Literature DB >> 25659617

Enantioselective synthesis of dictyoceratin-A (smenospondiol) and -C, hypoxia-selective growth inhibitors from marine sponge.

Yuji Sumii1, Naoyuki Kotoku2, Akinori Fukuda1, Takashi Kawachi1, Yuta Sumii1, Masayoshi Arai1, Motomasa Kobayashi3.   

Abstract

Total syntheses of (+)-dictyoceratin-C (1) and (+)-dictyoceratin-A (smenospondiol) (2), hypoxia-selective growth inhibitors isolated from marine sponge, were executed. The absolute stereochemistry of the each compound was determined through the enantioselective total syntheses of them. It revealed that the unnatural enantiomers of them also exhibited the hypoxia-selective growth inhibitory activity against human prostate cancer DU-145 cells.
Copyright © 2015 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  (+)-Dictyoceratin-A (smenospondiol); (+)-Dictyoceratin-C; Absolute stereochemistry; Hypoxia-selective growth inhibitor; Total synthesis

Mesh：

Substances：

Year:  2015        PMID： 25659617     DOI： 10.1016/j.bmc.2015.01.021

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  7 in total

1.  Enantioselective Total Synthesis and Structural Revision of Dysiherbol A.

Authors:  Julian Baars; Isabelle Grimm; Dirk Blunk; Jörg-Martin Neudörfl; Hans-Günther Schmalz
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-01       Impact factor: 15.336

Review 2.  Dactylospongia elegans-A Promising Drug Source: Metabolites, Bioactivities, Biosynthesis, Synthesis, and Structural-Activity Relationship.

Authors:  Sabrin R M Ibrahim; Sana A Fadil; Haifa A Fadil; Rawan H Hareeri; Sultan O Alolayan; Hossam M Abdallah; Gamal A Mohamed
Journal:  Mar Drugs       Date:  2022-03-23       Impact factor: 6.085

3.  Structure-Activity Relationship and in Vivo Anti-Tumor Evaluations of Dictyoceratin-A and -C, Hypoxia-Selective Growth Inhibitors from Marine Sponge.

Authors:  Yuji Sumii; Naoyuki Kotoku; Akinori Fukuda; Takashi Kawachi; Masayoshi Arai; Motomasa Kobayashi
Journal:  Mar Drugs       Date:  2015-12-16       Impact factor: 5.118

Review 4.  Bioactive Prenyl- and Terpenyl-Quinones/Hydroquinones of Marine Origin †.

Authors:  Pablo A García; Ángela P Hernández; Arturo San Feliciano; Mª Ángeles Castro
Journal:  Mar Drugs       Date:  2018-08-21       Impact factor: 5.118

5.  Target Identification of the Marine Natural Products Dictyoceratin-A and -C as Selective Growth Inhibitors in Cancer Cells Adapted to Hypoxic Environments.

Authors:  Takashi Kawachi; Shun Tanaka; Akinori Fukuda; Yuji Sumii; Andi Setiawan; Naoyuki Kotoku; Motomasa Kobayashi; Masayoshi Arai
Journal:  Mar Drugs       Date:  2019-03-08       Impact factor: 5.118

6.  Unexpected Racemization in the Course of the Acetalization of (+)-(S)-5-Methyl-Wieland-Miescher Ketone with 1,2-Ethanediol and TsOH under Classical Experimental Conditions.

Authors:  Francesca Leonelli; Irene Piergentili; Giulio Lucarelli; Luisa Maria Migneco; Rinaldo Marini Bettolo
Journal:  Int J Mol Sci       Date:  2019-12-05       Impact factor: 5.923

Review 7.  Marine Invertebrate Metabolites with Anticancer Activities: Solutions to the "Supply Problem".

Authors:  Nelson G M Gomes; Ramesh Dasari; Sunena Chandra; Robert Kiss; Alexander Kornienko
Journal:  Mar Drugs       Date:  2016-05-21       Impact factor: 5.118
  7 in total

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