Literature DB >> 25089179

The biology and synthesis of α-hydroxytropolones.

Christine Meck1, Michael P D'Erasmo1, Danielle R Hirsch1, Ryan P Murelli1.   

Abstract

α-Hydroxytropolones are a subclass of the troponoid family of natural products that are of high interest due to their broad biological activity and potential as treatment options for several diseases. Despite this promise, there have been scarce synthetic chemistry-driven optimization studies on the molecules. The following review highlights key developments in the biological studies conducted on α-hydroxytropolones to date, including the few synthetic chemistry-driven optimization studies. In addition, we provide an overview of the methods currently available to access these molecules. This review is intended to serve as a resource for those interested in biological activity of α-hydroxytropolones, and inspire the development of new synthetic methods and strategies that could aid in this pursuit.

Entities:  

Year:  2014        PMID： 25089179      PMCID： PMC4114738          DOI： 10.1039/C4MD00055B

Source DB:  PubMed          Journal:  Medchemcomm        ISSN： 2040-2503            Impact factor:   3.597


  45 in total

Review 1.  Aminoglycoside resistance in Pseudomonas aeruginosa.

Authors:  Keith Poole
Journal:  Antimicrob Agents Chemother       Date:  2005-02       Impact factor: 5.191

Review 2.  A fresh look at natural tropolonoids.

Authors:  Ronald Bentley
Journal:  Nat Prod Rep       Date:  2007-11-22       Impact factor: 13.423

3.  Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: synthesis of methoxytropolones and furans.

Authors:  Yvonne D Williams; Christine Meck; Noushad Mohd; Ryan P Murelli
Journal:  J Org Chem       Date:  2013-11-14       Impact factor: 4.354

4.  Synthesis, activity, and structural analysis of novel α-hydroxytropolone inhibitors of human immunodeficiency virus reverse transcriptase-associated ribonuclease H.

Authors:  Suhman Chung; Daniel M Himmel; Jian-Kang Jiang; Krzysztof Wojtak; Joseph D Bauman; Jason W Rausch; Jennifer A Wilson; John A Beutler; Craig J Thomas; Eddy Arnold; Stuart F J Le Grice
Journal:  J Med Chem       Date:  2011-06-02       Impact factor: 7.446

Review 5.  Bacterial resistance to aminoglycoside antibiotics.

Authors:  J Davies; G D Wright
Journal:  Trends Microbiol       Date:  1997-06       Impact factor: 17.079

6.  Computational study of the intramolecular proton transfer reactions of 3-hydroxytropolone (2,7-dihydroxycyclohepta-2,4,6-trien-1-one) and its dimers.

Authors:  Dilara Ozbakir Isin; Nihat Karakus
Journal:  J Mol Model       Date:  2010-03-16       Impact factor: 1.810

7.  HIV-1 reverse transcriptase can simultaneously engage its DNA/RNA substrate at both DNA polymerase and RNase H active sites: implications for RNase H inhibition.

Authors:  Greg L Beilhartz; Michaela Wendeler; Noel Baichoo; Jason Rausch; Stuart Le Grice; Matthias Götte
Journal:  J Mol Biol       Date:  2009-03-13       Impact factor: 5.469

8.  Transient kinetic analyses of the ribonuclease H cleavage activity of HIV-1 reverse transcriptase in complex with efavirenz and/or a β-thujaplicinol analogue.

Authors:  Brian D Herman; Nicolas Sluis-Cremer
Journal:  Biochem J       Date:  2013-10-15       Impact factor: 3.857

9.  Vinylogous ureas as a novel class of inhibitors of reverse transcriptase-associated ribonuclease H activity.

Authors:  Michaela Wendeler; Hsiu-Fang Lee; Alun Bermingham; Jennifer T Miller; Oleg Chertov; Marion K Bona; Noel S Baichoo; Maryam Ehteshami; John Beutler; Barry R O'Keefe; Matthias Götte; Mamuka Kvaratskhelia; Stuart Le Grice
Journal:  ACS Chem Biol       Date:  2008-10-03       Impact factor: 5.100

10.  RNase H active site inhibitors of human immunodeficiency virus type 1 reverse transcriptase: design, biochemical activity, and structural information.

Authors:  Thorsten A Kirschberg; Mini Balakrishnan; Neil H Squires; Tiffany Barnes; Katherine M Brendza; Xiaowu Chen; Eugene J Eisenberg; Weili Jin; Nilima Kutty; Stephanie Leavitt; Albert Liclican; Qi Liu; Xiaohong Liu; John Mak; Jason K Perry; Michael Wang; William J Watkins; Eric B Lansdon
Journal:  J Med Chem       Date:  2009-10-08       Impact factor: 7.446
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  30 in total

1.  Efficacy and cytotoxicity in cell culture of novel α-hydroxytropolone inhibitors of hepatitis B virus ribonuclease H.

Authors:  Elena Lomonosova; Jil Daw; Aswin K Garimallaprabhakaran; Nana B Agyemang; Yashkumar Ashani; Ryan P Murelli; John E Tavis
Journal:  Antiviral Res       Date:  2017-06-17       Impact factor: 5.970

Review 2.  Yellow-Cedar, Callitropsis (Chamaecyparis) nootkatensis, Secondary Metabolites, Biological Activities, and Chemical Ecology.

Authors:  Joseph J Karchesy; Rick G Kelsey; M P González-Hernández
Journal:  J Chem Ecol       Date:  2018-04-14       Impact factor: 2.626

3.  Biosynthesis of Tropolones in Streptomyces spp.: Interweaving Biosynthesis and Degradation of Phenylacetic Acid and Hydroxylations on the Tropone Ring.

Authors:  Xuefei Chen; Min Xu; Jin Lü; Jianguo Xu; Yemin Wang; Shuangjun Lin; Zixin Deng; Meifeng Tao
Journal:  Appl Environ Microbiol       Date:  2018-05-31       Impact factor: 4.792

4.  The Exonuclease Activity of Herpes Simplex Virus 1 UL12 Is Required for Production of Viral DNA That Can Be Packaged To Produce Infectious Virus.

Authors:  Lorry M Grady; Renata Szczepaniak; Ryan P Murelli; Takeshi Masaoka; Stuart F J Le Grice; Dennis L Wright; Sandra K Weller
Journal:  J Virol       Date:  2017-11-14       Impact factor: 5.103

5.  Traceless Solid-Phase α-Hydroxytropolone Synthesis.

Authors:  Michael P D'Erasmo; Takashi Masaoka; Jennifer A Wilson; Errol M Hunte; John A Beutler; Stuart F J Le Grice; Ryan P Murelli
Journal:  Medchemcomm       Date:  2016-07-07       Impact factor: 3.597

6.  Discovery and Development of a Three-Component Oxidopyrylium [5 + 2] Cycloaddition.

Authors:  Michael P D'Erasmo; Christine Meck; Chad A Lewis; Ryan P Murelli
Journal:  J Org Chem       Date:  2016-04-08       Impact factor: 4.354

7.  Restored iron transport by a small molecule promotes absorption and hemoglobinization in animals.

Authors:  Anthony S Grillo; Anna M SantaMaria; Martin D Kafina; Alexander G Cioffi; Nicholas C Huston; Murui Han; Young Ah Seo; Yvette Y Yien; Christopher Nardone; Archita V Menon; James Fan; Dillon C Svoboda; Jacob B Anderson; John D Hong; Bruno G Nicolau; Kiran Subedi; Andrew A Gewirth; Marianne Wessling-Resnick; Jonghan Kim; Barry H Paw; Martin D Burke
Journal:  Science       Date:  2017-05-12       Impact factor: 47.728

8.  Synthetic α-Hydroxytropolones Inhibit Replication of Wild-Type and Acyclovir-Resistant Herpes Simplex Viruses.

Authors:  Peter J Ireland; John E Tavis; Michael P D'Erasmo; Danielle R Hirsch; Ryan P Murelli; Mark M Cadiz; Bindi S Patel; Ankit K Gupta; Tiffany C Edwards; Maria Korom; Eileen A Moran; Lynda A Morrison
Journal:  Antimicrob Agents Chemother       Date:  2016-03-25       Impact factor: 5.191

9.  Hydroxylated tropolones inhibit hepatitis B virus replication by blocking viral ribonuclease H activity.

Authors:  Gaofeng Lu; Elena Lomonosova; Xiaohong Cheng; Eileen A Moran; Marvin J Meyers; Stuart F J Le Grice; Craig J Thomas; Jian-kang Jiang; Christine Meck; Danielle R Hirsch; Michael P D'Erasmo; Duygu M Suyabatmaz; Ryan P Murelli; John E Tavis
Journal:  Antimicrob Agents Chemother       Date:  2014-12-01       Impact factor: 5.191

10.  A Complex Mechanism Involving LysR and TetR/AcrR That Regulates Iron Scavenger Biosynthesis in Pseudomonas donghuensis HYS.

Authors:  Min Chen; Panning Wang; Zhixiong Xie
Journal:  J Bacteriol       Date:  2018-06-11       Impact factor: 3.490
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