N-Sulfonated-N-Heterocycles: Synthesis, Chemistry, and Biological Applications

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N-Sulfonated-N-Heterocycles
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Contents
About the authors
1 Synthesis of N-sulfonated aziridines
1.1 Introduction
1.2 Synthesis of N-sulfonated aziridines via transferring of nitrogen to alkenes
1.2.1 The addition of nitrene species to alkenes
1.2.1.1 Nitrene transfer reactions using sulfonylimino iodinanes as nitrene precursors
1.2.1.2 Nitrene transfer reactions using sulfonamides as nitrene precursors
1.2.1.3 Nitrene transfer reactions using N-sulfonyl azides as nitrene precursors
1.2.1.4 Nitrene transfer reactions using haloamine-T as nitrene precursors
1.2.2 The addition of nitrogen-centered radical species to alkenes
1.3 Synthesis of N-sulfonated aziridines via transferring of carbon to N-sulfonyl imines
1.3.1 Direct aza-Darzens reaction
1.3.2 Reaction of N-sulfonyl imines with sulfonium ylides
1.4 Synthesis of N-sulfonated aziridines via intramolecular cyclization of amine derivatives
References
2 Chemistry of N-sulfonated aziridines and their use in polymerization reactions
2.1 Introduction
2.2 Chemistry of N-sulfonated aziridines
2.2.1 Ring-opening of N-sulfonated aziridines to acyclic amine derivatives
2.2.1.1 To β-phenylethylamine derivatives
2.2.1.2 To vicinal diamines
2.2.1.3 To allyl amines and enamines
2.2.1.4 To Ketimines
2.2.2 Ring-opening of N-sulfonated aziridines to other cyclic N-sulfonated aza-heterocycles
2.2.2.1 To N-sulfonated four-membered heterocycles
2.2.2.2 To N-sulfonated five-membered heterocyclic ring
2.2.2.3 To N-sulfonated six-membered heterocyclic ring
2.2.2.4 To N-sulfonated seven-membered heterocyclic ring
2.3 Uses of N-sulfonated aziridines in living aza-anionic polymerization
2.3.1 Bis(trimethylsilyl)amides-catalyzed anionic ring-opening polymerization of N-sulfonated aziridines
2.3.1.1 Copolymerization of different N-sulfonylaziridine monomers
2.3.2 Organocatalytic ring-opening polymerization of N-sulfonated aziridines
2.3.3 Synthesis of copolymers and block copolymers of N-sulfonylaziridine monomers with different well-known monomers
2.3.4 Functionalized poly(sulfonylaziridine)s prepared via APOR polymerization of N-sulfonylaziridine
2.3.4.1 Polyaziridine-based linear in-chain functionalized polymers
2.3.4.2 Polyaziridine-based linear chain-end functionalized polymers: Telechelic polyaziridines
2.3.4.3 Recent synthetic developments of polyaziridine-based macromolecular architectural polymers
2.3.5 Desulfonation: easy access of linear polyamides from polyaziridine prepared via the anionic polymerization of N-sulfo...
References
3 Synthesis of N-sulfonated azetidines and β-lactemes and their applications
3.1 Introduction
3.2 Synthesis of sulfonyl-activated azetidines and azetidin-2-ones
3.2.1 Ring expansion of sulfonyl-activated azidirine
3.2.1.1 To sulfonyl-activated azetidine
3.2.1.2 To sulfonyl-activated azetidin-2-ones (sulfonyl-activated β-lactam)
3.2.2 Synthesis of N-sulfonylazetidines via cycloaddition reactions
3.2.3 Synthesis of sulfonyl-activated azetidines and azetidin-2-ones via intramolecular cyclization of amine derivatives or...
3.2.3.1 To N-sulfonyl azetidines
3.2.3.2 N-sulfonyl azetidinone (N-sulfonyl β-lactam)
3.2.4 Synthesis of N-sulfonyl azetidine via ring contraction of 2-pyrrol-one
3.2.5 Synthesis of bicyclic β-lactams via a crossed-benzoin/oxy-cope rearrangement
3.3 Chemistry of sulfonyl-activated azetidine and azetidin-2-ones
3.3.1 To acyclic amine derivatives
3.3.2 To benzosultams
3.4 Sulfonyl-activated azetidine and azetidin-2-ones in polymerization application
3.4.1 Synthesis of poly(N-sulfonylaziridine)s via anionic polymerization
3.4.2 Synthesis of β-lactam-containing polymers via metathesis polymerization
References
4 N-Sulfonated N-azoles: Synthesis, chemistry and biological applications
4.1 Introduction
4.2 N-Sulfonated pyrroles
4.2.1 Synthesis
4.2.1.1 N-Sulfonyl triazole as a α-imino metallocarbene precursor in the synthesis of N-sulfonyl pyrroles and their derivatives
4.2.1.2 Transannulation reactions of N-sulfonyl triazoles with alkynes
4.2.1.3 Transannulation reactions of N-sulfonyl triazoles with alkenes
4.2.1.4 N-sulfonyl aziridines as a precursor for synthesis N-sulfonyl pyrroles and their derivatives
4.2.1.5 N-Sulfonyl ynamides as a precursor in the synthesis of fused N-sulfonyl pyrroles and their derivatives
4.2.2 Biological activity of N-tosyl pyrroles
4.2.2.1 Anticancer activity
4.2.2.2 Antiviral activity
4.3 Synthesis of N-tosyl isoxazoles and their derivatives
4.3.1 Synthesis
4.4 Synthesis of N-tosyl oxazoles and their derivatives
4.4.1 Synthesis
4.5 Synthesis of N-tosyl-1,2-thiazole and its derivatives
4.5.1 Synthesis
4.6 Synthesis of N-tosyl thiazole and its derivatives
4.6.1 Synthesis
References
5 Synthesis of N-sulfonated N-diazoles, their chemistry and biological assessments
5.1 Introduction
5.2 Synthesis of N-sulfonylimidazole and its derivatives
5.3 Uses of N-sulfonylimidazole derivatives
5.4 Chemistry of N-sulfonylpyrazoles
5.4.1 Synthesis of N-sulfonylated pyrazoles
5.5 Chemistry of N-sulfonylthiadiazole derivatives
5.5.1 Chemistry of thiadiazole moiety
5.6 Synthesis of 1,3,4-thiadiazole and 1,2,3-thiadiazole derivatives
5.7 Chemistry of N-sulfonyl-1,3,4-oxadiazoles
References
6 Synthesis, chemistry and uses of N-sulfonated N-triazoles and N-tetrazoles
6.1 Introduction
6.2 Synthesis of N-sulfonyl-1,2,3-triazoles
6.3 Reactions of N-sulfonyl-1,2,3-triazoles
6.3.1 Reactions with alcoholic compounds
6.3.2 Reactions with ketones
6.3.3 Reactions with substituted ether
6.3.4 Reaction with cyclohexane
6.3.5 Reactions with different amines
6.3.6 Reaction with bromocyanide
6.3.7 Hydrolysis
6.3.8 Miscellaneous reactions
6.3.9 Ring expansion
6.4 Chemistry of 1,2,4-triazoles
6.4.1 Synthesis of N-sulfonylated 1,2,4-triazoles
6.5 Biological activity of some N-sulfonyltriazoles
6.6 Chemistry of N-sulfonyl-1,2,3,4-tetrazoles
6.6.1 Synthesis of N-sulfonyl-1,2,3,4-tetrazoles
References
7 Synthetic approaches and biological evaluation of N-sulfonated N-azines
7.1 Introduction
7.2 Synthesis of N-sulfonyl pyridinone derivatives and their biological activities
7.2.1 Synthesis of N-sulfonyl 2-pyridinones
7.2.2 Synthesis of N-sulfonyl dihydro 2-pyridinones
7.2.3 Synthesis of N-sulfonyl tetrahydro 2-pyridinones
7.2.4 Synthesis of N-sulfonyl 3-pyridinones
7.2.5 Synthesis of N-sulfonyl 4-pyridinones
7.2.6 Synthesis of N-sulfonyl 2-quinolone and their derivatives
7.2.7 Synthesis of N-sulfonyl isoquinolone and their derivatives
7.2.8 Synthesis of N-sulfonyl pyridinone-fused heterocycles
7.3 Synthesis of N-sulfonyl pyridine derivatives and their biological activities
7.3.1 Synthesis of N-sulfonyl di- and tetrahydropyridines
7.3.2 Synthesis of N-sulfonyl pipyridines
7.3.3 Synthesis of N-sulfonyl quinolines
7.3.4 Synthesis of N-sulfonyl isoquinolines and their derivatives
7.3.5 Synthesis of N-sulfonyl pyridine-fused heterocycles
7.4 Synthesis of N-sulfonyl oxazine derivatives and their biological activities
7.4.1 Synthesis of N-sulfonyl 1,4-oxazines
7.4.1.1 Synthesis of N-sulfonyl di- and tetrahydro-1,4-oxazines
7.4.1.2 Synthesis of N-sulfonyl 1,4-benzoxazines
7.4.2 Synthesis of N-sulfonyl 1,3-oxazines
7.5 Synthesis of N-sulfonyl thiazine derivatives
7.5.1 Synthesis of N-sulfonyl 1,4-thiazines
7.5.2 Synthesis of N-sulfonyl 1,4-benzothiazines
References
8 Synthesis of N-sulfonated N-diazines, N-triazines and N-tetrazines; their uses and biological applications
8.1 Introduction
8.2 N-Sulfonyldiazines
8.2.1 N-Sulfonyl-1,4-diazines (N-sulfonyl pyrazines)
8.2.2 N-Sulfonyl-1,2-diazines (N-sulfonyl pyridazines)
8.2.3 N-Sulfonyl-1,3-diazines (N-sulfonyl pyrimidines)
8.3 N-Sulfonyl-triazines
8.3.1 N-Sulfonyl-1,2,4-triazines
8.3.2 N-Sulfonyl-1,3,5-triazines
8.3.3 N-Sulfonyl-1,2,3-triazines
8.4 N-Sulfonated tetrazines
References
9 Synthesis of N-sulfonated N-azepines
9.1 Introduction
9.2 N-Sulfonyl azepines
9.2.1 Metal-catalyzed intermolecular cyclization
9.2.1.1 Palladium-catalyzed reactions
9.2.1.2 Copper-catalyzed reactions
9.2.1.3 Silver catalyzed reactions
9.2.2 Metal-catalyzed intramolecular cyclization
9.2.2.1 Palladium-catalyzed reactions
9.2.2.2 Gold catalyzed reactions
9.2.2.3 Iridium catalyzed reactions
9.2.3 Other synthetic pathways
9.3 N-Sulfonyl dihydroazepines
9.3.1 Metal-catalyzed intermolecular cyclization
9.3.1.1 Palladium-catalyzed reactions
9.3.1.2 Silver catalyzed reactions
9.3.1.3 Rhodium-catalyzed reactions
9.3.2 Metal-catalyzed intramolecular cyclization
9.3.2.1 Palladium-catalyzed reactions
9.3.2.2 Gold catalyzed reactions
9.3.2.3 Silver catalyzed reactions
9.3.2.4 Rhodium-catalyzed reactions
9.3.2.5 Ruthenium catalyzed reactions
9.3.2.6 Platinum-catalyzed reactions
9.3.3 Other synthetic pathways
9.4 N-Sulfonyl tetrahydroazepines
9.4.1 Metal-catalyzed intermolecular cyclization
9.4.1.1 Rhodium-catalyzed reactions
9.4.2 Metal-catalyzed intramolecular cyclization
9.4.2.1 Pallidum catalyzed reactions
9.4.2.2 Gold catalyzed reactions
9.4.2.3 Rhodium-catalyzed reactions
9.4.2.4 Ruthenium catalyzed reactions
9.4.2.5 Molybdenum catalyzed reactions
9.4.2.6 Silver catalyzed reactions
9.4.3 Other synthetic pathways
References
10 Synthesis of N-sulfonated N-benzoazoles and their use in medicinal chemistry
10.1 Introduction
10.2 Chemistry of N-sulfonyl indoles
10.2.1 Biological activities of N-sulfonated indoles
10.2.1.1 Antiparasitic effect
10.2.1.2 5-HT6-antagonism
10.2.1.3 Anti-apoptotic effect
10.2.1.4 Retinoic acid receptor-related orphan receptor γ (ROR γ) agonists
10.2.1.5 Antipsychotics activity
10.2.1.6 anti-HIV-1 activity
10.3 Synthesis of N-sulfonyl benzoxazole
10.3.1 Synthesis of N-sulfonyl-1,2-benzoxazole
10.3.2 Synthesis of N-sulfonyl-1,3-benzoxazole
10.4 Synthesis of N-sulfonyl benzothiazoles
10.4.1 Synthesis of N-sulfonyl-1,2-benzothiazoles
10.4.2 Synthesis of N-sulfonyl-1,3-benzothiazoles
References
11 N-Sulfonated N-benzodiazoles and N-benzotriazoles: Synthesis and medicinal activity
11.1 Introduction
11.2 N-Sulfonyl benzimidazole
11.2.1 Synthesis of N- sulfonyl benzimidazole
11.2.2 Biological activities of N-sulfonyl benzimidazole derivatives
11.2.2.1 Antiinflammatory activity
11.2.2.2 Antitumor activity
11.2.2.3 Antitrypanosoma cruzi activity
11.2.2.4 Antiviral activity
11.2.2.5 5HT6 receptor antagonists
11.2.2.6 Antibacterial and urease inhibitory activity
11.2.2.7 Antimycobacterium activity
11.2.2.8 Anti-HIV mutant strains
11.2.2.9 Apoptosis enhancement activity
11.2.2.10 Inhibitors of NOD1-induced nuclear factor-jB activation
11.2.2.11 Anti-hepatitis B virus activity
11.3 N-Sulfonyl indazoles
11.3.1 Chemistry of N-sulfonyl indazoles
11.3.2 Biological activities of N-sulfonyl benzimidzole
11.3.2.1 5-HT6 antagonists
11.3.2.2 Antiepilepsy
11.3.2.3 HDAC inhibitor activity
11.4 N-Sulfonyl triazoles
11.4.1 Chemistry of N-sulfonyl triazoles
11.4.2 Biological activities of N-sulfonyl benzotriazoles
11.4.2.1 Sodium hydrogen exchanger inhibitory activity
11.4.2.2 Platelet aggregation inhibition activity
11.4.2.3 Antibacterial activity
References
12 N-Sulfonated N-benzoazines: Synthesis and medicinal chemistry
12.1 Introduction
12.2 N-Sulfonyl-cinnolines
12.2.1 Medicinal chemistry aspects
12.2.2 Synthetic aspects
12.3 N-Sulfonyl-phthalazine
12.3.1 Medicinal chemistry aspects
12.3.2 Synthetic aspects
12.3.2.1 Synthesis of N-methyl/phenylsulfonyl phthalazine
12.3.2.2 Synthesis of 3,4-dihydrobenzo[f]phthalazines
12.4 N-Sulfonyl-quinazolines
12.4.1 Medicinal chemistry aspects
12.4.2 Synthetic aspects
12.4.2.1 The preparation of dihydroquinazolines via metal-free [4+2] cycloaddition of ynamides with nitriles
12.4.2.2 Synthesis of imidazo- and pyrimido [1,2-b]-1,2-benzothiazine-6,6-dioxides
12.5 N-Sulfonyl-quinolines, – isoquinolines and their derivatives
12.5.1 Medicinal chemistry aspects
12.5.2 Synthetic aspects
12.6 N-Sulfonyl-quinolinones
12.6.1 Medicinal chemistry aspects
12.6.2 Synthetic aspects
12.6.2.1 Sulfonyl chalcones and their quinolinone derivatives
12.6.2.2 One-pot synthesis of aryl-sulfonyl quinolone derivatives
12.6.2.3 Synthesis of N-sulfonyl γ and δ-lactams via transition metal-free oxidative catalysis
12.6.2.4 Synthesis of N-sulfonyl-oxoquinoline heterocycles
12.7 N-Sulfonyl quinoxaline
12.7.1 Medicinal chemistry aspect
12.7.2 Synthetic aspects
12.7.2.1 Synthesis N-arylsulfonylquinoxaline
12.7.2.2 Synthesis of N1-arylsulfonyl-2-quinoxalinones
12.7.2.3 Synthesis of multisubstituted dihydroquinoxalin-2-one
References
13 Patents and applications of N-sulfonated N-heterocycles
13.1 Introduction
13.2 Three membered N-sulfonyl heterocycles
13.2.1 N-Sulfonyl aziridine
13.3 Four-membered N-sulfonyl heterocycles
13.3.1 N-Sulfonyl-azetidine and azetidine derivatives
13.3.1.1 Medical applications of azetidine derivatives
13.3.1.2 N-Sulfonyl azetidine derivatives for the treatment of hyperlipidemia
13.3.1.3 N-Sulfonyl azetidine derivatives for the treatment of muscular degradation disorders
13.3.1.4 N-Sulfonyl azetidine derivatives for the treatment of cardiac diseases
13.3.1.5 N-Sulfonyl azetidine derivatives for the treatment of cancer
13.3.1.6 N-Sulfonyl azetidine derivatives for the treatment of inflammation and related disorders
13.4 Five membered N-sulfonyl heterocycles
13.4.1 N-Sulfonyl imidazole and imidazoline derivatives
13.4.1.1 Medical applications of imidazole and imidazoline derivatives
13.4.1.2 N-Sulfonyl imidazole and imidazoline derivatives for the treatment of cancer
13.4.2 N-Sulfonyl pyrazole derivatives
13.4.2.1 Medical applications of pyrazole derivatives
13.4.3 N-sulfonated pyrrole and pyrrolidine
13.4.3.1 Medical applications of pyrrole and pyrrolidine derivatives
13.4.3.2 N-Sulfonyl pyrrole for pain management
13.4.3.3 N-Sulfonyl dihydro pyrrole and pyrrolidine for cancer treatment
13.5 Six membered N-sulfonyl heterocycles
13.5.1 N-Sulfonyl piperazine derivatives
13.5.1.1 Medical applications of piperazine derivatives
13.5.1.2 N-Sulfonyl piperazine for pain management
13.5.1.3 N-Sulfonyl piperazine for the treatment of Alzheimer’s disease
13.5.1.4 Treatment of diseases correlated to the production of reactive oxygen species
13.5.2 N-Sulfonyl piperidine derivatives
13.5.2.1 Medical applications of piperazine derivatives
13.5.2.2 N-Sulfonyl piperidine for the treatment of Alzheimer’s disease
13.5.2.3 N-Sulfonyl piperidine as ATP citrate lyase inhibitors
13.5.3 N-Sulfonyl pyrazine derivatives
13.5.3.1 Medical applications of pyrazine derivatives
13.5.3.2 N-Sulfonyl pyrazine derivatives for pain management
13.6 Fused N-sulfonyl heterocycles
13.6.1 N-Sulfonyl azaindoles
13.6.1.1 Medical applications of azaindole derivatives
13.6.1.2 N-Sulfonyl azaindole derivatives for treatment of inflammation
13.6.1.3 N-Sulfonyl azaindoles for treatment of HIV
13.6.1.4 N-sulfonyl azaindole for pain management
13.6.2 N-Sulfonyl benzimidazole
13.6.2.1 Medical applications of benzimidazole derivatives
13.6.2.2 N-Sulfonyl benzimidazole derivatives for the treatment of obesity
13.6.2.3 N-Sulfonyl benzimidazole derivatives as anticancer agents
13.6.2.4 N-Sulfonyl benzimidazole derivatives as antibacterial agents
13.6.2.5 N-Sulfonyl benzimidazole derivatives as antiviral agents
13.6.2.6 N-Sulfonyl benzimidazole derivative as immuno-modulators
13.6.3 N-Sulfonyl benzotriazole derivatives
13.6.3.1 Medical applications of benzotriazole derivatives
13.6.3.2 N-Sulfonyl benzotriazole derivatives as anticancer agents
13.6.3.3 N-Sulfonyl benzotriazole derivatives for treatment of HIV
13.6.3.4 N-Sulfonyl benzotriazole derivatives as phosphate transport inhibitors
13.6.3.5 N-Sulfonyl benzotriazole derivatives as human melanin-concentrating hormone receptor antagonists
13.6.3.6 N-Sulfonyl benzotriazole derivatives in the industry
13.6.3.6.1 Manufacturing a photo thermographic film
13.6.3.6.2 Process for manufacturing novel colorant compound
13.6.4 N-Sulfonyl indole derivatives
13.6.4.1 Medical applications of indole derivatives
13.6.4.2 N-Sulfonyl indole for inflammation-related disorders
13.6.4.3 N-Sulfonyl indole derivatives for the treatment of peptic ulcer
13.6.4.4 N-Sulfonyl indole derivatives for the treatment of Hepatitis B
13.6.4.5 N-Sulfonyl indole derivatives as anticancer agents
13.6.4.6 N-Sulfonyl indole derivatives for the treatment of Parkinson’s disease
13.6.4.7 N-Sulfonyl indole derivatives for the treatment of obesity
13.6.4.8 Other medical uses of N-sulfonyl indole
13.6.5 N-Sulfonyl quinoline and N-sulfonyl isoquinoline derivatives
13.6.5.1 Medical applications of quinoline and isoquinoline derivatives
13.6.5.2 N-Sulfonyl quinoline and N-sulfonyl isoquinoline derivatives for the treatment of cancer
13.6.6 Other N-Sulfonyl heterocycles
References
Index
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