Literature DB >> 21082793

Divergent route to access structurally diverse 4-quinolones via mono or sequential cross-couplings.

R Matthew Cross1, Roman Manetsch.   

Abstract

A divergent route was developed to access 3-iodo- and 6-chloro-3-iodo-4(1H)-quinolones for further elaboration via mono and/or sequential Suzuki-Miyaura cross-coupling to generate novel and medicinally important 4(1H)-quinolones. Copper- and palladium-catalyzed cyanations were used to functionalize the 4-quinolone core further.

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Year:  2010        PMID： 21082793     DOI： 10.1021/jo1014504

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  12 in total

1.  4(1H)-Quinolones with liver stage activity against Plasmodium berghei.

Authors:  Alexis N Lacrue; Fabián E Sáenz; R Matthew Cross; Kenneth O Udenze; Andrii Monastyrskyi; Steven Stein; Tina S Mutka; Roman Manetsch; Dennis E Kyle
Journal:  Antimicrob Agents Chemother       Date:  2012-11-05       Impact factor: 5.191

2.  4(1H)-pyridone and 4(1H)-quinolone derivatives as antimalarials with erythrocytic, exoerythrocytic, and transmission blocking activities.

Authors:  Andrii Monastyrskyi; Dennis E Kyle; Roman Manetsch
Journal:  Curr Top Med Chem       Date:  2014       Impact factor: 3.295

3.  Lead optimization of 3-carboxyl-4(1H)-quinolones to deliver orally bioavailable antimalarials.

Authors:  Yiqun Zhang; Julie A Clark; Michele C Connelly; Fangyi Zhu; Jaeki Min; W Armand Guiguemde; Anupam Pradhan; Lalitha Iyer; Anna Furimsky; Jason Gow; Toufan Parman; Farah El Mazouni; Margaret A Phillips; Dennis E Kyle; Jon Mirsalis; R Kiplin Guy
Journal:  J Med Chem       Date:  2012-04-18       Impact factor: 7.446

4.  Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1H-indoles, and quinolin-4(1H)-ones.

Authors:  Keith C Coffman; Teresa A Palazzo; Timothy P Hartley; James C Fettinger; Dean J Tantillo; Mark J Kurth
Journal:  Org Lett       Date:  2013-04-04       Impact factor: 6.005

5.  Progress in the Optimization of 4(1H)-Quinolone Derivatives as Antimalarials Targeting the Erythrocytic, the Exoerythrocytic and the Transmitting Stages of the Malaria Parasite.

Authors:  Fabian Brockmeyer; Roman Manetsch
Journal:  Chimia (Aarau)       Date:  2017-04-26       Impact factor: 1.656

6.  Synthesis, antimalarial activity, and structure-activity relationship of 7-(2-phenoxyethoxy)-4(1H)-quinolones.

Authors:  R Matthew Cross; Niranjan K Namelikonda; Tina S Mutka; Lisa Luong; Dennis E Kyle; Roman Manetsch
Journal:  J Med Chem       Date:  2011-11-23       Impact factor: 8.039

7.  Aminoalkoxycarbonyloxymethyl Ether Prodrugs with a pH-Triggered Release Mechanism: A Case Study Improving the Solubility, Bioavailability, and Efficacy of Antimalarial 4(1H)-Quinolones with Single Dose Cures.

Authors:  Andrii Monastyrskyi; Fabian Brockmeyer; Alexis N LaCrue; Yingzhao Zhao; Steven P Maher; Jordany R Maignan; Vivian Padin-Irizarry; Yana I Sakhno; Prakash T Parvatkar; Ami H Asakawa; Lili Huang; Debora Casandra; Sherwin Mashkouri; Dennis E Kyle; Roman Manetsch
Journal:  J Med Chem       Date:  2021-05-12       Impact factor: 8.039

8.  A New Scalable Synthesis of ELQ-300, ELQ-316, and other Antiparasitic Quinolones.

Authors:  Sovitj Pou; Rozalia A Dodean; Lisa Frueh; Katherine M Liebman; Rory T Gallagher; Haihong Jin; Robert T Jacobs; Aaron Nilsen; David R Stuart; J Stone Doggett; Michael K Riscoe; Rolf W Winter
Journal:  Org Process Res Dev       Date:  2021-08-04       Impact factor: 3.858

9.  Orally bioavailable 6-chloro-7-methoxy-4(1H)-quinolones efficacious against multiple stages of Plasmodium.

Authors:  R Matthew Cross; David L Flanigan; Andrii Monastyrskyi; Alexis N LaCrue; Fabián E Sáenz; Jordany R Maignan; Tina S Mutka; Karen L White; David M Shackleford; Ian Bathurst; Frank R Fronczek; Lukasz Wojtas; Wayne C Guida; Susan A Charman; Jeremy N Burrows; Dennis E Kyle; Roman Manetsch
Journal:  J Med Chem       Date:  2014-10-22       Impact factor: 7.446

10.  Synthesis and biological activities of the respiratory chain inhibitor aurachin D and new ring versus chain analogues.

Authors:  Xu-Wen Li; Jennifer Herrmann; Yi Zang; Philippe Grellier; Soizic Prado; Rolf Müller; Bastien Nay
Journal:  Beilstein J Org Chem       Date:  2013-07-31       Impact factor: 2.883
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