TY - JOUR
T1 - Synthesis of 1,8-dioxooctahydroxanthene derivatives using ionic liquids, quantum chemical studies and anticancer activity
AU - Sangwan, Reetu
AU - Saini, Monika
AU - Verma, Ruchi
AU - Kumar, Saurabh
AU - Banerjee, Monisha
AU - Jain, Sudha
N1 - Funding Information:
The authors are thankful to the Department of Chemistry, University of Lucknow, Lucknow (U.P.) for supporting UV, IR and NMR spectroscopic and computational facilities, SAIF Division, CSIR- Central Drug Research Institute, Lucknow for MASS spectral analysis. The cell culture facility developed from project grant of Centre of Excellence, Higher Education, Govt of UP is duly acknowledged. Financial support from the University Grants Commission (UGC) and Council of Scientific and Industrial Research (CSIR), New Delhi is gratefully acknowledged. Reetu Sangwan is supported by CSIR (FILE NO 09/107(0369)2014-EMR-I). Ruchi Verma is thankful to UGC fellowship (RGNF) (file no.F117.1/2014-15/RGNF-2014-15-SC-UTT-78865). Saurabh Kumar is grateful to ICMR for research grant.
Funding Information:
The authors are thankful to the Department of Chemistry, University of Lucknow, Lucknow (U.P.) for supporting UV, IR and NMR spectroscopic and computational facilities, SAIF Division, CSIR- Central Drug Research Institute , Lucknow for MASS spectral analysis. The cell culture facility developed from project grant of Centre of Excellence, Higher Education, Govt of UP is duly acknowledged. Financial support from the University Grants Commission ( UGC ) and Council of Scientific and Industrial Research ( CSIR ), New Delhi is gratefully acknowledged. Reetu Sangwan is supported by CSIR (FILE NO 09/107(0369)2014-EMR-I ). Ruchi Verma is thankful to UGC fellowship (RGNF) (file no. F117.1/2014-15/RGNF-2014-15-SC-UTT-78865 ). Saurabh Kumar is grateful to ICMR for research grant.
Publisher Copyright:
© 2020
PY - 2020/5/15
Y1 - 2020/5/15
N2 - An eco friendly and efficient method for the synthesis of 1,8-dioxooctahydroxanthene derivatives in excellent yield (∼90%) using ionic liquids 1-butyl-3-methylimidazoliumtetrafluoroborate (BMIF), 1-butyl-3-methylimidazoliumbromide (BMIB) and 1-butyl-3-methylimidazoliumchloride (BMIC) under solvent free condition has been developed for the first time. All the synthesized compounds (3a-3k) were fully characterized by analysis of spectral data (FT-IR, 1H NMR, 13C NMR, UV–Vis and mass spectroscopy). Quantum chemical studies were also done for one of the synthesized compound, 3,3,6,6-tetramethyl-9-(2,3,4-trimethoxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione (3a). All the synthesized compounds (3a-3k) were assayed for in vitro antitumor activities against human lung cancer cell line (A549). In cell proliferation experiments, 9-(3,4-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione (3k) was found to be most potent agent and significantly inhibited the tested cancer cell line A549 (IC50 3.88) with 88.77% inhibiton at 10 mM concentration.
AB - An eco friendly and efficient method for the synthesis of 1,8-dioxooctahydroxanthene derivatives in excellent yield (∼90%) using ionic liquids 1-butyl-3-methylimidazoliumtetrafluoroborate (BMIF), 1-butyl-3-methylimidazoliumbromide (BMIB) and 1-butyl-3-methylimidazoliumchloride (BMIC) under solvent free condition has been developed for the first time. All the synthesized compounds (3a-3k) were fully characterized by analysis of spectral data (FT-IR, 1H NMR, 13C NMR, UV–Vis and mass spectroscopy). Quantum chemical studies were also done for one of the synthesized compound, 3,3,6,6-tetramethyl-9-(2,3,4-trimethoxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione (3a). All the synthesized compounds (3a-3k) were assayed for in vitro antitumor activities against human lung cancer cell line (A549). In cell proliferation experiments, 9-(3,4-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione (3k) was found to be most potent agent and significantly inhibited the tested cancer cell line A549 (IC50 3.88) with 88.77% inhibiton at 10 mM concentration.
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U2 - 10.1016/j.molstruc.2020.127786
DO - 10.1016/j.molstruc.2020.127786
M3 - Article
AN - SCOPUS:85079347556
SN - 0022-2860
VL - 1208
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
M1 - 127786
ER -
