Synthesis and molecular docking studies of new chromane (2-(4-hydroxybenzyl) 3,5,7-trihydroxychroma-4-one) and its O-substituted analogues
Keywords:
chroman-4-one, anti-inflammatory, analgesic, molecular docking, COX 2Abstract
A series of 3-(O-R) substituted compounds (SI-SX) of 2-(4-hydroxybenzyl) 3,5,7-trihydroxychroma-4-one were synthesized from easily accessible starting materials such as, p-hydroxybenzaldehyde and ethyl bromopyruvate. All the ten derivatives (SI-SX) were synthesized in appropriate yields, and they were characterized by IR, 1H NMR and C NMR. Molecular docking of all the derivatives were performed using Molegro virtual docker tool 6.0.2 (MVD) tool. CYCLOOXYGENASE-2 (COX2) or PROSTAGLANDIN SYNTHASE-2 was taken as the target protein and was downloaded from Research Collaboratory for Structural Bioinformatics (RCSB) Protein Data Bank (PDB) (https://www.rcsb.org/structure/1CX2) with PDBID: ICX2, 10.2210/pdb1CX2/pdb). The 3D images of ligand protein interactions were extracted using the software, MVD 6.0.2 visualizer interface. Among all the derivatives, SII, SVI has shown good moldock score values -77.59 and -75.75 with high number of interactions (09) towards the target protein, indicating its ability to act as an anti-inflammatory and analgesic activity.
Downloads
References
Ali, K. A., Abdelhafez, N. A. A., Ragab, E. A., Ibrahim, A. A., & Amr, A. E. (2015). Design and synthesis of novel fused heterocycles using 4-chromanone as synthon. Russian Journal of General Chemistry, 85(12), 2853-2860.
Alipour, E., Mousavi, Z., Safaei, Z., Pordeli, M., Safavi, M., Firoozpour, L., ... & Foroumadi, A. (2014). Synthesis and cytotoxic evaluation of some new [1, 3] dioxolo [4, 5-g] chromen-8-one derivatives. DARU Journal of Pharmaceutical Sciences, 22(1), 1-6.
Alizadeh, B. H., Saeedi, M., Dehghan, G., Foroumadi, A., & Shafiee, A. (2015). Synthesis of some novel pyrano [2, 3-f] chromenone derivatives. Journal of the Iranian Chemical Society, 12(4), 605-612.
Alizadeh, S. R., & Ebrahimzadeh, M. A. (2022). O-Substituted Quercetin derivatives: structural classification, drug design, development, and biological activities, a review. Journal of Molecular Structure, 132392.
Christophe Carola H., Ralf Rosskopf M. (2010): Use of chroman-4-one derivatives.: United States Patent application publication., US 2010/0028278 A1,1, 1–24
Gažák, R., Svobodová, A., Psotová, J., Sedmera, P., Přikrylová, V., Walterová, D., & Křen, V. (2004). Oxidised derivatives of silybin and their antiradical and antioxidant activity. Bioorganic & medicinal chemistry, 12(21), 5677-5687.
Hu, C., Zhou, Z., Xiang, Y., Song, X., Wang, H., Tao, K., & Ye, X. (2018). Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives. Medicinal Chemistry Research, 27(1), 194-205.
Jarapula, R., Gangarapu, K., Manda, S., & Rekulapally, S. (2016). Synthesis, in vivo anti-inflammatory activity, and molecular docking studies of new isatin derivatives. International journal of medicinal chemistry, 2016.
Kamboj, S., & Singh, R. (2021). Chromanone-A prerogative therapeutic scaffold: an overview. Arabian Journal for Science and Engineering, 1-37.
Kaur, N., Kishore, L., & Singh, R. (2016). Antidiabetic effect of new chromane isolated from Dillenia indica L. leaves in streptozotocin induced diabetic rats. Journal of Functional Foods, 22, 547-555.
Kurumbail, R. G., Stevens, A. M., Gierse, J. K., McDonald, J. J., Stegeman, R. A., Pak, J. Y., ... & Stallings, W. C. (1996). Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature, 384(6610), 644-648.
Li H.J., Luan X.H., Zhao Y.M. (2004). Facile synthesis of 3-Omethylquercetin. Chin J Org Chem 24:1619–1621.
Li, N. G., Shi, Z. H., Tang, Y. P., Yang, J. P., & Duan, J. A. (2009). An efficient partial synthesis of 4′-O-methylquercetin via regioselective protection and alkylation of quercetin. Beilstein Journal of Organic Chemistry, 5(1), 60.
Li, N. G., Shi, Z. H., Tang, Y. P., Yang, J. P., Lu, T. L., Zhang, F., ... & Duan, J. A. (2011). Synthetic studies on the construction of 7-O-methylquercetin through regioselective protection and alkylation of quercetin. Chinese Chemical Letters, 22(1), 5-8.
Novoa, R. B. (2021). State of the art and future applications of digital health in Chile. International Journal of Health & Medical Sciences, 4(3), 355-361. https://doi.org/10.31295/ijhms.v4n3.1772
Panche, A. N., Diwan, A. D., & Chandra, S. R. (2016). Flavonoids: an overview. Journal of nutritional science, 5.
Ratnawati, I. G. A. A., Sutapa, G. N., & Ratini, N. N. (2018). The concentration of radon gas in air-conditioned indoor: Air quality can increase the potential of lung cancer. International Journal of Physical Sciences and Engineering, 2(2), 111–119. https://doi.org/10.29332/ijpse.v2n2.169
Shaikh, M. M., Kruger, H. G., Bodenstein, J., Smith, P., & du Toit, K. (2012). Anti-inflammatory activities of selected synthetic homoisoflavanones. Natural Product Research, 26(16), 1473-1482.
Shi, Z. H., Li, N. G., Tang, Y. P., Shi, Q. P., Tang, H., Li, W., ... & Duan, J. A. (2014). Biological evaluation and SAR analysis of O-methylated analogs of quercetin as inhibitors of cancer cell proliferation. Drug development research, 75(7), 455-462.
Shi, Z. H., Li, N. G., Tang, Y. P., Yang, J. P., & Duan, J. A. (2012). Metabolism-based synthesis, biologic evaluation and SARs analysis ofáO-methylated analogs of quercetin as thrombin inhibitors. European journal of medicinal chemistry, 54, 210-222.
Waller, C. P., Thumser, A. E., Langat, M. K., Crouch, N. R., & Mulholland, D. A. (2013). COX-2 inhibitory activity of homoisoflavanones and xanthones from the bulbs of the Southern African Ledebouria socialis and Ledebouria ovatifolia (Hyacinthaceae: Hyacinthoideae). Phytochemistry, 95, 284-290.
Wang, Q. Q., Shi, J. B., Chen, C., Huang, C., Tang, W. J., & Li, J. (2016). Hesperetin derivatives: synthesis and anti-inflammatory activity. Bioorganic & Medicinal Chemistry Letters, 26(5), 1460-1465.
Widana, I.K., Sumetri, N.W., Sutapa, I.K., Suryasa, W. (2021). Anthropometric measures for better cardiovascular and musculoskeletal health. Computer Applications in Engineering Education, 29(3), 550–561. https://doi.org/10.1002/cae.22202
Winekenstädde, D., Angelis, A., Waltenberger, B., Schwaiger, S., Tchoumtchoua, J., König, S., ... & Stuppner, H. (2015). Phytochemical profile of the aerial parts of Sedum sediforme and anti-inflammatory activity of myricitrin. Natural Product Communications, 10(1), 1934578X1501000122.
Zhao, J.W.; Chen, D.S.; Deng, C.S., et al. (2017): Evaluation of anti-infammatory activity of compounds isolated from the rhizome of Ophiopogon japonicas. BMC Complement Altern. Med. 17(1), 1–12
Zheng, C., Wang, L., Han, T., Xin, H., Jiang, Y., Pan, L., ... & Qin, L. (2016). Pruinosanones AC, anti-inflammatory isoflavone derivatives from Caragana pruinosa. Scientific reports, 6(1), 1-8.
Published
How to Cite
Issue
Section
Copyright (c) 2022 International journal of health sciences
![Creative Commons License](http://i.creativecommons.org/l/by-nc-nd/4.0/88x31.png)
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
Articles published in the International Journal of Health Sciences (IJHS) are available under Creative Commons Attribution Non-Commercial No Derivatives Licence (CC BY-NC-ND 4.0). Authors retain copyright in their work and grant IJHS right of first publication under CC BY-NC-ND 4.0. Users have the right to read, download, copy, distribute, print, search, or link to the full texts of articles in this journal, and to use them for any other lawful purpose.
Articles published in IJHS can be copied, communicated and shared in their published form for non-commercial purposes provided full attribution is given to the author and the journal. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgment of its initial publication in this journal.
This copyright notice applies to articles published in IJHS volumes 4 onwards. Please read about the copyright notices for previous volumes under Journal History.