Helvetica Chimica Acta p. 559 - 570 (2002)
Update date:2022-07-29
Topics:
Khan, Khalid Mohammed
Rahat, Shagufta
Choudhary, Muhammad Iqbal
Atta-ur-Rahman
Ghani, Usman
Perveen, Shahnaz
Khatoon, Shagufta
Dar, Ahsana
Malik, Abdul
To evaluate the effect of substituents on biological activities of electron-rich N-containing heterocycles, the variably 2-substituted 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles 26-33 were synthesized and evaluated for antibacterial, antifungal, and enzyme-inhibition activities. The target compounds were obtained from alkyl 4- or 3-hydroxy benzoates 1 and 2, respectively, and from methyl indoleacetate 3. The phenolic OH group of benzoates 1 and 2 were substituted with p-toluenesulfonyl (→ 4 and 5), benzoyl (→ 6 and 7), and benzyl groups (→ 8 and 9) and then converted to 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles. To establish structure-activity relationships (SAR), a pharmacological screening of the intervening intermediates was also conducted, which revealed that the intermediate hydrazide 11 possesses significant antimicrobial and MAO-A inhibiting properties and intermediates 12, 24, 28, and 29 appreciable antifungal activities. Compound 7 inhibits α-chymotrypsin.
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Doi:10.1021/ja0123812
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