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A Concise Synthesis of the DNA‐Intercalating and Antimalarial Alkaloid Cryptolepine and Its Fluorescence Behaviour in Solvents of Different Polarities
Author(s) -
Lai Tapan Kumar,
Chatterjee Asima,
Banerji Julie,
Sarkar Deboleena,
Chattopadhyay Nitin
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890212
Subject(s) - chemistry , alkaloid , intercalation (chemistry) , combinatorial chemistry , dna , fluorescence , condensation , yield (engineering) , molecule , organic chemistry , biochemistry , physics , materials science , quantum mechanics , metallurgy , thermodynamics
A microwave‐induced rapid and facile synthesis of the DNA‐intercalating and antimalarial drug cryptolepine is described. The key step in this synthesis involves the aqueous‐phase base‐catalyzed condensation of isatin and 1‐acetyl‐1 H ‐indol‐3‐yl acetate which has been simplified and expedited by dielectric heating, employing an ordinary domestic microwave oven. The method transforms the synthesis of an important drug molecule from a prohibitively lengthy process to a matter of a few minutes with a much improved yield. Dual absorption and fluorescence is observed from the molecular system in solvents of different polarity thus providing valuable insight into its binding modes toward protein or DNA.