Synthesis and Biological Evaluation of 2-(4,5,6,7-Tetrahydrobenzo[c]Isoxazol-3-yl)-4H-Chromen-4-Ones

References

• J. Zhu, J. Mo, H. Z. Lin, Y. Chen, and H. P. Sun, “The Recent Progress of Isoxazole in Medicinal Chemistry,” Bioorganic & Medicinal Chemistry 26, no. 12 (2018): 3065–75.
   PubMed Web of Science ®Google Scholar
• A. Oubella, Y. A. Itto, A. Auhmani, A. Riahi, A. Robert, J. C. Dara, H. Morjani, C. A. Parish, and M. Esseffar, “Diastereoselective Synthesis and Cytotoxic Evaluation of New Isoxazoles and Pyrazoles with Monoterpenic Skeleton,” Journal of Molecular Structure 1198, (2019): 126924.
   Web of Science ®Google Scholar
• J. P. Nie, Z. Qu, Y. Chen, J. H. Chen, Y. Jiang, M. Jin, Y. Yu, W. Y. Niu, H. Duan, and N. Qin, “Discovery and anti-Diabetic Effects of Novel Isoxazole Based Flavonoid Derivatives,” Fitoterapia 142, (2020): 104499.
   PubMed Web of Science ®Google Scholar
• K. A. E. Abdelall, “Synthesis and Biological Evaluations of Novel Isoxazoles and Furoxan Derivative as anti-Inflammatory Agents,” Bioorganic Chemistry 94, (2020): 103441.
   PubMed Web of Science ®Google Scholar
• D. Zhang, J. Jia, L. Meng, W. Xu, L. Tang, and J. Wang, “Synthesis and Preliminary Antibacterial Evaluation of 2-Butyl Succinate-Based Hydroxamate Derivatives Containing Isoxazole Rings,” Archives of Pharmacal Research 33, no. 6 (2010): 831–42.
   PubMed Web of Science ®Google Scholar
• Maria M. M. Santos, Natália Faria, Jim Iley, Simon J. Coles, Michael B. Hursthouse, M. Luz Martins, and Rui Moreira, “Reaction of Naphthoquinones with Substituted Nitromethanes. Facile Synthesis and Antifungal Activity of naphtho[2,3-d]isoxazole-4,9-diones,” Bioorganic & Medicinal Chemistry Letters 20, no. 1 (2010): 193–5.
   PubMed Web of Science ®Google Scholar
• Ki Deok Shin, Mi-Young Lee, Dae-Seop Shin, Sangku Lee, Kwang-Hee Son, Sukhoon Koh, Young-Ki Paik, Byoung-Mog Kwon, and Dong Cho Han, “Blocking Tumor Cell Migration and Invasion with Biphenyl Isoxazole Derivative KRIBB3, a Synthetic Molecule That Inhibits Hsp27 Phosphorylation,” The Journal of Biological Chemistry 280, no. 50 (2005): 41439–48.
   PubMed Web of Science ®Google Scholar
• Z. Yang, P. Li, and X. Gan, “Novel Pyrazole-Hydrazone Derivatives Containing an Isoxazole Moiety: Design, Synthesis, and Antiviral Activity,” Molecules 23, (2018): 1798.
   Web of Science ®Google Scholar
• N. V. Balaji, B. HariBabu, V. U. Rao, G. V. Subbaraju, K. P. Nagasree, and M. M. K. Kumar, “Synthesis, Screening and Docking Analysis of Hispolon Pyrazoles and Isoxazoles as Potential Antitubercular Agents,” Current Topics in Medicinal Chemistry 19, no. 9 (2019): 662–82.
   PubMed Web of Science ®Google Scholar
• W. Li, J. Li, H. Shen, J. Cheng, Z. Li, and X. Xu, “Synthesis, Nematicidal Activity and Docking Study of Novel Chromone Derivatives Containing Substituted Pyrazole,” Chinese Chemical Letters 29, no. 6 (2018): 911–4.
   Web of Science ®Google Scholar
• Y. Duan, Y. Jiang, F. Guo, L. Chen, L. Xu, W. Zhang, and B. Liu, “The Antitumor Activity of Naturally Occurring Chromones: A Review,” Fitoterapia 135, (2019): 114–29.
   PubMed Web of Science ®Google Scholar
• C. Demetgul, and N. Beyazit, “Synthesis, Characterization and Antioxidant Activity of Chitosan-Chromone Derivatives,” Carbohydrate Polymers 181, (2018): 812–7.
   PubMed Web of Science ®Google Scholar
• J. N. Modranka, E. Nawrot, and J. Graczyk, “In Vivo Antitumor, in Vitro Antibacterial Activity and Alkylating Properties of Phosphorohydrazine Derivatives of Coumarin and Chromone,” European Journal of Medicinal Chemistry 41, no. 11 (2006): 1301–9.
   PubMed Web of Science ®Google Scholar
• C. Sun, C. Chen, S. Xu, J. Wang, Y. Zhu, D. Kong, H. Tao, M. Jin, P. Zheng, and W. Zhu, “Synthesis and Anticancer Activity of Novel 4-Morpholino-7,8-Dihydro-5H-Thiopyrano[4,3-d]Pyrimidine Derivatives Bearing Chromone Moiety,” Bioorganic & Medicinal Chemistry 24, no. 16 (2016): 3862–9.
   PubMed Web of Science ®Google Scholar
• P. Baruah, M. A. Rohman, S. O. Yesylevskyy, and S. Mitra, “Therapeutic Potency of Substituted Chromones as Alzheimer's Drug: Elucidation of Acetylcholinesterase Inhibitory Activity through Spectroscopic and Molecular Modelling Investigation,” BioImpacts: BI 9, no. 2 (2019): 79–88. BI,
   PubMed Web of Science ®Google Scholar
• H. Liu, R. Xu, L. Feng, W. Guo, N. Cao, C. Qian, P. Teng, L. Wang, X. Wu, Y. Sun, et al. “A Novel Chromone Derivative with anti-Inflammatory Property via Inhibition of ROS-Dependent Activation of TRAF6-ASK1-p38 Pathway,” PLoS One 7, no. 8 (2012): e37168.
   PubMedGoogle Scholar
• N. C. Netzer, T. Kupper, H. W. Voss, and A. H. Eliasson, “The Actual Role of Sodium Cromoglycate in the Treatment of Asthma-a Critical Review,” Sleep & Breathing = Schlaf & Atmung 16, no. 4 (2012): 1027–32.
   PubMed Web of Science ®Google Scholar
• J. Sheikh, H. Juneja, V. Ingle, P. Ali, and T. B. Hadda, “Synthesis and in Vitro Biology of Co(II), Ni(II), Cu(II) and Zinc(II) Complexes of Functionalized Beta-Diketone Bearing Energy Buried Potential Antibacterial and Antiviral O,O Pharmacophore Sites,” Journal of Saudi Chemical Society 17, no. 3 (2013): 269–76.
   Web of Science ®Google Scholar
• T. V. Deepthi, and P. Venugopalan, “Synthesis, Characterization and Biological Studies on NiII and CuII Complexes of Two Novel α,β-Unsaturated 1,3-Diketones Related to Curcuminoids,” Inorganica Chimica Acta 450, (2016): 243–50.
   Web of Science ®Google Scholar
• V. Porchezhiyan, D. Kalaivani, J. Shobana, and S. E. Noorjahan, “Synthesis, Docking and in Vitro Evaluation of l-Proline Derived 1,3-Diketones Possessing anti-Cancer and anti-Inflammatory Activities,” Journal of Molecular Structure 1206, (2020): 127754.
   Web of Science ®Google Scholar
• T. Nishiyama, S. Shiotsu, and H. Tsujita, “Antioxidative Activity and Active Site of 1,3-Indandiones with the β-Diketone Moiety,” Polymer Degradation and Stability 76, no. 3 (2002): 435–9.
   Web of Science ®Google Scholar
• P. V. Badadhe, L. R. Patil, S. S. Bhagat, A. V. Chate, D. W. Shinde, M. D. Nikam, and C. H. Gill, “Synthesis and Antimicrobial Screening of Some Novel Chromones and Pyrazoles with Incorporated Isoxazole Moieties,” Journal of Heterocyclic Chemistry 50, (2013): n/a–1004.
   Web of Science ®Google Scholar
• W. Wang, L. Deng, C. Hu, Y. Zhang, Y. Li, and S. Zuo, “Synthesis of Isoxazole‐Linked Norcantharidin Analogues of Substituted Chromones,” Journal of Heterocyclic Chemistry 54, no. 3 (2017): 1806–11.
   Web of Science ®Google Scholar
• (a) S. G. Dengale, H. N. Akolkar, B. K. Karale, N. R. Darekar, S. D. Mhaske, M. H. Shaikh, D. N Raut and K. K. Deshmukh, “Synthesis of 3‐(trifluoromethyl)‐1‐ (perfluorophenyl)‐1H‐pyrazol‐5(4H)‐one derivatives via Knoevenagel condensation and their biological evaluation,” Journal of the Chinese Chemical Society, 68 (2021): 657-668;
   Google Scholar
  (b) S. P. Kunde, K. G. Kanade, B. K. Karale, H. N. Akolkar, S. S. Arbuj, P. V. Randhavane, S. T. Shinde, M. H. Shaikh and A. K. Kulkarni, “Nanostructured N doped TiO2 efficient stable catalyst for Kabachnik-Fields reaction under microwave irradiation,” RSC Advances, 10 (2020): 26997–27005;
   PubMed Web of Science ®Google Scholar
  (c) H. N. Akolkar, S. J Takate, K. K. Deshmukh, B. K. Karale, N. R. Darekar, V. M. Khedkar and M. H. Shaikh “Design, Synthesis and Biological Evaluation of Novel Furan & Thiophene Containing Pyrazolyl Pyrazolines as Antimalarial Agents,” Polycyclic Aromatic Compounds, https://doi.org/10.1080/10406638.2020.1821231;
   Google Scholar
  (d) M. H. Shaikh, D. D. Subhedar, S. V. Akolkar, A. A, Nagargoje, V. M. Khedkar, D. Sarkar and B. B. Shingate, “Tetrazoloquinoline-1, 2, 3-Triazole Derivatives as Antimicrobial Agents: Synthesis, Biological Evaluation and Molecular Docking Study,” Polycyclic Aromatic Compounds, https://doi.org/10.1080/10406638.2020.1821229.
   Google Scholar
• (a) Schrodinger Suite 2015-4 QM-Polarized Ligand Docking protocol; Glide version 6.9, Schrodinger, LLC, New York, NY,2006; Jaguar version 9.0, Schrodinger, LLC, New York, NY, 2015; QSite version 6.9, Schrodinger, LLC, New York, NY, 2015;
   Google Scholar
  (b) R. A. Friesner, R. B. Murphy, M. P. Repasky, L. L. Frye, J. R. Greenwood, T. A. Halgren, P. C. Sanschagrin and D. T. Mainz, “Extra precision glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes,” Journal of Medicinal Chemistry, 2149 (2006): 6177–6196 and related references cited theirin.
   PubMed Web of Science ®Google Scholar
• S. Zhang, Y. Luo, L. Q. He, Z. J. Liu, A. Q. Jiang, Y. H. Yang, and H. L. Zhu, “Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel 1,3,4-Oxadiazole Derivatives Possessing Benzotriazole Moiety as FAK Inhibitors with Anticancer Activity,” Bioorganic & Medicinal Chemistry 21, no. 13 (2013): 3723–9.
   PubMed Web of Science ®Google Scholar
• Molinspiration Chemoinformatics Brastislava, Slovak Republic, Available from: http://www.molinspiration.com/cgi-bin/properties 2014.
   Google Scholar
• (a) P. Padmanabhan and S. N. Jangle, “Evaluation of in-vitro anti-inflammatory activity of herbal preparation, a combination of four medicinal plants,” International Journal of Basic and Applied Medical Sciences, 2 (2012): 109–116;
   Google Scholar
  (b) Y. Mizushima and M. Kobayashi, “Interaction of anti‐inflammatory drugs with serum proteins, especially with some biologically active proteins,” Journal of Pharmacy and Pharmacology, 20 (1968): 169–73;
   PubMed Web of Science ®Google Scholar
  (c) G. Elias and M. N. Rao, “Inhibition of albumin denaturation and anti-inflammatory activity of dehydrozingerone and its analogs,” Indian Journal of Experimental Biology, 26 (1988): 540–542;
   PubMed Web of Science ®Google Scholar
  (d) S. F. D. Nguemnang, E. G. Tsafack, M. Mbiantcha, A. Gilbert, A. D. Atsamo, N. W. Yousseu, M. M. V. Matah, C. F. Adjouzem, “In vitro anti-inflammatory and in vivo antiarthritic activities of aqueous and ethanolic extracts of Dissotis thollonii Cogn. (Melastomataceae) in rats,” Evidence-Based Complementary and Alternative Medicine 15(2019);
   Google Scholar
  (e) K. D. P. P. Gunathilake, K. K. D. S. Ranaweera and H. P. Vasantha Rupasinghe, “In vitro anti-inflammatory properties of selected green leafy vegetables”, Biomedicines 6 (2018): 107–116;
   Web of Science ®Google Scholar
  (f) N. H. Grant, H. E. Alburn and C. Kryzanauskas, “Stabilization of serum albumin by anti-inflammatory drugs,” Biochemical Pharmacology 19 (1970): 715–722.
   PubMed Web of Science ®Google Scholar
• C. A. Lipinski, L. Lombardo, B. W. Dominy, and P. J. Feeney, “Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings,” Advanced Drug Delivery Reviews 46, no. 1-3 (2001): 3–26.
   PubMed Web of Science ®Google Scholar
• Yuan H. Zhao, Michael H. Abraham, Joelle Le, Anne Hersey, Chris N. Luscombe, Gordon Beck, Brad Sherborne, and Ian Cooper, “Rate Limited Steps of Human Oral Absorption and QSAR Studies,” Pharmaceutical Research 19, no. 10 (2002): 1446–57.
   PubMed Web of Science ®Google Scholar
• Drug-likeness and molecular property prediction, available from: http://www.molsoft.com/mprop/
   Google Scholar