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Synthesis and structure activity relationships of 1 substituted aminomethyl 3 phenyl methyl 1 3 dihydroisobenzofurans and 4 substituted amino 1 phenylmethylisochromans a new class of antihistaminics



Synthesis and structure activity relationships of 1 substituted aminomethyl 3 phenyl methyl 1 3 dihydroisobenzofurans and 4 substituted amino 1 phenylmethylisochromans a new class of antihistaminics



Indian Journal of Chemistry Section B Organic Chemistry Including Medicinal Chemistry 23(12): 1261-1267



The title compounds have been synthesized from the common intermediates 1-phenyl/methyl-4-bromo-3-isochromanones (10/11) which have been prepared from 2-benzoyl/acetyl-phenylacetic acids (6/7) by NaBH4 reduction followed by bromination of 1-phenyl/methyl-3-isochromanones (8/9) thus obtained. The alkaline hydrolysis of 10/11 yields a mixture of trans- and cis-3-phenyl/methyl 1,3-dihydroisobenzofuran-1-carboxylic acids (12/13). These acids (12/13) on treatment with dimethylamine give the corresponding amides (14/15) which on diborane reduction afford the required mixture of trans- and cis-1-(N,N-dimethylaminomethyl)-3-phenyl/methyl-1,3-dihydroisobenzofurans (16/17). Condensation of different amines with 10/11 give the corresponding mixtures of cis- and trans-1-phenyl/methyl-4-substituted-amino-3-isochromanones (23, 24, 27-30) which on diborane reduction afford 1-phenyl/methyl-4-substituted-aminoisochromans (31-34). These compounds show significant antihistaminic activity (H1) and the most potent compound is 16.

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