N-Methyl-1h- Indole-2-Carboxamide From the Marine Fungus Cladosporium Cladosporioides

Abstract

The crystal structure of N-methyl-1H-indole-2-carboxamide C 10 H 10 N 2 O was determined by single crystal X-ray diffraction. The structure can be described as consisting of an indole group and as substituent, linked at C2, the N-methylcarboxamide group. The molecular structure is essentially planar. The crystal packing results in N-H-O hydrogen bonds which join the molecules into centrosymmetric dimeric rings. The knowledge of the crystal structure allows a complete assignment of the 1 H and 13 C-NMR spectra. The N-methyl-1H-indole-2-carboxamide is the first indole derivative isolated from marine fungus.

Secondary metabolites of fungi from marine habitats

“…N-Methyl-1H-indole-2-carboxamide (656) from the fungus Cladosporium cladosporioides, isolated from the Chilean sponge Cliona sp., has apparently never been reported as a natural product before, but has now been described and its structure determined by single-crystal X-ray diffraction. 451 Two new indole derivatives, 2-(1H-indol-3-yl)ethyl 2-hydroxypropanoate (657) and 2-(1H-indol-3-yl)ethyl 5-hydroxypentanoate (658), were reported from the yeast Pichia membranifaciens, isolated from the Japanese sponge Halichondria okadai. 452 ZZF51(A) (660) is a copper complex of two fusaric acid (5butylpicolinic acid) moieties produced by the fungus Fusarium sp., an endophyte of the Chinese mangrove plant Castaniopsis fissa.…”

Conotoxins: Review and Docking Studies to determine potentials of Conotoxin as an Anticancer Drug Molecule

“…Valine is a nonpolar amino acid with a large side chain which makes it hydrophobic in nature. The indole and hydroxyl groups have shown to form covalent bonds, and in certain studies it has been observed that such a bond increases cytotoxicity of some compounds [52]. Valine having large uncharged side chain is less reactive, which is also evident from the bond length.…”

Natural Products from Chilean and Antarctic Marine Fungi and Their Biomedical Relevance

“…Compound 10 is the first indole derivative isolated from a marine fungus ( Cladosporium cladosorioides) . The crystal structure of N-methyl-1H-indole-2-carboxamide ( 10 ) ( Figure 4 ) was determined by single-crystal X-ray diffraction [ 27 ].…”