Literature DB >> 9868151

Chemistry of puupehenone: 1,6-conjugate addition to its quinone-methide system.

J K Zjawiony1, P Bartyzel, M T Hamann.   

Abstract

The marine natural product puupehenone (1), isolated in good yields from sponges of the genus Hyrtios, has been shown to undergo stereospecific 1,6-conjugate addition to its quinone-methide system. Several nucleophilic agents such as hydrogen cyanide, Grignard reagents, and nitroalkanes were studied, producing structurally diverse compounds. This lead optimization study was initiated due to the bioactivity of puupehenone and its natural analogues, which includes numerous previous reports of potential anticancer and antiinfective activity.

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Year:  1998        PMID: 9868151     DOI: 10.1021/np9802062

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  5 in total

1.  Synthesis and Evaluation of Marine Natural Product-Inspired Meroterpenoids with Selective Activity toward Dormant Mycobacterium tuberculosis.

Authors:  Anshupriya Si; Alexander D Landgraf; Sandra Geden; Steven J Sucheck; Kyle H Rohde
Journal:  ACS Omega       Date:  2022-06-27

2.  Puupehanol, a sesquiterpene-dihydroquinone derivative from the marine sponge Hyrtios sp.

Authors:  Wen-Hui Xu; Yuanqing Ding; Melissa R Jacob; Ameeta K Agarwal; Alice M Clark; Daneel Ferreira; Zong-Suo Liang; Xing-Cong Li
Journal:  Bioorg Med Chem Lett       Date:  2009-09-11       Impact factor: 2.823

Review 3.  Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order Dictyoceratida.

Authors:  Dusan Sladić; Miroslav J Gasić
Journal:  Molecules       Date:  2006-01-31       Impact factor: 4.411

Review 4.  Pleiotropic Role of Puupehenones in Biomedical Research.

Authors:  Beatriz Martínez-Poveda; Ana R Quesada; Miguel Ángel Medina
Journal:  Mar Drugs       Date:  2017-10-21       Impact factor: 5.118

5.  Puupehenone, a Marine-Sponge-Derived Sesquiterpene Quinone, Potentiates the Antifungal Drug Caspofungin by Disrupting Hsp90 Activity and the Cell Wall Integrity Pathway.

Authors:  Siddharth K Tripathi; Qin Feng; Li Liu; David E Levin; Kuldeep K Roy; Robert J Doerksen; Scott R Baerson; Xiaomin Shi; Xuewen Pan; Wen-Hui Xu; Xing-Cong Li; Alice M Clark; Ameeta K Agarwal
Journal:  mSphere       Date:  2020-01-08       Impact factor: 4.389

  5 in total

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