Analogs of Antifungal Indoles Isolated from Aporpium Caryae with Activity Against Sudden-Death Syndrome of Soybean

Abstract

Based on the precedent discovery of a weak antifungal indole isolated from Aporpium caryae, which increased its activity when changing the N-alkyl chain, nineteen N-alkyl

Exploring novel fluorine rich fuberidazole derivatives as hypoxic cancer inhibitors: design, synthesis, pharmacokinetics, molecular docking and DFT evaluations

“…To synthesize fuberidazole derivatives 5a-p, a facile and green route was adopted in which 3,4,5-trifluorobenzene-1,2-diamine 1 was treated with furan-2-carbaldehyde derivatives 2 using PEG 400 as a greener medium giving intermediate 3a-d confirmed by elemental analysis and 1 H and 13 C NMR (see Table S1, Figs S1 and S8). The intermediate 3a-d were then reacted with RCl 4 and sodium hydride in the presence of a minimum quantity of acetone as a solvent for five hours at room temperature, which afforded fuberidazole derivatives 5a-p in good to excellent yields (Scheme 1).…”

“…Therefore, we purified them by preparative TLC and column chromatography. The structures of 5a-p were assigned according to FT-IR, multinuclear ( 1 H and 13 C NMR) and CHN analysis. In the FTIR spectrum of 5a-p, the absence of the -NH 2 absorption band confirmed the formation of the imidazole ring.…”

“…Benzimidazoles nucleus contained in fuberidazoles is a very popular nitrogen-containing heterocycle. They have anticonvulsant (12), antifungal (13), antiviral (14), and anticancer (15) activities. The structural resemblance of fuberidazole to the naturally occurring nucleotides allows it to target the polymers in the living world leading to a vast impact in biological systems (16).…”

“…collect the infrared spectra. The 1 H NMR (300 MHz) and 13 C NMR (75.43 MHz) spectra were collected on a Bruker AM-250 spectrometer utilizing CDCl 3 and DMSO as internal standards. A UV-Visible spectrophotometer was used to obtain UV-Visible absorption spectra, model UV-1700.…”

Synthesis of Substituted 2-Phenyl-1H-indoles and their Fungicidal Activity

“…Indoles also form a part of drugs like indomethacin (which is used as an anti-inflammatory, an antipyretic and an analgesic), indoxole (an anti-inflammatory and anti-pyretic) and the naturally occurring hallucinogen dimethyltryptamine (N,N-DMT). Indoles and its derivatives are known to posses biological activities e.g., anticancer, antifungal, anticonvulsant, anti-inflammatory and analgesic [2,[14][15][16] etc.…”