepatol. (1997) [Pubmed]
  19. [[[(Thienylcarbonyl)alkyl]oxy]phenyl]- and [[[(pyrrylcarbonyl)alkyl]oxy]phenyl]oxazoline derivatives with potent and selective antihuman rhinovirus activity. Massa, S., Corelli, F., Artico, M., Mai, A., Ragno, R., De Montis, A., Loi, A.G., Corrias, S., Marongiu, M.E., La Colla, P. J. Med. Chem. (1995) [Pubmed]
  20. Acyl substitution at the ortho position of anilides enhances oral bioavailability of thiophene sulfonamides: TBC3214, an ETA selective endothelin antagonist. Wu, C., Decker, E.R., Blok, N., Li, J., Bourgoyne, A.R., Bui, H., Keller, K.M., Knowles, V., Li, W., Stavros, F.D., Holland, G.W., Brock, T.A., Dixon, R.A. J. Med. Chem. (2001) [Pubmed]
  21. 2-Amino-3-aroyl-4,5-alkylthiophenes: agonist allosteric enhancers at human A(1) adenosine receptors. Tranberg, C.E., Zickgraf, A., Giunta, B.N., Luetjens, H., Figler, H., Murphree, L.J., Falke, R., Fleischer, H., Linden, J., Scammells, P.J., Olsson, R.A. J. Med. Chem. (2002) [Pubmed]
  22. Synthesis, X-ray crystal structures, stabilities, and in vitro cytotoxic activities of new heteroarylacrylonitriles. Saczewski, F., Reszka, P., Gdaniec, M., Grünert, R., Bednarski, P.J. J. Med. Chem. (2004) [Pubmed]
  23. Characterization of cutaneous phototoxicity induced by topical alpha-terthienyl and ultraviolet A radiation. Rampone, W.M., McCullough, J.L., Weinstein, G.D., Towers, G.H., Berns, M.W., Abeysekera, B. J. Invest. Dermatol. (1986) [Pubmed]
  24. Thiophene systems. 5. Thieno[3,4-b][1,5]benzoxazepines, thieno[3,4-b][1,5]benzothiazepines, and thieno[3,4-b][1,4]benzodiazepines as potential central nervous system agents. Press, J.B., Hofmann, C.M., Eudy, N.H., Day, I.P., Greenblatt, E.N., Safir, S.R. J. Med. Chem. (1981) [Pubmed]
  25. Hydroxylation and formation of electrophilic metabolites of tienilic acid and its isomer by human liver microsomes. Catalysis by a cytochrome P450 IIC different from that responsible for mephenytoin hydroxylation. Dansette, P.M., Amar, C., Valadon, P., Pons, C., Beaune, P.H., Mansuy, D. Biochem. Pharmacol. (1991) [Pubmed]
  26. Genotoxicity of chryseno[4,5-bcd]thiophene and its sulfone derivative. Sinsheimer, J.E., Hooberman, B.H., Das, S.K., Savla, P.M., Ashe, A.J. Environ. Mol. Mutagen. (1992) [Pubmed]
  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. Adam, W., Bosio, S.G., Fröhling, B., Leusser, D., Stalke, D. J. Am. Chem. Soc. (2002) [Pubmed]
  28. Thiophene-based diamidine forms a "super" at binding minor groove agent. Mallena, S., Lee, M.P., Bailly, C., Neidle, S., Kumar, A., Boykin, D.W., Wilson, W.D. J. Am. Chem. Soc. (2004) [Pubmed]
  29. Highly selective, novel analogs of 4-[2-(diphenylmethoxy)ethyl]- 1-benzylpiperidine for the dopamine transporter: effect of different aromatic substitutions on their affinity and selectivity. Dutta, A.K., Coffey, L.L., Reith, M.E. J. Med. Chem. (1997) [Pubmed]
  30. Thienyl and thiazolyl acyclic analogues of 5-deazatetrahydrofolic acid. Hodson, S.J., Bigham, E.C., Duch, D.S., Smith, G.K., Ferone, R. J. Med. Chem. (1994) [Pubmed]
  31. Thiophene derivatives as new mechanism-based inhibitors of cytochromes P-450: inactivation of yeast-expressed human liver cytochrome P-450 2C9 by tienilic acid. López-Garcia, M.P., Dansette, P.M., Mansuy, D. Biochemistry (1994) [Pubmed]
  32. Isolation and genetic analysis of mutations allowing the degradation of furans and thiophenes by Escherichia coli. Abdulrashid, N., Clark, D.P. J. Bacteriol. (1987) [Pubmed]
  33. Carbonic anhydrase inhibitors: sulfonamides incorporating furan-, thiophene- and pyrrole-carboxamido groups possess strong topical intraocular pressure lowering properties as aqueous suspensions. Ilies, M., Supuran, C.T., Scozzafava, A., Casini, A., Mincione, F., Menabuoni, L., Caproiu, M.T., Maganu, M., Banciu, M.D. Bioorg. Med. Chem. (2000) [Pubmed]
  34. Synthesis of heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors: effects on the inhibitory activity of the replacement of the cyclopentene central core with pyrazole, thiophene or isoxazole ring. Balsamo, A., Coletta, I., Guglielmotti, A., Landolfi, C., Mancini, F., Martinelli, A., Milanese, C., Minutolo, F., Nencetti, S., Orlandini, E., Pinza, M., Rapposelli, S., Rossello, A. European journal of medicinal chemistry. (2003) [Pubmed]
  35. Synthesis and biological evaluation of novel macrocyclic bis-7-azaindolylmaleimides as potent and highly selective glycogen synthase kinase-3 beta (GSK-3 beta) inhibitors. Shen, L., Prouty, C., Conway, B.R., Westover, L., Xu, J.Z., Look, R.A., Chen, X., Beavers, M.P., Roberts, J., Murray, W.V., Demarest, K.T., Kuo, G.H. Bioorg. Med. Chem. (2004) [Pubmed]
  36. Electron-induced switching of the supramolecular chirality of optically active polythiophene aggregates. Goto, H., Yashima, E. J. Am. Chem. Soc. (2002) [Pubmed]
  37. Label-free electrochemical detection of protein based on a ferrocene-bearing cationic polythiophene and aptamer. Le Floch, F., Ho, H.A., Leclerc, M. Anal. Chem. (2006) [Pubmed]
  38. Molecular cloning and sequence of the thdF gene, which is involved in thiophene and furan oxidation by Escherichia coli. Alam, K.Y., Clark, D.P. J. Bacteriol. (1991) [Pubmed]
  39. Design and synthesis of push-pull chromophores for second-order nonlinear optics derived from rigidified thiophene-based pi-conjugating spacers. Raimundo, J.M., Blanchard, P., Gallego-Planas, N., Mercier, N., Ledoux-Rak, I., Hierle, R., Roncali, J. J. Org. Chem. (2002) [Pubmed]
WikiGenes - Universities