Issue 20, 2011
From the journal:

Organic & Biomolecular Chemistry

Syntheses of sulfur and selenium analogues of pachastrissaminevia double displacements of cyclic sulfate†

Hongjun Jeon,a   Hoon Bae,a   Dong Jae Baek,a   Young-Shin Kwak,b   Deukjoon Kima  and  Sanghee Kim*a  

* Corresponding authors

a College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea
E-mail: pennkim@snu.ac.kr
Fax: +82-2-888-0649
Tel: +82-2-880-2487

b Korea Research Institute of Bioscience & Biotechnology (KRIBB), Chungbuk 363-883, Korea
E-mail: yskwak@kribb.re.kr
Fax: +82-43-240-6009
Tel: +82-43-240-6108

Abstract

Bioisosteric analogues of pachastrissamine that contain sulfur and selenium atoms replacing the oxygen in the ring system, were efficiently prepared from a cyclic sulfate intermediate by sequential intermolecular and intramolecular SN2 displacement reactions of the dianions. The analogues exhibited cytotoxicities comparable to that of pachastrissamine.

Graphical abstract: Syntheses of sulfur and selenium analogues of pachastrissamine via double displacements of cyclic sulfate

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Article information

DOI
https://doi.org/10.1039/C1OB05920C
Article type
Paper
Submitted
08 Jun 2011
Accepted
19 Jul 2011
First published
30 Aug 2011

Org. Biomol. Chem., 2011,9, 7237-7242

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Syntheses of sulfur and selenium analogues of pachastrissamine via double displacements of cyclic sulfate

H. Jeon, H. Bae, D. J. Baek, Y. Kwak, D. Kim and S. Kim, Org. Biomol. Chem., 2011, 9, 7237 DOI: 10.1039/C1OB05920C

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