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Eight-Membered Rings With Two Heteroatoms 1,3

  • Authors: Parrino B.; Cascioferro S.; Carbone D.; Cirrincione G.; Diana P.
  • Publication year: 2022
  • Type: Capitolo o Saggio
  • Key words: 1,3-Diazocine; 2H-1,3-Oxazocine; 2H-1,3-Thiazocine; 4H-1,3-Dioxocin; 4H-1,3-Dithiocin; 4H-1,3-Oxathiocin; Anti-HIV agents; Anticancer agents; Biosynthetic pathways of 1, 3-heterocines; Cholesterylester transfer protein (CETP) inhibitors; Cold-menthol receptor TRPM8 modulators; Equilibrative nucleoside transporter 1 (ENT1) inhibitors; Histone deacetylase 6 inhibitors
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Eight-membered rings with two heteroatoms in a 1,3-relationship, namely 1,3-diazocine, 2H-1,3-oxazocine, 2H-1,3-thiazocine, 4H-1,3-dioxocin, 4H-1,3-oxathiocin, and 4H-1,3-dithiocin, are discussed in this chapter, that covers the literature from 2007 to October 2020 (SciFindern search) and reports the chemistry of uncondensed derivatives, heterocines fused to carbocycles and heterocycles, as well as bridged heterocines. Among eight-membered 1,3-diheterocines, 1,3-diazocines and 1,3-oxazocines are the two largest classes, based on the number of publications, mostly due to the studies of the synthesis of these cyclic systems, their pharmacological properties and/or their important industrial applications. The main change in this chapter, with respect to CHEC-III, is related to the introduction of “Biosynthesis” section, since Nature in recent years has made a significant contribution to the synthesis of secondary metabolites, especially for biologically active ones. In this paragraph, the natural sources and the proposed biosynthetic pathways are reported. “Experimental Structural Methods” paragraph it was avoided reporting the spectroscopic data (NMR, IR, UV etc.) as in the previous edition they were extensively provided and, in the latest period, they remained in the same range. Analogously, the same behavior was maintained for physical properties (solubility, melting points, chromatographic behavior, conformational issues) thanks to the coverage in “Thermodynamic Aspects” paragraph of CHEC-III, which remained substantially unchanged to-date. Some section headings (for example, ‘Reactivity of fully conjugated rings’) are missing, in the cases where no advances have been reported since 2007.