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Synthesis and Fragmentation Behavior Study of n-alkyl/benzyl Isatin Derivatives Present in Small/Complex Molecules: Precursor for the Preparation of Biological Active Heterocycles
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  • Journal title : Mass Spectrometry Letters
  • Volume 6, Issue 3,  2015, pp.65-70
  • Publisher : Korean Society Mass Spectrometry
  • DOI : 10.5478/MSL.2015.6.3.65
 Title & Authors
Synthesis and Fragmentation Behavior Study of n-alkyl/benzyl Isatin Derivatives Present in Small/Complex Molecules: Precursor for the Preparation of Biological Active Heterocycles
Kadi, Adnan A.; Al-Shakliah, Nasser S.; Motiur Rahman, A. F. M.;
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N-Alkyl/benzyl substituted isatin derivatives are intermediates and synthetic precursors for the preparation of biological 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 derivatives were synthesized from isatin and alkyl/benzyl halides in presence of K2CO3 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/MSn. N-Alkyl substituted isatin derivatives fragmented 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 fragments [RNCH2]+. 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.
Isatin;N-Alkyl/aryl isatin;Fragmentation behavior;Heterocycles;
 Cited by
Erdmann, O. L. Journal für Praktische Chemie 1840, 19, 321. crossref(new window)

Laurent, M. A. Ann. Chim. Phy. 1841, 3, 371.

Sandmeyer, T. Helvetica Chimica Acta 1919, 2, 234. crossref(new window)

Marvel, C. S.; Hiers, G. S. Org. Synth. 1925, 5, 71. crossref(new window)

Guo, Y.; Chen, F. Zhongcaoyao 1986, 17, 8.

Yoshikawa, M.; Murakami, T.; Kishi, A.; Sakurama, T.; Matsuda, H.; Nomura, M.; Matsuda, H.; Kubo, M. Chemical & Pharmaceutical Bulletin 1998, 46, 886. crossref(new window)

Bergman, J.; Lindström, J.-O.; Tilstam, U. Tetrahedron 1985, 41, 2879. crossref(new window)

Silva, J. F. M. d.; Garden, S. J.; Pinto, A. C. Journal of the Brazilian Chemical Society 2001, 12, 273. crossref(new window)

Sumpter, W. C. Chem. Rev. 1944, 34, 393. crossref(new window)

Popp, F. D. Adv. Heterocycl. Chem. 1975, 18, 1. crossref(new window)

French, K. H. V. Journal of Applied Chemistry 1952, 2, 664. crossref(new window)

Rahman, A. F. M. M.; Angawi, R. F.; Kadi, A. A. Food Chem. 2015, 173, 489. crossref(new window)

Rahman, A. F. M. M.; Attwa, M. W.; Ahmad, P.; Baseeruddin, M.; Kadi, A. A. Mass Spectrom. Lett. 2013, 4, 30. crossref(new window)

Abdelhameed, A. S.; Attwa, M. W.; Abdel-Aziz, H. A.; Kadi, A. A. Chem. Cent. J. 2013, 7, 16. crossref(new window)

Abdelhameed, A. S.; Kadi, A. A.; Abdel-Aziz, H. A.; Angawi, R. F.; Attwa, M. W.; Al-Rashood, K. A. Sci. World J. 2014, 1. crossref(new window)

Katritzky, A. R.; Fan, W.-Q.; Liang, D.-S.; Li, Q.-L. J. Heterocy. Chem. 1989, 26, 1541. crossref(new window)

Horner, L.; Klüpfel, K. Justus Liebigs Annalen der Chemie 1955, 591, 69. crossref(new window)

SoltaniRad, M. N.; Khalafi-Nezhad, A.; Babamohammadi, S.; Behrouz, S. Helvetica Chimica Acta 2010, 93, 2454. crossref(new window)

Shmidt, M.; Reverdito, A.; Kremenchuzky, L.; Perillo, I.; Blanco, M. Molecules 2008, 13, 831. crossref(new window)

Nguyen, D. T.; Nguyen, T. K. G. J. Chem. 2013, 5.

Mulla, S. A. R.; Pathan, M. Y.; Chavan, S. S. RSC Adv. 2013, 3, 20281. crossref(new window)

Kaku, H.; Takuwa, T.; Kageyama, M.; Nozawa, K.; Doihara, H. WO2009123080A1, 2009.

Chafeev, M.; Chowdhury, S.; Fraser, R.; Fu, J.; Hou, D.; Kamboj, R.; Liu, S.; Sun, S.; Sun, J.; Sviridov, S.; Bagherzadeh, M. S.; Chakka, N.; Hsieh, T.; Raina, V. WO2006113864A2, 2006.

Diaz, P.; Xu, J.; Astruc-Diaz, F.; Pan, H.-M.; Brown, D. L.; Naguib, M. J. Med. Chem. 2008, 51, 4932. crossref(new window)

Rahman, A. F. M. M.; Park, S.-E.; Kadi, A. A.; Kwon, Y. J. Med. Chem. 2014, 57, 9139. crossref(new window)