Water mediated procedure for preparation of stereoselective oximes as inhibitors of MRCK kinase

Stereoselective aldoximes, preferably Z form have been obtained from α-cyano substituted carbonyl conjugated alkenes. This reaction occurs through Michael addition type reaction followed by retro-Knoevenagel reaction without transition-metal catalysis via C–C bond cleavage. These oximes are evaluate...

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Bibliographic Details
Published in:Journal of molecular structure 2020-11, Vol.1220, p.128699, Article 128699
Main Authors: Shrivash, Manoj Kumar, Singh, Shilipi, Shukla, Akhilesh Kumar, Luqman, Suaib, Pandey, Jyoti, Misra, Krishna
Format: Article
Language:English
Subjects:
Cancer cell lines
C–C bond Cleavage
MRCK kinase
Retro-knoevenagel reaction
Stereoselective synthesis
Z-Oximes
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Summary:Stereoselective aldoximes, preferably Z form have been obtained from α-cyano substituted carbonyl conjugated alkenes. This reaction occurs through Michael addition type reaction followed by retro-Knoevenagel reaction without transition-metal catalysis via C–C bond cleavage. These oximes are evaluated against cancer cell lines employing mechanistic study. Two oximes showed significant cytotoxic activity, which through in silico studies were found to inhibit MRCK Kinase, responsible for metastatic spread of cancer mortality. [Display omitted] •Water mediated and base catalyzed C–C bond cleavage.•A novel and facile stereoselective strategy for synthesis of Z oximes.•Metal free, mild and time economic condition.•Good air and moisture tolerance broad substrate scope high stereoselective.•Small molecule inhibit MRCK kinase,thereby may have good anticancer property.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2020.128699