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Chemical Compound Review

Sulfamide     sulfamide

Synonyms: Sulfamamide, sulfamoylamine, NSC-252, Sulfuryl amide, NSC252, ...
 
 
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Disease relevance of NSC252

  • Inhibitors of the C(2)-symmetric HIV-1 protease: nonsymmetric binding of a symmetric cyclic sulfamide with ketoxime groups in the P2/P2' side chains [1].
  • Heparinoids with different sulfamide contents indicated that the anticoagulant activity (35.3-41.3 units/mg) is independent of the sulfamide content, while an increase in sulfamide content lowered the toxicity [2].
  • Generalized cutaneous depigmentation following sulfamide-induced drug eruption [3].
 

High impact information on NSC252

  • In other cases, the sulfamide moiety is important for inducing desired physico-chemical properties to the drug-like compounds incorporating it, such as enhanced water solubility, better bioavailability, etc., because of the intrinsic properties of this highly polarized moiety when attached to an organic scaffold [4].
  • Long chain saturated and unsaturated alkyl sulfamide and propyl sulfamide derivatives, analogs of oleoylethanolamide, have been synthesized and evaluated in vivo and in vitro as peroxisome proliferator activated receptor alpha (PPARalpha) activators [5].
  • These results indicate that the sulfamide moiety is not particularly suitable for obtaining potent carbonic anhydrase inhibition [6].
  • Comparison of sulfamate and sulfamide groups for the inhibition of carbonic anhydrase-II by using topiramate as a structural platform [6].
  • Sulfamide-based inhibitors for carboxypeptidase A. Novel type transition state analogue inhibitors for zinc proteases [7].
 

Chemical compound and disease context of NSC252

  • The toxicity to mice and/or houseflies decreases in the following order: TETS much greater than the heterotetracyclic compound hexamethylenetrisulfohexamine (HEXS) and two TETS analogues in which one sulfamide group is replaced with o-phenylenediamine or 1,1-dimethyl-1,2-diaminoethane much greater than seven other hetero(homo)adamantanes [8].
  • To identify structural features associated with a certain resistance profile, the inhibitory properties of a series of symmetric and asymmetric cyclic sulfamide, cyclic urea and linear transition-state analogue inhibitors of HIV-1 protease were investigated using wild-type and mutant enzyme [9].
 

Anatomical context of NSC252

 

Associations of NSC252 with other chemical compounds

 

Gene context of NSC252

References

  1. Inhibitors of the C(2)-symmetric HIV-1 protease: nonsymmetric binding of a symmetric cyclic sulfamide with ketoxime groups in the P2/P2' side chains. Hultén, J., Andersson, H.O., Schaal, W., Danielson, H.U., Classon, B., Kvarnström, I., Karlén, A., Unge, T., Samuelsson, B., Hallberg, A. J. Med. Chem. (1999) [Pubmed]
  2. Synthesis of new heparinoids with high anticoagulant activity. Hatanaka, K., Yoshida, T., Miyahara, S., Sato, T., Ono, F., Uryu, T., Kuzuhara, H. J. Med. Chem. (1987) [Pubmed]
  3. Generalized cutaneous depigmentation following sulfamide-induced drug eruption. Martínez-Ruiz, E., Ortega, C., Calduch, L., Molina, I., Montesinos, E., Revert, A., Cardá, C., Navarro, V., Jordá, E. Dermatology (Basel) (2000) [Pubmed]
  4. Therapeutic potential of sulfamides as enzyme inhibitors. Winum, J.Y., Scozzafava, A., Montero, J.L., Supuran, C.T. Medicinal research reviews. (2006) [Pubmed]
  5. Novel sulfamide analogs of oleoylethanolamide showing in vivo satiety inducing actions and PPARalpha activation. Cano, C., Pavón, J., Serrano, A., Goya, P., Paez, J.A., de Fonseca, F.R., Macias-Gonzalez, M. J. Med. Chem. (2007) [Pubmed]
  6. Comparison of sulfamate and sulfamide groups for the inhibition of carbonic anhydrase-II by using topiramate as a structural platform. Maryanoff, B.E., McComsey, D.F., Costanzo, M.J., Hochman, C., Smith-Swintosky, V., Shank, R.P. J. Med. Chem. (2005) [Pubmed]
  7. Sulfamide-based inhibitors for carboxypeptidase A. Novel type transition state analogue inhibitors for zinc proteases. Park, J.D., Kim, D.H., Kim, S.J., Woo, J.R., Ryu, S.E. J. Med. Chem. (2002) [Pubmed]
  8. Recognition of tetramethylenedisulfotetramine and related sulfamides by the brain GABA-gated chloride channel and a cyclodiene-sensitive monoclonal antibody. Esser, T., Karu, A.E., Toia, R.F., Casida, J.E. Chem. Res. Toxicol. (1991) [Pubmed]
  9. Resistance profiles of cyclic and linear inhibitors of HIV-1 protease. Ahlsén, G., Hultén, J., Shuman, C.F., Poliakov, A., Lindgren, M.T., Alterman, M., Samuelsson, B., Hallberg, A., Danielson, U.H. Antivir. Chem. Chemother. (2002) [Pubmed]
  10. Protonophoretic activity of hypoglycemic sulfonylureas in black lipid membranes. Deleers, M., Brasseur, R. Pharmacological research communications. (1986) [Pubmed]
  11. Carbonic anhydrase inhibitors: inhibition of isozymes I, II and IV by sulfamide and sulfamic acid derivatives. Scozzafava, A., Banciu, M.D., Popescu, A., Supuran, C.T. J. Enzym. Inhib. (2000) [Pubmed]
  12. Identification of nonpeptidic small-molecule inhibitors of interleukin-2. Waal, N.D., Yang, W., Oslob, J.D., Arkin, M.R., Hyde, J., Lu, W., McDowell, R.S., Yu, C.H., Raimundo, B.C. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  13. Carbonic anhydrase inhibitors: N-cyanosulfonamides, a new class of high affinity isozyme II and IV inhibitors. Supuran, C.T., Scozzafava, A., Briganti, F. J. Enzym. Inhib. (1999) [Pubmed]
  14. Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV. Casini, A., Antel, J., Abbate, F., Scozzafava, A., David, S., Waldeck, H., Schäfer, S., Supuran, C.T. Bioorg. Med. Chem. Lett. (2003) [Pubmed]
  15. Potent and selective, sulfamide-based human beta 3-adrenergic receptor agonists. Dow, R.L., Paight, E.S., Schneider, S.R., Hadcock, J.R., Hargrove, D.M., Martin, K.A., Maurer, T.S., Nardone, N.A., Tess, D.A., DaSilva-Jardine, P. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  16. Design, synthesis, and in vitro evaluation of inhibitors of human leukocyte elastase based on a functionalized cyclic sulfamide scaffold. Zhong, J., Gan, X., Alliston, K.R., Groutas, W.C. Bioorg. Med. Chem. (2004) [Pubmed]
  17. Tyrosyl sulfamide derivatives as ligands for affinity adsorption of anti FVIII antibodies. Dahri, L., Boisson-Vidal, C., Muller, D., Jozefonvicz, J. Journal of biomaterials science. Polymer edition. (1994) [Pubmed]
 
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