Sulfones. I. The Isomeric X,x'-Diaminodiphenyl Sulfones

Baker, B. R.; Kadish, Arthur F.; Querry, Merle V.

doi:10.1021/jo01148a027

Cited by 11 publications

(8 citation statements)

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“…3,3'-Diaminodiphenyl sulphone (3,3'DDS) and 3,4diaminodiphenyl sulphone (3,4DDS) were synthesized according to the methods of Baker et al (1950). 4,4-Diaminodiphenyl sulphone (DDS) was supplied by the Sigma Chemical Co. Ltd (Poole, UK).…”

Section: Methodsmentioning

confidence: 99%

“…4,4-Diaminodiphenyl sulphone (DDS) was supplied by the Sigma Chemical Co. Ltd (Poole, UK). 3,3'-Diaminodiphenyl sulphone (3,3'DDS) and 3,4diaminodiphenyl sulphone (3,4DDS) were synthesized according to the methods of Baker et al (1950). 4-Acetyl 4aminodiphenyl sulphone (MADDS), 4,4-diacetyl diphenyl sulphone (DADDS), 4,4'-diaminodiphenyl thioether, (DDT); 4-acetyl-4aminodiphenyl thioether (MADDT) and 4,4-diacetyl diaminodiphenyl thioether (DADDT) were synthesized according to the methods of Raiziss et al(1939).…”

Section: Methodsmentioning

confidence: 99%

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An Investigation into the Haematological Toxicity of Structural Analogues of Dapsone In-vivo and In-vitro

Coleman

Tingle

Hussain

et al. 1991

Journal of Pharmacy and Pharmacology

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With microsomes prepared from a single human liver, 4,4'-diaminodiphenyl sulphone (DDS), 4-acetyl-4-aminodiphenyl sulphone (MADDS), 4-acetyl-4-aminodiphenyl thioether (MADDT) and 4,4'-diacetyldiphenyl thioether (DADDT) caused significantly greater methaemoglobin formation compared with control. In-vitro in the rat, the pattern of toxicity was slightly different:DADDT was not haemotoxic, whilst 3,4'-diaminodiphenyl sulphone (3,4'DDS) and 3,3'-diaminodiphenyl sulphone (3,3'DDS) as well as DDS, MADDS and MADDT were significantly greater than control. 4,4' Acetyl diphenyl sulphone (DADDS), 4,4' diaminodiphenyl thioether (DDT), 4,4'-diaminodiphenyl ether (DDE) and 4,4' diaminooctofluorodiphenyl sulphone (F8DDS) did not cause significant methaemoglobinaemia in either human or rat liver microsomes. DDS, MADDS, and MADDT were not significantly different in haemotoxicity generation in-vitro in the presence of human microsomes. In the rat in-vitro, DDS, MADDS, and 3,4'DDS did not differ significantly in red cell toxicity, and were the most potent methaemoglobin formers. The 3,3'DDS and MADDT derivatives were both significantly less toxic compared with DDS. None of the compounds tested caused haemoglobin oxidation in the absence of NADPH in-vitro. In the whole rat, DDS, MADDS and MADDT caused significantly higher levels of methaemoglobin compared with control. None of the remaining compounds caused methaemoglobin formation which was significantly greater than control. DDS and MADDS were the most potent methaemoglobin formers tested, in-vivo and in-vitro.(ABSTRACT TRUNCATED AT 250 WORDS)

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

An Investigation into the Haematological Toxicity of Structural Analogues of Dapsone In-vivo and In-vitro

Coleman

Tingle

Hussain

et al. 1991

Journal of Pharmacy and Pharmacology

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“…Recently, 3,3'-diamino diphenyl sulfone dissolved in ethanol was mixed directly with monophosphoric acid to prepare a new organic-inorganic hybrid crystal material, [C48H51N8O8S4](HPO4)H2PO4, which has a noncentrosymmetric structure and can be a good candidate for nonlinear optic applications 6 . The easiest method of introducing an amino group in 3-position appeared to be by nitration of the proper sulfone, a meta-directing group, followed by reduction 7 . In industry, 3,3'diamino diphenyl sulfone is synthesized via reduction of 3,3'dinitro diphenyl sulfone generated from the nitration reaction of diphenyl sulfone (DPS) as shown in Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Quality Control of 3,3'-Diamino Diphenyl Sulfone by High Performance Liquid Chromatography

Wei-qun¹,

Lian²,

Jun-qin³

et al. 2014

Asian J. Chem.

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An effective reversed-phase high performance liquid chromatographic method has been developed to separate industrial 3,3'-diamino diphenyl sulfone and its related substances. Separation was achieved on a reversed-phase C18 column with methanol-water (40/60, v/v) as the mobile phase and detection was operated by UV absorption at a wavelength of 250 nm. One unknown impurity, 3,4'-diamino diphenyl sulfone, was identified by the combination of liquid chromatography-mass spectrometry and relationship between RP-HPLC retention and hydrophobicity of the compounds studied. Partial related impurities, 4,4'-diamino diphenyl sulfone, 3,4'-diamino diphenyl sulfone and 3-amino-3'-nitro diphenyl sulfone were determined under the proposed chromatographic condition with relative standard deviations lower than 4.4 %. On the basis of good separation and reliable determination of related substances in 3,3'-diamino diphenyl sulfone, the chromatographic fingerprint of industrial 3,3'-diamino diphenyl sulfone was established, by which quality assessment of 3,3'-diamino diphenyl sulfone could be facilitated for industrial use.

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“…Numbers 4, 5, and 6 were recrystallized from Methyl Cellosolve-water. 1 The crude yield, m.p. 124-126°.…”

mentioning

confidence: 99%

“…242-243°and crude yield, 66%. 1 Melts at 165°, resolidifies and remelts at 185°when crystallized from alcohol. = Contains one-half molecule benzene of crystallization.…”

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confidence: 99%