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Chemical Compound Review

benzoxazol     benzooxazole

Synonyms: BENZOXAZOLE, Benzooxazole, benzoxazoline, SureCN7903, PubChem21884, ...
 
 
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Disease relevance of benzooxazole

 

High impact information on benzooxazole

  • In particular, introduction of heterobicycles such as benzoxazole resulted in more potent chymase-inhibitory activity [6].
  • More importantly, the results suggest that the benzoxazole inactivation pathway may be important physiologically and may have influenced the distribution of amine oxidases and catalase in cells [7].
  • Several heterocycles, including oxazoline and benzoxazole, afforded extremely potent inhibitors of HNE (1p-r) with nanomolar to subnanomolar Ki values [8].
  • 3,4-Dihydro-4-oxo-3-[(5,7-difluoro-2-benzoxazolyl)methyl]-1- phthalazineacetic acid (124) was the best of the benzoxazole series (IC50 = 3.2 x 10(-9) M); it suppressed accumulation of sorbitol in rat sciatic nerve by 78% at an oral dose of 10 mg/kg [2].
  • In general, inhibitory activity against 5-LO, LTD4, and OA was broadest for benzthiazole-containing analogues (benzthiazole greater than benzimidazole much greater than benzoxazole, benzofuran) [9].
 

Biological context of benzooxazole

  • Detailed structure-activity relationship studies on the benzoxazole moiety and substituents at the 2-position of the pyrimidinone ring revealed that 2r (Y-40079) had the most potent chymase-inhibitory activity (K(i) = 4.85 nM) [6].
  • Molecular recognition between ligands and nucleic acids: novel pyridine- and benzoxazole-containing agents related to Hoechst 33258 that exhibit altered DNA sequence specificity deduced from footprinting analysis and spectroscopic studies [10].
  • Palladium-catalyzed aminations of the electron-rich furanyl, thiophenyl, and indolyl halides and of the related 2-halogenated thiazoles, benzimidazole, and benzoxazole have been shown to occur with a subset of amines [11].
  • The in vitro metabolites were identified by NMR and MS as 5 alpha-hydroxyethyl- (major), 5,6-dihydrodiol-, 6'-hydroxy-, 6-hydroxymethyl-, and 5-vinyl analogs, and a benzoxazole ring hydrolysis product [12].
  • In the second series of compounds based on Hoechst 33258, the structure obtained by replacing the two benzimidazoles in the parent compound by a combination of pyridoimidazole and benzoxazole, exhibits changes in the carbonyl frequency region of poly dG.poly dC which is attributed to the ligand interaction at the minor groove of GC base pairs [13].
 

Anatomical context of benzooxazole

  • In contrast, a simplified analogue in which the carbomethoxy-substituted benzoxazole ring was replaced with a carbomethoxy group was almost as active as UK-1 against the four cancer cell lines examined but lacked activity against S. aureus [14].
  • Several modified 2-piperazinyl benzoxazole derivatives, which exhibit an agonistic effect on gastrointestinal motility, were synthesized and their effects on the contraction of guinea-pig ileum were examined [15].
 

Associations of benzooxazole with other chemical compounds

 

Gene context of benzooxazole

  • Benzoxazole- and benzothiazole-diones were at least 50 times more potent in inhibiting CDC25C than their benzimidazole-indazole- or isoindole-dione counterparts [18].
  • Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff's bases [21].
  • The thermal decomposition of benzoxazole diluted in argon was studied behind reflected shock waves in a 2 in. i.d. single-pulse shock tube over the temperature range 1000-1350 K and at overall densities of approximately 3 x 10(-5) mol/cm(3) [22].
  • Synthesis and pharmacological characterization of a new benzoxazole derivative as a potent 5-HT3 receptor agonist [23].
  • Benzoxazole benzenesulfonamides as allosteric inhibitors of fructose-1,6-bisphosphatase [24].

References

  1. Orally active benzoxazole derivative as 5-HT3 receptor partial agonist for treatment of diarrhea-predominant irritable bowel syndrome. Yoshida, S., Shiokawa, S., Kawano, K., Ito, T., Murakami, H., Suzuki, H., Sato, Y. J. Med. Chem. (2005) [Pubmed]
  2. Potent, orally active aldose reductase inhibitors related to zopolrestat: surrogates for benzothiazole side chain. Mylari, B.L., Beyer, T.A., Scott, P.J., Aldinger, C.E., Dee, M.F., Siegel, T.W., Zembrowski, W.J. J. Med. Chem. (1992) [Pubmed]
  3. AJI9561, a new cytotoxic benzoxazole derivative produced by Streptomyces sp. Sato, S., Kajiura, T., Noguchi, M., Takehana, K., Kobayashi, T., Tsuji, T. J. Antibiot. (2001) [Pubmed]
  4. Synthesis and microbiological activity of some N-(o-hydroxyphenyl)benzamides and phenylacetamides as the possible metabolites of antimicrobial active benzoxazoles: part II. Sener, E.A., Bingöl, K.K., Oren, I., Arpaci, O.T., Yaçin, I., Altanlar, N. Farmaco (2000) [Pubmed]
  5. Induction of apoptosis and necrosis by resistance modifiers benzazoles and benzoxazines on tumour cell line mouse lymphoma L5718 Mdr+cells. Varga, A., Aki-Sener, E., Yalcin, I., Temiz-Arpaci, O., Tekiner-Gulbas, B., Cherepnev, G., Molnar, J. In Vivo (2005) [Pubmed]
  6. Synthesis, structure-activity relationships, and pharmacokinetic profiles of nonpeptidic alpha-keto heterocycles as novel inhibitors of human chymase. Akahoshi, F., Ashimori, A., Sakashita, H., Yoshimura, T., Imada, T., Nakajima, M., Mitsutomi, N., Kuwahara, S., Ohtsuka, T., Fukaya, C., Miyazaki, M., Nakamura, N. J. Med. Chem. (2001) [Pubmed]
  7. Catalytic turnover of substrate benzylamines by the quinone-dependent plasma amine oxidase leads to H2O2-dependent inactivation: evidence for generation of a cofactor-derived benzoxazole. Lee, Y., Shepard, E., Smith, J., Dooley, D.M., Sayre, L.M. Biochemistry (2001) [Pubmed]
  8. Peptidyl alpha-ketoheterocyclic inhibitors of human neutrophil elastase. 2. Effect of varying the heterocyclic ring on in vitro potency. Edwards, P.D., Wolanin, D.J., Andisik, D.W., Davis, M.W. J. Med. Chem. (1995) [Pubmed]
  9. Leukotriene D4 antagonists and 5-lipoxygenase inhibitors. Synthesis of benzoheterocyclic [(methoxyphenyl)amino]oxoalkanoic acid esters. Musser, J.H., Kubrak, D.M., Chang, J., DiZio, S.M., Hite, M., Hand, J.M., Lewis, A.J. J. Med. Chem. (1987) [Pubmed]
  10. Molecular recognition between ligands and nucleic acids: novel pyridine- and benzoxazole-containing agents related to Hoechst 33258 that exhibit altered DNA sequence specificity deduced from footprinting analysis and spectroscopic studies. Bathini, Y., Rao, K.E., Shea, R.G., Lown, J.W. Chem. Res. Toxicol. (1990) [Pubmed]
  11. Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides. Hooper, M.W., Utsunomiya, M., Hartwig, J.F. J. Org. Chem. (2003) [Pubmed]
  12. Metabolism of 3-[2-(benzoxazol-2-yl)ethyl]-5-ethyl-6-methylpyridin-2 (1H)-one (L-696,229), an HIV-1 reverse transcriptase inhibitor, by rat liver slices and in humans. Balani, S.K., Kauffman, L.R., Arison, B.H., Olah, T.V., Goldman, M.E., Varga, S.L., O'Brien, J.A., Ramjit, H.G., Rooney, C.S., Hoffman, J.M. Drug Metab. Dispos. (1994) [Pubmed]
  13. FTIR study of specific binding interactions between DNA minor groove binding ligands and polynucleotides. Adnet, F., Liquier, J., Taillandier, E., Singh, M.P., Rao, K.E., Lown, J.W. J. Biomol. Struct. Dyn. (1992) [Pubmed]
  14. Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1. Kumar, D., Jacob, M.R., Reynolds, M.B., Kerwin, S.M. Bioorg. Med. Chem. (2002) [Pubmed]
  15. A new 5-HT3 receptor ligand. II. Structure-activity analysis of 5-HT3 receptor agonist action in the gut. Yamada, M., Sato, Y., Kobayashi, K., Konno, F., Soneda, T., Watanabe, T. Chem. Pharm. Bull. (1998) [Pubmed]
  16. Peptidyl alpha-ketoheterocyclic inhibitors of human neutrophil elastase. 3. In vitro and in vivo potency of a series of peptidyl alpha-ketobenzoxazoles. Edwards, P.D., Zottola, M.A., Davis, M., Williams, J., Tuthill, P.A. J. Med. Chem. (1995) [Pubmed]
  17. Design, synthesis, and evaluation of alpha-ketoheterocycles as class C beta-lactamase inhibitors. Kumar, S., Pearson, A.L., Pratt, R.F. Bioorg. Med. Chem. (2001) [Pubmed]
  18. Synthesis and biological evaluation of novel heterocyclic quinones as inhibitors of the dual specificity protein phosphatase CDC25C. Lavergne, O., Fernandes, A.C., Bréhu, L., Sidhu, A., Brézak, M.C., Prévost, G., Ducommun, B., Contour-Galcera, M.O. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
  19. Benzoxazole benzenesulfonamides are novel allosteric inhibitors of fructose-1,6-bisphosphatase with a distinct binding mode. von Geldern, T.W., Lai, C., Gum, R.J., Daly, M., Sun, C., Fry, E.H., Abad-Zapatero, C. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
  20. Vibrational analysis of structure activity relationships (SAR) in molecular binding. Pivonka, D. Applied spectroscopy. (2004) [Pubmed]
  21. Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff's bases. Sondhi, S.M., Singh, N., Kumar, A., Lozach, O., Meijer, L. Bioorg. Med. Chem. (2006) [Pubmed]
  22. Thermal reactions of benzoxazole. Single pulse shock tube experiments and quantum chemical calculations. Lifshitz, A., Tamburu, C., Suslensky, A., Dubnikova, F. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  23. Synthesis and pharmacological characterization of a new benzoxazole derivative as a potent 5-HT3 receptor agonist. López-Tudanca, P.L., Labeaga, L., Innerárity, A., Alonso-Cires, L., Tapia, I., Mosquera, R., Orjales, A. Bioorg. Med. Chem. (2003) [Pubmed]
  24. Benzoxazole benzenesulfonamides as allosteric inhibitors of fructose-1,6-bisphosphatase. Lai, C., Gum, R.J., Daly, M., Fry, E.H., Hutchins, C., Abad-Zapatero, C., von Geldern, T.W. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
 
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