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Vol. 29 No. 7 (2017): Vol 29 Issue 7

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Synthesis and Antiproliferative Activity of Some Dihydro-1H-furo[2,3-c]pyrazole-Flavone Hybrids

https://doi.org/10.14233/ajchem.2017.20550
Venkata Swamy Tangeti
Department of Chemistry, Raghu Engineering College, Visakhapatnam-531 162, India; Vector Control Research Center (ICMR), Puducherry-605 006, India
D. Vasundhara
Department of Chemistry, Raghu Institute of Technology, Visakhapatnam-531 162, India
K.V.V.V. Satyanarayana
Department of Chemistry, Raghu Engineering College, Visakhapatnam-531 162, India
Kaja Srinivas Pavan Kumar
GVK Biosciences Pvt. Ltd., Nacharam, Hyderabad-500 076, India

Corresponding Author(s) : Venkata Swamy Tangeti

swamychempcu@gmail.com

Asian Journal of Chemistry, Vol. 29 No. 7 (2017): Vol 29 Issue 7

Abstract

A new series of dihydro-1H-furo[2,3-c]pyrazole-flavone hybrids were synthesized from one-pot four-component reaction of b-keto ester (1), hydrazine (2), 7-hydroxy 8-formyl flavones (3), pyridiniumylide (4) in presence of NEt3 as catalyst under ethanol reflux conditions and their antiproliferative properties were evaluated against human cancer cell lines, namely, laryngeal carcinoma (Hep2), lung adenocarcinoma (A549) and cervical cancer (HeLa). The best among them, furo[2,3-c]pyrazole-flavone with C4'-methoxy substitution was selected for further structure activity relationship (SAR) studies. Among the derivatives, (4S,5S)-ethyl 4-(7-hydroxy-5-methoxy-4-oxo-2-(2,4,6-trimethoxyphenyl)-4H-chromen-8-yl)-3-methyl-4,5-dihydro-1H-furo[2,3-c]pyrazole-5-carboxylate (8r) showed most potent cytotoxic activity against all three cancer cell lines. Toxicity studies revealed that the dihydro-1H-furo[2,3-c]pyrazole-flavones are specifically target the cancer cell lines.

Keywords

Furo[2,3-c]pyrazole-flavone hybrids Pyridiniumylide 7-Hydroxy 8-formyl flavone Antiproliferative
Tangeti, V. S., Vasundhara, D., Satyanarayana, K., & Pavan Kumar, K. S. (2017). Synthesis and Antiproliferative Activity of Some Dihydro-1H-furo[2,3-c]pyrazole-Flavone Hybrids. Asian Journal of Chemistry, 29(7), 1525–1532. https://doi.org/10.14233/ajchem.2017.20550
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