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Chemical Compound Review: 

BENZANILIDE     N-phenylbenzamide

Synonyms: SureCN31966, AGN-PC-00KBUL, ARONIS003508, CHEMBL115523, NSC-3131, ...
 
 
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Disease relevance of N-phenylbenzamide

 

High impact information on N-phenylbenzamide

  • Encainide, a new benzanilide derivative with high potency and a good therapeutic/toxic ratio, was evaluated with the use of standard His bundle recording techniques to determine its effects on the cardiac conduction system in closed chest animals [2].
  • Compounds with alkoxy groups (especially ethoxy group) at the 2'-position of benzanilide possessed potent affinity and selectivity for the V1A receptor versus V2 receptor [3].
  • A series of compounds structurally related to 2-phenyl-4'-(2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-carbonyl) benzanilide was synthesized and demonstrated to have arginine vasopressin (AVP) antagonist activity for both V1A and V2 receptors [4].
  • Synthesis of benzanilide derivatives which have dual alpha 1-adrenoceptor antagonistic action and steroid 5 alpha-reductase inhibitory activity and their structure-activity relationships is described [5].
  • 3. Hydrolysis of benzanilide and related compounds was inhibited by anthelmintic organophosphates [6].
 

Anatomical context of N-phenylbenzamide

  • TZ181 (7a), having a benzanilide skeleton, exhibited differentiation-inducing activity in HL-60 cell assay, while TZ191 (7b), the N-methylated analog of TZ181 (7a), TZ245 (9) and TZ335 (10) acted as retinoid synergists like the RXR-selective ligand, LGD1069 (5) [7].
 

Analytical, diagnostic and therapeutic context of N-phenylbenzamide

  • Metalation of benzanilide with n-butyllithium, addition of 4-(dimethylamino)cyclohexanone, and acidification afforded a mixture of cis- and trans-4-(dimethylamino)spiro[cyclohexane-1,1'(3'H)-isobenzofuran]-3'-ones (1a,b), which were separated by fractional crystallization [8].

References

  1. Effects of encainide on the determinants of cardiac excitability in sheep Purkinje fibers. Arnsdorf, M.F., Schmidt, G.A., Sawicki, G.J. J. Pharmacol. Exp. Ther. (1985) [Pubmed]
  2. Canine electrophysiology of encainide, a new antiarrhythmic drug. Sami, M., Mason, J.W., Oh, G., Harrison, D.C. Am. J. Cardiol. (1979) [Pubmed]
  3. Preparation of non-peptide, highly potent and selective antagonists of arginine vasopressin V1A receptor by introduction of alkoxy groups. Shimada, Y., Taniguchi, N., Matsuhisa, A., Yatsu, T., Tahara, A., Tanaka, A. Chem. Pharm. Bull. (2003) [Pubmed]
  4. Nonpeptide arginine vasopressin antagonists for both V1A and V2 receptors: synthesis and pharmacological properties of 2-phenyl-4'-(2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-carbonyl) benzanilide derivatives. Matsuhisa, A., Koshio, H., Sakamoto, K., Taniguchi, N., Yatsu, T., Tanaka, A. Chem. Pharm. Bull. (1998) [Pubmed]
  5. Synthesis of benzanilide derivatives as dual acting agents with alpha 1-adrenoceptor antagonistic action and steroid 5-alpha reductase inhibitory activity. Yoshida, K., Horikoshi, Y., Eta, M., Chikazawa, J., Ogishima, M., Fukuda, Y., Sato, H. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
  6. The metabolism of niclosamide and related compounds by Moniezia expansa, Ascaris lumbricoides var suum, and mouse- and sheep-liver enzymes. Douch, P.G., Gahagan, H.M. Xenobiotica (1977) [Pubmed]
  7. Novel thiazolidinedione derivatives with retinoid synergistic activity. Ebisawa, M., Kawachi, E., Fukasawa, H., Hashimoto, Y., Itai, A., Shudo, K., Kagechika, H. Biol. Pharm. Bull. (1998) [Pubmed]
  8. Synthesis of spiro[isobenzofuran-1(3H),4'-piperidines] as potential central nervous system agents. 6. Synthesis, 13C NMR, and biological evaluation of cis- and trans-4-amino-3'-arylspiro[cyclohexane-1,1'(3'H)-isobenzofuran] derivatives. Martin, L.L., Worm, M., Agnew, M.N., Kruse, H., Wilker, J.C., Geyer, H.M. J. Med. Chem. (1981) [Pubmed]
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