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Title: Synthesis of novel spiropiperidine derivatives and their antimicrobial and antioxidant activities
Authors: Srinivasan, Rajagopalan
Narayana, Badiadka
Sarojini, Balladka Kunhanna
Raj, Channa Govindaraju Darshan
Keywords: Spiro piperidines;Pyrazolones;Antimicrobial;Antioxidant
Issue Date: Nov-2018
Publisher: NISCAIR-CSIR, India
Abstract: A series of novel spiro-piperidinyl pyrazolones are synthesized by the reaction of N-Boc protected ethyl nipecotate with heteroaryl and alkyl aldehydes in presence of lithium diisopropyl amide (LDA) to yield corresponding β-hydroxy ester, followed by MnO2 oxidation to give β-keto ester. Further reaction of β-keto ester with hydrazine hydrate results in the formation of spiro-piperidinyl pyrazolone scaffold 5a-d which upon N-benzylation followed by deprotection yields compounds 7a-s. The pyrazolone-NH group has been alkylated in compound 5a with ethyl chloroacetate followed by hydrolysis and amide coupling to afford compounds 9a-d. The furan ring in compound 5a is oxidized to carboxylic acid with KMnO4 and coupled with amines to prepare amide derivatives 11a-c. All the synthesized compounds are evaluated for their in vitro antibacterial and antioxidant activity. Compounds 7a-d and 7g-s are found to possess high antibacterial activity and compounds 7a,7b, 9a, 9b, 11a and 11c are found to be potent antioxidants.
Page(s): 1391-1408
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.57B(11) [November 2018]

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