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Title: Derivatization and biological activity studies of 3-chloro-3-chlorosulfenyl spiro tetrahydropyran/tetrahydrothiopyran-4,2'-chroman-4'-one
Authors: Hegab, Mohamed I
Tolan, Hala E M
Morsy, Eman M H
I S, Abdelsalam
Saleh, Alaa M
Gad, Farouk A
Abdel-Megeid, Farouk M E
Keywords: α-Chloro-β-oxosulfenyl chlorides;oxadithiin derivatives;sulfonamides;antioxidant;antimicrobial activity
Issue Date: Nov-2021
Publisher: NIScPR-CSIR, India
Abstract: The adducts 4a,b-7a,b have been obtained either by reducing α-chloro-β-oxosulfenyl chlorides 2a,b with iodide ion in the presence of dienes namely, 2-methyl-1,3-butadiene (isoperene), 2,3-dimethyl-1,3-butadiene, 1,2,3,4- tetrachlorocyclopentadiene, or 1,3-cyclohexadiene, respectively; or by thermolysis of oxadithiin derivatives 3a,b in the presence of the same aforementioned dienes presumably via the formation of the same intermediate A in both cases of compounds 2a,b and 3a,b. It is observed that α-chloro-β-oxosulfenyl chlorides 2a,b undergo straight forward substitution with potassium cyanide to give 8a,b. Direct oxidation of 2a,b with H2O2/AcOH affords 3,3-dichloropyran-4-ones 9a,b, while conversion of 2a,b to the sulfonamides 10a,b followed by oxidation provides 3-chloropyranones 11a,b. Antioxidant and antimicrobial evaluation of compounds 4a,b-6a,b shows moderate activiy. MIC of the derivative 6b reveals a remarkable inhibition of the pathogenic gram positive bacteria (Staphylococcus aureus ) as well as gram negative E coli.
Page(s): 1502-1510
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.60B(11) [November 2021]

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