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Chemical Compound Review

Benzoimide     isoindole-1,3-dione

Synonyms: Ftalimmide, Phthalimid, phtalimide, PHTHALIMIDE, Phenylimide, ...
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Disease relevance of NSC3108

  • Design and optimization of tricyclic phtalimide analogues as novel inhibitors of HIV-1 integrase [1].
  • Allergic contact dermatitis from N-(cyclohexylthio) phthalimide in a playground fitter [2].
  • Three representative examples N-[2-pyridinyl-1-oxide) methyl] phthalimide 8, 1-[N-2-phthalimidoethyl]-3,4-dihydroiso-quinoline 12, and 1-[N-(2-(1,2,3,4-tetrahydro-2-quinolinyl)] ethylphthalimide 14 were shown to inhibit L1210 leukemia DNA synthesis whereas RNA synthesis was not inhibited at 25-100 uM [3].
  • The two compounds containing a phthalimide moiety (compounds 3a and 3b) showed significant and selective cytotoxicity against the breast cancer cell line MDA-MB231 [4].
  • However, a comparison of these N-substituted adamantylester imides with the series published previously, indicated that the incorporation of L-alanine and L-phenylalanine into the phthalimide moiety was the best choice regardless of the series and leads to antimicrobial activity against Staphylococcus aureus strains [5].

Psychiatry related information on NSC3108


High impact information on NSC3108

  • The chemical efficiencies of these processes are not significantly affected by (1) the lengths of the peptide chains separating the phthalimide and alpha-amidosilane or alpha-amidocarboxylate centers and (2) the nature of the penultimate cation radical alpha-heterolytic fragmentation process (i.e., desilylation vs decarboxylation) [7].
  • On the contrary, (S)-thalidomide is preferentially metabolized by hydroxylation in the phthalimide moiety, resulting in the formation of (S)-5-hydroxythalidomide [8].
  • As a second step in this process, altering the phthalimide moiety to optimize interactions in the guanine-binding pocket of GPRT is expected to lead to compounds with promising activity against G. lamblia PRT [9].
  • Previous structure-activity relationships (SAR) revealed two positively charged centers and two lateral phthalimide moieties in a defined arrangement to be essential of a high allosteric potency [10].
  • Hexane-bisammonium-type compounds containing lateral phthalimide moieties are well-established ligands of the common allosteric binding site of muscarinic M(2) receptors [10].

Biological context of NSC3108

  • Kinetics of self-decomposition and hydrogen atom transfer reactions of substituted phthalimide N-oxyl radicals in acetic acid [11].
  • Crucial to this success was a very unorthodox phthalimide cleavage procedure, C8 azidation prior to aziridination and late stage alkylation of the 5' amino group with iodoethanol necessitated by the high degree of lability endowed by the aryl azide moiety [12].
  • In this analogous series of phthalimide derivatives, minor chemical changes affected dramatically the compounds' pharmacokinetics [13].
  • Development of new CoMFA and CoMSIA 3D-QSAR models for anti-inflammatory phthalimide-containing TNFalpha modulators [14].
  • Hexane-bisammonium-type compounds containing lateral phthalimide moieties are known to have a rather high affinity for the allosteric site of muscarinic M2 receptors [15].

Anatomical context of NSC3108


Associations of NSC3108 with other chemical compounds


Gene context of NSC3108

  • Design and synthesis of phthalimide-type histone deacetylase inhibitors [22].
  • This led us to explore the possibility of using expression of one of the major stress genes, hsp70, in Drosophila as a biomarker against phthalimide group of chemicals, which may accordingly provide an early indication of exposure to these hazardous chemicals [23].
  • Replacement of the phthalimide moiety by substituted benzamides led to retention of 5-HT1A affinity but to no improvement in selectivity, whereas replacement by alkyl amides proved beneficial, leading to an improvement in affinity and selectivity [24].
  • Some phthalimide analogs, included PP-33 [2-(2,6-diisopropylphenyl)-1H-isoindole-1,3-dione] and its 4,5,6,7-tetrafluora derivative FPP-33), also showed such an inducer-specific bidirectional TNF-alpha production-regulating activity [25].
  • A novel pyrolysis GC-ECD technique that quantified the thermal degradation product phthalimide had pg sensitivity suitable to detect the trace amounts of Folpet that permeated [26].

Analytical, diagnostic and therapeutic context of NSC3108


  1. Design and optimization of tricyclic phtalimide analogues as novel inhibitors of HIV-1 integrase. Verschueren, W.G., Dierynck, I., Amssoms, K.I., Hu, L., Boonants, P.M., Pille, G.M., Daeyaert, F.F., Hertogs, K., Surleraux, D.L., Wigerinck, P.B. J. Med. Chem. (2005) [Pubmed]
  2. Allergic contact dermatitis from N-(cyclohexylthio) phthalimide in a playground fitter. Loffeld, A., Foulds, I.S. Contact Derm. (2004) [Pubmed]
  3. The cytotoxicity of N-Pyridinyl and N-quinolinyl substituted derivatives of phthalimide and succinimide. Hall, I.H., Wong, O.T., Scovill, J.P. Biomed. Pharmacother. (1995) [Pubmed]
  4. New lipophilic phthalimido- and 3-phenoxybenzyl sulfonates: inhibition of antigen 85C mycolyltransferase activity and cytotoxicity. Kovac, A., Wilson, R.A., Besra, G.S., Filipic, M., Kikelj, D., Gobec, S. Journal of enzyme inhibition and medicinal chemistry. (2006) [Pubmed]
  5. Synthesis and antimicrobial activity of new adamantane derivatives III. Orzeszko, A., Kamińska, B., Starościak, B.J. Farmaco (2002) [Pubmed]
  6. Influence of new gamma-aminobutyric acid amide derivatives and its phthalimide precursors on the central nervous system activity in mice. Mendyk, A., Sałat, K., Librowski, T., Czarneck, R., Malawska, B. Polish journal of pharmacology. (2001) [Pubmed]
  7. A synthetic strategy for the preparation of cyclic peptide mimetics based on SET-promoted photocyclization processes. Yoon, U.C., Jin, Y.X., Oh, S.W., Park, C.H., Park, J.H., Campana, C.F., Cai, X., Duesler, E.N., Mariano, P.S. J. Am. Chem. Soc. (2003) [Pubmed]
  8. In vitro biotransformation of (R)- and (S)-thalidomide: application of circular dichroism spectroscopy to the stereochemical characterization of the hydroxylated metabolites. Meyring, M., Mühlbacher, J., Messer, K., Kastner-Pustet, N., Bringmann, G., Mannschreck, A., Blaschke, G. Anal. Chem. (2002) [Pubmed]
  9. Virtual screening of combinatorial libraries across a gene family: in search of inhibitors of Giardia lamblia guanine phosphoribosyltransferase. Aronov, A.M., Munagala, N.R., Kuntz, I.D., Wang, C.C. Antimicrob. Agents Chemother. (2001) [Pubmed]
  10. Structure-activity relationships in a series of bisquaternary bisphthalimidine derivatives modulating the muscarinic M(2)-receptor allosterically. Botero Cid, H.M., Tränkle, C., Baumann, K., Pick, R., Mies-Klomfass, E., Kostenis, E., Mohr, K., Holzgrabe, U. J. Med. Chem. (2000) [Pubmed]
  11. Kinetics of self-decomposition and hydrogen atom transfer reactions of substituted phthalimide N-oxyl radicals in acetic acid. Cai, Y., Koshino, N., Saha, B., Espenson, J.H. J. Org. Chem. (2005) [Pubmed]
  12. Efficient synthesis of azide-bearing cofactor mimics. Comstock, L.R., Rajski, S.R. J. Org. Chem. (2004) [Pubmed]
  13. Comparative pharmacokinetic and pharmacodynamic analysis of phthaloyl glycine derivatives with potential antiepileptic activity. abu Salach, O., Hadad, S., Haj-Yehia, A., Sussan, S., Bialer, M. Pharm. Res. (1994) [Pubmed]
  14. Development of new CoMFA and CoMSIA 3D-QSAR models for anti-inflammatory phthalimide-containing TNFalpha modulators. Avila, C.M., Romeiro, N.C., Sperandio da Silva, G.M., Sant'anna, C.M., Barreiro, E.J., Fraga, C.A. Bioorg. Med. Chem. (2006) [Pubmed]
  15. Probing the size of a hydrophobic binding pocket within the allosteric site of muscarinic acetylcholine M2-receptors. Bender, W., Staudt, M., Tränkle, C., Mohr, K., Holzgrabe, U. Life Sci. (2000) [Pubmed]
  16. Cytotoxicity of imides-N-alkyl semicarbazones, thiosemicarbazones, acetylhydrazones and related derivatives. Hall, I.H., Wong, O.T., Chapman, J.M. Anticancer Drugs (1995) [Pubmed]
  17. Evaluation of the anticancer property of a new alpha-methylene-gamma-lactone derivative of phthalimide. Sanyal, U., Dutta, S., Das, H. Neoplasma (1995) [Pubmed]
  18. The effects of cyclic imides on lipoprotein receptor binding and degradation of rat and human cells and effects on regulatory enzymes of lipid metabolism. Wong, O.T., Williams, W.L., Oswald, B.S., Hall, I.H. Res. Commun. Chem. Pathol. Pharmacol. (1992) [Pubmed]
  19. Amino acid-derived phthalimide and saccharin derivatives as inhibitors of human leukocyte elastase, cathepsin G, and proteinase 3. Groutas, W.C., Chong, L.S., Venkataraman, R., Kuang, R., Epp, J.B., Houser-Archield, N., Huang, H., Hoidal, J.R. Arch. Biochem. Biophys. (1996) [Pubmed]
  20. Antihyperlipidemic activity of phthalimide analogues in rodents. Hall, I.H., Voorstad, P.J., Chapman, J.M., Cocolas, G.H. Journal of pharmaceutical sciences. (1983) [Pubmed]
  21. Immunomodulatory assays to study structure-activity relationships of thalidomide. Shannon, E.J., Morales, M.J., Sandoval, F. Immunopharmacology (1997) [Pubmed]
  22. Design and synthesis of phthalimide-type histone deacetylase inhibitors. Shinji, C., Nakamura, T., Maeda, S., Yoshida, M., Hashimoto, Y., Miyachi, H. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  23. Induction of hsp70 in transgenic Drosophila: biomarker of exposure against phthalimide group of chemicals. Nazir, A., Saxena, D.K., Kar Chowdhuri, D. Biochim. Biophys. Acta (2003) [Pubmed]
  24. Analogues of the 5-HT1A serotonin antagonist 1-(2-methoxyphenyl)-4-[4-(2-phthalimido)butyl]piperazine with reduced alpha 1-adrenergic affinity. Raghupathi, R.K., Rydelek-Fitzgerald, L., Teitler, M., Glennon, R.A. J. Med. Chem. (1991) [Pubmed]
  25. Inducer-specific bidirectional regulation by thalidomide and phenylphthalimides of tumor necrosis factor-alpha production. Miyachi, H., Azuma, A., Hioki, E., Iwasaki, S., Kobayashi, Y., Hashimoto, Y. Biochem. Biophys. Res. Commun. (1996) [Pubmed]
  26. Folpet permeation through nitrile gloves. Zainal, H., Que Hee, S.S. Applied occupational and environmental hygiene. (2003) [Pubmed]
  27. Metabolic and toxic behaviours of phthalimide derivatives in albino rat II. Placental passage of chloromethyl phthalimide, oxymethyl phthalimide and phthalimide--their fetal metabolism. Ackermann, H., Faust, H., Kagan, Y.S., Voronina, V.H. Arch. Toxicol. (1978) [Pubmed]
  28. Design, synthesis, conformational analysis and nucleic acid hybridisation properties of thymidyl pyrrolidine-amide oligonucleotide mimics (POM). Hickman, D.T., Tan, T.H., Morral, J., King, P.M., Cooper, M.A., Micklefield, J. Org. Biomol. Chem. (2003) [Pubmed]
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