title: Synthesis and anti-tuberculosis activity of the marine natural product caulerpin and its analogues.
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 (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).
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Delegación Coyoacán, México D.F. C.P. 04510, Mexico. qfbcicc@hotmail.com.
authors.forename: Cristina I
authors.initials: CI
authors.lastname: Canché Chay
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Delegación Coyoacán, México D.F. C.P. 04510, Mexico. chio746_@hotmail.com.
authors.forename: Rocío
authors.initials: R
authors.lastname: Gómez Cansino
authors.affiliation: Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México, Ciudad Universitaria, Delegación Coyoacán, México D.F. C.P. 04510, Mexico. espitia@biomedicas.unam.mx.
authors.forename: Clara I
authors.initials: CI
authors.lastname: Espitia Pinzón
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Delegación Coyoacán, México D.F. C.P. 04510, Mexico. rube_to83@hotmail.com.
authors.forename: Rubén O
authors.initials: RO
authors.lastname: Torres-Ochoa
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Delegación Coyoacán, México D.F. C.P. 04510, Mexico. robmar@unam.mx.
authors.forename: Roberto
authors.initials: R
authors.lastname: Martínez
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D046068:Caulerpa / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D009169:Mycobacterium tuberculosis / Q000187:drug effects*
chemical_list: D000995:Antitubercular Agents; D001688:Biological Products; D007211:Indoles; C000392:caulerpin