Encyclopedia

  • Chapter 3 Indoles
  • Add time:07/16/2019         Source:sciencedirect.com

    Publisher SummaryIndole is perhaps the single most visible heterocycle in all of chemistry. It is embodied in a myriad of natural products, pharmaceutical agents, and a growing list of polymers. In addition to the hundreds of well-known indole plant alkaloids (e.g. yohimbine, reserpine, strychnine, ellipticine, lysergic acid, physostigmine), the indole ring is present in an array of other organisms. The indigo analog Tyrian Purple is the ancient Egyptian dye produced by Mediterranean mollusks, and a bromine-containing triindole is found in an Orina sponge. Sciodole is a Tricholoma fungal product and the plant growth hormone 4-chloroindole-3-acetic acid (4-Cl-IAA) is utilized by peas, beans, lentils, and other plants. Another chlorine-containing fungal metabolite is pennigritrem, produced by Penicillium nigricans. The funnel-web spider employs the toxic argiotoxin 659 in chemical defense. The central importance of the indole derivatives serotonin and the amino acid tryptophan in living organisms has inspired chemists to design and synthesize thousands of indole-containing pharmaceuticals. Three new antimigraine drugs—competitors of the highly effective Sumatriptan—are Naramig, Zomig, and Maxalt. The antiemetics Nasea and Anzemet are potent and highly selective 5-HT3 receptor antagonists for the treatment of chemotherapy-induced nausea and vomiting. Lescol is an HMG-CoA reductase inhibitor, and Somatuline is an indole cyclic peptide for the treatment of acromegaly by acting as a growth hormone inhibitor.

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