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Chemical Compound Review

pyridone     1H-pyridin-2-one

Synonyms: PYRIDON, alpha-Pyridone, Pyridone-2, CHEMBL662, Pyridin-2-ol, ...
 
 
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Disease relevance of Pyridinol

  • The structure-based design, chemical synthesis, and biological evaluation of various 2-pyridone-containing human rhinovirus (HRV) 3C protease (3CP) inhibitors are described [1].
  • Synthesis and evaluation of 2-pyridinone derivatives as HIV-1 specific reverse transcriptase inhibitors. 1. Phthalimidoalkyl and -alkylamino analogues [2].
  • The alpha-pyridone (H-T), PPB, 1-MeCyt (H-T) dimer, and 1-MeUra monomer complexes are inert to chloride ion and inactive against mouse sarcoma S-180 [3].
  • 2-Hydroxypyridine metabolism and pigment formation in three Arthrobacter species [4].
  • ABT-719, which represents the new 2-pyridone compound class, has promise for the treatment of urinary tract infections, as suggested by the significant efficacy seen against experimental pyelonephritis caused by E. coli, P. aeruginosa and susceptible and resistant enterococci [5].
 

High impact information on Pyridinol

  • In an approach to helical self-aggregation, C2-symmetric cavity compounds based on the fusion of the bicyclo[3.3.1]nonane and indole framework and incorporating two 2-pyridone hydrogen-bonding motifs, compounds (-)-4 (pyrrole N-butyl) and (-)-5 (pyrrole N-decyl), have been synthesized [6].
  • The 2-pyridone antibacterial agents: bacterial topoisomerase inhibitors [7].
  • Since their alpha-pyridone moieties are responsible for their key interactions with the active site via hydrogen bonding, and possibly via C-H.pi interactions, all three maintain similar positions and orientations with respect to it [8].
  • The modified complexes were chemically synthesized with the substitution of a single 2-pyridone (2P) base analogue for residues U4, U7, and U16 [9].
  • ABT-255 is a novel 2-pyridone antibacterial agent which demonstrates in vitro potency and in vivo efficacy against drug-susceptible and drug-resistant M. tuberculosis strains [10].
 

Chemical compound and disease context of Pyridinol

 

Biological context of Pyridinol

  • 2-Hydroxypyridine, the hydrolysis product of the putative pyridine-2-diazonium intermediate, generated after oxidative demethylation, was formed in high yields from 2-NMPY [16].
  • The effect of the dimerization, by hydrogen-bond (HB) complexation, on the tautomerism of 2-hydroxypyridine and a series 2-aminopyridines has been carried using ab initio methods [17].
  • Conjugate addition of lithium amides to (S)-N-acryloyl- or (S)-N-2'-alkylacryloyloxazolidinones and alkylation or protonation of the resulting enolates with 2-pyridone respectively provides a highly stereoselective and product complementary route to a range of (R)- and (S)-2-alkyl-3-aminopropionic acids in good yield and in high ee [18].
  • Similarly, only 2-hydroxypyridine induced the expression of a xenobiotic response element-directed reporter gene in transfected HepG2 cells [19].
  • Pharmacokinetics and bioavailability of pyridinol carbamate in humans [20].
 

Anatomical context of Pyridinol

 

Associations of Pyridinol with other chemical compounds

 

Gene context of Pyridinol

  • The effect was seen even at a 4 : 1 ratio of 2-pyridone and monomeric Abeta-peptide [26].
  • Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. Part 7: structure-activity studies of bicyclic 2-pyridone-containing peptidomimetics [27].
 

Analytical, diagnostic and therapeutic context of Pyridinol

  • Optimization of the 2-pyridone-containing compounds is shown to provide several highly active 3CP inhibitors (k(obs)/[I] > 500,00 M(-1) s(-1)) that function as potent antirhinoviral agents (EC(50) = <0.05 microM) against multiple virus serotypes in cell culture [1].
  • The optimization of the pharmacokinetic performance of various 2-pyridone-containing human rhinovirus (HRV) 3C protease (3CP) inhibitors following oral administration to either beagle dogs or CM-monkeys is described [28].
  • Photochemistry of N-isopropoxy-substituted 2(1H)-pyridone and 4-p-tolylthiazole-2(3H)-thione: alkoxyl-radical release (spin-trapping, EPR, and transient spectroscopy) and its significance in the photooxidative induction of DNA strand breaks [29].
  • Long term lathyrism and atherogenic diet in the rat. Protective action of pyridinol carbamate [30].

References

  1. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 6. Structure-activity studies of orally bioavailable, 2-pyridone-containing peptidomimetics. Dragovich, P.S., Prins, T.J., Zhou, R., Brown, E.L., Maldonado, F.C., Fuhrman, S.A., Zalman, L.S., Tuntland, T., Lee, C.A., Patick, A.K., Matthews, D.A., Hendrickson, T.F., Kosa, M.B., Liu, B., Batugo, M.R., Gleeson, J.P., Sakata, S.K., Chen, L., Guzman, M.C., Meador, J.W., Ferre, R.A., Worland, S.T. J. Med. Chem. (2002) [Pubmed]
  2. Synthesis and evaluation of 2-pyridinone derivatives as HIV-1 specific reverse transcriptase inhibitors. 1. Phthalimidoalkyl and -alkylamino analogues. Hoffman, J.M., Wai, J.S., Thomas, C.M., Levin, R.B., O'Brien, J.A., Goldman, M.E. J. Med. Chem. (1992) [Pubmed]
  3. Cytotoxicity of platinum (II) dinuclear complexes with 1-alkylthymine ligands against mouse sarcoma 180 cells. Rekonen, P., Dohta, Y., Kodaka, M., Okada, T., Okamoto, K., Okuno, H. J. Med. Chem. (1997) [Pubmed]
  4. 2-Hydroxypyridine metabolism and pigment formation in three Arthrobacter species. Kolenbrander, P.E., Weinberger, M. J. Bacteriol. (1977) [Pubmed]
  5. Efficacy of ABT-719, a 2-pyridone antimicrobial, against enterococci, Escherichia coli, and Pseudomonas aeruginosa in experimental murine pyelonephritis. Meulbroek, J.A., Oleksijew, A., Tanaka, S.K., Alder, J.D. J. Antimicrob. Chemother. (1996) [Pubmed]
  6. An approach to helical tubular self-aggregation using C2-symmetric self-complementary hydrogen-bonding cavity molecules. Stoncius, S., Orentas, E., Butkus, E., Ohrström, L., Wendt, O.F., Wärnmark, K. J. Am. Chem. Soc. (2006) [Pubmed]
  7. The 2-pyridone antibacterial agents: bacterial topoisomerase inhibitors. Li, Q., Mitscher, L.A., Shen, L.L. Medicinal research reviews. (2000) [Pubmed]
  8. X-ray structures of Torpedo californica acetylcholinesterase complexed with (+)-huperzine A and (-)-huperzine B: structural evidence for an active site rearrangement. Dvir, H., Jiang, H.L., Wong, D.M., Harel, M., Chetrit, M., He, X.C., Jin, G.Y., Yu, G.L., Tang, X.C., Silman, I., Bai, D.L., Sussman, J.L. Biochemistry (2002) [Pubmed]
  9. Critical nature of a specific uridine O2-carbonyl for cleavage by the hammerhead ribozyme. Bevers, S., Ha, S.B., McLaughlin, L.W. Biochemistry (1999) [Pubmed]
  10. In vivo efficacy of ABT-255 against drug-sensitive and -resistant Mycobacterium tuberculosis strains. Oleksijew, A., Meulbroek, J., Ewing, P., Jarvis, K., Mitten, M., Paige, L., Tovcimak, A., Nukkula, M., Chu, D., Alder, J.D. Antimicrob. Agents Chemother. (1998) [Pubmed]
  11. Synthesis and evaluation of 2-pyridinone derivatives as specific HIV-1 reverse transcriptase inhibitors. 3. Pyridyl and phenyl analogs of 3-aminopyridin-2(1H)-one. Wai, J.S., Williams, T.M., Bamberger, D.L., Fisher, T.E., Hoffman, J.M., Hudcosky, R.J., MacTough, S.C., Rooney, C.S., Saari, W.S., Thomas, C.M. J. Med. Chem. (1993) [Pubmed]
  12. Progression of occlusive atherosclerosis. Long-term administration of pyridinol carbamate. Redisch, W., Clauss, R.H., Rouen, L.R., Katz, M.C., Terry, E.N. Archives of surgery (Chicago, Ill. : 1960) (1975) [Pubmed]
  13. Disturbances of purine nucleotide metabolism in uremia. Rutkowski, B., Swierczynski, J., Slominska, E., Szolkiewicz, M., Smolenski, R.T., Marlewski, M., Butto, B., Rutkowski, P. Semin. Nephrol. (2004) [Pubmed]
  14. Studies on the activity of three palladium(II) compounds of the form: Trans-PdL(2)Cl(2) where L=2-hydroxypyridine, 3-hydroxypyridine, and 4-hydroxypyridine. Huq, F., Tayyem, H., Beale, P., Yu, J.Q. J. Inorg. Biochem. (2007) [Pubmed]
  15. Biochemical criteria for the evaluation of drug efficiency on adjuvant arthritis and nephrotoxic serum nephritis in the rat: studies with phenylbutazone, L-Asparaginase, colchicine, lysine acetylsalicylate, and pyridinol carbamate. Sternberg, M., Peyroux, J., Grochulski, A., Engler, R., Feret, J., Moisy, M., Lagrue, G., Jayle, M.F. Can. J. Physiol. Pharmacol. (1975) [Pubmed]
  16. Metabolism of carcinogenic and non-carcinogenic N-nitroso-N-methylaminopyridines. I. Investigations in vitro. Heydt, G., Eisenbrand, G., Preussmann, R. Carcinogenesis (1982) [Pubmed]
  17. Influence of intermolecular hydrogen bonds on the tautomerism of pyridine derivatives. Alkorta, I., Elguero, J. J. Org. Chem. (2002) [Pubmed]
  18. Asymmetric synthesis of 2-alkyl- and 2-aryl-3-aminopropionic acids (beta2-amino acids) from (S)-N-acryloyl-5,5-dimethyloxazolidin-2-one SuperQuat derivatives. Beddow, J.E., Davies, S.G., Smith, A.D., Russell, A.J. Chem. Commun. (Camb.) (2004) [Pubmed]
  19. CYP1A1 induction by pyridine and its metabolites in HepG2 cells. Iba, M.M., Nguyen, T., Fung, J. Arch. Biochem. Biophys. (2002) [Pubmed]
  20. Pharmacokinetics and bioavailability of pyridinol carbamate in humans. Sassard, J., Bernard, N., Legheand, J., Cuisinaud, G., Traeger, J. Journal of pharmaceutical sciences. (1979) [Pubmed]
  21. Protective effect of pyridinol carbamate in dermal and aortic connective tissue lesions induced by chronic lathyrism. Bouissou, H., Pieraggi, M.T., Julian, M. Pharmacological research communications. (1978) [Pubmed]
  22. Determination of pyridinol carbamate in plasma using high-performance liquid chromatography. Bernard, N., Brazier, J.L., Sassard, J. J. Chromatogr. (1978) [Pubmed]
  23. Metabolism of metyrapone. III. Formation of an alpha-pyridone metabolite by rat hepatic soluble enzymes. Damani, L.A., Crooks, P.A., Cowan, D.A. Drug Metab. Dispos. (1981) [Pubmed]
  24. 2-hydroxypyridine <--> 2-pyridone tautomerization: catalytic influence of formic acid. Hazra, M.K., Chakraborty, T. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  25. One-electron oxidation of "photo-Fenton" reagents and inhibition of lipid peroxidation. Tobin, D., Arvanitidis, M., Bisby, R.H. Biochem. Biophys. Res. Commun. (2002) [Pubmed]
  26. Microwave-assisted decarboxylation of bicyclic 2-pyridone scaffolds and identification of Abeta-peptide aggregation inhibitors. Aberg, V., Norman, F., Chorell, E., Westermark, A., Olofsson, A., Sauer-Eriksson, A.E., Almqvist, F. Org. Biomol. Chem. (2005) [Pubmed]
  27. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. Part 7: structure-activity studies of bicyclic 2-pyridone-containing peptidomimetics. Dragovich, P.S., Prins, T.J., Zhou, R., Johnson, T.O., Brown, E.L., Maldonado, F.C., Fuhrman, S.A., Zalman, L.S., Patick, A.K., Matthews, D.A., Hou, X., Meador, J.W., Ferre, R.A., Worland, S.T. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
  28. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 8. Pharmacological optimization of orally bioavailable 2-pyridone-containing peptidomimetics. Dragovich, P.S., Prins, T.J., Zhou, R., Johnson, T.O., Hua, Y., Luu, H.T., Sakata, S.K., Brown, E.L., Maldonado, F.C., Tuntland, T., Lee, C.A., Fuhrman, S.A., Zalman, L.S., Patick, A.K., Matthews, D.A., Wu, E.Y., Guo, M., Borer, B.C., Nayyar, N.K., Moran, T., Chen, L., Rejto, P.A., Rose, P.W., Guzman, M.C., Dovalsantos, E.Z., Lee, S., McGee, K., Mohajeri, M., Liese, A., Tao, J., Kosa, M.B., Liu, B., Batugo, M.R., Gleeson, J.P., Wu, Z.P., Liu, J., Meador, J.W., Ferre, R.A. J. Med. Chem. (2003) [Pubmed]
  29. Photochemistry of N-isopropoxy-substituted 2(1H)-pyridone and 4-p-tolylthiazole-2(3H)-thione: alkoxyl-radical release (spin-trapping, EPR, and transient spectroscopy) and its significance in the photooxidative induction of DNA strand breaks. Adam, W., Hartung, J., Okamoto, H., Marquardt, S., Nau, W.M., Pischel, U., Saha-Möller, C.R., Spehar, K. J. Org. Chem. (2002) [Pubmed]
  30. Long term lathyrism and atherogenic diet in the rat. Protective action of pyridinol carbamate. Pieraggi, M.T., De Graeve, J., Julian, M., Thiers, J.C., Bouissou, H. Virchows Archiv. A, Pathological anatomy and histology. (1980) [Pubmed]
 
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