title: Benzofuran-, benzothiophene-, indazole- and benzisoxazole-quinones: excellent substrates for NAD(P)H:quinone oxidoreductase 1.
abstract: A series of heterocyclic quinones based on benzofuran, benzothiophene, indazole and benzisoxazole has been synthesized, and evaluated for their ability to function as substrates for recombinant human NAD(P)H:quinone oxidoreductase (NQO1), a two-electron reductase upregulated in tumor cells. Overall, the quinones are excellent substrates for NQO1, approaching the reduction rates observed for menadione.
authors: Department of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, UK.
authors: Jeffery J
authors: JJ
authors: Newsome
authors: Mary
authors: M
authors: Hassani
authors: Elizabeth
authors: E
authors: Swann
authors: Jane M
authors: JM
authors: Bibby
authors: Howard D
authors: HD
authors: Beall
authors: Christopher J
authors: CJ
authors: Moody
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D045744:Cell Line, Tumor; D057075:Enzyme Assays; D006801:Humans; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000037:antagonists & inhibitors* / Q000737:chemistry; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D001572:Benzofurans; D007191:Indazoles; D010080:Oxazoles; D011809:Quinones; D013876:Thiophenes; D016660:NAD(P)H Dehydrogenase (Quinone); C447479:NQO1 protein, human
references: Eur J Med Chem. 2008 Sep;43(9):1858-64
references: 18222567
references: Free Radic Biol Med. 2010 Sep 15;49(6):919-62
references: 20493944
references: Org Biomol Chem. 2008 Feb 21;6(4):637-56
references: 18264564
references: Biochem Pharmacol. 2001 Jun 15;61(12):1509-16
references: 11377380
references: Cancer Metastasis Rev. 1993 Jun;12(2):83-101
references: 8375023
references: Chemistry. 2004 Oct 11;10(20):5243-50
references: 15372585
references: Bioorg Med Chem. 2010 Jan 1;18(1):134-41
references: 19959367
references: Org Biomol Chem. 2007 Nov 21;5(22):3665-73
references: 17971996
references: Org Biomol Chem. 2011 Oct 7;9(19):6700-6
references: 21808774
references: Bioorg Med Chem. 2004 Apr 1;12(7):1667-87
references: 15028260
references: J Mol Biol. 2004 Jul 30;341(1):281-302
references: 15312779
references: J Med Chem. 2000 Aug 10;43(16):3157-67
references: 10956224
references: J Med Chem. 2001 Sep 27;44(20):3311-9
references: 11563930
references: Org Biomol Chem. 2007 May 21;5(10):1629-40
references: 17571194
references: ACS Med Chem Lett. 2012 Jun 06;3(7):550-4
references: 24900508
references: J Chem Soc Perkin 1. 1977;(6):653-7
references: 16021
references: Bioorg Med Chem Lett. 2009 Aug 15;19(16):4878-81
references: 19616945
references: Structure. 2001 Aug;9(8):659-67
references: 11587640
references: J Med Chem. 1998 Nov 19;41(24):4755-66
references: 9822546
references: Biochemistry. 2001 Dec 18;40(50):15135-42
references: 11735396
references: Front Biosci. 2000 Jul 01;5:D639-48
references: 10877993
references: Nat Rev Cancer. 2007 Jul;7(7):495-507
references: 17568790
references: Chemistry. 2007;13(11):3218-26
references: 17200920
references: Bioorg Med Chem. 2012 May 15;20(10):3223-32
references: 22522008
references: Bioorg Med Chem Lett. 2000 Oct 2;10(19):2193-5
references: 11012027
references: Biochemistry. 2003 Dec 23;42(50):15003-8
references: 14674777
references: J Med Chem. 1999 Oct 7;42(20):4071-80
references: 10514277