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Chemical Compound Review

CHEMBL14047     2-phenylguanidine

Synonyms: SureCN256023, SureCN467577, CHEBI:113403, LS-73864, ZINC04276940, ...
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High impact information on Phenylguanidine

  • The x-ray crystal structure of the uPA B-chain complexed with this inhibitor revealed a surprising binding mode consisting of the expected insertion of the phenylguanidine moiety into the S1 pocket, but with the adamantyl residue protruding toward the hydrophobic S1' enzyme subsite, thus exposing the ureido group to hydrogen-bonding interactions [1].
  • This new crystal form contains an accessible active site that facilitates compound soaking, which was used to determine the co-crystal structures of urokinase in complex with the small molecule inhibitors amiloride, 4-iodo-benzo(b)thiophene-2-carboxamidine and phenylguanidine at 2 [2].
  • A series of phenylguanidine analogues represented by 10, 12, and 21 were synthesized and found to have high binding affinities for the human melanocortin-5 receptor [3].
  • The present work describes the interaction of phenylguanidine and cyclohexylguanidine with receptor structures of the isolated guinea-pig ileum [4].

Analytical, diagnostic and therapeutic context of Phenylguanidine


  1. (4-aminomethyl)phenylguanidine derivatives as nonpeptidic highly selective inhibitors of human urokinase. Sperl, S., Jacob, U., Arroyo de Prada, N., Stürzebecher, J., Wilhelm, O.G., Bode, W., Magdolen, V., Huber, R., Moroder, L. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  2. Re-engineering of human urokinase provides a system for structure-based drug design at high resolution and reveals a novel structural subsite. Nienaber, V., Wang, J., Davidson, D., Henkin, J. J. Biol. Chem. (2000) [Pubmed]
  3. Phenylguanidines as selective nonpeptide melanocortin-5 receptor antagonists. Chen, C., Yu, J., Fleck, B.A., Hoare, S.R., Saunders, J., Foster, A.C. J. Med. Chem. (2004) [Pubmed]
  4. Guanidines as analogs of histamine and antihistamines on the isolated guinea-pig ileum. Rezende, L., Diniz, C.R., Mares-Guia, M. Gen. Pharmacol. (1976) [Pubmed]
  5. Antiparasitic agents. 4. Injectable phenylguanidine anthelmintics. Cruthers, L.R., Haugwitz, R.D., Maurer, B.V. Experientia (1980) [Pubmed]
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