Synthesis of 4, 6-difluoro-5-hydroxy-(α-methyl) tryptamine and 4, 6-difluoro-5-hydroxy-(β-methyl) tryptamine as potential selective monoamine oxidase B inhibitors

HJC Chen, T Applewhite, B Jayachandran…

Index: Chen, Hauh-Jyun Candy; Applewhite, Terrence; Jayachandran; Kirk, Kenneth L. Journal of Fluorine Chemistry, 1998 , vol. 92, # 1 p. 41 - 44

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Citation Number: 5

Abstract

Condensation of 4-nitro-1-pentanal and 4-nitropentanal 3-methylbutanal with 3, 5-difluoro-4- methoxyphenylhydrazine afforded 4, 6-difluoro-5-methoxy-3-(2′-nitro) propylindole 4a and 4, 6-difluoro-5-methoxy-3-(1′-methyl-2′-nitro) ethylindole 4b, respectively, in one step. Reduction of the nitro group with lithium aluminum hydride followed by removal of the methyl ether with boron tribromide produced the title compounds. They were inactive as MAO B ...

~17%

Structure activity relationships of 5-, 6-, and 7-methyl-sub...

[Yamashita, Dennis S.; Marquis, Robert W.; Xie, Ren; Nidamarthy, Sirishkumar D.; Oh, Hye-Ja; Jeong, Jae U.; Erhard, Karl F.; Ward, Keith W.; Roethke, Theresa J.; Smith, Brian R.; Cheng; Geng, Xiaoliu; Lin, Fan; Offen, Priscilla H.; Wang, Bing; Nevins, Neysa; Head, Martha S.; Haltiwanger, R. Curtis; Sarjeant, Amy A. Narducci; Liable-Sands, Louise M.; Zhao, Baoguang; Smith, Ward W.; Janson, Cheryl A.; Gao, Enoch; Tomaszek, Thaddeus; McQueney, Michael; James, Ian E.; Gress, Catherine J.; Zembryki, Denise L.; Lark, Michael W.; Veber, Daniel F. Journal of Medicinal Chemistry, 2006 , vol. 49, # 5 p. 1597 - 1612]