• P-ISSN2233-4203
  • E-ISSN2093-8950

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  • P-ISSN 2233-4203
  • E-ISSN 2093-8950

Synthesis and Fragmentation Behavior Study of n-alkyl/benzyl Isatin Derivatives Present in Small/Complex Molecules: Precursor for the Preparation of Biological Active Heterocycles

Mass Spectrometry Letters, (P)2233-4203; (E)2093-8950
2015, v.6 no.3, pp.65-70
https://doi.org/10.5478/MSL.2015.6.3.65
Kadi Adnan A. (King Saud University)
Al-Shakliah Nasser S. (King Saud University)
Rahman A. F. M. Motiur (King Saud University)
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Abstract

N-Alkyl/benzyl substituted isatin derivatives are intermediates and synthetic precursors for the preparation of biolog- ical active heterocycles. N-alkyl/benzyl isatins have showed various biological activities, such as cytotoxicity, antiviral, caspase inhibition, cannabinoid receptor 2 agonists for the treatment of neuropathic pain, etc. In this study, N-alkyl/benzyl isatin deriva- tives were synthesized from isatin and alkyl/benzyl halides in presence of K 2 CO 3 in DMF and excellent to quantitative yields (~95%) were obtained. Isatins and benzyl-isatins were condensed with fluorescein hydrazide to form fluorescein hydrazone. All the compounds were subjected to their fragmentation behavior study using LC/MS n . N-Alkyl substituted isatin derivatives frag- mented at nitrogen-carbon (N-C) bond, hence gave daughter ion as [RN+H] + . Whereas, N-benzyl substituted isatin derivatives fragmented at carbon-carbon (C-C) bond of alkyl chain which linked with nitrogen molecules, therefore gave N-methyl frag- ments [RNCH 2 ] + . This study demonstrated that, isatin moiety present in a small/large molecule or in a matrix of reaction mixture with/without N-alkyl/benzyl substituents can be identified by mass spectroscopic fragmentation behavior study.

keywords
Isatin N-Alkyl/aryl isatin Fragmentation behavior Heterocycles


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Submission Date
2015-04-30
Revised Date
2015-08-10
Accepted Date
2015-08-17
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