An efficient and convenient method to synthesize highly functionalized 3,7'-bisindole derivatives has been developed via a Michael addition and cyclic condensation reaction of heterocyclic ketene aminals (HKAs) with 2-(1H-indol-3-yl)cyclohexa-2,5-diene-1,4-dione derivatives in ethanol-based solvents at room temperature. This strategy provides an efficient, environmentally friendly approach for ...

Two molecules of the amino acid L-tryptophan are the biosynthetic precursors to a class of natural products named the "bisindoles." Hundreds of these bisindole molecules have been isolated from natural sources, and many of these molecules have potent medicinal properties. Recent studies have clarified the biosynthetic construction of six bisindole molecules, revealing novel enzymatic mechanisms...

Leucofoline and leuconoline, representing the first members of the aspidospermatan-aspidospermatan and eburnane-sarpagine subclasses of the bisindole alkaloids, respectively, were isolated from the Malayan Leuconotis griffithii. The structures of these bisindole alkaloids were established using NMR and MS analysis, and in the case of leuconoline, confirmed by X-ray diffraction analysis. Both al...

New bisindole alkaloids, hyrtinadines C (1) and D (2), have been isolated from an Okinawan marine sponge Hyrtios sp. The structures of hyrtinadines C (1) and D (2) were elucidated based on analyses of the spectral data. Hyrtinadines C (1) and D (2) were the relatively rare alkaloids possessing a 3,4-fused azepinoindole skeleton. Hyrtinadines C (1) and D (2) showed antimicrobial activity.

Bisindole natural products consist of two monomeric indole alkaloid units as their obligate constituents. Bisindoles are more potent with respect to their biological activity than their corresponding monomeric units. In addition, the synthesis of bisindoles are far more challenging than the synthesis of monomeric indole alkaloids. Herein is reviewed the enantiospecific total and partial synthes...

Two new bisindole alkaloids, 12?-O-demethyl-vobtusine-5-lactam and isovobtusine-N-oxide (1 2), were isolated from the leaves of Voacanga grandifolia, together with two known alkaloids. Their structures elucidated on basis 1D 2D NMR data. 1 2 showed potent antimalarial activity against Plasmodium falciparum 3D7 very low cytotoxic a human cell line, HepG2 cells.

The diversity-oriented synthesis of bisindole derivatives to construct concise libraries using consecutive cross-coupling reactions and prepare new sulfonamide type fluorous protecting groups is presented.

The potential implication of photochromic materials with absorption and reactivity in the near-infrared region is far-reaching. In this work, three novel bisindole-containing diarylethene derivatives 1o–3o have been successfully synthesized and their photochromic behaviour exhibits a strong bathochromic shift effect compared with bisbenzothiophene diarylethene 4o. These new bisindole-diarylethe...

Nine bisindole alkaloids, comprising four belonging to the macroline-sarpagine group, and five belonging to the macroline-pleiocarpamine group, were isolated from the stem-bark extracts of Alstonia angustifolia (Apocynacea). Their structures were established using NMR and MS analyses.

Four new bisindole alkaloids of the Strychnos-Strychnos type, leucoridines A-D (1-4), were isolated from the stem-bark extract of Leuconotis griffithii. Alkaloids 1-4 showed moderate cytotoxicity against drug-sensitive and vincristine-resistant human KB cells.