An Efficient, Eco-Friendly Synthesis of Pyran Annulated Indole Analogs under Conventional Heating and Microwave Irradiation, and Their Anticancer and Antioxidant Activity

• Published in: Russian journal of general chemistry Vol. 88; no. 10; pp. 2190 - 2196
• Main Authors: Rathod, A. S., Biradar, J. S.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-10-2018; Springer; Springer Nature B.V
• Subjects: Analogs; Anticancer properties; Antioxidants; Cancer; Care and treatment; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Cytotoxicity; Malononitrile; NMR; Nuclear magnetic resonance; Phenols; phenols; indole; pyran; catalyst; anticancer and antioxidant activities; MW-irradiation; green synthesis
• ISSN: 1070-3632; 1608-3350
• DOI: 10.1134/S1070363218100262

A rapid, facile, green, eco-friendly, cost effective, and efficient method for the synthesis of pyran annulated indole analogs via one-pot, three components reaction is developed. According to the developed method 2,5-disubstituted-1
H
-indol-3-carboxaldehyde, malononitrile and various phenols react under MW assisted solvent-free conditions. These compounds can be also prepared under a conventional method that is characterized by some disadvantages in comparison with the above approach. Structures of products are confirmed by FT-IR,
1
H and
13
C NMR, and mass spectral data. The in vitro antioxidant and cytotoxic activities of the products are evaluated against three tumor cell lines and discussed in terms of structure―activity analysis. Among the screened compounds
3d
,
4a
,
4b
,
5a
, and
5b
exhibit excellent antioxidant activity. Compounds
4b
,
5a
, and
5b
demonstrate strong cytotoxic activity.