ChemInform Abstract: Synthesis and in vivo Antitumor and Antiviral Activities of 2′‐Deoxyribofuranosyl and Arabinofuranosyl Nucleosides of Certain Purine‐6‐sulfenamides, ‐sulfinamides and ‐sulfonamides.

Revankar, Ganapathi R.; Hanna, Naeem B.; Ramasamy, K.; Larson, S. B.; Smee, D. F.; Finch, Robert A.; Avery, Thomas L.; Robins, Roland K.

doi:10.1002/chin.199047250

Cited by 2 publications

(2 citation statements)

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“…In the quest for searching for an exclusive application of alternating current protocols in organic synthesis, we discovered that the radical-radical cross-coupling to form an N-S bond represents a suitable class of reaction, that could not be delivered via DC electrolysis (Figure 1E and 1F). N-S bonds are versatile structural components, because they are ubiquitous structural motifs present in many valuable molecules (Figure 2A), [25][26][27][28][29][30][31][32][33] and also valuable reagents in organic transformations. [34][35][36][37][38][39][40] Over the past decades, methods for N-S bonds containing compounds synthesis have been largely developed.…”

Section: (B) Previous Methods For N-s Bonds Formation (C) Our Design For N-s Bonds Formationmentioning

confidence: 99%

Radical–Radical Cross-Coupling Assisted N–S Bond Formation Using Alternating Current Protocol

Yuan

Wang

et al. 2022

CCS Chem

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Alternating current (AC) electrolysis is a promising, yet challenging, and under-developed protocol in organic synthesis. To achieve as high atom-efficiency as possible and avoid the use of external oxidant, the electrochemistry has become a standard organic synthesis tool. Herein, AC-based protocol is a superior option than its counterpart (DC: direct current), especially for those reactions that cannot be accomplished by DC.With an aim to achieve this objective, we have employed the AC electrolysis successfully to deliver the unprecedented cross-coupling of sulfonyl or acyl substituted aniline derivatives with thiophenols/thiols under exogenous-oxidant-and catalyst-free conditions. Numerous N-S bonds containing compounds (Total 40 number) have been prepared in up to 93% yield and good selectivity. Interestingly, no reactivity has been noted using DC electrolysis or traditional chemical approaches under our reaction conditions. Mechanistic studies indicated that disulfide is the key intermediate in this alternating current mediated radical-radical crosscoupling reaction. Therefore, the current work does not only provide an efficient method for N-S bonds formation, but also pave new sustainable avenues to innovation in organic synthesis.

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Section: (B) Previous Methods For N-s Bonds Formation (C) Our Design For N-s Bonds Formationmentioning

confidence: 99%

Radical–Radical Cross-Coupling Assisted N–S Bond Formation Using Alternating Current Protocol

Yuan

Wang

et al. 2022

CCS Chem

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“…Revankar et al [69] reported elimination of 2'-deoxy-6-thioinosine and 9-β-Darabinofuranosyl-6-thiopurine with chloramine to prepare corresponding 6sulfenamides which on oxidation by excess metachloroperbenzoic acid (mCPBA) produced corresponding sulfonamide in 48% yield (scheme 19). (mCPBA) was used as an oxidizing agent for the oxidation of sulfur to produce the corresponding sulfone.…”

Section: Scheme 18; Synthesis Of Sulfonamide From Sulfonic Acid Usingmentioning

confidence: 99%

Sulfonamides: Synthesis and the recent applications in Medicinal Chemistry

et al. 2020

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This review spotlights on sulfonamides from different sides, including history, structure-activity relationship, chemistry, methods of classification and up to date ways for their synthesis. Moreover, the review includes a discussion of the varied pharmacological effects of sulfonamides. Sulfonamides have a good range of pharmacological activities like oral diuretics (furosemide, indapamide, chlorthalidone, thiazides); anticancer (E7070), carbonic anhydrase (CA) inhibitors (CAIs) (acetazolamide, dichlorophenamide, dorzolamide and brinzolamide), antiepileptics (zonisamide and sulthiame), for rheumatoid arthritis (Sulfasalazine) antiviral (Darunavir) anti-inflammatory (celecoxib), antibacterial (Sulfadizine), as ophthamologicals (Dorzolamide) anticonvulsant (Zonisamide) cycloxygenase 2 (COX2) inhibitors (valdecoxib). These days, novel pills are launched, like apricoxib and pazopanib, which additionally include this organization. The sulfonamides competitively inhibit vitamin Bc synthesis in microorganisms and subsequently inhibit multiplication of bacteria but donot actively kill them. They need been used against most gram-positive and lots of gram-negative bacteria, also as some fungi.

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ChemInform Abstract: Synthesis and in vivo Antitumor and Antiviral Activities of 2′‐Deoxyribofuranosyl and Arabinofuranosyl Nucleosides of Certain Purine‐6‐sulfenamides, ‐sulfinamides and ‐sulfonamides.

Abstract: The amination products (III) from the thiopurines (I) are oxidized to the corresponding (R,S)‐sulfoxides (IV) or sulfones (V).

Cited by 2 publications

References 1 publication

Radical–Radical Cross-Coupling Assisted N–S Bond Formation Using Alternating Current Protocol

Radical–Radical Cross-Coupling Assisted N–S Bond Formation Using Alternating Current Protocol

Sulfonamides: Synthesis and the recent applications in Medicinal Chemistry

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