Synthesis, DFT Study and Antibacterial Activity of some Isoxazoline Derivatives Containing 1,4-benzothiazin-3-one Nucleus Obtained Using 1,3-dipolar Cycloaddition Reaction

Document Type : Research Article

Authors

1 Laboratoire de Chimie Appliquée et Environnement, équipe de Chimie Bioorganique Appliquée, Faculté des Sciences, Université Ibn Zohr, Agadir, MOROCCO

2 Laboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Centre de Recherche des Sciences des Médicaments, Mohammed V University in Rabat, Faculté des Sciences, Av. Ibn Battouta, BP 10140 Rabat, MOROCCO

3 Laboratoire de Chimie Organique et Etudes Physico-Chimique, ENS Takaddoum, Université Mohammed V, Rabat, MOROCCO

4 Laboratoire National de Contrôle des Médicaments, Direction du Médicament et de la Pharmacie, Ministère de la Santé, Rabat, MOROCCO

5 Laboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fès, MOROCCO

6 Département de bactériologie, Institut national d’hygiène, avenue Ibn Batouta, B.P. 769, Agdal, Rabat, 11000, MOROCCO

7 Department of Chemistry, Tulane University, New Orleans, LA 70118, USA

Abstract

Novel series of isoxazoline derivatives containing 1,4-benzothiazin-3-one ring (6a-h) were synthesized via 1,3-dipolar cycloaddition reactions of arylnitrile oxides 5a-d on 4-allyl-2-(substituted)-1,4-benzothiazin-3-ones 3 and 4 led to polyheterocyclic. Systems. During our work,
we mainly focused on the reactivity of nitrile oxides with carbon-carbon extracyclic double bond of the allyl group. The reaction leads exclusively to cycloadducts 6a-h with a good yield. The compounds were characterized using s spectral data (1H-NMR, 13C-NMR) and for some structures were also confirmed via single-crystal X-ray diffraction techniques. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311G(d,p) level are compared with the experimentally determined molecular structure in the solid-state. The HOMO—LUMO behavior was elucidated. The results are in agreement with the experimental data. The newly synthesized compounds 1, 2, 3, 4, 6a-g using cycloaddition reactions were evaluated in vitro for their antibacterial activities against some Gram-positive and Gram-negative microbial strains. Several compounds tested showed significant activity.

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Main Subjects

References

1] Trapani G., Reho A., Morlacchi F., Latrofa A., Marchini P., Venturi F., Cantalamessa F., Synthesis and Antiinflammatory Activity of Various 1,4-Benzothiazine Derivatives, Farmaco. Ed.  Sci, 40(5): 369-376 (1985).
[2] Gupta S., Ajmera N., Meena P., Gautam N., Kumar A., Gautam D.C., Synthesis and Biological Evaluation of New 1,4-Thiazine Containing Heterocyclic Compounds, Jordan. J. Chem, 4: 209-221 (2009).
[3] Armenise D., Trapani G., Arrivo V., Laraspata, E., Morlacchi F., Research on Potentially Bioactive
Aza and Thiaza Polycyclic Compounds Containing a Bridgehead ANitrogen Atom. Synthesis and Antimicrobial Activity of Some 1,4-benzothiazines and Pyrrolobenzothiazines, J. Heterocycl. Chem, 37: 1611-1616 (2000).
[4] Gowda J., Khader A.M.A., Kalluraya B., Shree P., Shabaraya A.R., Synthesis, Characterization and Pharmacological Activity of 4-{[1-substituted aminomethyl-4-arylideneamino-5-sulfanyl-4,5-dihydro-1H -1,2,4-triazol-3-yl] methyl}-2H-1,4-benzothiazin-3(4H)-ones, Eur. J. Med. Chem, 46: 4100-4106 (2011).
[5] Shamsuzzaman A.M., Dar H., Khanam M., Gatoo, A., Anticancer and Antimicrobial Evaluation of Newly Synthesized Steroidal 5,6 Fused Benzothiazines, Arab. J. Chem, 7: 461-468 (2014).
[6] Armenise D., Muraglia M., Florio M.A., Laurentis N.D., Rosato A., Carrieri A., Corbo F., Franchini C., 4H-1,4-Benzothiazine, Dihydro-1,4-benzothiazinones and 2-Amino-5-fluorobenzenethiol Derivatives: Ciprofloxacin-Treated Mammalian Cells, Mol. Pharmacol. Mol. Pharmacol, 50: 1178–1188 (2012).
[7] Bansode T.N., Shelke J.V., Dongre V.G., Synthesis and Antimicrobial Activity of some New N-acyl Substituted Phenothiazines, Eur. J. Med. Chem, 44: 5094-5098 (2009).
[8] Sebbar N.K., Ellouz M., Essassi E.M., Ouzidan Y., Mague J.T., Crystal structure of 4-benzyl-2Hbenzo[b][1,4]thiazin-3(4H)-one. Acta Cryst, E7: o999 (2015).
[9] Sebbar N.K., Zerzouf A., Essassi E.M., Saadi M., El Ammari L., (2Z)-2-Benzylidene-4-(prop-2- yn-1 -yl)-2H-1,4-benzothiazin-3(4H)-one, Acta Cryst, E70: o614 (2014).
[10] Sebbar N.K., Zerzouf A., Essassi E.M., Saadi M., El Ammari L., 4-(Prop-2-ynyl)-2H-1,4- benzothiazin- 3(4H)-one, Acta Cryst, E70: o641 (2014).
[11] Thomas L., Gupta A., Gupta V., Synthesis of 2-amino-5-chloro-3-(trifluoromethyl)benzenethiol and Conversion into 4H-1,4-benzothiazines and Their Sulfones, J. Fluorine Chem, 122: 207-213 (2003).
[12] Sebbar N.K., El Fal M., Essassi E.M., Saadi M., El Ammari L., (2Z)-2-Benzyl­idene-4-n-butyl-3,4-di­hydro-2H-1,4-benzo­thia­zin-3-one, Acta Cryst, E70: o686 (2014).
[13] Sebbar N.K., Zerzouf A., Essassi E.M., Saadi M., El Ammari L., 4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth­yl]-2H-1,4-benzo­thia­zin-3(4H)-one, Acta Cryst, E70: o160–o161 (2014).
[14] Dixit Y., Dixit R., Gautam N., Gautam D. C., Synthesis and Antimicrobial Activities of Novel Biologically Active Heterocycles: 10H-Phenothiazines, Their Ribofuranosides, and Sulfone Derivatives, Nucleosides Nucleotides Nucleic Acids, 28: 998-1006 (2009).
[15] Ellouz M., Sebbar N.K., Essassi E.M., Ouzidan Y., Mague J.T., Crystal structure of (Z)-ethyl 2-{5-[(2-benzyl­idene-3-oxo-2,3-di­hydro­benzo[b][1,4]thia­zin-4-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate, Acta Cryst, E71: o1022-o1023 (2015).
[16] Chakib I., Elmsellem H., Sebbar N.K., Essassi E.M., Fichtali I., Zerzouf A., Ouzidan Y., Aouniti A.,
El Mahi B., Hammouti B., Investigation of (4Z)-4-(2H-1,4-benzothiazin-3(4H)-ylidene)-5-methyl-2- phenyl-2,4-dihydro-3H-pyrazol-3-one as a New Corrosion Inhibitors in Molarhydrochloricacid: Computational Calculations, Der Pharma Chemica, 8: 422-433 (2016).
[17] Fringuelli R, Schiaffella F, Bistoni F, Pitzurra L, Vecchiarelli A, Azole Derivatives of 1,4- Benzothiazine as Antifungal Agents, Bioorg Med Chem, 6: 103-108 (1998).
[18] Warren B. K., Knaus E.E., Pyridine and Reduced Pyridine Analogues of 10H-pyrido[3,4- b][1,4]benzothiazines with Analgesic Activity Analogues à Noyau Pyridinique Plus ou Moins Hydrogéné de 10H-pyrido[3,4-b]benzothiazine-1,4 à activité analgésique, Eur. J. Med. Chem, 22: 411–415 (1987).
[19] Armenise D., Muraglia M., Florio M.A., De Laurentis N., Rosato A., Carrieri A., Corbo F., Franchini C., 4H‐1,4‐Benzothiazine, Dihydro‐1,4‐benzothiazinones and 2‐Amino‐5‐fluorobenzenethiol Derivatives: Design, Synthesis and in vitro Antimicrobial Screening, Arch. Pharm. Chem. Life Sci, 345: 407-416 (2012).
[20] Sabatini S, Kaatz G. W, Rossolini G. M, Brandim D, Fravolini A, Rossolini G. M, Brandini D, Fravolini A, From Phenothiazine to 3-phenyl-1,4-Benzothiazine Derivatives as Inhibitors of
the Staphylococcus Aureus Nor A Multidrug Efflux Pump, J.Med.Chem, 51: 4321–4330 (2008).
[21] Jacquot Y, Bermont L, Giorgi H, Refouvelet B, Adessi G. L, Daubrosse, E, Xicluna, A, Substituted Benzopyranobenzothiazinones. Synthesis and Estrogenic Activity on MCF-7 Breast Carcinoma Cells, Eur.J. Med. Chem, 36: 127–136 (2001).
[22] Munirajasekhar D., Himaja M., Sunil V Mali., Synthesis and Anthelimintic Activity of 2-amino-6-Substituted Benzothiazoles, Int. Res. J. Pharm, 2; 114-117 (2011).
[23] Sperry J., Wright D., Furans, Thiophenes and Related Heterocycles in Drug Discovery, Curr. Opin. Drug Discov. Dev, 8: 723-740 (2005).
[24] Tangallapally R.P., Sun D., Rakesh N., Budha N., Lee E.B R., Lenaerts A.J.M., Meibohm B., Lee R.E., Discovery of Novel Isoxazolines as Anti-Tuberculosis Agents, Bioorg Med Chem Lett, 17: 6638-6642 (2007).
[25] Kozikowski A.P., The Isoxazoline Route to the Molecules of Nature, Acc. Chem. Res, 410-416 (1984).
[26] Sheldrick G.M., A Short History of SHELX, Acta.Crystallogr; A64: 112-122 (2008).
[27] Sheldrick, G.M., Program SHELXTL97. Siemens Analytical X-Ray Instruments, Inc., Madison, Wisconsin, USA, (1997).
[28] Becke A.D., Density-Functional Thermochemistry. III. The Role of Exact Exchange, Chem. Phys, 98: 5648 (1993).
[29] Frisch M.J. Trucks G.W. Schlegel H.B. Scuseria G.E., Robb M.A. Cheeseman J.R. Scalmani G. Barone V. Mennucci B. Petersson G.A. Nakatsuji H. Caricato M. Li, X. Hratchian H.P. Izmaylov A.F. Bloino J. Zheng G. Sonnenberg J.L. Hada M. Ehara M. Toyota  K. Fukuda R. Hasegawa J. Ishida M. Nakajima T. Honda Y. Kitao O. Nakai H. Vreven T. Montgomery J.A., Jr. Peralta J. E. Ogliaro F. Bearpark M. Heyd J.J. Brothers E. Kudin K.N. Staroverov V.N. Kobayashi R. Normand J. Raghavachari K. Rendell A. Burant J.C. Iyengar S.S. Tomasi J. Cossi, M. Rega N. Millam J. M. Klene M. Knox J.E. Cross J.B. Bakken V. Adamo C. Jaramillo J. Gomperts R. Stratmann R.E. Yazyev O. Austin A.J. Cammi R. Pomelli C. Ochterski J.W. Martin R.L. Morokuma K. Zakrzewski V.G. Voth G.A. Salvador P. Dannenberg J.J. Dapprich S. Daniels A.D. Farkas Ö. Foresman J.B. Ortiz J.V. Cioslowski J. Fox D.J. Gaussian 09, Revision E.01, Gaussian, Inc., Wallingford CT, (2009).
[30] Becke A.D., Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior, Phys. Rev, A38: 3098 (1988).
[31] Lee C., Yang W., Parr R.G., Development of the Colle-Salvetti Correlation-Energy Formula into
a Functional of the Electron Density, Phys. Rev, B37: 785 (1988).
[32] Arthington-Skaggs B.A., Motley M., Morrison C.J., Comparative Evaluation of PASCO and National Committee for Clinical Laboratory Standards M27-A Broth Microdilution Methods for Antifungal Drug Susceptibility Testing of Yeasts, J. Clin Microbiology, 38: 2254 (2000).
[33] Bandiera T., Albini F.M., Albini E., Synthesis and Antifungal Activity of Some Allylamine Derivatives, J. Heterocyclic Chem, 24: 1597 (1987).
[34] Ellouz M., Sebbar N. K., Fichtali I., Ouzidan Y., Mennane Z., Charof R., Mague J. T., Urrutigoïty M., Essassi E.M., Synthesis and Antibacterial Activity of New 1 ,2, 3-t Riazolylm ethyl- 2H -1 ,4- Benzothiazin-3(4H)-one Derivatives, Chem. Cent. J, 12: 123 (2018).
[35] Sebbar N.K.,  Ellouz M.,  Essassi E.M.,  Saadi M.,  El Ammari L., 4-[(3-Phenyl-4,5-di­hydro­isoxazol-5-yl)meth­yl]-2H-benzo[b][1,4]thia­zin-3(4H)-one, IUCrData, 2016, 1, x161012.
[36] Sebbar N.K.,  Ellouz M.,  Essassi E. M.,  Saadi M., El Ammari L., Crystal Structure of (E)-2-benzyl­idene-4-[(3-phenyl-4,5-di­hydro­isoxazol-5-yl)meth­yl]-2H-benzo[b][1,4]thia­zin-3(4H)-one, Acta. Cryst,  E71: o423-o424 (2015).
[37] Sebbar N.K., Mekhzoum M.E.M., Essassi E.M., Zerzouf A., Talbaoui A., Bakri Y., Saadi M., Ammari L.E., Novel 1,4-benzothiazine Derivatives: Synthesis, Crystal Structure, and Anti-Bacterialproperties, Res. Chem. Intermed, 42(9): 6845–6862 (2016).
[38] Dunstan W.R., DymondT.S., XLV.—Contributions from the Research Laboratory of the Pharmaceutical Society of Great Britain. The Action of Alkalis on the Nitro-Compounds of the Paraffin Series, Formation of Isoxazoles, J. Chem. Soc, 59: 410-33 (1891).
[39] Rescifina A., Varrica M.G., Carnovale C., Romeo G., ChiacchioU., Novelisoxazole Polycyclic Aromatic Hydrocarbons as DNA Intercalating Agents, Eur. J. Med. Chem, 51: 163-73 (2012).
[40] Lang J. S.A., Lin Y.I. Isoxazoles and Their Benzo Derivatives, Compr. Heterocycl. Chem. II, 6: 1-130 (1984).
[41] Lambein F, Kuo YH, Parijs RV., Isoxazolin-5-ones, Chemistry and Biology of a New Class of Plant Products, Heterocycles, 4: 567-93 (1976).
[42] Gasparrini F, Giovannoli M, Misiti D, Natile G., Palmieri G., Maresca L., Gold(III)-catalyzed One-Pot Synthesis of isoxazoles from terminal alkynes and nitric acid. Isoxazole, J. Am. Chem. Soc., 115 (10): 4401–4402 (1993).
[43] Badadhe P.V., Chavan N.M., Mandhane P.G., Joshi R.S., Nagargoje D.R., Gill C.H., Synthesis and Characterization of Some Novel Isoxazolines and Pyrazolines as Potent Antimicrobial Agents, Indian. J. Chem, 50B: 879-84 (2011).
[44] Pardasani R.T., Pardasani P., Komal A., Sonali V., Rahul J., Synthesis, Configurational Analysis and Antimicrobial Activity of Imidazolidinone, Thiazolidinedione and Isoxazolone Derivatives of 9,10-Phenanthrenequinone, Indian. J. Chem, 50B: 83-8 (2011).
Iranian Journal of Chemistry and Chemical Engineering
Volume 39, Issue 4 - Serial Number 102
July and August 2020
Pages 53-67

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