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

Marine Drugs

Cristina I. Canché Chay¹  Rocío Gómez Cansino¹  Clara I. Espitia Pinzón²  Rubén O. Torres-Ochoa¹ 

[1] Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Delegación Coyoacán, México D.F. C.P. 04510, Mexico; E-Mails:;Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México, Ciudad Universitaria, Delegación Coyoacán, México D.F. C.P. 04510, Mexico.; E-Mail:

关键词: synthesis;    caulerpin;    analogues;    anti-tuberculosis activity;   

DOI  :  10.3390/md12041757

来源: mdpi

【 摘 要 】

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 (1b–1g) 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 (4a–4g). 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).

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.