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Chemical Compound Review

Hydrindene     2,3-dihydro-1H-indene

Synonyms: Indane, INDAN, PubChem20379, ARONIS23879, I1804_ALDRICH, ...
 
 
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Disease relevance of indane

  • Both prepubertal and adult rats were treated with a single oral dose of either 60 mg or 120 mg of dl-6-(N-pipecolinomethyl)-5-hydroxy indane maleate (PMHI) per kg of body weight [1].
 

High impact information on indane

  • The catalytic domain of the myosin head was labeled at Cys-707 with indane dione spin label; the regulatory domain was labeled at the single cysteine residue of the essential light chain and exchanged into myosin [2].
  • In negative-mode laser-desorption time-of-flight (LD-TOF) mass spectra, the expanded radialenes exhibited peaks due to the corresponding cyclo[n]carbon anions (n = 18, 24, 30, and 36) formed by the stepwise loss of the aromatic indane fragments [3].
  • Orientation of intermediate nucleotide states of indane dione spin-labeled myosin heads in muscle fibers [4].
  • We obtained electron paramagnetic resonance spectra of an indane dione spin label (InVSL) bound to Cys 707 (SH1) of the myosin head, in skinned rabbit psoas muscle fibers [4].
  • Orientational dynamics of indane dione spin-labeled myosin heads in relaxed and contracting skeletal muscle fibers [5].
 

Biological context of indane

  • (R)-Proline catalyzes the amination reaction of functionalized indane carboxaldehydes and allows for the efficient enantioselective synthesis (>99% ee) of the metabotropic glutamate receptor ligands (S)-AIDA and (S)-APICA [6].
  • Synthesis and QSAR study of the anticancer activity of some novel indane carbocyclic nucleosides [7].
 

Anatomical context of indane

  • The indane series was more effective in producing contractions of the ileum than the other compounds [8].
  • A set of 14 indane carbocyclic nucleosides were synthesized and experimentally assayed for their inhibitory effects in the proliferation of murine leukemia (L1210/0) and human T-lymphocyte (Molt4/C8, CEM/0) cells [7].
 

Associations of indane with other chemical compounds

 

Gene context of indane

  • Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties [10].
  • To identify what chemical features might promote effective antagonism, we replaced Arg1 and Pro7 with structurally constrained and proteolytic-resistant residues, such as Bip (biphenylalanine), Dip (diphenylalanine) or 2Ind (indane amino acid) [11].
  • To find novel compounds superior to MSI-78, we have further designed, synthesizing 1,1-di(4-aminobutyl)-6-benzylindane (PM4) and 1,1-dibenzyl-6-(4-aminobutyl) indane (PM5), and tested their inhibitory ability of the growth of S. aureus [12].

References

  1. Studies on the antitesticular action of DL-6-(N-2-pipecolinomethyl)-5-hydroxy-indane (PMHI) in the rat. Fang, V.S., Anderson, W.A. Endocrinology (1976) [Pubmed]
  2. Independent mobility of catalytic and regulatory domains of myosin heads. Adhikari, B., Hideg, K., Fajer, P.G. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  3. Expanded radialenes with bicyclo[4.3.1]decatriene units: new precursors to cyclo[n]carbons. Tobe, Y., Umeda, R., Iwasa, N., Sonoda, M. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  4. Orientation of intermediate nucleotide states of indane dione spin-labeled myosin heads in muscle fibers. Roopnarine, O., Thomas, D.D. Biophys. J. (1996) [Pubmed]
  5. Orientational dynamics of indane dione spin-labeled myosin heads in relaxed and contracting skeletal muscle fibers. Roopnarine, O., Thomas, D.D. Biophys. J. (1995) [Pubmed]
  6. Organocatalytic enantioselective synthesis of metabotropic glutamate receptor ligands. Suri, J.T., Steiner, D.D., Barbas, C.F. Org. Lett. (2005) [Pubmed]
  7. Synthesis and QSAR study of the anticancer activity of some novel indane carbocyclic nucleosides. Yao, S.W., Lopes, V.H., Fernández, F., García-Mera, X., Morales, M., Rodríguez-Borges, J.E., Cordeiro, M.N. Bioorg. Med. Chem. (2003) [Pubmed]
  8. In vitro actions of NN-dimethyl-2-aminoindane and related compounds. Little, H.J., Rees, J.M. J. Pharm. Pharmacol. (1980) [Pubmed]
  9. Examination of the in vitro (anti)estrogenic, (anti)androgenic and (anti)dioxin-like activities of tetralin, indane and isochroman derivatives using receptor-specific bioassays. Schreurs, R.H., Sonneveld, E., van der Saag, P.T., van der Burg, B., Seinen, W. Toxicol. Lett. (2005) [Pubmed]
  10. Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties. Chazalette, C., Masereel, B., Rolin, S., Thiry, A., Scozzafava, A., Innocenti, A., Supuran, C.T. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  11. Cyclic and linear bradykinin analogues: implications for B2 antagonist design. Hsieh, K.H., Stewart, J.M. J. Pept. Res. (1999) [Pubmed]
  12. Biological activities of 1,1,6-trisubstituted indanes: beyond magainin 2. Numao, N., Hirota, Y., Iwahori, A., Kidokoro, S., Sasatsu, M., Kondo, I., Itoh, S., Itoh, E., Katoh, T., Shimozono, N., Yamazaki, A., Takao, K., Kobayashi, S. Biol. Pharm. Bull. (1999) [Pubmed]
 
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