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Chemical Compound Review

Chromane     chroman

Synonyms: Chroman, benzoxane, SureCN8447, ACMC-1AH0G, AG-F-65462, ...
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Disease relevance of chroman

  • The spiro products may be formed by ozone addition to the chroman ring and subsequent rearrangement to ring-opened hydroxyacid products, which yield spiro products by ring closure due to dehydration [1].
  • Chroman amide and nicotinyl amide derivatives: inhibition of lipid peroxidation and protection against head trauma [2].

Psychiatry related information on chroman


High impact information on chroman

  • Chiral chroman moiety of siccanin was prepared based on our recent development of the Pd-catalyzed asymmetric allylic alkylation (AAA) of phenol trisubstituted allyl carbonates [4].
  • In actuality, alpha-tocopherol is one member of a class of phytochemicals that are distinguished by varying methylation of a chroman head group [5].
  • We explored the pharmacological properties of trans-6-cyano-4-(N-ethylsulfonyl-N-methylamino)-3-hydroxy-2,2-dime thyl- chromane (293B), a chromanol compound, on the K+ current produced by direct intranuclear injection of KvLQT1 and IsK cDNA plasmids in COS-7 cells [6].
  • These modifications include variations in the phenone side chain, substitution with prenyl, allyl, and benzyl in the 4-position of the phlorophenone nucleus, and ring cyclizations via etherification to give furan and chroman compounds [7].
  • Inhibitory effect of chroman carboxamide on interleukin-6 expression in response to lipopolysaccharide by preventing nuclear factor-kappaB activation in macrophages [8].

Biological context of chroman


Anatomical context of chroman


Associations of chroman with other chemical compounds


Gene context of chroman

  • Taken together, this study demonstrated that chroman KL-1156 compound interfered with nuclear translocation step of NF-kappaB p65, which was attributable to its anti-inflammatory action [14].
  • 7. KL-1156 compound attenuated LPS-induced synthesis of both mRNA and protein of inducible nitric oxide synthase (iNOS), in parallel, and inhibited LPS-induced iNOS promoter activity, indicating that the chroman compound down-regulated iNOS expression at transcription level [14].


  1. Reactions of vitamin E and its model compound 2,2,5,7,8-pentamethylchroman-6-ol with ozone. Liebler, D.C., Matsumoto, S., Iitaka, Y., Matsuo, M. Chem. Res. Toxicol. (1993) [Pubmed]
  2. Chroman amide and nicotinyl amide derivatives: inhibition of lipid peroxidation and protection against head trauma. Vajragupta, O., Toasaksiri, S., Boonyarat, C., Wongkrajang, Y., Peungvicha, P., Watanabe, H., Boonchoong, P. Free Radic. Res. (2000) [Pubmed]
  3. Antidepressant-like effects of alnespirone (S 20499) in the learned helplessness test in rats. Mac Sweeney, C.P., Lesourd, M., Gandon, J.M. Eur. J. Pharmacol. (1998) [Pubmed]
  4. Biomimetic enantioselective total synthesis of (-)-siccanin via the Pd-catalyzed asymmetric allylic alkylation (AAA) and sequential radical cyclizations. Trost, B.M., Shen, H.C., Surivet, J.P. J. Am. Chem. Soc. (2004) [Pubmed]
  5. New perspectives on vitamin E: gamma-tocopherol and carboxyelthylhydroxychroman metabolites in biology and medicine. Hensley, K., Benaksas, E.J., Bolli, R., Comp, P., Grammas, P., Hamdheydari, L., Mou, S., Pye, Q.N., Stoddard, M.F., Wallis, G., Williamson, K.S., West, M., Wechter, W.J., Floyd, R.A. Free Radic. Biol. Med. (2004) [Pubmed]
  6. KvLQT1 potassium channel but not IsK is the molecular target for trans-6-cyano-4-(N-ethylsulfonyl-N-methylamino)-3-hydroxy-2,2-dimethyl- chromane. Loussouarn, G., Charpentier, F., Mohammad-Panah, R., Kunzelmann, K., Baró, I., Escande, D. Mol. Pharmacol. (1997) [Pubmed]
  7. Synthesis and antimicrobial activity of a series of caespitin derivatives. Van der Schyf, C.J., Dekker, T.G., Fourie, T.G., Snyckers, F.O. Antimicrob. Agents Chemother. (1986) [Pubmed]
  8. Inhibitory effect of chroman carboxamide on interleukin-6 expression in response to lipopolysaccharide by preventing nuclear factor-kappaB activation in macrophages. Kim, B.H., Lee, K.H., Chung, E.Y., Chang, Y.S., Lee, H., Lee, C.K., Min, K.R., Kim, Y. Eur. J. Pharmacol. (2006) [Pubmed]
  9. Effects of chroman derivatives on platelet aggregation induced by some aggregating agents in rabbits. Aida, Y., Kasama, T., Fukaya, H., Takeuchi, N., Sugiyama, K., Tobinaga, S. Clin. Exp. Pharmacol. Physiol. (1998) [Pubmed]
  10. Influence of tocopherol, its chromane compound, phytyl chains and superoxide dismutase on increased vascular resistance and permeability due to arachidonate metabolism in isolated rabbit lung. Seeger, W., Wolf, H., Stähler, G., Neuhof, H., Róka, L. Prostaglandins (1982) [Pubmed]
  11. Discovery of thiochroman and chroman derivatives as pure antiestrogens and their structure-activity relationship. Kanbe, Y., Kim, M.H., Nishimoto, M., Ohtake, Y., Kato, N., Tsunenari, T., Taniguchi, K., Ohizumi, I., Kaiho, S., Morikawa, K., Jo, J.C., Lim, H.S., Kim, H.Y. Bioorg. Med. Chem. (2006) [Pubmed]
  12. Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates. Boyd, D.R., Sharma, N.D., Bowers, N.I., Boyle, R., Harrison, J.S., Lee, K., Bugg, T.D., Gibson, D.T. Org. Biomol. Chem. (2003) [Pubmed]
  13. Troglitazone-induced intracellular oxidative stress in rat hepatoma cells: a flow cytometric assessment. Narayanan, P.K., Hart, T., Elcock, F., Zhang, C., Hahn, L., McFarland, D., Schwartz, L., Morgan, D.G., Bugelski, P. Cytometry. Part A : the journal of the International Society for Analytical Cytology. (2003) [Pubmed]
  14. Inhibitory mechanism of chroman compound on LPS-induced nitric oxide production and nuclear factor-kappaB activation. Kim, B.H., Reddy, A.M., Lee, K.H., Chung, E.Y., Cho, S.M., Lee, H., Min, K.R., Kim, Y. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  15. N-acyl-3-amino-5-methoxychromans: a new series of non-indolic melatonin analogues. Sugden, D. Eur. J. Pharmacol. (1994) [Pubmed]
  16. The selective labelling of central 5-HT1A receptor binding sites by [3H]5-methoxy-3-(di-n-propylamino)chroman. Cossery, J.M., Gozlan, H., Spampinato, U., Perdicakis, C., Guillaumet, G., Pichat, L., Hamon, M. Eur. J. Pharmacol. (1987) [Pubmed]
  17. Comparative antioxidant activity of tocotrienols and the novel chromanyl-polyisoprenyl molecule FeAox-6 in isolated membranes and intact cells. Palozza, P., Verdecchia, S., Avanzi, L., Vertuani, S., Serini, S., Iannone, A., Manfredini, S. Mol. Cell. Biochem. (2006) [Pubmed]
  18. Effect of 3,4-trans-2,2-dimethyl-3-phenyl-4-P-(beta-pyrrolidinoethoxy) phenyl -7-methoxy chroman (centchroman) on the biochemistry of the fallopian tube and uterus of rhesus monkeys (Macaca mulatta). Imam, S.K., Srivastava, K., Dasgupta, P.R., Kar, A.B. Contraception. (1975) [Pubmed]
  19. A cytotoxic butenolide, two new dolabellane diterpenoids, a chroman and a benzoquinol derivative formosan Casearia membranacea. Chang, K.C., Duh, C.Y., Chen, I.S., Tsai, I.L. Planta Med. (2003) [Pubmed]
  20. Chemoprotective potentials of homoisoflavonoids and chalcones of Dracaena cinnabari: modulations of drug-metabolizing enzymes and antioxidant activity. Machala, M., Kubínová, R., Horavová, P., Suchý, V. Phytotherapy research : PTR. (2001) [Pubmed]
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