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Green Synthesis of Novel Class of Benzazocine Derivatives, their Crystal Structures and Anticancer Activity

[ Vol. 14 , Issue. 1 ]

Author(s):

Raza Murad Ghalib, Rokiah Hashim, Othman Sulaiman, Ali Jawad, Sayed Hasan Mehdi, Goran A. Bogdanovic, Srecko R. Trifunovic, Fumio Kawamura, B. M. Khadeer Ahamed and Amin Malik Shah Abdul Majid   Pages 127 - 136 ( 10 )

Abstract:


Background: Heterocyclic molecules have been synthesized by a green & facile strategy. These molecules contain a 8-membered azocine ring. The structures have been determined by spectral analysis and single crystal X-ray analysis. These compounds have anticancer activity.

Method: A mixture of ninhydrin and acetone/ethylmethylketone in acetic acid in molar ratio 1:1 were heated on water bath for 15 minutes. The reaction mixtures were dried on rotary evaporator and crystallized with chloroform- n-hexane (1:1 v/v) to give the colorless crystals of 1 And 2 respectively. Compounds 3 and 4 were synthesized by adding o-phenylenediamine to the completed reaction mixtures of 1 and 2 and each was further heated on water bath for 5 minutes. The dried reaction mixtures were chromatographed over a silica gel column and crystalized as 3 and 4.

Results: This strategy resulted novel class of anticancer benzazocines (3 & 4).

Conclusion: This method features mild reaction conditions and simple operation. The synthesis completes in two steps; from ninhydrin to 1 & 2 and from 1 & 2 to 3 & 4. The same basic skeleton of 3 & 4 and the same synthesis procedure clearly shows the general applicability of this reaction that is also proved enough by single crystal Xray analysis and the strategy can be applicable for a wide range of other substrates. The obtained compounds are potential anticancer agents.

Keywords:

Synthesis, crystal structures, benzazocine, methylated molecules, anticancer activity.

Affiliation:

Department of Chemistry, Faculty of Sciences and Arts –Khulais, University of Jeddah, Khulais P.O. Box 355, Postal Code 21921, Kingdom of Saudi Arabia.

Graphical Abstract:



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