Chapter 11 Colchicine and Related Compounds
1968; Elsevier BV; Linguagem: Inglês
10.1016/s1876-0813(08)60123-2
ISSN1876-0813
Autores Tópico(s)Synthesis of heterocyclic compounds
ResumoThe long-established use of colchicine in the treatment of gout, the discovery of its antimitotic activity, and the chemical studies culminating in the elucidation of the structure of this unusual molecule continue to stimulate widespread investigations by chemists, biologists, and pharmacologists. Recent work on colchicine and related alkaloids has had two major foci—the total synthesis and the biosynthesis of colchicine. In addition, structures have been unambiguously determined for α- and β-lumicolchicine, as well as for several other natural and photochemical compounds. Studies on the optical rotatory dispersion (ORD)-, nuclear magnetic resonance (NMR)-, and mass-spectra of colchicine and related compounds have appeared that may be of diagnostic value to future investigations in the field. The results of recent isolation studies have been summarized in this chapter. It discusses the synthesis of colchicine degradation products and related spectroscopic examination—optical rotation and optical rotatory dispersion, nuclear magnetic resonance, and mass spectra. Both colchicine and isocolchicine exhibit double negative cotton effects (330 and 280 mμ). Recently, NMR-analysis has contributed to the structural elucidation of colchicine-type compounds and also to the transformation products, oxycolchicine and lumicolchicines. A number of colchicine derivatives have been analyzed by mass spectroscopy under conditions that allowed clear fragmentation patterns to be observed in the high mass region. The Treatment of colchicine with chromic acid furnishes oxycolchicine that contains extra oxygen and shows no loss of carbon.
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