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Literature DB >> 19795052

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

Peter Wipf¹, Tingting Mo, Steven J Geib, Diana Caridha, Geoffrey S Dow, Lucia Gerena, Norma Roncal, Erin E Milner.

Abstract

Two novel SF5 analogs of the antimalarial agent mefloquine were synthesized in 5 steps and 10-23% overall yields and found to have improved activity and selectivity against malaria parasites. This work also represents the first report of SF5-substituted quinolines.

Entities: Chemical Disease Gene Species

Mesh：

Substances：
Antimalarials
Mefloquine

Year: 2009 PMID： 19795052 PMCID： PMC2929370 DOI： 10.1039/b911483a

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

20 in total

1. Methyl- and (Trifluoromethyl)alkene Peptide Isosteres: Synthesis and Evaluation of Their Potential as beta-Turn Promoters and Peptide Mimetics.

Authors: Peter Wipf; Todd C. Henninger; Steven J. Geib
Journal: J Org Chem Date: 1998-09-04 Impact factor: 4.354

Review 2. Medical need, scientific opportunity and the drive for antimalarial drugs.

Authors: Robert G Ridley
Journal: Nature Date: 2002-02-07 Impact factor: 49.962

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

Authors: John T Welch; Dong Sung Lim
Journal: Bioorg Med Chem Date: 2007-08-15 Impact factor: 3.641

4. Neuropsychiatric side effects after the use of mefloquine.

Authors: T Weinke; M Trautmann; T Held; G Weber; D Eichenlaub; K Fleischer; W Kern; H D Pohle
Journal: Am J Trop Med Hyg Date: 1991-07 Impact factor: 2.345

5. Multidrug-resistance gene (P-glycoprotein) is expressed by endothelial cells at blood-brain barrier sites.

Authors: C Cordon-Cardo; J P O'Brien; D Casals; L Rittman-Grauer; J L Biedler; M R Melamed; J R Bertino
Journal: Proc Natl Acad Sci U S A Date: 1989-01 Impact factor: 11.205

6. Antimalarials. 7. Bis(trifluoromethyl)- -(2-piperidyl)-4-quinolinemethanols.

Authors: C J Ohnmacht; A R Patel; R E Lutz
Journal: J Med Chem Date: 1971-10 Impact factor: 7.446

7. Mefloquine (WR 142,490) in the treatment of human malaria.

Authors: C M Trenholme; R L Williams; R E Desjardins; H Frischer; P E Carson; K H Rieckmann; C J Canfield
Journal: Science Date: 1975-11-21 Impact factor: 47.728

8. Chemical insights from high-resolution X-ray photoelectron spectroscopy and ab initio theory: propyne, trifluoropropyne, and ethynylsulfur pentafluoride.

Authors: L J Saethre; N Berrah; J D Bozek; K J Børve; T X Carroll; E Kukk; G L Gard; R Winter; T D Thomas
Journal: J Am Chem Soc Date: 2001-10-31 Impact factor: 15.419

Review 9. Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents.

Authors: M Foley; L Tilley
Journal: Pharmacol Ther Date: 1998-07 Impact factor: 12.310

10. Severe psychiatric side effects observed during prophylaxis and treatment with mefloquine.

Authors: C Hennequin; P Bourée; N Bazin; F Bisaro; A Feline
Journal: Arch Intern Med Date: 1994-10-24

13 in total

1. Synthesis and Optimization of K_v7 (KCNQ) Potassium Channel Agonists: The Role of Fluorines in Potency and Selectivity.

Authors: Ruiting Liu; Thanos Tzounopoulos; Peter Wipf
Journal: ACS Med Chem Lett Date: 2019-05-08 Impact factor: 4.345

2. Optimized quinoline amino alcohols as disruptors and dispersal agents of Vibrio cholerae biofilms.

Authors: Brian León; F P Jake Haeckl; Roger G Linington
Journal: Org Biomol Chem Date: 2015-08-21 Impact factor: 3.876

3. Synthesis and evaluation of 7-substituted 4-aminoquinoline analogues for antimalarial activity.

Authors: Jong Yeon Hwang; Takashi Kawasuji; David J Lowes; Julie A Clark; Michele C Connelly; Fangyi Zhu; W Armand Guiguemde; Martina S Sigal; Emily B Wilson; Joseph L Derisi; R Kiplin Guy
Journal: J Med Chem Date: 2011-09-26 Impact factor: 7.446

4. Structure-Activity Study of Bioisosteric Trifluoromethyl and Pentafluorosulfanyl Indole Inhibitors of the AAA ATPase p97.

Authors: Celeste Alverez; Michelle R Arkin; Stacie L Bulfer; Raffaele Colombo; Marina Kovaliov; Matthew G LaPorte; Chaemin Lim; Mary Liang; William J Moore; R Jeffrey Neitz; Yongzhao Yan; Zhizhou Yue; Donna M Huryn; Peter Wipf
Journal: ACS Med Chem Lett Date: 2015-10-23 Impact factor: 4.345

5. 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

6. 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

Review 7. Chemical modulation of Kv7 potassium channels.

Authors: Matteo Borgini; Pravat Mondal; Ruiting Liu; Peter Wipf
Journal: RSC Med Chem Date: 2021-01-14

8. A small-fish model for behavioral-toxicological screening of new antimalarial drugs: a comparison between erythro- and threo-mefloquine.

Authors: Hans Maaswinkel; Liqun Zhu; Wei Weng
Journal: BMC Res Notes Date: 2015-04-02

9. 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

10. Synthesis of SF5-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes.

Authors: Petr Beier; Tereza Pastýříková
Journal: Beilstein J Org Chem Date: 2013-02-21 Impact factor: 2.883