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Volumn 34, Issue 1, 2015, Pages 15-25

Synthesis, crystal structure and spectroscopic properties of 1,2-Benzothiazine derivatives: An experimental and DFT study

Author keywords

1,2 benzothiazine; B3LYP 6 31+G (d); Crystal structures; Density functional theory (DFT); HUMO LUMO

Indexed keywords


EID: 84920903770     PISSN: 02545861     EISSN: None     Source Type: Journal    
DOI: 10.14102/j.cnki.0254-5861.2011-0423     Document Type: Article
Times cited : (15)

References (43)
  • 1
    • 3142677266 scopus 로고    scopus 로고
    • Benzothiazines in synthesis. Toward the synthesis of pseudopteroxazole
    • Harmata, M.; Hong, X.; Barnes, C. L. Benzothiazines in synthesis. Toward the synthesis of pseudopteroxazole. Org. Lett. 2004, 6, 2201-2203.
    • (2004) Org. Lett. , vol.6 , pp. 2201-2203
    • Harmata, M.1    Hong, X.2    Barnes, C.L.3
  • 2
    • 0035059899 scopus 로고    scopus 로고
    • Comparison by magnetic resonance imaging of the effects of two different non-steroidal anti-inflammatory drugs on edema following the surgical extraction of impacted third molars
    • Yaltirik, M.; Oral, C. K.; Oral, I.; Kasaboglu, G.; Cebi, V. Comparison by magnetic resonance imaging of the effects of two different non-steroidal anti-inflammatory drugs on edema following the surgical extraction of impacted third molars. Turk. J. Med. Sci. 2001, 31, 151-154.
    • (2001) Turk. J. Med. Sci. , vol.31 , pp. 151-154
    • Yaltirik, M.1    Oral, C.K.2    Oral, I.3    Kasaboglu, G.4    Cebi, V.5
  • 3
    • 0037147639 scopus 로고    scopus 로고
    • Microwave promoted regeneration of carbonyl compounds from oximes using N,N-dichloro poly(styrene-co-divinylbenzene)sulphonamide resin
    • Park, M. S.; Chang, E. S.; Lee, M. S.; Kwon, S. K. Microwave promoted regeneration of carbonyl compounds from oximes using N,N-dichloro poly(styrene-co-divinylbenzene)sulphonamide resin. Bull. Korean Chem. Soc. 2002, 23, 1836-1838.
    • (2002) Bull. Korean Chem. Soc. , vol.23 , pp. 1836-1838
    • Park, M.S.1    Chang, E.S.2    Lee, M.S.3    Kwon, S.K.4
  • 5
    • 85163210290 scopus 로고
    • Uber benzo-polymethylen-verbindungen, X.: Oxydativer abbau von tetralin und substituierten tetralinen zu phthalonsauren und phthalsauren
    • Braun, J. V. Uber benzo-polymethylen-verbindungen, X.: oxydativer abbau von tetralin und substituierten tetralinen zu phthalonsauren und phthalsauren. Chem. Ber. 1923, 56, 2332-2343.
    • (1923) Chem. Ber. , vol.56 , pp. 2332-2343
    • Braun, J.V.1
  • 7
    • 79955573819 scopus 로고    scopus 로고
    • Microwave assisted synthesis and structure-activity relationship of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides as anti-microbial agents
    • Ahmad, N.; Zia-ur-Rehman, M.; Siddiqui, H. L.; Ullah, M. F.; Parvez, M. Microwave assisted synthesis and structure-activity relationship of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides as anti-microbial agents. Eur. J. Med. Chem. 2011, 46, 2368-2377.
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 2368-2377
    • Ahmad, N.1    Zia-Ur-Rehman, M.2    Siddiqui, H.L.3    Ullah, M.F.4    Parvez, M.5
  • 8
    • 35549005006 scopus 로고    scopus 로고
    • Remarkable accelerating effect of Ag-salt on intramolecular cyclization of o-(1-alkynyl)benzenesulfonamides
    • Barange, D. K.; Nishad, T. C.; Swamy, N. K.; Bandameedi, V.; Kumar, D. A. Remarkable accelerating effect of Ag-salt on intramolecular cyclization of o-(1-alkynyl)benzenesulfonamides. J. Org. Chem. 2007, 72, 8547-8550.
    • (2007) J. Org. Chem. , vol.72 , pp. 8547-8550
    • Barange, D.K.1    Nishad, T.C.2    Swamy, N.K.3    Bandameedi, V.4    Kumar, D.A.5
  • 10
    • 84864416307 scopus 로고    scopus 로고
    • Synthesis and pharmacological activity of N-(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides on rat uterus, rat aorta and rat pancreatic β-cells
    • Khelili, S.; Kihal, N.; Yekhlef, M.; De Tullio, P.; Lebrun, P.; Pirotte, B. Synthesis and pharmacological activity of N-(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides on rat uterus, rat aorta and rat pancreatic β-cells. Eur. J. of Med. Chem. 2012, 54, 873-878.
    • (2012) Eur. J. of Med. Chem. , vol.54 , pp. 873-878
    • Khelili, S.1    Kihal, N.2    Yekhlef, M.3    De Tullio, P.4    Lebrun, P.5    Pirotte, B.6
  • 11
    • 0010757902 scopus 로고
    • Synthesis of new fluorinated 4H-1,4-benzothiazines as possible anticancer agents
    • Gupta, R. R.; Kumar, R.; Gutam, R. K. Synthesis of new fluorinated 4H-1,4-benzothiazines as possible anticancer agents. J. Fluorine Chem. 1985, 28, 381-385.
    • (1985) J. Fluorine Chem. , vol.28 , pp. 381-385
    • Gupta, R.R.1    Kumar, R.2    Gutam, R.K.3
  • 12
    • 0036625014 scopus 로고    scopus 로고
    • Efficacy of oral doxepin and piroxicam treatment for interstitial cystitis
    • Wammack, R.; Remzi, M.; Seitz, C.; Djavan, B.; Marberger, M. Efficacy of oral doxepin and piroxicam treatment for interstitial cystitis. Eur. Urol. 2002, 41, 596-601.
    • (2002) Eur. Urol. , vol.41 , pp. 596-601
    • Wammack, R.1    Remzi, M.2    Seitz, C.3    Djavan, B.4    Marberger, M.5
  • 14
    • 0033071447 scopus 로고    scopus 로고
    • Synthesis and analgesic and anti-inflammatory activities of 1,2-benzothiazine derivatives
    • Lee, E. B.; Kwon, S. K.; Kim, S. G. Synthesis and analgesic and anti-inflammatory activities of 1,2-benzothiazine derivatives. Arch. Pharm. Res. 1999, 22, 44-47.
    • (1999) Arch. Pharm. Res. , vol.22 , pp. 44-47
    • Lee, E.B.1    Kwon, S.K.2    Kim, S.G.3
  • 16
    • 60549084163 scopus 로고    scopus 로고
    • A facile synthesis of novel biologically active 4-hydroxy-N′-(benzylidene)-2H-benzo[e][1,2]thiazine-3-carbohydrazide 1,1-dioxides
    • Zia-ur-Rehman, M.; Choudary, J. A.; Elsegood, M. R. J.; Siddiqui, H. L.; Khan, K. M. A facile synthesis of novel biologically active 4-hydroxy-N′-(benzylidene)-2H-benzo[e][1,2]thiazine-3-carbohydrazide 1,1-dioxides. Eur. J. Med. Chem. 2009, 44, 1311-1316.
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 1311-1316
    • Zia-Ur-Rehman, M.1    Choudary, J.A.2    Elsegood, M.R.J.3    Siddiqui, H.L.4    Khan, K.M.5
  • 19
    • 0019944528 scopus 로고
    • Piroxicam and other anti-inflammatory oxicams
    • Lombardino, J. G.; Wiseman, E. H. Piroxicam and other anti-inflammatory oxicams. Med. Res. Rev. 1982, 2, 127-152.
    • (1982) Med. Res. Rev. , vol.2 , pp. 127-152
    • Lombardino, J.G.1    Wiseman, E.H.2
  • 21
    • 67349149369 scopus 로고    scopus 로고
    • Synthesis and structure analysis of cyclodehydration product of piroxicam: A metabolite detected in dogs and monkeys
    • Pal, S.; Bindu, P.; Dubey, P. K.; Chakraborty, S.; Mukherjee, A. K. Synthesis and structure analysis of cyclodehydration product of piroxicam: a metabolite detected in dogs and monkeys. Eur. J. Med. Chem. 2009, 44, 3368-3371.
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 3368-3371
    • Pal, S.1    Bindu, P.2    Dubey, P.K.3    Chakraborty, S.4    Mukherjee, A.K.5
  • 22
    • 0026025917 scopus 로고
    • Investigation of piroxicam polymorphism
    • Vrecer, F.; Srcic, S.; Korbar, J. S. Investigation of piroxicam polymorphism. Int. J. Pharm. 1991, 68, 35-41.
    • (1991) Int. J. Pharm. , vol.68 , pp. 35-41
    • Vrecer, F.1    Srcic, S.2    Korbar, J.S.3
  • 23
    • 18744374968 scopus 로고    scopus 로고
    • Mechanochromism of piroxicam accompanied by intermolecular proton transfer probed by spectroscopic methods and solid-phase changes
    • Sheth, A. R.; Lubach, J. W.; Munson, E. J.; Muller, F. X.; Grant, D. J. W. Mechanochromism of piroxicam accompanied by intermolecular proton transfer probed by spectroscopic methods and solid-phase changes. J. Am. Chem. Soc. 2005, 127, 6641-6651.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 6641-6651
    • Sheth, A.R.1    Lubach, J.W.2    Munson, E.J.3    Muller, F.X.4    Grant, D.J.W.5
  • 24
    • 0037473468 scopus 로고    scopus 로고
    • Characterization of piroxicam crystal modifications
    • Vrecer, F.; Vrbinc, M.; Meden, A. Characterization of piroxicam crystal modifications. Intl. J. Pharm. 2003, 256, 3-15.
    • (2003) Intl. J. Pharm. , vol.256 , pp. 3-15
    • Vrecer, F.1    Vrbinc, M.2    Meden, A.3
  • 25
    • 84878714539 scopus 로고    scopus 로고
    • 4-hydroxy-2H-1, 2-benzothiazine-3-carbohydrazide 1, 1-dioxide-oxalohydrazide (1: 1): X-ray structure and DFT calculations
    • Arshad, M. N.; Şahin, O.; Zia-ur-Rehman, M.; Khan, I. U.; Asiri, A. M.; Rafique, H. M. 4-hydroxy-2H-1, 2-benzothiazine-3-carbohydrazide 1, 1-dioxide-oxalohydrazide (1: 1): X-ray structure and DFT calculations. J. Struct. Chem. 2013, 54, 437-442.
    • (2013) J. Struct. Chem. , vol.54 , pp. 437-442
    • Arshad, M.N.1    Şahin, O.2    Zia-Ur-Rehman, M.3    Khan, I.U.4    Asiri, A.M.5    Rafique, H.M.6
  • 26
    • 84861716582 scopus 로고    scopus 로고
    • Synthesis and antioxidant activity of new series of 2,1-benzothiazine-2,2-dioxide hydrazine derivatives
    • Shafiq, M.; Khan, I. U.; Zia-ur-Rehman, M.; Asghar, M. N.; Asiri, A. M.; Arshad, M. N. Synthesis and antioxidant activity of new series of 2,1-benzothiazine-2,2-dioxide hydrazine derivatives. Asian J. Chem. 2012, 24, 4799-4803.
    • (2012) Asian J. Chem. , vol.24 , pp. 4799-4803
    • Shafiq, M.1    Khan, I.U.2    Zia-Ur-Rehman, M.3    Asghar, M.N.4    Asiri, A.M.5    Arshad, M.N.6
  • 28
    • 84897544648 scopus 로고    scopus 로고
    • A possible route toward expert systems in supramolecular chemistry: 2-periodic H-bond patterns in molecular crystals
    • Zolotarev, P. N.; Arshad, M. N.; Asiri, A. M.; Al-amshany, Z. M.; Blatov, V. A. A possible route toward expert systems in supramolecular chemistry: 2-periodic H-bond patterns in molecular crystals. Cryst. Growth Des. 2014, 16, 1938-1949.
    • (2014) Cryst. Growth Des. , vol.16 , pp. 1938-1949
    • Zolotarev, P.N.1    Arshad, M.N.2    Asiri, A.M.3    Al-Amshany, Z.M.4    Blatov, V.A.5
  • 29
    • 84890461282 scopus 로고    scopus 로고
    • Crystallographic studies of dehydration phenomenon in methyl 3-hydroxy-2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1λ6-benzo[e][1,2]thiazine-3-carboxylate
    • Arshad, M. N.; Şahin, O.; Zia-ur-Rehman, M.; Shafiq, M.; Khan, I. U.; Asiri, A. M.; Khan, S. B.; Alamry, K. A. Crystallographic studies of dehydration phenomenon in methyl 3-hydroxy-2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1λ6-benzo[e][1,2]thiazine-3-carboxylate. J. Chem. Cryst. 2013, 43, 671-677.
    • (2013) J. Chem. Cryst. , vol.43 , pp. 671-677
    • Arshad, M.N.1    Şahin, O.2    Zia-Ur-Rehman, M.3    Shafiq, M.4    Khan, I.U.5    Asiri, A.M.6    Khan, S.B.7    Alamry, K.A.8
  • 30
    • 80051478885 scopus 로고    scopus 로고
    • 6-Bromo-1-methyl-4-[2-(4-methylbenzylidene) hydrazinylidene]-3H-26, 1-benzothiazine-2, 2-dione
    • Shafiq, M.; Khan, I. U.; Zia-ur-Rehman, M.; Arshad, M. N.; Asiri, A. M. 6-Bromo-1-methyl-4-[2-(4-methylbenzylidene) hydrazinylidene]-3H-26, 1-benzothiazine-2, 2-dione. Acta Cryst. E 2011, 67, po2092-po2092.
    • (2011) Acta Cryst. E , vol.67 , pp. po2092-po2092
    • Shafiq, M.1    Khan, I.U.2    Zia-Ur-Rehman, M.3    Arshad, M.N.4    Asiri, A.M.5
  • 31
    • 70349769432 scopus 로고    scopus 로고
    • N-[2-(Aminocarbonyl) phenyl]-4-hydroxy-2-methyl-2H-1, 2-benzothiazine-3-carboxamide 1, 1-dioxide
    • Arshad, M. N.; Zia-ur-Rehman, M.; Khan, I. U. N-[2-(Aminocarbonyl) phenyl]-4-hydroxy-2-methyl-2H-1, 2-benzothiazine-3-carboxamide 1, 1-dioxide. Acta Cryst. E 2009, 65, po2596-po2596.
    • (2009) Acta Cryst. E , vol.65 , pp. po2596-po2596
    • Arshad, M.N.1    Zia-Ur-Rehman, M.2    Khan, I.U.3
  • 32
    • 77952081749 scopus 로고    scopus 로고
    • Methyl 2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
    • Arshad, M. N.; Zia-Ur-Rehman, M.; Khan, I. U. Methyl 2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide. Acta Cryst. E 2010, 66, po1070-po1070.
    • (2010) Acta Cryst. E , vol.66 , pp. po1070-po1070
    • Arshad, M.N.1    Zia-Ur-Rehman, M.2    Khan, I.U.3
  • 33
    • 37549039510 scopus 로고    scopus 로고
    • A short history of SHELX
    • Sheldrick, G. M. A short history of SHELX. Acta Cryst. A 2008, 64, 112-122.
    • (2008) Acta Cryst. A , vol.64 , pp. 112-122
    • Sheldrick, G.M.1
  • 36
    • 0141452964 scopus 로고    scopus 로고
    • WinGX suite for small-molecule single-crystal crystallography
    • Farrugia, L. J. WinGX suite for small-molecule single-crystal crystallography. J. Appl. Crystallogr. 1999, 30, 837-838.
    • (1999) J. Appl. Crystallogr. , vol.30 , pp. 837-838
    • Farrugia, L.J.1
  • 41
    • 84890021933 scopus 로고
    • The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors
    • Boys, S. F.; Bernardi, F. The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Mol. Phys. 1970, 19, 553-566.
    • (1970) Mol. Phys. , vol.19 , pp. 553-566
    • Boys, S.F.1    Bernardi, F.2
  • 42
    • 1842692143 scopus 로고
    • General definition of ring puckering coordinates
    • Cremer, D.; Pople, J.A. General definition of ring puckering coordinates. J. Am. Chem. Soc. 1975, 97, 1354-1358.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 1354-1358
    • Cremer, D.1    Pople, J.A.2
  • 43
    • 84872847177 scopus 로고    scopus 로고
    • Synthesis, crystal structure, vibration spectral, and DFT studies of 4-aminoantipyrine and its derivatives
    • Li, Y.; Li, Y.; Wang, H.; Xiong, X.; Wei, P.; Li, F. Synthesis, crystal structure, vibration spectral, and DFT studies of 4-aminoantipyrine and its derivatives. Molecules 2013, 18, 877-893.
    • (2013) Molecules , vol.18 , pp. 877-893
    • Li, Y.1    Li, Y.2    Wang, H.3    Xiong, X.4    Wei, P.5    Li, F.6


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