Efficient Method for Synthesis of 2-Acetylbenzo(b)thiophene and Its Derivatives, the Key Synthons for 5-Lipoxygenase Inhibitors

REFERENCES

• (a) Burney , P. G. J. ; Chinn , S. ; Rona , R. J. Has the prevalence of asthma increased in children? Evidence from the national study of health and growth 1973–1986 . BMJ 1990 , 300 , 1306 – 1310 ; (b) Jackson , R. J. ; Sears , M. R. ; Beaglehole , R. ; Rey , H. H. International trends in asthma mortality: 1970 to 1985 . Chest 1988 , 94 , 914 – 918 ; (c) Weiss , K. B. ; Gergen , P. J. ; Hodgson , T. A. Economic evaluation of asthma in the United States . N. Engl. J. Med. 1992 , 326 , 1391 – 1396 .
   PubMed Web of Science ®Google Scholar
• Barnes , P. J. ; Chung , K. F. ; Page , C. P. Inflammatory mediators and asthma . Pharmacol. Rev. 1988 , 40 , 49 – 84 ; (b) Piacentini , G. L. ; Kaliner , M. A. The potential roles of leukotrienes in bronchial asthma . Am. Rev. Respir. Dis. 1982 , 126 , 449 – 451 .
   PubMed Web of Science ®Google Scholar
• (a) Samuelson , B. Leukotrienes: Mediators of immediate hypersensitivity reactions and inflammation . Science 1983 , 220 , 568 – 575 ; (b) Henderson , W. R. The role of leukotrienes in inflammation . Ann. Intern. Med. 1994 , 121 , 684 – 697 .
   PubMed Web of Science ®Google Scholar
• (a) Werz , O. ; Steinhilber , D. Therapeutic options for 5-lipoxygenase inhibitors . Pharmacol. Ther. 2006 , 112 , 701 – 718 ; (b) Romano , M. ; Claria , J. Cyclooxygenase-2 and 5-lipoxygenase converging functions on cell proliferation and tumor angiogenesis: Implications for cancer therapy . FASEB J. 2003 , 17 , 1986 – 1995 ; (c) Spanbroek , R. ; Habenicht , A. J. The potential role of antileukotriene drugs in atherosclerosis . Drug News Perspect. 2003 , 16 , 485 – 489 ; (d) Werz , O. ; Steinhilber , D. Development of 5-lipoxygenase inhibitors: Lessons from cellular enzyme regulation . Biochem. Pharmacol. 2005 , 70 , 327 – 333 ; (e) Awni , W. M. ; Granneman , G. R. ; Locke , C. S. ; Brandwein , S. R. ; Dube , L. M. Population pharmacokinetics of zileution, a selective 5-lipoxygenase inhibitor, in patients with rheumatoid arthritis . Eur. J. Clin. Pharmacol. 1995 , 48 , 155 – 160 .
   PubMed Web of Science ®Google Scholar
• (a) Werz , O. ; Steinhilber , D. Pharmacological intervention with 5-lipoxygenase: New insights and novel compounds . Expert Opin. Ther. Patients 2005 , 15 , 505 – 519 ; (b) Funk , C. D. Leukotriene modifiers as potential therapeutics for cardiovascular disease . Nat. Rev. Drug Discovery 2005 , 4 , 664 – 672 ; (c) Yoshimura , R. ; Matsuyama , M. ; Kuratsukuri , K. ; Tsuchida , K. ; Takemoto , Y. ; Nakatani , T. Novel approach to anticancer therapies for prostate cancer: Lipoxygenese as new target in the treatment of prostate cancer . Drugs Future 2005 , 30 , 351 – 357 .
   Web of Science ®Google Scholar
• (a) Carter , G. W. ; Young , P. R. ; Albert , D. H. ; Bouska , J. ; Dyer , R. ; Bell , R. L. ; Summers , J. B. ; Brooks , D. W. 5-Lipoxygenase inhibitory activity of zileuton . J. Pharmacol. Exper. Ther. 1991 , 256 , 929 – 937 ; (b) Belle , R. L. ; Young , P. R. ; Albert , D. ; Lanni , C. ; Summers , J. B. ; Brooks , D. W. ; Rubin , P. ; Carter , G. W. The discovery and development of zileuton: An orally active 5-lipoxygenase inhibitor . Int. J. Immunopharmac. 1992 , 14 , 505 – 510 ; (b) McGill , K. A. ; Busse , W. W. Zileuton . Lancet 1996 , 348 , 519 – 524 .
   PubMed Web of Science ®Google Scholar
• (a) Onuchina , O. A. ; Zaitsev , S. A. ; Levina , V. I. ; Grigor'ev , N. B. ; Chernyshev , V. V. ; Granik , V. G. Acyl migration during alkylation of acetoxyurea derivatives . Pharm. Chem. J. 2007 , 41 , 160 – 165 ; (b) Stewart , A. O. ; Bhatia , P. A. ; Martin , J. G. ; Summers , J. B. ; Rodriques , K. E. ; Martin , M. B. ; Holms , J. H. ; Moore , J. L. ; Craig , R. A. ; Kolosa , T. ; Ratajczyk , J. D. ; Mazdiyasni , H. ; Kerdesky , F. A. J. ; DeNinno , S. L. ; Maki , R. G. ; Bouska , J. B. ; Young , P. R. ; Lanni , C. ; Bell , R. L. ; Carter , G. W. ; Brooks , C. D. W. Structure–activity relationship of N-hydroxyurea 5-lipoxygenase inhibitors . J. Med. Chem. 1997 , 40 , 1955 – 1968 .
   Google Scholar
• For synthesis of zileuton (1), see (a) Guinchard , X. ; Dennis , J.-N. Reactions of in situ generated N-Boc nitrones with aromatic and heteroaromatic Grignard reagents: Application to the synthesis of zileuton . J. Org. Chem. 2008 , 73 , 2028 – 2031 ; (b) Ren-yun , W. ; Zhen , C. ; Yu-ling , L. Synthesis of zileuton, an anti-asthmatic drug . Zhongguo Xinyao Zazhi 2004 , 13 , 1133 – 1134 ; (c) Copp , R. R. ; Fohey , B. T. ; Lannoye , G. Acid-catalyzed addition of N-hydroxyurea to 1-aryl alcohol derivatives: A new synthesis of zileuton . Synth. Commun. 2001 , 31 , 3081 – 3086 ; (d) Ku , Y.-Y. ; Patel , R. ; Roden , B. A. ; Sawick , D. P. Synthesis of substituted heterocycles: Simple method for the introduction of the N-hydroxyurea functionality . Tetrahedron Lett. 1994 , 35 , 6017 – 6020 ; (e) Rohloff , J. C. ; Alfredson , T. V. ; Schwartz , M. A. Enantioselective synthesis of 5-LO inhibitors using a gulofuranose auxiliary . Tetrahedron Lett. 1994 , 35 , 1011 – 1014 ; (f) Basha , A. ; Henry , R. ; McLaughlin , M. A. ; Ratajczyk , J. D. ; Wittenberger , S. J. Addition of organometallic reagents to N-glycosyl nitrones. Enantioselective synthesis of (+)-(R)- and (–)-(S)-Zileuton . J. Org. Chem. 1994 , 59 , 6103 – 6106 ; (g) Basha , A. ; Brooks , D. W. Synthesis of 5-lipoxygenase inhibitor zileuton from thiophenol . J. Org. Chem. 1993 , 58 , 1293 – 1294 ; (h) Kolosa , T. ; Brooks , D. W. Practical synthesis of 2-acetylbenzo(b)thiophene. Synth. Commun. 1993 , 23 , 743 – 748 ; (i) Garigipati , R. ; Sorenson , M. ; Erhard , K. ; Adams , J. Resolution of hydroxyureas . Tetrahedron Lett. 1993 , 34 , 5537 – 5540 ; (j) Hsiao , C.-N. ; Kolasa , T. Synthesis of chiral zileuton, a potent and selective inhibitor of 5-lipoxygenase . Tetrahedron Lett. 1992 , 33 , 2629 – 2632 .
   Google Scholar
• (a) Brooks , D. W. ; Summers , J. B. ; Rodriques , K. E. ; Maki , R. G. ; Dellaria , F. ; Holms , J. H. ; Moore , J. L. Preparation of N-(benzo[b]thienylalkyl)-N-hydroxy amides and ureas with polar substituents as 5-lipoxygenase inhibitors. U.S. Patent 4,873,259, 1991; (b) Hengeveld , J. ; Leese , E. H. ; Moon , B. S. ; Abad , D. M. ; Allen , K. A. ; Bauer , P. E. ; Murphey , D. B. ; Fohey , B. T. ; Copp Jr. , R. R. ; Lannoye , G. S. ; Mittag , R. M. Synthesis and isolation of N-(aryl or heteroaryl)-alkyl-N-hydroxyurea. U.S. Patent 6,080,874, 2000.
   Google Scholar
• From 2-thiobenzoic acid, see (a) Smiles , S. ; McClelland , E. W. Derivatives of 3-oxo(1)thionaphthalene . J. Chem. Soc. (London) 1921 , 119 , 1810 – 1816 ; (b) Hsiao , C. N. ; Bhagavatula , L. ; Pariza , R. L. A practical synthesis of 2-carbonylbenzo(b)thiophenes . Synth. Commun. 1990 , 20 , 1687 – 1695 ; (c) Learolini , R. ; Pedulli , G. F. ; Tundo , A. ; Zanardi , G. Reaction pathways for the cyclization of ortho-thioalkyl and ortho-thioaryl substituted phenyl radicles with alkenes: Reaction of o-methylthioarenediazonium tetrafluroborates with alkynes to give 2-substituted benzo(b)thiophenes . J. Chem. Soc., Chem. Commun . 1985 , 1390 – 1391 .
   Google Scholar
• From 2-thiobenzaldehyde, see (a) Rahman , L. K. A. ; Scrowston , R. M. 7-Substituted benzo(bothiophenes and 1,2-benzisothiazoles, part 1: Hydroxy- or methoxy- derivatives . J. Chem. Soc., Perkin Trans. 1 1983 , 2973 – 2977 ; (b) Kasmai , H. S. ; Machke , S. G. An efficient and convenient synthesis of 2-mercaptobenzaldehyde . Synthesis 1989 , 763 – 765 .
   Google Scholar
• Dickman , D. A. ; Horrom , B. W. ; Roden , B. A. ; Chemburkar , S. R. Process for the production of 2-acetylbenzo(b)thiophenes . U.S. Patent 5,169,961, 1992.
   Google Scholar
• Dickman , D. A. ; Chemburkar , S. R. ; Konocapaki , D. B. ; Elisseou , E. M. Oxidative cleavage of aryl or alkyl tert-butyl sulfides with dimethyl sulfoxide/hydrobromic acid to form symmetrical aryl or alkyl disulfides . Synthesis 1993 , 573 – 574 .
   Google Scholar
• Li , Z. ; Yuequin , Z. ; Liu , Z. ; Si , S. ; Yang , Z. ; Shao , H. ; Yang , J. Preparation of thiophene, furan, and indole derivatives as regulators of bone morphogenetic protein for treatment of osteoporosis . Faming Zhuanli Shenqing Gongkai Shuomingshu Chin. Patent 1,807,411, 2006.
   Google Scholar
• Clark , P. D. ; Clarke , K. ; Scrowston , R. M. ; Sutton , T. Substitution reactions of benzo(b)thiophen derivatives, part VIII: Reactions of some substituted compounds and of 4-chlorobenzo(b)thiophen and its 3-methyl derivatives . J. Chem. Res., Synop. 1978 , 10 .
   Google Scholar