ChemInform Abstract: Explosive Hazard of Esters of Sulfonic Acids.

Collin, D. T.; Wilson, D. R.

doi:10.1002/chin.198724090

ChemInform

1987

DOI: 10.1002/chin.198724090

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ChemInform Abstract: Explosive Hazard of Esters of Sulfonic Acids.

D. T. Collin¹,

D. R. Wilson²

Abstract: 090ChemInform Abstract The cyclobutylmethyl sulfonate (Ia) decomposes explosively on heating to produce the cyclopentene (II) and the sulfonic acid (III). The compounds (Ib) and (IV) perform similar but less energetic cleavage reactions.

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2023

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“…1.86 g (65%) of a white solid; 1 H NMR (400 MHz,5-(Cyclobutylmethylthio)-2H-tetrazole (65h).Prepared from cyclobutylmesylate (63h) 37. (Note: Cyclobutylmethylmesylate is an explosion hazard38 ) The crude product was purified by trituration with diethyl ether/heptane. 1.20 g, 100% of a white solid;1 H NMR (400 MHz, CDCl3): δ = 3.35 (d, J = 7.6 Hz, 1H), 2.70-2.59 (m, 1H), 2.14-2.05 (m, 2H), 1.90-1.65 (m, 4H).…”

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Discovery of 1,3,4-oxadiazoles with slow-action activity againstPlasmodium falciparummalaria parasites

Andrews

Fisher

Firmin

et al. 2023

Preprint

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To achieve malaria eradication, new preventative agents that act differently to front-line treatment drugs are needed. To identify potential chemoprevention starting points we screened a sub-set of the CSIRO Australia Compound Collection for compounds with slow-action in vitro activity against Plasmodium falciparum. This work identified N,N-dialkyl-5-alkylsulfonyl-1,3,4-oxadiazol-2-amines as a new antiplasmodial chemotype (e.g., 1 96 h IC50 550 nM) with a different action to delayed-death slow-action drugs. Structure activity relationship analysis of analogues identified multiple compounds with potent and selective in vitro activity against drug-sensitive and multi-drug resistant Plasmodium parasites (e.g., 31 and 32 96 h IC50 <40 nM; SI >2,500). However subsequent studies in mice with lead compound 1, which had the best microsomal stability of the compounds assessed, demonstrated rapid clearance (T1/2 <1.6 h) and poor oral in vivo efficacy. This indicates that improvements in the pharma-cokinetic profile of N,N-dialkyl-5-alkylsulfonyl-1,3,4-oxadiazol-2-amines would be needed for the development of this chemotype for malaria chemoprophylaxis.

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mentioning

confidence: 99%

Discovery of 1,3,4-oxadiazoles with slow-action activity againstPlasmodium falciparummalaria parasites

Andrews

Fisher

Firmin

et al. 2023

Preprint

View full text Add to dashboard Cite

show abstract

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ChemInform Abstract: Explosive Hazard of Esters of Sulfonic Acids.

Abstract: 090ChemInform Abstract The cyclobutylmethyl sulfonate (Ia) decomposes explosively on heating to produce the cyclopentene (II) and the sulfonic acid (III). The compounds (Ib) and (IV) perform similar but less energetic cleavage reactions.

Cited by 1 publication

References 0 publications

Discovery of 1,3,4-oxadiazoles with slow-action activity againstPlasmodium falciparummalaria parasites

Discovery of 1,3,4-oxadiazoles with slow-action activity againstPlasmodium falciparummalaria parasites

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