Literature DB >> 24900603

Identification and optimization of an aminoalcohol-carbazole series with antimalarial properties.

Jérôme Molette1, Julie Routier1, Nada Abla1, Dominique Besson2, Agnes Bombrun1, Reto Brun3, Howard Burt1, Katrin Georgi1, Marcel Kaiser3, Solomon Nwaka2, Mathilde Muzerelle1, Alexander Scheer1.   

Abstract

Recent observations on the emergence of artemisinin resistant parasites have highlighted the need for new antimalarial treatments. An HTS campaign led to the identification of the 1-(1-aminopropan-2-ol)carbazole analogues as potent hits against Plasmodium falciparum K1 strain. The SAR study and optimization of early ADME and physicochemical properties direct us to the selection of a late lead compound that shows good efficacy when orally administrated in the in vivo P. berghei mouse model.

Entities:  

Keywords:  IC50; Malaria; Plasmodium berghei; Plasmodium falciparum; SAR; WHO; carbazole; hERG

Year:  2013        PMID： 24900603      PMCID： PMC4027556          DOI： 10.1021/ml400015f

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  29 in total

Review 1.  Medicinal chemistry of hERG optimizations: Highlights and hang-ups.

Authors:  Craig Jamieson; Elizabeth M Moir; Zoran Rankovic; Grant Wishart
Journal:  J Med Chem       Date:  2006-08-24       Impact factor: 7.446

2.  Evidence of artemisinin-resistant malaria in western Cambodia.

Authors:  Harald Noedl; Youry Se; Kurt Schaecher; Bryan L Smith; Duong Socheat; Mark M Fukuda
Journal:  N Engl J Med       Date:  2008-12-08       Impact factor: 91.245

Review 3.  Artemisinin-based combination therapies: a vital tool in efforts to eliminate malaria.

Authors:  Richard T Eastman; David A Fidock
Journal:  Nat Rev Microbiol       Date:  2009-11-02       Impact factor: 60.633

4.  3- and 4-carbazole dialkylaminocarbinols as potential antimalarial agents.

Authors:  V H Brown; M Keyanpour-Rad; J I DeGraw
Journal:  J Med Chem       Date:  1971-06       Impact factor: 7.446

5.  Antimalarial drug resistance and combination chemotherapy.

Authors:  N White
Journal:  Philos Trans R Soc Lond B Biol Sci       Date:  1999-04-29       Impact factor: 6.237

6.  Discovery of a proneurogenic, neuroprotective chemical.

Authors:  Andrew A Pieper; Shanhai Xie; Emanuela Capota; Sandi Jo Estill; Jeannie Zhong; Jeffrey M Long; Ginger L Becker; Paula Huntington; Shauna E Goldman; Ching-Han Shen; Maria Capota; Jeremiah K Britt; Tiina Kotti; Kerstin Ure; Daniel J Brat; Noelle S Williams; Karen S MacMillan; Jacinth Naidoo; Lisa Melito; Jenny Hsieh; Jef De Brabander; Joseph M Ready; Steven L McKnight
Journal:  Cell       Date:  2010-07-09       Impact factor: 41.582

7.  The global distribution of clinical episodes of Plasmodium falciparum malaria.

Authors:  Robert W Snow; Carlos A Guerra; Abdisalan M Noor; Hla Y Myint; Simon I Hay
Journal:  Nature       Date:  2005-03-10       Impact factor: 49.962

8.  Malaria-infected mice are cured by oral administration of new artemisinin derivatives.

Authors:  Gary H Posner; Wonsuk Chang; Lindsey Hess; Lauren Woodard; Sandra Sinishtaj; Aimee R Usera; William Maio; Andrew S Rosenthal; Alvin S Kalinda; John G D'Angelo; Kimberly S Petersen; Remo Stohler; Jacques Chollet; Josefina Santo-Tomas; Christopher Snyder; Matthias Rottmann; Sergio Wittlin; Reto Brun; Theresa A Shapiro
Journal:  J Med Chem       Date:  2008-01-31       Impact factor: 7.446

9.  Artemisinin resistance in Plasmodium falciparum malaria.

Authors:  Arjen M Dondorp; François Nosten; Poravuth Yi; Debashish Das; Aung Phae Phyo; Joel Tarning; Khin Maung Lwin; Frederic Ariey; Warunee Hanpithakpong; Sue J Lee; Pascal Ringwald; Kamolrat Silamut; Mallika Imwong; Kesinee Chotivanich; Pharath Lim; Trent Herdman; Sen Sam An; Shunmay Yeung; Pratap Singhasivanon; Nicholas P J Day; Niklas Lindegardh; Duong Socheat; Nicholas J White
Journal:  N Engl J Med       Date:  2009-07-30       Impact factor: 91.245

Review 10.  Predicting and tuning physicochemical properties in lead optimization: amine basicities.

Authors:  Martin Morgenthaler; Eliane Schweizer; Anja Hoffmann-Röder; Fausta Benini; Rainer E Martin; Georg Jaeschke; Björn Wagner; Holger Fischer; Stefanie Bendels; Daniel Zimmerli; Josef Schneider; François Diederich; Manfred Kansy; Klaus Müller
Journal:  ChemMedChem       Date:  2007-08       Impact factor: 3.466
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  8 in total

1.  Long-Lasting and Fast-Acting in Vivo Efficacious Antiplasmodial Azepanylcarbazole Amino Alcohol.

Authors:  Nada Abla; Sridevi Bashyam; Susan A Charman; Béatrice Greco; Philip Hewitt; Maria Belén Jiménez-Díaz; Kasiram Katneni; Holger Kubas; Didier Picard; Yuvaraj Sambandan; Laura Sanz; Dennis Smith; Tai Wang; Paul Willis; Sergio Wittlin; Thomas Spangenberg
Journal:  ACS Med Chem Lett       Date:  2017-11-28       Impact factor: 4.345

2.  Design, synthesis, and biological evaluation of novel carbazole derivatives as potent DNMT1 inhibitors with reasonable PK properties.

Authors:  Ennian Li; Kai Wang; Bei Zhang; Siqi Guo; Senhao Xiao; Qi Pan; Xiaowan Wang; Weiying Chen; Yunshan Wu; Hesong Xu; Xiangqian Kong; Cheng Luo; Shijie Chen; Bo Liu
Journal:  J Enzyme Inhib Med Chem       Date:  2022-12       Impact factor: 5.756

3.  Novel carbazole aminoalcohols as inhibitors of β-hematin formation: Antiplasmodial and antischistosomal activities.

Authors:  Weisi Wang; Qiang Li; Yufen Wei; Jian Xue; Xiao Sun; Yang Yu; Zhuo Chen; Shizhu Li; Liping Duan
Journal:  Int J Parasitol Drugs Drug Resist       Date:  2017-04-02       Impact factor: 4.077

4.  Antibiotic activities of propanolamine containing 1,4-benzoxazin-3-ones against phytopathogenic bacteria.

Authors:  Jiarui Rao; Liwei Liu; Dan Zeng; Mingwei Wang; Meng Xiang; Song Yang
Journal:  RSC Adv       Date:  2020-01-02       Impact factor: 4.036

5.  Jejucarbazoles A-C, carbazole glycosides with indoleamine 2,3-dioxygenase 1 inhibitory activity from Streptomyces sp. KCB15JA151.

Authors:  Gil Soo Kim; Jun-Pil Jang; Mincheol Kwon; Tae Hoon Oh; Kyung Taek Heo; Byeongsan Lee; Jung-Sook Lee; Sung-Kyun Ko; Young-Soo Hong; Jong Seog Ahn; Jae-Hyuk Jang
Journal:  RSC Adv       Date:  2021-06-01       Impact factor: 3.361

6.  Discovery of a Carbazole-Derived Lead Drug for Human African Trypanosomiasis.

Authors:  Sarah M Thomas; Andrei Purmal; Michael Pollastri; Kojo Mensa-Wilmot
Journal:  Sci Rep       Date:  2016-08-26       Impact factor: 4.379

7.  In situ epoxide generation by dimethyldioxirane oxidation and the use of epichlorohydrin in the flow synthesis of a library of β-amino alcohols.

Authors:  Peter J Cossar; Jennifer R Baker; Nicholas Cain; Adam McCluskey
Journal:  R Soc Open Sci       Date:  2018-04-04       Impact factor: 2.963

8.  Visible Light Induced Metal-Free Carbene N-Carbazolation.

Authors:  Claire Empel; Frederic W Patureau; Rene M Koenigs
Journal:  J Org Chem       Date:  2019-08-15       Impact factor: 4.354
  8 in total

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