InChI=1S/C13H15ClO5S/c1-13(2)7-9(12(15)19-13)8-18-20(16,17)11-5-3-10(14)4-6-11/h3-6,9H,7-8H2,1-2H3 |
HDBZILYPRPDNTH-UHFFFAOYSA-N |
CC1(C)CC(COS(=O)(=O)c2ccc(Cl)cc2)C(=O)O1 |
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Outgoing
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3-[(4-chlorophenylsulfonyloxy)methyl]-5,5-dimethylbutyrolactone
(CHEBI:59149)
is a
arenesulfonate ester
(CHEBI:38094)
3-[(4-chlorophenylsulfonyloxy)methyl]-5,5-dimethylbutyrolactone
(CHEBI:59149)
is a
butan-4-olide
(CHEBI:22950)
3-[(4-chlorophenylsulfonyloxy)methyl]-5,5-dimethylbutyrolactone
(CHEBI:59149)
is a
monochlorobenzenes
(CHEBI:83403)
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(5,5-dimethyl-2-oxooxolan-3-yl)methyl 4-chlorobenzene-1-sulfonate
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(5,5-dimethyl-2-oxotetrahydrofuran-3-yl)methyl 4-chlorobenzenesulfonate
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IUPAC
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3-(4-chlorobenzenesulfonyl)oxymethyl-5,5-dimethyldihydro-2(3H)-furanone
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ChEBI
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3-[(4-chlorobenzenesulfonyl)oxymethyl]-5,5-dimethyldihydro-2(3H)-furanone
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ChEBI
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Franot C, Roberts DW, Basketter DA, Benezra C, Lepoittevin JP (1994) Structure-activity relationships for contact allergenic potential of gamma,gamma-dimethyl-gamma-butyrolactone derivatives. 2. Quantitative structure-skin sensitization relationships for alpha-substituted-alpha-methyl-gamma,gamma-dimethyl-gamma-butyrolactone s. Chemical research in toxicology 7, 307-312 [PubMed:8075361] [show Abstract] A skin sensitization cross-challenge dataset for a series of alpha-(X-substituted-methyl)-gamma,gamma-dimethyl-gamma-butyrolactones is analyzed in terms of the relative alkylation index (RAI) model. The data analyzed consist of guinea pig sensitization response data for tests in which one lactone derivative is used for the induction stage and then the animals are challenged with another lactone derivative to elicit the response. RAI values are based on calculated log P (octanol/water) values together with measured relative rate constants for reactions of the lactones with n-butylamine to form alpha-methylene-gamma,gamma-dimethyl-gamma-butyrolactone. Plots of biological response against RAI for induction (RAIi) for sets of data in which the same compound is used for challenge have the double-sigmoid shape typical of sensitization response--RAIi plots, with some points in the overload region. Relative elicitation potential (REP) values, defined in terms of the biological response when sensitized animals are challenged with the compound in question relative to the response when the same animals are challenged with a chosen reference compound, are obtained. Consistent with the RAI model, plots of REP against RAIc, the RAI value corresponding to challenge, are linear and the slopes of plots corresponding to different reference compounds are, within the limits of experimental error, in the same ratio as the REP values of the reference compounds. Finally, multiple linear regression analysis gives a quantitative structure-activity relationship (QSAR) covering the complete set of cross-challenge data, relating the biological responses to the RAIi and RAIc values.(ABSTRACT TRUNCATED AT 250 WORDS) | Franot C, Roberts DW, Smith RG, Basketter DA, Benezra C, Lepoittevin JP (1994) Structure-activity relationships for contact allergenic potential of gamma,gamma-dimethyl-gamma-butyrolactone derivatives. 1. Synthesis and electrophilic reactivity studies of alpha-(omega-substituted-alkyl)-gamma,gamma-dimethyl-gamma-butyrolacton es and correlation of skin sensitization potential and cross-sensitization patterns with structure. Chemical research in toxicology 7, 297-306 [PubMed:8075360] [show Abstract] A series of alpha-(X-substituted-methyl)-gamma,gamma-dimethyl-gamma-butyrolactones (series 1), a series of alpha-(2-X-substituted-ethyl)-gamma,gamma-dimethyl-gamma-butyrolactones (series 2), where X is a leaving group, and the compound alpha-(3-bromopropyl)-gamma,gamma-butyrolactone (3) were synthesized. Their reactions as electrophiles toward n-butylamine, used as a model for nucleophilic groups on skin proteins whose in vivo chemical modification leads to skin sensitization, were investigated. The compounds of series 1 were shown to react via a two-stage elimination--Michael addition sequence whereby the elements of HX are eliminated to form alpha-methylene-gamma,gamma-dimethyl-gamma-butyrolactone, which reacts more slowly with n-butylamine to give alpha-[(N-butylamino)methyl]-gamma,gamma-dimethyl-gamma-butyrolactone. The compounds of series 2 and compound 3 were shown to react with n-butylamine via a single-stage substitution reaction to give respectively alpha-[2-(N-butylamino)ethyl]- and alpha-[3-(N-butylamino)propyl]-gamma,gamma-dimethyl-gamma-butyrolactones . Rate constants for these reactions have been determined, and it is found that substitution reactions of series 2 and compound 3 are slower than Michael addition of alpha-methylene-gamma,gamma-dimethyl-gamma-butyrolactone, which in turn is slower than the elimination reactions of series 1. The results of guinea pig skin sensitization tests on these compounds were found to be consistent with the above findings in that the compounds of series 1 were found to be in general much stronger sensitizers than those of series 2 and compound 3. The results of cross-challenge tests indicate that sensitizing compounds from series 2 were cross-reactive with both series 1 and compound 3 but that compound 3 is only weakly cross-reactive with series 1. These observations indicated that for these compounds a difference of two carbon atoms between the determinant groups transferred to protein had a markedly greater effect than a difference of one carbon atom on antigenic specificity. |
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