Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions

References (87)

1. 1 Southon, I.W., and Buckingham, J. (1989). Dictionary of Alkaloids, Chapman & Hall.
2. 2 Gothelf, 1998, Asymmetric 1,3-Dipolar Cycloaddition Reactions [DOI]
3. 3 Huisgen, 1963, Kinetics and Mechanism of 1,3-Dipolar Cycloadditions [DOI]
4. 4 Huisgen, 1976, 1,3-Dipolar cycloadditions. 76. Concerted nature of 1,3-dipolar cycloadditions and the question of diradical intermediates [DOI]
5. 5 Firestone, 1968, Mechanism of 1,3-dipolar cycloadditions [DOI]
6. 6 Firestone, 1977, The diradical mechanism for 1,3-dipolar cycloadditions and related thermal pericyclic reactions [DOI]
7. 7 Firestone, 2013, The Low Energy of Concert in Many Symmetry Allowed Cycloadditions Supports a Stepwise Diradical Mechanism [DOI]
8. 8 Kozikowski, 1984, The isoxazoline route to the molecules of nature [DOI]
9. 9 Kumar, 2014, A Simple, Efficient One Pot Synthesis of 2-Isoxazoline Derivatives and their Antimicrobial Activity
10. 10 Diana, 1985, Isoxazoles with antipi cornavirus activity [DOI]
11. 11 Antczak, 2001, A new acivicin prodrug designed for tumor-Targeted delivery [DOI]
12. 12 Prajapti, 2015, Synthesis and biological evaluation of novel Δ2-isoxazoline fused cyclopentane derivatives as potential antimicrobial and anticancer agents [DOI]
13. 13 Zhang, 2012, Synthesis and biological activities of novel isoxazoline-linked pseudodisaccharide derivatives [DOI]
14. 14 Abdelall, 2019, Synthesis and biological evaluations of novel isoxazoles and furoxan derivative as anti-inflammatory agents [DOI]
15. 15 Zhu, 2018, The recent progress of isoxazole in medicinal chemistry [DOI]
16. 16 Zadrozna, 2000, 4,5-Dihydroisoxazoles: Testing of antimicrobial activity [DOI]
17. 17 Liu, 2020, Stereoselective Synthesis of CF3-Containing Spiro oxindoles via 1,3-Dipolar Cycloaddition by Dipeptide Based Phosphonium Salt Catalysis [DOI]
18. 18 Gui, 2020, Recent Advances in the Construction of Trifluoromethyl Containing Spiro oxindoles through Cycloaddition Reactions [DOI]
19. 19 Uno, 2020, Synthesis of Highly Functionalized 12-Membered Trifluoromethyl Heterocycles via a Nonde carboxyl ative Pd-Catalyzed [6 + 6] Annulation [DOI]
20. 20 Bigelow, 1947, The Action of Elementary Fluorine upon Organic Compounds [DOI]
21. 21 Yoshimura, 2016, Advances in Synthetic Applications of Hypervalent Iodine Compounds [DOI]
22. 22 Muller, 2007, Fluorine in Pharmaceuticals: Looking Beyond Intuition [DOI]
23. 23 Aggarwal, 2013, Synthesis and antimicrobial activity of 3-(2-thienyl)-4-arylazo-5-hydroxy-5-trifluoromethyl-Δ2-isoxazolines and 3-(2-thienyl)-4-arylazo-5-trifluoromethylisoxazoles [DOI]
24. 24 Filler, R., and Kobayashi, Y. (1982). Biomedicinal Aspects of Fluorine Chemistry, Elsevier.
25. 25 Giovannoni, 2003, [(3-Chlorophenyl)piperazinylpropyl]pyridazinones and Analogues as Potent Antinociceptive Agents [DOI]
26. 26 Karthikeyan, 2009, Synthesis and antinociceptive activity of pyrazolyl isoxazolines and pyrazolyl isoxazoles [DOI]
27. 27 Kamal, 2011, Synthesis and biological evaluation of 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydroquinazolinone hybrids as anticancer agents [DOI]
28. 28 Patrizia, 2010, Synthesis and antitumor activity of 2,5-bis(3′-indolyl)-furans and 3,5-bis(3′-indolyl)-isoxazoles, nortopsentin analogues [DOI]
29. 29 Isanbor, 2006, Fluorine in medicinal chemistry: A review of anti-cancer agents [DOI]
30. 30 Bukovsky, 2019, Steric and electronic effects of CF3 conformations in acene(CF3)n derivatives [DOI]
31. 31 Haranahalli, 2019, Recent progress in the strategic incorporation of fluorine into medicinally active compounds [DOI]
32. 32 Agbaje, 2011, Lewis acid mediated diastereoselective synthesis of fused fluorinated spiroketal as potential biologically active compounds [DOI]
33. 33 Jbeily, 2017, Fluorophilicity and lipophilicity of fluorinated rhodamines determined by their partition coefficients in biphasic solvent systems [DOI]
34. 34 Ojima, I. (2009). Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell. [DOI]
35. 35 Wang, 2014, Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001–2011) [DOI]
36. 36 Koldobskii, 2020, Polyfluorinated esters of 4-chloro-2-oxobut-3-ynoic acid. Cycloaddition reactions of hexafluoro isopropyl 4-chloro-2-oxobut-3-ynoate, an incredibly electrophilic alkyne [DOI]
37. 37 Bigotti, 2009, Functionalized fluoroalkyl heterocycles by 1,3-dipolar cycloadditions with γ-fluoro-α-nitroalkenes [DOI]
38. 38 2010, Fluorine in health care: Organofluorine containing blockbuster drugs [DOI]
39. 39 McGrath, 2010, Graphical Journey of Innovative Organic Architectures That Have Improved Our Lives [DOI]
40. 40 Zhou, 2016, Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas [DOI]
41. 41 Domingo, L.R. (2016). Molecular Electron Density Theory: A Modern View of Reactivity in Organic Chemistry. Molecules, 21. [DOI]
42. 42 Domingo, 2019, Unravelling the Mysteries of the [3 + 2] Cycloaddition Reactions [DOI]
43. 43 Domingo, 2014, A DFT analysis of the participation of zwitterionic TACs in polar [3 + 2] cycloaddition reactions [DOI]
44. 44 Zeroual, 2019, An MEDT study of the mechanism and selectivities of the [3 + 2] cycloaddition reaction of tomentosin with benzonitrile oxide [DOI]
45. 45 Zeroual, 2019, An investigation of the molecular mechanism, chemoselectivity and regioselectivity of cycloaddition reaction between acetonitrile N-Oxide and 2,5-dimethyl-2H-[1,2,3]diazaphosphole: A MEDT study [DOI]
46. 46 Yoshimura, 2013, Hypervalent Iodine Catalyzed Generation of Nitrile Oxides from Oximes and their Cycloaddition with Alkenes or Alkynes [DOI]
47. 47 Becke, 1993, Density-functional thermochemistry. III. The role of exact exchange [DOI]
48. 48 Hehre, W.J., Radom, L., Schleyer, P.R., and Pople, J.A. (1986). Ab Initio Molecular Orbital Theory, Wiley.
49. 49 Fisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). Gaussian 09, Revision A.02, Fox, Gaussian, Inc.
50. 50 Schlegel, 1982, Optimization of equilibrium geometries and transition structures [DOI]
51. 51 Fukui, 1970, Formulation of the reaction coordinate [DOI]
52. 52 Gonzalez, 1991, Improved algorithms for reaction path following: Higher order implicit algorithms [DOI]
53. 53 Tomasi, 1994, Molecular Interactions in Solution: An Overview of Methods Based on Continuous Distributions of the Solvent [DOI]
54. 54 Barone, 1998, Geometry optimization of molecular structures in solution by the polarizable continuum model [DOI]
55. 55 Domingo, 2014, A new C–C bond formation model based on the quantum chemical topology of electron density [DOI]
56. 56 Reed, 1988, Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint [DOI]
57. 57 Domingo, L.R., Ríos-Gutiérrez, M., and Pérez, P. (2016). Applications of the Conceptual Density Functional Theory Indices to Organic Chemistry Reactivity. Molecules, 21. [DOI]
58. 58 Becke, 1990, A simple measure of electron localization in atomic and molecular systems [DOI]
59. 59 Noury, 1999, Computational tools for the electron localization function topological analysis [DOI]
60. 60 Krokidis, 1997, Characterization of Elementary Chemical Processes by Catastrophe Theory [DOI]
61. 61 Lefebre, 2018, The Independent Gradient Model: A New Approach for Probing Strong and Weak Interactions in Molecules from Wave Function Calculations [DOI]
62. 62 1999, Density-functional theory beyond the Hohenberg-Kohn theorem [DOI]
63. 63 Salah, 2021, MEDT study of the 1,3-DC reaction of diazomethane with Psilostachyin and investigation about the interactions of some pyrazoline derivatives with protease (Mpro) of nCoV-2 [DOI]
64. 64 Lu, 2012, Multiwfn: A multifunctional wave function analyzer [DOI]
65. 65 Silvi, 1994, Classification of chemical bonds based on topological analysis of electron localization functions [DOI]
66. 66 Parr, R.G., and Yang, W. (1989). Density Functional Theory of Atoms and Molecules, Oxford University Press.
67. 67 Parr, 1999, Electrophilicity Index [DOI]
68. 68 Domingo, 2008, Understanding the Reactivity of Captodative Ethylenes in Polar Cycloaddition Reactions. A Theoretical Study [DOI]
69. 69 Aurell, 2004, A theoretical study on the regioselectivity of 1,3-dipolar cycloadditions using DFT-based reactivity indexes [DOI]
70. 70 Domingo, L.R., Ríos-Gutiérrez, M., and Castellanos Soriano, J. (2020). Understanding the Origin of the Regioselectivity in Non-Polar [3 + 2] Cycloaddition Reactions through the Molecular Electron Density Theory. Org. Chem., 1. [DOI]
71. 71 Domingo, 2013, Understanding the local reactivity in polar organic reactions through electrophilic and nucleophilic Parr functions [DOI]
72. 72 Zeroual, 2020, A molecular electron density theory investigation of the molecular mechanism, regioselectivity, stereoselectivity and chemoselectivity of cycloaddition reaction between acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole [DOI]
73. 73 Domingo, 2008, Understanding the Participation of Quadricyclane as Nucleophile in Polar [2σ + 2σ + 2π] Cycloadditions toward Electrophilic π Molecules [DOI]
74. 74 Didelot, 2007, Anti-Cancer Therapeutic Approaches Based on Intracellular and Extracellular Heat Shock Proteins [DOI]
75. 75 Tumma, 2019, Design, Synthesis, Molecular Docking, and Biological Evaluation of Pyrazole 1-Carbothiamide incorporated Isoxazole Derivatives [DOI]
76. 76 Loh, 2010, Inhibition of HIV-1 Replication by Isoxazolidine and Isoxazole Sulfonamides [DOI]
77. 77 Panda, 2009, Synthesis, Antiinflammatory and Antibacterial Activity of Novel Indolyl-isoxazoles [DOI]
78. 78 Durgamma, 2016, Synthesis and Antioxidant Activity of Amido-Linked Benzoxazolyl/Benzothiazolyl/BenzimidazolylPyrazoles and Isoxazoles [DOI]
79. 79 Makarov, 2005, Novel [(biphenyloxy)propyl]isoxazole derivatives for inhibition of human rhinovirus 2 and coxsackie virus B3 replication [DOI]
80. 80 Basha, 2015, Synthesis and antimicrobial activity of thiazolyl pyrazoles and isoxazoles [DOI]
81. 81 Arrieta, 1998, Efficient tautomerization hydrazone-azomethine imine under microwave irradiation. Synthesis of [4,3′] and [5,3′]bipyrazoles [DOI]
82. 82 Berman, 2000, The Protein Data Bank [DOI]
83. 83 Burley, 2019, RCSB Protein Data Bank: Biological macromolecular structures enabling research and education in fundamental biology, biomedicine, biotechnology and energy [DOI]
84. 84 Goodsell, 1990, Automated Docking of Substrates to Proteins by Simulated Annealing [DOI]
85. 85 Morris, 1998, Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function [DOI]
86. 86 Katritzky, 1996, Correlation of Boiling Points with Molecular Structure. 1. A Training Set of 298 Diverse Organics and a Test Set of 9 Simple Inorganics [DOI]
87. 87 Solis, 1981, Minimization by Random Search Techniques [DOI]

Cited by 34

Showing 19 of 34 known citations — external sources report more than can currently be individually listed.

Related research

• A Novel Catalytic Synthesis of Flavones under Autoclave Conditions and Comparative Study of Anti-cancer Activity — shares topic coverage
• Thermostability and in-vitro Antibacterial Activity of Aqueous Extracts of Tetrapleura tetraptera Pods on Multidrug Resistant Clinical Isolates — shares topic coverage
• Acute Toxicity, Phytochemistry and Anti-diarrheal Effects of Celtis integrifolia Lam. Aqueous Leaf Extract in Wistar Albino Rats — shares topic coverage
• Understanding the Reactivity of Trimethylsilyldiazoalkanes Participating in [3+2] Cycloaddition Reactions towards Diethylfumarate with a Molecular Electron Density Theory Perspective — shares topic coverage
• Understanding the Origin of the Regioselectivity in Non-Polar [3+2] Cycloaddition Reactions through the Molecular Electron Density Theory — shares topic coverage