Structural Studies of 2-Pentyl/Pentenyl-Substituted Methyl 4-Hydroxy-2H-1,2-Benzothiazine-3-Carboxylate-1,1-Dioxide

Muhammad Nadeem ARSHAD; Muhammad ZIA-UR-REHMAN; Islam Ullah KHAN; Ghulam MUSTAFA; Muhammad SHAFIQ; Hafiz Muhammad RAFIQUE; Kevin Travis HOLMAN

Authors

Muhammad Nadeem ARSHAD Chemistry Department & Center of Excellence for Advanced Materials Research, Faculty of Science, King Abdulaziz University, Jeddah 21589
Muhammad ZIA-UR-REHMAN 2Applied Chemistry Research Center, PCSIR Laboratories Complex, Ferozpur Road Lahore 54600
Islam Ullah KHAN Materials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000
Ghulam MUSTAFA Department of Chemistry, University of Gujrat, Gujrat 50781
Muhammad SHAFIQ Department of Chemistry, Government College University, Faisalabad 38040
Hafiz Muhammad RAFIQUE X-ray Diffraction and Crystallography Laboratory, Department of Physics, School of Physical Sciences, University of the Punjab, Quaid-e-Azam Campus, Lahore 54590
Kevin Travis HOLMAN Department of Chemistry, 240 Reiss Science Building, Georgetown University, 37th and Oth Streets NW, Washington, DC 20057-1227

Keywords:

1, 2-benzothiazine, single crystal, structure studies, X-rays, oxicam

Abstract

Crystal structures of methyl 2-pentyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide 1 and methyl 2-pentenyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide 2 have been determined after their synthesis from saccharin. 1 and 2 crystallize in a monoclinic and orthorhombic crystal system, respectively. The asymmetric unit of both contains one molecule of each compound and shows intramolecular O-H×××O interactions generating six membered ring motifs S¹₁(6). Intermolecular hydrogen bonding interactions have been observed in the molecule with the pentyl side chain. The thiazine ring in both molecules adopts a half chair conformation with a r.m.s. deviation of 0.2049 Å and 0.2161 Å.

Downloads

Download data is not yet available.

Author Biographies

Muhammad Nadeem ARSHAD, Chemistry Department & Center of Excellence for Advanced Materials Research, Faculty of Science, King Abdulaziz University, Jeddah 21589

Ghulam MUSTAFA, Department of Chemistry, University of Gujrat, Gujrat 50781

Materials Chemistry Laboratory, Department of Chemistry, GC University, Lahore-54000, Pakistan.

References

JG Lombardino, EH Wiseman and W Mclamore. Synthesis and antiinflammatory activity of some 3-carboxamides of 2-alkyl-4-hydroxy-2H-1,2-benzothiazine 1,1-dioxide. J. Med. Chem. 1971; 14, 1171-5.

AR Sheth, S Bates, FX Muller and DJW Grant. Local structure in amorphous phases of piroxicam from powder X-ray diffractometry. Crys. Growth Des. 2005; 5, 571-8.

M Zia-ur-Rehman, JA Choudary, MRJ Elsegood, HL Siddiqui and S Ahmad. N-[2-(Aminocarbonyl)phenyl]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide dimethyl sulfoxide solvate. Acta Cryst. 2007; E63, o900-1.

M Zia-ur-Rehman, JA Choudary and S Ahmad. An Efficient Synthesis of 2-Alkyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides. Bull. Korean Chem. Soc. 2005; 26, 1771-5.

M Zia-ur-Rehman, JA Choudary, S Ahmad and HL Siddiqui. Synthesis of potential biologically active 1,2-benzothiazin-3-yl-quinazolin-4(3H)-ones. Chem. Pharm. Bull. 2006; 54, 1175-8.

M Zia-ur-Rehman, JA Choudary, MRJ Elsegood, HL Siddiqui and KM Khan. 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, 1311-6.

M Ahmad, HL Siddiqui, M Zia-ur-Rehman and M Parvez. Anti-oxidant and anti-bacterial activities of novel N'-arylmethylidene-2-(3, 4-dimethyl-5, 5-dioxidopyrazolo[4,3-c][1,2]benzothiazin-2(4H)-yl) acetohydrazides. Eur. J. Med. Chem. 2010; 45, 698-704.

MN Arshad, IU Khan, M Zia-ur-Rehman and M Shafiq. Antioxidant potential of new methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide derivatives. Asian J. Chem. 2011; 23, 2801-5.

N Ahmad, M Zia-ur-Rehman, HL Siddiqui and M Parvez. 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. M. Eur. J. Med. Chem. 2011; 46, 2368-77.

M Shafiq, M Zia-ur-Rehman, IU Khan, MN Arshad and SA Khan. Synthesis of novel anti-bacterial 2,1-benzothiazine 2,2-dioxides derived from methyl anthranilate. J. Chil. Chem. Soc. 2011; 56, 527-31.

Z Otwinowski and W Minor. Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol. 1997; 276, 307-26.

R Hooft. COLLECT: Data Collection Software. Nonius BV, Delft, The Netherlands, 1998.

MN Arshad, IU Khan, M Zia-ur-Rehman, SA Ahmad and HM Rafique. Methyl 4-hydroxy-2-methoxycarbonylmethyl-1,1-dioxo-1,2-dihydro-1λ6,2-benzothiazine-3-carboxylate. Acta Cryst. 2011; E67, o2527.

J Bernstein, RE Davis, L Shimoni and NL Chang. Patterns in hydrogen bonding: functionality and graph set analysis in crystals. Angew. Chem. Int. Ed. Engl. 1995; 34, 1555-73.