Literature DB >> 17765553

The synthesis and biological activity of pentafluorosulfanyl analogs of fluoxetine, fenfluramine, and norfenfluramine.

John T Welch1, Dong Sung Lim.   

Abstract

The trifluoromethyl group of fluoxetine 1 and fenfluramine and norfenfluramine, 2 and 3, was substituted by the pentafluorosulfanyl group. On examination of the efficacy of the pentafluorosulfanyl containing compounds as inhibitors of 5-hydroxytryptamine receptors, it was found that substitution could lead to enhanced selectivity and in the case of the pentafluorosulfanyl analog of fenfluramine, 18, it significantly enhanced potency against the 5-HT(2b), 5-HT(2c), and 5-HT(6) receptors.

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Year:  2007        PMID： 17765553     DOI： 10.1016/j.bmc.2007.08.012

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  10 in total

1.  Pentafluorosulfanyl-containing flufenamic acid analogs: Syntheses, properties and biological activities.

Authors:  Christine M M Hendriks; Trevor M Penning; Tianzhu Zang; Dominik Wiemuth; Stefan Gründer; Italo A Sanhueza; Franziska Schoenebeck; Carsten Bolm
Journal:  Bioorg Med Chem Lett       Date:  2015-09-08       Impact factor: 2.823

2.  Microbial biotransformation of aryl sulfanylpentafluorides.

Authors:  Emma Kavanagh; Michael Winn; Cliona Nic Gabhann; Neil K O'Connor; Petr Beier; Cormac D Murphy
Journal:  Environ Sci Pollut Res Int       Date:  2013-07-20       Impact factor: 4.223

3.  Synthesis and biological evaluation of the first pentafluorosulfanyl analogs of mefloquine.

Authors:  Peter Wipf; Tingting Mo; Steven J Geib; Diana Caridha; Geoffrey S Dow; Lucia Gerena; Norma Roncal; Erin E Milner
Journal:  Org Biomol Chem       Date:  2009-08-07       Impact factor: 3.876

4.  Use of Fluorinated Functionality in Enzyme Inhibitor Development: Mechanistic and Analytical Advantages.

Authors:  David B Berkowitz; Kannan R Karukurichi; Roberto de la Salud-Bea; David L Nelson; Christopher D McCune
Journal:  J Fluor Chem       Date:  2008-09       Impact factor: 2.050

5.  Synthesis of Phthalocyanines with a Pentafluorosulfanyl Substituent at Peripheral Positions.

Authors:  Norihito Iida; Kenta Tanaka; Etsuko Tokunaga; Satoru Mori; Norimichi Saito; Norio Shibata
Journal:  ChemistryOpen       Date:  2015-07-24       Impact factor: 2.911

6.  Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes.

Authors:  Norbert Vida; Jiří Václavík; Petr Beier
Journal:  Beilstein J Org Chem       Date:  2016-01-20       Impact factor: 2.883

7.  Photoredox Catalytic α-Alkoxypentafluorosulfanylation of α-Methyl- and α-Phenylstyrene Using SF6.

Authors:  David Rombach; Hans-Achim Wagenknecht
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-26       Impact factor: 15.336

8.  Amine-borane complex-initiated SF5Cl radical addition on alkenes and alkynes.

Authors:  Audrey Gilbert; Pauline Langowski; Marine Delgado; Laurent Chabaud; Mathieu Pucheault; Jean-François Paquin
Journal:  Beilstein J Org Chem       Date:  2020-12-16       Impact factor: 2.883

9.  In Vitro, In Vivo, and Absorption, Distribution, Metabolism, and Excretion Evaluation of SF5-Containing N,N'-Diarylureas as Antischistosomal Agents.

Authors:  Alexandra Probst; Eugènia Pujol; Cécile Häberli; Jennifer Keiser; Santiago Vázquez
Journal:  Antimicrob Agents Chemother       Date:  2021-07-26       Impact factor: 5.191

10.  An eccentric rod-like linear connection of two heterocycles: synthesis of pyridine trans-tetrafluoro-λ6-sulfanyl triazoles.

Authors:  Prajwalita Das; Kiyoteru Niina; Tomoya Hiromura; Etsuko Tokunaga; Norimichi Saito; Norio Shibata
Journal:  Chem Sci       Date:  2018-05-14       Impact factor: 9.825
  10 in total

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