Synthesis and anti-BVDV activity of novel δ-sultones in vitro: Implications for HCV therapies

Progress in the synthesis of δ-sultones

“…A broad variety of enolate-type nucleophilic addition reactions to access differently ring-sized sultones have been reported in the past [ 12 , 13 , 88 – 95 ], either via cyclization/addition of sulfonate-based carbanions to an adjacent electrophilic position (e.g., an ester or an aldehyde) or by adding enolates to activated electrophilic sulfuric acid species. In 1972 already, Timoney et al carried out the base-mediated cyclization of mesylates 68 to access the bicyclic δ-sultones 69 , albeit in low yield [ 88 ].…”

“…In an analogous fashion, the intramolecular aldol-type cyclization of ortho-formyl substituted O-mesylated phenol derivatives 70 has been successfully employed by several groups to access the valuable δ-sultones 71 (Scheme 14 ), which can then serve as building blocks for a variety of further transformations and as intermediates en route to potentially biologically active molecules [ 90 – 92 ]. One interesting example highlighting the potential of these cyclization approaches was reported in 2014 [ 12 ], where a broad variety of the potential anti BVDV (bovine viral diarrhea virus) active bicyclic δ-sultones 74 was access in a straightforward manner starting from lactones 73 under the basic conditions.

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Updating the CSIC Reaction (2003–2020)

“…[6] However, Xu and colleagues (reference 12 in Waser's review) used and cited the CSICr without complexes and prejudices. [7] Other authors neglected also the new name reaction to figure it: "…Aldol-Type Condensations and Related Processes…On the other hand, the intramolecular condensations of alkanesulfonates, derived from cyanohydrins, in the presence of different bases lead directly to β-amino α,β-unsaturated γ-sultone…", [8] or were totally reluctant to use the CSICr name, [9] still preferring the aldol reaction name, even in transformations using simple, non-carbohydrate precursors [10] following years later the original and pioneering approach proposed by Marco-Contelles [1,11] to extend the scope of the original sugar-like CSICr discovered by Gómez de las Heras et al [4] Then, since the beginning it was clear for us that a full survey of the real progresses of CSICr would be a difficult task, almost impossible. Consequently, and advancing our apologies for involuntary oversights and uncited articles, we decided to update and summarize the developments of CSICr from 2003, including SciFinder ® search as noted above, the contributions for the most dedicated CSICr practitioners, highlighting author contributions who cited the CSICr name reaction in the context of their research, [12] or communications citing [13] the seminal review.…”

Actinobacteria from Termite Mounds Show Antiviral Activity against Bovine Viral Diarrhea Virus, a Surrogate Model for Hepatitis C Virus

“…There are no available vaccines for the prevention of HCV infection, and current therapy involves a combination of interferon-R (PEG-INF) and ribavirin (1- β -D-ribofuranosyl-1,2,4 triazole-3-carboxamide), a nucleoside analog [ 5 , 6 ]. In addition to its costliness, this treatment is only effective for HCV genotype 1-infected patients and produces numerous side effects, including psychiatric disorders, hemolytic anemia, and changes in blood cell counts, leading to discontinuation [ 5 , 7 ]. Protease inhibitors (PI), including boceprevir and telaprevir, have revolutionized the treatment of HCV genotype 1 infections; however, combination treatments using PIs have been associated with adverse events, which also lead to the early termination of therapy [ 8 ].…”