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Side chain SAR of bicyclic β-lactamase inhibitors (BLIs). 2. N-Alkylated and open chain analogs of MK-8712

Helen Chen, Timothy A Blizzard, Seongkon Kim, Jane Wu, Katherine Young, Young-Whan Park, Aimie M Ogawa, Susan Raghoobar, Ronald E Painter, Doug Wisniewski, Nichelle Hairston, Paula Fitzgerald, Nandini Sharma, Giovanna Scapin, Jun Lu, Jeff Hermes, Milton L Hammond
Bioorganic & Medicinal Chemistry Letters 2011 July 15, 21 (14): 4267-70
21676616
The bridged monobactam β-lactamase inhibitor MK-8712 (1) effectively inhibits class C β-lactamases. Side chain N-alkylated and ring-opened analogs of 1 were prepared and evaluated for combination with imipenem to overcome class C β-lactamase mediated resistance. Although some analogs were more potent inhibitors of AmpC, none exhibited better synergy with imipenem than 1.

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