The conversions of isothiazolium salts into thiophenecarboxylic ester derivatives

McKinnon, David M.; Duncan, K. Ann; Millar, Lesley M.

doi:10.1139/v84-271

Cited by 9 publications

(2 citation statements)

References 3 publications

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“…Yields and essential analytical data are reported in the Supporting Information. Analytical data for compounds 42 – 46 , 50 – 53 matched the data already published. − …”

Section: Methodssupporting

confidence: 66%

Accepting the Invitation to Open Innovation in Malaria Drug Discovery: Synthesis, Biological Evaluation, and Investigation on the Structure–Activity Relationships of Benzo[b]thiophene-2-carboxamides as Antimalarial Agents

Pieroni¹,

Azzali²,

Basilico

et al. 2017

J. Med. Chem.

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Malaria eradication is a global health priority, but current therapies are not always suitable for providing a radical cure. Artemisinin has paved the way for the current malaria treatment, the so-called Artemisinin-based Combination Therapy (ACT). However, with the detection of resistance to ACT, innovative compounds active against multiple parasite species and at multiple life stages are needed. GlaxoSmithKline has recently disclosed the results of a phenotypic screening of an internal library, publishing a collection of 400 antimalarial chemotypes, termed the "Malaria Box". After analysis of the data set, we have carried out a medicinal chemistry campaign in order to define the structure-activity relationships for one of the released compounds, which embodies a benzothiophene-2-carboxamide core. Thirty-five compounds were prepared, and a description of the structural features responsible for the in vitro activity against different strains of P. falciparum, the toxicity, and the metabolic stability is herein reported.

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“…Yields and essential analytical data are reported in the Supporting Information. Analytical data for compounds 42 – 46 , 50 – 53 matched the data already published. − …”

Section: Methodssupporting

confidence: 66%

Accepting the Invitation to Open Innovation in Malaria Drug Discovery: Synthesis, Biological Evaluation, and Investigation on the Structure–Activity Relationships of Benzo[b]thiophene-2-carboxamides as Antimalarial Agents

Pieroni¹,

Azzali²,

Basilico

et al. 2017

J. Med. Chem.

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“…Synthesis of 2-(alkoxycarbonyl)-3-aminothiophenes has been achieved by treatment of either β-chlorocinnamonitriles with thioglycolic acid esters in the presence of a base or a base-catalyzed cyclization of β-alkylthio-α-cyanocinnamonitriles . Treatment of 2,5-diphenylisothiazolium perchlorate with dimethylsulfonium carbethoxymethylide gave 2-(ethoxycarbonyl)-5-phenyl-3-(phenylamino)thiophenes as a minor product …”

mentioning

confidence: 99%

Reactions of Thioaroylketene S,N-Acetals with 1,3-Dicarbonyl Compounds in the Presence of Mercury(II) Acetate: A General Route to 2-Acyl- and 2-Aroyl-3-(alkylamino)-5- arylthiophenes and 2-(Ethoxycarbonyl)-3- (methylamino)-5-arylthiophenes

1998

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Acyl-and aroylketene S,N-acetals have been extensively studied by Junjappa and co-workers 1 and utilized for the synthesis of a variety of heteroatom compounds. Surprisingly, much less attention has been focused on their analogues, thioaroylketene S,N-acetals 1. 2 This might be due to the difficulty of access to the compounds 1. Recently, we reported a facile and convenient method for the synthesis of compounds 1, which involves the reactions of 2-alkyl-3-(alkylthio)-5-arylisothiazolium iodides with NaBH 4 in a mixture of CHCl 3 and EtOH at room temperature. 3 We have shown that compounds 1 are useful for the synthesis of various heterocyclic compounds. 4 As a part of our study on exploring the synthetic potential of compounds 1, 3-(methylamino)-3-(methylthio)-1-phenylthioxopropene (1a) (0.172 mmol) was treated with mercury(II) acetate (0.172 mmol) in acetone (10 mL) for 1 h at room temperature in order to obtain information about a possible interaction between mercury(II) ion and the thione sulfur. Chromatography (silica gel, 70-230 mesh, ASTM) of the reaction mixture gave 2-acetyl-3-(methylamino)-5-phenylthiophene (2a) in 75% yield. The involvement of acetone as a reagent in this reaction prompted us to investigate the reactions of 1 with readily enolizable 1,3-dicarbonyl compounds. We report the preliminary results.

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Five‐Membered Heterocycles: 1,2‐Azoles. Part 2. Isoxazoles and Isothiazoles

Silva

Tomé

Melo

et al. 2011

Modern Heterocyclic Chemistry

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The conversions of isothiazolium salts into thiophenecarboxylic ester derivatives

Cited by 9 publications

References 3 publications

Accepting the Invitation to Open Innovation in Malaria Drug Discovery: Synthesis, Biological Evaluation, and Investigation on the Structure–Activity Relationships of Benzo[b]thiophene-2-carboxamides as Antimalarial Agents

Accepting the Invitation to Open Innovation in Malaria Drug Discovery: Synthesis, Biological Evaluation, and Investigation on the Structure–Activity Relationships of Benzo[b]thiophene-2-carboxamides as Antimalarial Agents

Reactions of Thioaroylketene S,N-Acetals with 1,3-Dicarbonyl Compounds in the Presence of Mercury(II) Acetate: A General Route to 2-Acyl- and 2-Aroyl-3-(alkylamino)-5- arylthiophenes and 2-(Ethoxycarbonyl)-3- (methylamino)-5-arylthiophenes

Five‐Membered Heterocycles: 1,2‐Azoles. Part 2. Isoxazoles and Isothiazoles

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