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Mar. Drugs 2014, 12(4), 1757-1772; doi:10.3390/md12041757
Article

Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues

1
, 1
, 2
, 1
 and 1,*
1 Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Delegación Coyoacán, México D.F. C.P. 04510, Mexico 2 Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México, Ciudad Universitaria, Delegación Coyoacán, México D.F. C.P. 04510, Mexico
* Author to whom correspondence should be addressed.
Received: 7 January 2014 / Revised: 6 February 2014 / Accepted: 27 February 2014 / Published: 27 March 2014
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Abstract

Caulerpin (1a), a bis-indole alkaloid from the marine algal Caulerpa sp., was synthesized in three reaction steps with an overall yield of 11%. The caulerpin analogues (1b1g) were prepared using the same synthetic pathway with overall yields between 3% and 8%. The key reaction involved a radical oxidative aromatic substitution involving xanthate (3) and 3-formylindole compounds (4a4g). All bis-indole compounds synthesized were evaluated against the Mycobacterium tuberculosis strain H37Rv, and 1a was found to display excellent activity (IC50 0.24 µM).
Keywords: synthesis; caulerpin; analogues; anti-tuberculosis activity synthesis; caulerpin; analogues; anti-tuberculosis activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Chay, C.I.C.; Cansino, R.G.; Pinzón, C.I.E.; Torres-Ochoa, R.O.; Martínez, R. Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues. Mar. Drugs 2014, 12, 1757-1772.

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