A New Synthesis of 3-Arylthioindoles

Atkinson, J. G.; Hamel, P.; Girard, Yves

doi:10.1055/s-1988-27615

Cited by 59 publications

(31 citation statements)

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“…The required 3-arylthio intermediates were obtained by Atkinson reaction from appropriate 1H-indole-2-carboxylic acids and arylthiodisulfides in the presence of sodium hydride, and subsequent transformation of acids 28 in the corresponding methyl esters with (trimethylsilyl) diazomethane (SupplementaRy FiguRe 5) [44]. In an improved procedure, the esters of the indole were treated with N-(arylthio)succinimides in the presence of boron trifluoride diethyl etherate to furnish esters 29.…”

Section: Indolylarylsulfonesmentioning

confidence: 99%

Arylsulfone-Based HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors

et al. 2013

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HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) represent one of the most significant classes of drugs for the treatment of AIDS/HIV infection. Over the past two decades several potent arylsulfone-based HIV-1 NNRTIs and related analogs have been developed. This review provides an essential overview of the structure-activity relationships of the arylsulfone-based HIV-1 NNRTIs. Furthermore, structural information useful for the design and development of new sulfur containing NNRTIs with enhanced antiretroviral activity against HIV-1 wild type and clinically relevant drug resistant HIV-1 mutant strains will be discussed.

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Section: Indolylarylsulfonesmentioning

confidence: 99%

Arylsulfone-Based HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors

et al. 2013

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“…3-Phenylthio-1H-indole (113) was synthesized by reacting indole with 1,1 0 -diphenyldisulfide in the presence of NaH in anhydrous DMF, following the procedure reported by Atkinson. 55 Using this method methyl 3-phenylthio-1H-indole-2-carboxylate (114) was obtained in poor yield starting from methyl indole-2-carboxylate. To improve the yield, compound 113 was synthesized using N-phenylthiosuccinimide in the presence of boron trifluoride diethyl etherate, as previously reported for compound 117.…”

Section: H Arylthioindolesmentioning

confidence: 99%

Indole, a core nucleus for potent inhibitors of tubulin polymerization

Brancale

Silvestri

2006

Medicinal Research Reviews

338

134

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Microtubules are the basic components of cell structure, which take part in a wide number of pivotal cellular functions. Drugs that are able to modulate the microtubule assembly either by inhibition of tubulin polymerization or by blocking microtubule disassembly are of great interest in anti-cancer therapy. Several tubulin polymerization inhibitors characterized by the presence of an indole nucleus have been obtained from natural sources or have been prepared by semi-synthesis. In the last decade an ever increasing number of synthetic indoles have been reported. We have reviewed anti-tubulin agents obtained by synthesis having an indole as core nucleus. The synthesis, the biological activity, and the structure - activity relationship aspects of 3-formyl-2-phenylindoles, heterocombretastatins, diarylindoles, 2-aroylindoles, D-24851, 2-aryl-3-aroylindoles, 3-aroyl- and 1-aroylindoles, and arylthioindoles are discussed.

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“…2-Phenylsulfonylindole (1a) and 3-phenylsulfonylindole (1b), which we propose for use as the synthetic equivalents of unsubstituted indole in N-alkylation reactions, may be obtained readily by oxidation of the corresponding sulfides 2a [20] and 2b [21] As described by Broggini et al [22], the oxidation of indol-3-yl phenyl sulfide (2b) by 3-chloroperbenzoic acid leads to the corresponding sulfone 1b in high yield. The use of the same reagent for oxidation of isomeric sulfide 2a yielded corresponding sulfone 1a in only 52% yield.…”

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confidence: 81%

“…Indol-2-yl Phenyl Sulfide (2a) [20] and Indol-3-yl Phenyl Sulfide (2b) [21] were prepared according to previously described by Hamel et al…”

Section: Methodsmentioning

confidence: 99%

2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions

Карчава

Шулева

Ovcharenko

et al. 2010

Chem Heterocycl Comp

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The N-alkylation of 2-and 3-phenylsulfonylindoles under various conditions and the subsequent removal of the activating phenylsulfonyl group by reductive desulfonylation using Raney nickel leads to N-alkylindoles in high yield. 2-Phenylsulfonylindole readily undergoes the Mitsunobu reaction, while isomeric 3-phenylsulfonylindole is relatively inert under these conditions.In medicinal chemistry, indole derivatives form one of the most important classes of heterocyclic compounds [1]. This importance is due to the wide distribution of the indole fragment in the structures of natural and synthetic biologically active compounds with a broad range of activities. An enormous variety of efficient synthetic methods for construction of the bicyclic indole system and its modifications is already known [2, 3]. Nevertheless, the search for new, reliable, and simple synthetic transformations for indole derivatives remains a subject of current research.The direct N-alkylation of indole is clearly the most attractive method for obtaining N-alkyl derivatives. The initial generation of the indolyl anion is usually required for the success of this reaction. However, the ambident properties of the indolyl anion facilitate formation of N-alkylation, C-alkylation, and N,C-dialkylation products [2,4,5]. The selectivity of the reaction of the indolyl anion and the alkylating agent depends significantly on the nature of the cation, solvent, and structure of the alkylating agent. Although high selectivity for this reaction may be achieved by varying these factors, the problem of selective preparation of an indole N-alkylation product requires a specific solution in each concrete case [2, 6-8]. Special synthetic methods based on the use of phase-transfer catalysis [9][10][11], ionic liquids as the solvent [12,13], other special solvents [14,15], bases [16], and alkylating agents [17], as well as microwave irradiation have been proposed to resolve this problem. Furthermore, generation of the indolyl anion from an N-unsubstituted indole and indole derivatives lacking electron-withdrawing substituents requires the use of a stoichiometric amount of strong bases, which significantly limits the range of functional group tolerating the reaction conditions. It is also important to note _______ * Dedicated to Professor V. I. Minkin on the occasion of his seventieth birthday.

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A New Synthesis of 3-Arylthioindoles

Cited by 59 publications

References 0 publications

Arylsulfone-Based HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors

Arylsulfone-Based HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors

Indole, a core nucleus for potent inhibitors of tubulin polymerization

2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions

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