Literature DB >> 18251547

Synthesis of pyranicin and its inhibitory action with bovine heart mitochondrial complex I.

Yasunao Hattori1, Shin-ichi Furuhata, Motonori Okajima, Hiroyuki Konno, Masato Abe, Hideto Miyoshi, Tetsuhisa Goto, Hidefumi Makabe.   

Abstract

Total synthesis of pyranicin was achieved using Cl2Pd(CH3CN)2-catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of this compound for mitochondrial NADH-ubiquinone oxidoreductase (complex I) was slightly poorer than that of ordinary mono-THF acetogenins such as cis-solamin.

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Year:  2008        PMID: 18251547     DOI: 10.1021/ol702902w

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


  4 in total

1.  A concise and modular synthesis of pyranicin.

Authors:  Nolan D Griggs; Andrew J Phillips
Journal:  Org Lett       Date:  2008-10-10       Impact factor: 6.005

2.  Catalyst-directed diastereo- and site-selectivity in successive nucleophilic and electrophilic allylations of chiral 1,3-diols: protecting-group-free synthesis of substituted pyrans.

Authors:  Inji Shin; Gang Wang; Michael J Krische
Journal:  Chemistry       Date:  2014-08-28       Impact factor: 5.236

3.  Asymmetric total synthesis of pyranicin.

Authors:  Michael T Crimmins; Danielle L Jacobs
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

4.  A novel thiophene-3-carboxamide analog of annonaceous acetogenin exhibits antitumor activity via inhibition of mitochondrial complex I.

Authors:  Akinobu Akatsuka; Naoto Kojima; Mutsumi Okamura; Shingo Dan; Takao Yamori
Journal:  Pharmacol Res Perspect       Date:  2016-07-12
  4 in total

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