Literature DB >> 21676615

Efficient synthesis of 3-O-thia-cPA and preliminary analysis of its biological activity toward autotaxin.

Ryo Tanaka1, Masaru Kato, Takahiro Suzuki, Atsuo Nakazaki, Emi Nozaki, Mari Gotoh, Kimiko Murakami-Murofushi, Susumu Kobayashi.   

Abstract

The efficient synthesis of 3-O-thia-cPAs (4a-d), sulfur analogues of cyclic phosphatidic acid (cPA), has been achieved. The key step of the synthesis is an intramolecular Arbuzov reaction to construct the cyclic thiophosphate moiety. The present synthetic route enables the synthesis of 4a-d in only four steps from the commercially available glycidol. Preliminary biological experiments showed that 4a-d exhibited a similar inhibitory effect on autotaxin (ATX) as original cPA.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID: 21676615     DOI: 10.1016/j.bmcl.2011.05.083

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  4 in total

1.  2-Carba-lysophosphatidic acid is a novel β-lysophosphatidic acid analogue with high potential for lysophosphatidic acid receptor activation and autotaxin inhibition.

Authors:  Keiko Fukasawa; Mari Gotoh; Akiharu Uwamizu; Takatsugu Hirokawa; Masaki Ishikawa; Yoshibumi Shimizu; Shinji Yamamoto; Kensuke Iwasa; Keisuke Yoshikawa; Junken Aoki; Kimiko Murakami-Murofushi
Journal:  Sci Rep       Date:  2021-08-30       Impact factor: 4.379

2.  Protection of neuroblastoma Neuro2A cells from hypoxia-induced apoptosis by cyclic phosphatidic acid (cPA).

Authors:  Mari Gotoh; Katsura Sano-Maeda; Hiromu Murofushi; Kimiko Murakami-Murofushi
Journal:  PLoS One       Date:  2012-12-12       Impact factor: 3.240

Review 3.  Chemical evolution of autotaxin inhibitors.

Authors:  Harald M H G Albers; Huib Ovaa
Journal:  Chem Rev       Date:  2012-02-15       Impact factor: 60.622

4.  Structural evidence of the species-dependent albumin binding of the modified cyclic phosphatidic acid with cytotoxic properties.

Authors:  Bartosz Sekula; Anna Ciesielska; Przemyslaw Rytczak; Maria Koziołkiewicz; Anna Bujacz
Journal:  Biosci Rep       Date:  2016-06-03       Impact factor: 3.840

  4 in total

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