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Literature DB >> 11843581

Regiocontrolled synthesis of the trimeric quinone framework of conocurvone.

Ashkan Emadi¹, John S Harwood, Sahar Kohanim, Kenneth W Stagliano.

Abstract

[reaction: see text] The trimeric quinone framework of conocurvone is crucial for its potent anti-HIV activity. A new synthesis of trimeric quinones based on stepwise substitution of the halogens in 2,3-dihaloquinones by hydroxyquinone anions is described. Chlorinated biquinones are key intermediates that undergo regiospecific substitution reactions to yield trimeric quinone monomethyl ethers.

Entities: Chemical

Mesh：

Substances：

Year: 2002 PMID： 11843581 DOI： 10.1021/ol010272m

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

8 in total

1. Dimeric naphthoquinones, a novel class of compounds with prostate cancer cytotoxicity.

Authors: Ashley E Ross; Ashkan Emadi; Luigi Marchionni; Paula J Hurley; Brian W Simons; Edward M Schaeffer; Milena Vuica-Ross
Journal: BJU Int Date: 2010-12-22 Impact factor: 5.588

2. Synthesis, characterization and antineoplastic activity of bis-aziridinyl dimeric naphthoquinone - A novel class of compounds with potent activity against acute myeloid leukemia cells.

Authors: Brandon A Carter-Cooper; Steven Fletcher; Dana Ferraris; Eun Yong Choi; Dahlia Kronfli; Smaraki Dash; Phuc Truong; Edward A Sausville; Rena G Lapidus; Ashkan Emadi
Journal: Bioorg Med Chem Lett Date: 2016-11-17 Impact factor: 2.823

3. Metabolic and electrochemical mechanisms of dimeric naphthoquinones cytotoxicity in breast cancer cells.

Authors: Ashkan Emadi; Anne Le; Cynthia J Harwood; Kenneth W Stagliano; Farin Kamangar; Ashley E Ross; Charles R Cooper; Chi V Dang; Judith E Karp; Milena Vuica-Ross
Journal: Bioorg Med Chem Date: 2011-10-08 Impact factor: 3.641

4. A chemical genetic screen for modulators of asymmetrical 2,2'-dimeric naphthoquinones cytotoxicity in yeast.

Authors: Ashkan Emadi; Ashley E Ross; Kathleen M Cowan; Yolanda M Fortenberry; Milena Vuica-Ross
Journal: PLoS One Date: 2010-05-26 Impact factor: 3.240

5. Hydroxylated Dimeric Naphthoquinones Increase the Generation of Reactive Oxygen Species, Induce Apoptosis of Acute Myeloid Leukemia Cells and Are Not Substrates of the Multidrug Resistance Proteins ABCB1 and ABCG2.

Authors: Rena G Lapidus; Brandon A Carter-Cooper; Mariola Sadowska; Eun Yong Choi; Omasiri Wonodi; Nidal Muvarak; Karthika Natarajan; Lakshmi S Pidugu; Anil Jaiswal; Eric A Toth; Feyruz V Rassool; Arash Etemadi; Edward A Sausville; Maria R Baer; Ashkan Emadi
Journal: Pharmaceuticals (Basel) Date: 2016-01-19

Regiocontrolled synthesis of the trimeric quinone framework of conocurvone.

1. Dimeric naphthoquinones, a novel class of compounds with prostate cancer cytotoxicity.

2. Synthesis, characterization and antineoplastic activity of bis-aziridinyl dimeric naphthoquinone - A novel class of compounds with potent activity against acute myeloid leukemia cells.

3. Metabolic and electrochemical mechanisms of dimeric naphthoquinones cytotoxicity in breast cancer cells.

4. A chemical genetic screen for modulators of asymmetrical 2,2'-dimeric naphthoquinones cytotoxicity in yeast.

5. Hydroxylated Dimeric Naphthoquinones Increase the Generation of Reactive Oxygen Species, Induce Apoptosis of Acute Myeloid Leukemia Cells and Are Not Substrates of the Multidrug Resistance Proteins ABCB1 and ABCG2.

6. A direct interaction between NQO1 and a chemotherapeutic dimeric naphthoquinone.

7. Pseudo-cyclic face-to-face rigid structure caused by the intramolecular ion pair effect.

8. A survey on the reactivity of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone with amino compounds.