An efficient synthesis and biological study of substituted 8-chloro-5-methoxy/8-chloro-4H-1,4-benzothiazines, their sulphones and ribofuranosides

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• 作者：NISHIDHA KHANDELWAL (1)
  ABHILASHA (1)
  NAVEEN GAUTAM (1)
  D C GAUTAM (1)
  
• 关键词：4H ; 1 ; 4 ; benzothiazines ; sulphones ; ribofuranosides ; antimicrobial activity ; anthelmintic activity
• 刊名：Journal of Chemical Sciences
• 出版年：2013
• 出版时间：January 2013
• 年：2013
• 卷：125
• 期：1
• 页码：85-93
• 全文大小：411KB
• 参考文献：1. Clercq E D 1985 / Nucleos. Nucleot. Nucl. 4(1) 3 10.1080/07328318508077826">CrossRef
  2. Gupta R R 1988 / Phenothiazines and 1, 4-benzothiazines chemical and biomedical aspects, Amsterdam: Elsevier, 160
  3. Gupta V, Gautam R K, Jain S K and Gupta R R 1990 / Phosphorus Sulphur 47(1) 225 10.1080/10426509008046864">CrossRef
  4. Gupta A, Saraswat V, Mukherji S K and Gupta R?R 1993 / Phosphorus Sulphur 85(1) 101 10.1080/10426509308038187">CrossRef
  5. Kumar N, Singh G and Yadav A K 2001 / Heteroatom. Chem. 12(1) 52 10.1002/1098-1071(2001)12:1<52::AID-HC11>3.0.CO;2-0">CrossRef
  6. Sharma P R, Gupta V, Gautam D C and Gupta R?R 2003 / Phosphorus Sulphur 178(7) 1483 10.1080/10426500307883">CrossRef
  7. Gautam N, Hans D and Gautam D C 2005 / Oriental J. Chem. 21(2) 299
  8. Kachee T L, Gupta V, Gautam D C and Gupta R R 2005 / Phosphorus Sulphur 180(10) 2225 10.1080/104265090917790">CrossRef
  9. Gautam V, Sharma M, Panwar M, Gautam N, Kumar A, Sharma I K and Gautam D C 2009 / Phosphorus Sulphur 184(11) 3090 10.1080/10426500802704225">CrossRef
  10. Gupta S, Ajmera N, Meena P, Gautam N, Kumar A and Gautam D C 2009 / Jordan J. Chem. 4(3) 209
  11. Cuendet M, Hostettmann K, Potterat O and Dyatmiko W 1997 / Helv. Chim. Acta 80(4) 1144 10.1002/hlca.19970800411">CrossRef
  12. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M and Rice-Evans C 1999 / Free Radical Biol. Med. 26 1231 10.1016/S0891-5849(98)00315-3">CrossRef
  13. Braca A, Tommasi N D, Basi L D, Pizza C, Politi M and Morelli I 2001 / Nat. Prod. J. 64(7) 892 10.1021/np0100845">CrossRef
  14. Kolaczowski M, Michalak K and Motoashi N 2003 / Int. J. Antimicrob. Agents 22(3) 279 10.1016/S0924-8579(03)00214-0">CrossRef
  15. Omar K, Geronikaki A, Zoumpoulakis P, Camoutsis C, Sokovic M, Ciric A and Glamoclija J 2010 / Biol. Med. 18 426
  
• 作者单位：NISHIDHA KHANDELWAL (1)
  ABHILASHA (1)
  NAVEEN GAUTAM (1)
  D C GAUTAM (1)
  
  1. Department of Chemistry, University of Rajasthan, Jawahar LaL Nehru Marg, Jaipur, 302 004, India
  
• ISSN：0973-7103

文摘

8-Chloro-5-methoxy/8-chloro-4H-1,4-benzothiazines were synthesized by condensation followed by oxidative cyclisation of 2-amino-6-chloro-3-methoxy/2-amino-3-chlorobenzenethiol with β–diketones/β–ketoesters in the presence of dimethyl sulphoxide. By treating 4H-1,4-benzothiazines with 30% hydrogen peroxide in glacial acetic acid, 4H-1,4-benzothiazine-1,1-dioxides (sulphones) were synthesized. The 4H-1,4-benzothiazines have also been used as a base to prepare ribofuranosides by the reaction with β–D-ribofuranose-1-acetate-2,3,5-tribenzoate. All the synthesized compounds have been characterized by spectral and elemental analysis and have been examined for antimicrobial and anthelmintic activity. Graphical Abstract 4H-1,4-benzothiazines, the nitrogen and sulphur containing heterocycles are prepared by condensation followed by oxidative cyclization of 2-aminobenzenethiols with β-diketones/β-ketoester in dimethylsulphoxide. These compounds were then used as base to prepare ribofuranosides and their sulphones.