Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Letter Article

[BMIM]BF4 Mediated Multi-component Synthesis of Phenyl-4-(1Hpyrazol- 5-yl)-1H-pyrazolo[3,4-b]quinolin-5(4H)-ones and Evaluation of their Anti-cancer Activity

Author(s): A. Srinivas, A.J. Shree* and S.S.K. Goud

Volume 21, Issue 2, 2024

Published on: 12 September, 2023

Page: [124 - 130] Pages: 7

DOI: 10.2174/1570178620666230831162320

Price: $65

Abstract

Pyrazolo bridged quinolones scaffolds are an important building block in many of the medicinally active new chemical entities. In the current work, synthesis of phenyl-4-(1H-pyrazol-5-yl) conjugated with 1H-pyrazolo[3,4-b]quinolin-5(4H)-ones derivatives has been achieved by one-pot threecomponent reaction of 3-methyl-1-phenyl-1H-pyrazol-5-amine 1, 5,5-dimethylcyclohexane-1,3-diones 2, and 1H-pyrazole-5-carbaldehydes 3 using [BMIM]BF4 as green reaction medium with good yields. Furthermore, the synthesized compounds were evaluated for cytotoxic potential towards HeLa and DU145 cells. Of the eight derivatives, compound 4d exhibited good cytotoxicity with an IC50 value of 8.5 and 8.9 μM against DU145 and HeLa cells, respectively. The molecular docking studies revealed that compound 4d displayed good binding energy (-8.4 kcal/mol) against human checkpoint kinase 1.

« Previous Next »
Graphical Abstract

[1]
Ramesh, V.; Rao, G.P.C.; Ramachandran, D.; Chakravarthy, A.K. Eur. Chem. Bull., 2019, 8(9), 318-321.
[http://dx.doi.org/10.17628/ecb.2019.8.318-321]
[2]
Sheldon, R. Chem. Commun., 2001, (23), 2399-2407.
[http://dx.doi.org/10.1039/b107270f] [PMID: 12239988]
[3]
Toda, F.; Tanaka, K. Chem. Rev., 2000, 100, 1025.
[http://dx.doi.org/10.1021/cr940089p] [PMID: 11749257]
[4]
(a) Luo, Z.Y.; Zang, Q.S.; Oderaotoshi, Y.; Curran, D.P. Science, 2001, 291, 1766.;
(b) Masoud, M.; Arash, G.; Noorullah, H. J. Phys. Chem. Solids, 2023, 177, 111300.;
(c) Farzaneh, G.; Davood, A.; Masoud, M. J. Phys. Chem. Solids, 2023, 175, 111222.
[5]
Bharti, R.; Parvin, T. RSC Adv., 2015, 5(82), 66833-66839.
[http://dx.doi.org/10.1039/C5RA13093J]
[6]
Wasserscheid, P.; Keim, W. Angew. Chem. Int. Ed., 2000, 39(21), 3772-3789.
[http://dx.doi.org/10.1002/1521-3773(20001103)39:21<3772:AID-ANIE3772>3.0.CO;2-5]
[7]
Corma, A.; García, H. Chem. Rev., 2003, 103(11), 4307-4366.
[http://dx.doi.org/10.1021/cr030680z] [PMID: 14611265]
[8]
Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. Chem., 2002, 182-183, 419-437.
[http://dx.doi.org/10.1016/S1381-1169(01)00465-4]
[9]
Dyson, P.J.; Ellis, D.J.; Welton, T.; Parker, D.G. Chem. Commun., 1999, (1), 25-26.
[http://dx.doi.org/10.1039/a807447j]
[10]
Böhm, V.P.W.; Herrmann, W.A. Chemistry, 2000, 6(6), 1017-1025.
[http://dx.doi.org/10.1002/(SICI)1521-3765(20000317)6:6<1017:AID-CHEM1017>3.0.CO;2-8] [PMID: 10785822]
[11]
Stark, A.; MacLean, B.L.; Singer, R.D. J. Chem. Soc., Dalton Trans., 1999, (1), 63-66.
[http://dx.doi.org/10.1039/a806708b]
[12]
Judeh, Z.M.A.; Ching, C.B.; Bu, J.; McCluskey, A. Tetrahedron Lett., 2002, 43(29), 5089-5091.
[http://dx.doi.org/10.1016/S0040-4039(02)00998-X]
[13]
Bubun, B. ChemistrySelect, 2017, 2, 8362-8376.
[14]
Karthikeyan, C.; Malla, R.; Ashby, C.R., Jr; Amawi, H.; Abbott, K.L.; Moore, J.; Chen, J.; Balch, C.; Lee, C.; Flannery, P.C.; Trivedi, P.; Faridi, J.S.; Pondugula, S.R.; Tiwari, A.K. Cancer Lett., 2016, 376(1), 118-126.
[http://dx.doi.org/10.1016/j.canlet.2016.03.030] [PMID: 27012188]
[15]
Karnakar, K.; Narayana Murthy, S.; Ramesh, K.; Satish, G.; Nanubolu, J.B.; Nageswar, Y.V.D. Tetrahedron Lett., 2012, 53(23), 2897-2903.
[http://dx.doi.org/10.1016/j.tetlet.2012.03.135]
[16]
Mohamed, L.W.; Shaaban, M.A.; Zaher, A.F.; Alhamaky, S.M.; Elsahar, A.M. Bioorg. Chem., 2019, 83, 47-54.
[http://dx.doi.org/10.1016/j.bioorg.2018.10.014] [PMID: 30342385]
[17]
Sedlák, D.; Wilson, T.A.; Tjarks, W.; Radomska, H.S.; Wang, H.; Kolla, J.N. Leśnikowski, Z.J.; Špičáková, A.; Ali, T.; Ishita, K.; Rakotondraibe, L.H.; Vibhute, S.; Wang, D.; Anzenbacher, P.; Bennett, C.; Bartunek, P.; Coss, C.C. J. Med. Chem., 2021, 64(13), 9330-9353.
[http://dx.doi.org/10.1021/acs.jmedchem.1c00555] [PMID: 34181409]
[18]
Safaei-Ghomi, J.; Sadeghzadeh, R.; Shahbazi-Alavi, H. RSC Advances, 2016, 6(40), 33676-33685.
[http://dx.doi.org/10.1039/C6RA02906J]
[19]
Paul, S.; Das, A.R. Tetrahedron Lett., 2013, 54(9), 1149-1154.
[http://dx.doi.org/10.1016/j.tetlet.2012.12.079]
[20]
Bhattacharjee, D.; Kshiar, B.; Myrboh, B. RSC Advances, 2016, 6(98), 95944-95950.
[http://dx.doi.org/10.1039/C6RA22429F]
[21]
Khurana, J.M.; Chaudhary, A.; Nand, B.; Lumb, A. Tetrahedron Lett., 2012, 53(24), 3018-3022.
[http://dx.doi.org/10.1016/j.tetlet.2012.04.001]
[22]
Sowmiah, S.; Srinivasadesikan, V.; Tseng, M.C.; Chu, Y.H. Molecules, 2009, 14(9), 3780-3813.
[http://dx.doi.org/10.3390/molecules14093780] [PMID: 19783957]
[23]
Mosmann, T.; Immunol, J. Methods, 1983, 65, 55-63.
[24]
Kumar, R.N.; Poornachandra, Y.; Nagender, P.; Mallareddy, G.; Kumar, N.R.; Ranjithreddy, P.; Kumar, C.G.; Narsaiah, B. Eur. J. Med. Chem., 2016, 108, 68-78.
[http://dx.doi.org/10.1016/j.ejmech.2015.11.007] [PMID: 26629861]
[25]
Ghanbari-Ardestani, S.; Khojasteh-Band, S.; Zaboli, M.; Hassani, Z.; Mortezavi, M.; Mahani, M.; Torkzadeh-Mahani, M. J. Mol. Liq., 2019, 292, 111318.
[http://dx.doi.org/10.1016/j.molliq.2019.111318]
[26]
Wallace, A.C.; Laskowski, R.A.; Thornton, J.M. Protein Eng. Des. Sel., 1995, 8(2), 127-134.
[http://dx.doi.org/10.1093/protein/8.2.127]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy