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Chemical Compound Review

BUTENOLIDE     5H-furan-2-one

Synonyms: Crotonolactone, SureCN25302, furan-2-one, CHEMBL166223, CCRIS 5722, ...
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Disease relevance of NSC51296


Psychiatry related information on NSC51296


High impact information on NSC51296

  • Two of the enzymes, FPG and NEIL1 known to cleave normal abasic sites (1) by effecting beta,delta-elimination form cross-links to the butenolide lesion (4) [5].
  • It was also discovered that both the butenolide and ethylene glycol subunits play essential roles in the cytotoxicities against tumor cell lines, while the 10-substituted hydroxy group and the absolute configuration of methyl group at the butenolide moiety are less important for their activity [6].
  • Butenolide endothelin antagonists with improved aqueous solubility [7].
  • Further structural modifications around the butenolide ring led directly to the subnanomolar ETA selective antagonist PD156707, IC50's = 0.3 (ET(A)) and 780 nM (ET(B)) [8].
  • In this report we will describe the detailed structure-activity relationship (SAR) studies that led to the discovery of a potent series of butenolide ETA selective antagonists [8].

Biological context of NSC51296

  • These results indicate that the novel synthesized retinoidal butenolide KYN-54 inhibits oral carcinogenesis initiated with 4-NQO and such inhibition may be related to suppression of cell proliferation [9].
  • Dimerization of the resulting butenolide 11 is then achieved via alkyne metathesis using (tBuO)(3)W&tbd1;CCMe(3) as the catalyst [10].
  • A new strategy for the synthesis of bicyclic gamma-alkylidenebutenolides, butenolide-medium ring ether hybrids, is reported which involves Me(3)SiOTf-catalyzed cyclization of 1, 3-bis(trimethylsilyloxy)-1,3-butadienes with oxalyl chloride, Mitsunobu reaction, and subsequent ring-closing metathesis [11].
  • Dimerization of butenolide structures. A biomimetic approach to the dimeric sesquiterpene lactones (+/-)-biatractylolide and (+/-)-biepiasterolide [12].
  • Intraperitoneal administration of 2-buten-4-olide in doses of 30 to 100 mg/kg, decreased food intake dose-dependently by reducing meal frequency, meal size and eating rate, and prolonging meal duration, latency to eat the first meal after injection and post-prandial intermeal intervals [13].

Anatomical context of NSC51296


Associations of NSC51296 with other chemical compounds


Gene context of NSC51296


Analytical, diagnostic and therapeutic context of NSC51296


  1. Design, synthesis, and biological evaluation of novel nucleoside and nucleotide analogues as agents against DNA viruses and/or retroviruses. Hakimelahi, G.H., Ly, T.W., Moosavi-Movahedi, A.A., Jain, M.L., Zakerinia, M., Davari, H., Mei, H.C., Sambaiah, T., Moshfegh, A.A., Hakimelahi, S. J. Med. Chem. (2001) [Pubmed]
  2. 2-Buten-4-olide (2-B4O) inhibits experimental allergic encephalomyelitis (EAE) in Lewis rats. Naiki, M., Takeoka, Y., Yago, H., Kurimoto, Y., Gershwin, M.E., Suehiro, S. J. Autoimmun. (1995) [Pubmed]
  3. Dermal toxicity of Fusarium toxins in combinations. Bhavanishankar, T.N., Ramesh, H.P., Shantha, T. Arch. Toxicol. (1988) [Pubmed]
  4. 2-buten 4 olide affects feeding behavior of rhesus monkey. Mathur, R., Manchanda, S.K., Oomura, Y., Nayar, U. Prog. Neuropsychopharmacol. Biol. Psychiatry (1996) [Pubmed]
  5. Cross-linking of 2-deoxyribonolactone and its beta-elimination product by base excision repair enzymes. Kroeger, K.M., Hashimoto, M., Kow, Y.W., Greenberg, M.M. Biochemistry (2003) [Pubmed]
  6. Studies on mimicry of naturally occurring annonaceous acetogenins: non-THF analogues leading to remarkable selective cytotoxicity against human tumor cells. Zeng, B.B., Wu, Y., Jiang, S., Yu, Q., Yao, Z.J., Liu, Z.H., Li, H.Y., Li, Y., Chen, X.G., Wu, Y.L. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  7. Butenolide endothelin antagonists with improved aqueous solubility. Patt, W.C., Cheng, X.M., Repine, J.T., Lee, C., Reisdorph, B.R., Massa, M.A., Doherty, A.M., Welch, K.M., Bryant, J.W., Flynn, M.A., Walker, D.M., Schroeder, R.L., Haleen, S.J., Keiser, J.A. J. Med. Chem. (1999) [Pubmed]
  8. Structure-activity relationships in a series of orally active gamma-hydroxy butenolide endothelin antagonists. Patt, W.C., Edmunds, J.J., Repine, J.T., Berryman, K.A., Reisdorph, B.R., Lee, C., Plummer, M.S., Shahripour, A., Haleen, S.J., Keiser, J.A., Flynn, M.A., Welch, K.M., Reynolds, E.E., Rubin, R., Tobias, B., Hallak, H., Doherty, A.M. J. Med. Chem. (1997) [Pubmed]
  9. Inhibition of 4-nitroquinoline-1-oxide-induced rat oral carcinogenesis by dietary exposure of a new retinoidal butenolide, KYN-54, during the initiation and post-initiation phases. Makita, H., Tanaka, T., Ohnishi, M., Tamai, Y., Torihara, M., Yamahara, J., Mori, H., Satoh, K., Hara, A. Carcinogenesis (1995) [Pubmed]
  10. Concise synthesis of (S,S)-(+)-dehydrohomoancepsenolide. Fürstner, A., Dierkes, T. Org. Lett. (2000) [Pubmed]
  11. Efficient synthesis of butenolide-medium ring ether hybrids by a [3 + 2] cyclization-ring-closing metathesis strategy. Langer, P., Eckardt, T., Stoll, M. Org. Lett. (2000) [Pubmed]
  12. Dimerization of butenolide structures. A biomimetic approach to the dimeric sesquiterpene lactones (+/-)-biatractylolide and (+/-)-biepiasterolide. Bagal, S.K., Adlington, R.M., Baldwin, J.E., Marquez, R. J. Org. Chem. (2004) [Pubmed]
  13. Endogenous sugar acid derivative acting as a feeding suppressant. Plata-Salamán, C.R., Oomura, Y., Shimizu, N. Physiol. Behav. (1986) [Pubmed]
  14. Alteration of metabolism of acetylcholine induced by 2-deoxy-D-glucose in the gastroduodenum of the rat. Muramatsu, M., Chaki, S., Arai, I., Aihara, H. Neuropharmacology (1990) [Pubmed]
  15. Induction of Fos-like immunoreactivity in the rat hypothalamus by an endogenous feeding suppressant (2-buten-4-olide). Hisano, S., Uemura, N., Fukui, Y., Miki, M., Zhang, R. Neurosci. Lett. (1994) [Pubmed]
  16. Induction of Fos-like immunoreactivity in the lower brainstem and the spinal cord of the rat by intraperitoneal administration of an endogenous satiety substance, 2-buten-4-olide. Uemura, N., Hisano, S., Fukui, Y. Neurosci. Lett. (1997) [Pubmed]
  17. Effect of an endogenous satiety substance, 2-buten-4-olide, on gastric acid secretion and experimental ulceration in rats. Arai, I., Usuki-Ito, C., Muramatsu, M., Otomo, S., Shiraishi, T., Oomura, Y. Physiol. Behav. (1990) [Pubmed]
  18. Chemoprevention of azoxymethane-induced intestinal carcinogenesis by a novel synthesized retinoidal butenolide, 5-hydroxy-4-(2-phenyl-(E)-ethenyl)-2(5H)-furanone, in rats. Kawamori, T., Tanaka, T., Suzui, M., Okamoto, K., Tamai, Y., Torihara, M., Yamahara, J., Mori, H. Carcinogenesis (1995) [Pubmed]
  19. Supercritical fluid chromatography of Fusarium mycotoxins. Young, J.C., Games, D.E. J. Chromatogr. (1992) [Pubmed]
  20. Region-related Fos expression in hypothalamic dopaminergic neurons of rats by intraperitoneal administration of an endogenous satiety substance, 2-buten-4-olide. Hisano, S., Zhang, R., Uemura, N., Fukui, Y., Miki, T. Brain Res. (1995) [Pubmed]
  21. Characterization of [125I]-PD164333, an ETA selective non-peptide radiolabelled antagonist, in normal and diseased human tissues. Davenport, A.P., Kuc, R.E., Ashby, M.J., Patt, W.C., Doherty, A.M. Br. J. Pharmacol. (1998) [Pubmed]
  22. The short chain sugar acid, 2-buten-4-olide, activates oxytocin-secreting neurons but not arginine vasopressin-secreting neurons in the hypothalamus of rats. Kawasaki, M., Yamaga, C., Onaka, T., Saito, J., Mera, T., Hashimoto, H., Fujihara, H., Okimoto, N., Ohnishi, H., Nakamura, T., Ueta, Y. Brain Res. (2006) [Pubmed]
  23. Structure-activity relationships of a novel series of orally active nonpeptide ETA and ETA/B endothelin receptor-selective antagonists. Doherty, A.M., Patt, W.C., Repine, J., Edmunds, J.J., Berryman, K.A., Reisdorph, B.R., Walker, D.M., Haleen, S.J., Keiser, J.A., Flynn, M.A. J. Cardiovasc. Pharmacol. (1995) [Pubmed]
  24. A modular synthesis of annonaceous acetogenins. Marshall, J.A., Piettre, A., Paige, M.A., Valeriote, F. J. Org. Chem. (2003) [Pubmed]
  25. Selective inhibition of separated forms of cyclic nucleotide phosphodiesterase from rat heart by some cardio- or vaso-active butenolide derivatives. Némoz, G., Prigent, A.F., Picq, M., Pacheco, H. Biochem. Pharmacol. (1982) [Pubmed]
  26. 2-Buten-4-olide (2-B4O) inhibits type II collagen-induced arthritis in Lewis rats. Takeoka, Y., Naiki, M., Taguchi, N., Imai, H., Kurimoto, Y., Morita, S., Suehiro, S. Int. J. Immunopharmacol. (1993) [Pubmed]
  27. Central action of endogenous sugar acid (2-buten-4-olide): comparison with local anesthesia in hypothalamus. Ono, T., Nakamura, K., Fukuda, M., Kobayashi, T. Brain Res. Bull. (1990) [Pubmed]
  28. Influence of epicatechin reactions on the mechanisms of Maillard product formation in low moisture model systems. Totlani, V.M., Peterson, D.G. J. Agric. Food Chem. (2007) [Pubmed]
  29. The therapeutic potential of PD156707 and related butenolide endothelin antagonists. Maguire, J.J., Davenport, A.P. Expert opinion on investigational drugs. (1999) [Pubmed]
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