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Synthesis Crystal Structure and Spectral Properties of New Sulfonamides

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Abstract

In this paper, we report new sulfonamide derivatives, 4-((2,4-dichlorophenylsulfonamido)methyl)cyclohexanecarboxylic acid (1), ethyl 4-((naphthalene-2-sulfonamido)methyl)cyclohexanecarboxylate (2), and ethyl 4-((2,5-dichlorophenylsulfonamido)methyl)cyclohexanecarboxylate (3). The compounds were and characterized by FTIR, ESI-MS, and X-ray crystallography. Single crystal X-ray diffraction analysis shows that 1 crystallizes in the orthorhombic space group Pbcn, 2 in the monoclinic space group Cc and 3 in the monoclinic space group Cc. All three molecules feature hydrogen bonding.

Graphical Abstract

Three sulfonamide derivatives, 4-((2,4-dichlorophenylsulfonamido)methyl)cyclohexanecarboxylic acid (1), ethyl 4-((naphthalene-2-sulfonamido)methyl)cyclohexanecarboxylate (2) and ethyl 4-((2,5-dichlorophenylsulfonamido) methyl)cyclo-hexanecarboxylate (3) have been synthesized and their structures confirmed by single crystal X-ray diffraction. Hydrogen bonding in compound 1 involves carboxylic groups and N–H moieties as well as non-classical C–H···O interactions, while in 2 and 3, the N–H moiety and an oxygen atom of the sulfonamide functional group of neighboring molecules are involved.

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References

  1. Boufas W, Dupont N, Berredjem M, Berrezag K, Becheker I, Berredjem H, Aouf N-E (2014) Synthesis and antibacterial activity of sulfonamides. SAR and DFT studies. J Mol Struct 1074:180–185

    Article  CAS  Google Scholar 

  2. Zhong J, Gan X, Alliston KR, Lai Z, Yu H, Groutas CS, Wong T, Groutas WC (2004) Potential protease inhibitors based on a functionalized cyclic sulfamide scaffold. J Combin Chemi 6(4):556–563

    Article  CAS  Google Scholar 

  3. Winum JY, Scozzafava A, Montero JL, Supuran CT (2006) Therapeutic potential of sulfamides as enzyme inhibitors. Med Res Rev 26(6):767–792

    Article  CAS  Google Scholar 

  4. Cheng X-C, Wang Q, Fang H, Xu W-F (2008) Role of Sulfonamide Group in Matrix Metalloproteinase Inhibitors. Curr Med Chem 15(4):368–373. https://doi.org/10.2174/092986708783497300

    Article  CAS  PubMed  Google Scholar 

  5. Supuran CT, Scozzafava A (2002) Applications of carbonic anhydrase inhibitors and activators in therapy. Expert Opin Ther Pat 12(2):217–242

    Article  CAS  Google Scholar 

  6. Groutas WC, He S, Kuang R, Ruan S, Tu J, Chan H-K (2001) Inhibition of serine proteases by functionalized sulfonamides coupled to the 1, 2, 5-thiadiazolidin-3-one 1,1 dioxide scaffold. Bioorg Med Chem 9(6):1543–1548

    Article  CAS  Google Scholar 

  7. Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM (1997) Synthesis and biological evaluation of the 1, 5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1 H-pyrazol-1-yl] benzenesulfonamide (SC-58635, celecoxib). J Med Chem 40(9):1347–1365

    Article  CAS  Google Scholar 

  8. Talley JJ, Brown DL, Carter JS, Graneto MJ, Koboldt CM, Masferrer JL, Perkins WE, Rogers RS, Shaffer AF, Zhang YY (2000) 4-[5-Methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2. J Med Chem 43(5):775–777

    Article  CAS  Google Scholar 

  9. Abraham DJ (2003) Burger’s medicinal chemistry and drug discovery. Wiley, New York

    Book  Google Scholar 

  10. Markgren P-O, Schaal W, Hämäläinen M, Karlén A, Hallberg A, Samuelsson B, Danielson UH (2002) Relationships between structure and interaction kinetics for HIV-1 protease inhibitors. J Med Chem 45(25):5430–5439

    Article  CAS  Google Scholar 

  11. Rotella DP (2002) Phosphodiesterase 5 inhibitors: current status and potential applications. Nat Rev Drug Discov 1(9):674–682

    Article  CAS  Google Scholar 

  12. Crespo R, de Bravo MG, Colinas PA, Bravo RD (2010) In vitro antitumor activity of N-glycosyl sulfonamides. Bioorg Med Chem Lett 20(22):6469–6471

    Article  CAS  Google Scholar 

  13. Das B, Reddy VS, Reddy MR (2004) An efficient and selective tosylation of alcohols with p-toluenesulfonic acid. Tetrahedron Lett 45(36):6717–6719

    Article  CAS  Google Scholar 

  14. Danish M, Bibi A, Gilani K, Raza MA, Ashfaq M, Arshad MN, Asiri AM, Ayub K (2019) Antiradical, antimicrobial and enzyme inhibition evaluation of sulfonamide derived esters; synthesis, X-ray analysis and DFT studies. J Mol Struct 1175:379–388

    Article  CAS  Google Scholar 

  15. Armarego WL, Chai CLL (2013) Purification of laboratory chemicals. Elsevier, Burlington

    Google Scholar 

  16. CrysAlis P (2012) Agilent Technologies UK Ltd. Yarnton, Oxfordshire

  17. Altomare A, Burla MC, Camalli M, Cascarano GL, Giacovazzo C, Guagliardi A, Moliterni AG, Polidori G, Spagna R (1999) SIR97: a new tool for crystal structure determination and refinement. J Appl Crystallogr 32(1):115–119

    Article  CAS  Google Scholar 

  18. Sheldrick GM (2008) A short history of SHELX. Acta Crystallogr A 64(1):112–122

    Article  CAS  Google Scholar 

  19. Spek A (2001) PLATON, a multipurpose crystallographic tool. Utrecht University, Utrecht. There is no corresponding record for this reference

  20. Farrugia LJ (2012) WinGX and ORTEP for Windows: an update. J Appl Crystallogr 45(4):849–854

    Article  CAS  Google Scholar 

  21. Ha SHAD (2010) Synthesis of metal based derivatives of sulfonamides and their biological evaluation. Bahauddin Zakariya University, Multan

    Google Scholar 

  22. Stuart B (2000) Infrared spectroscopy. In: Kirk‐Othmer encyclopedia of chemical technology. Wiley, Hoboken

Download references

Acknowledgements

We are thankful to Higher Education Commission (HEC) of Pakistan for funding this work under the Project No. 20-2549/NRPU/R&D/HEC/12.

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Authors and Affiliations

  1. Department of Chemistry, Hafiz Hayat Campus, University of Gujrat, Gujrat, Pakistan

    Muhammad Danish, Arusa Akhtar & Muhammad Ashfaq

  2. Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589, Saudi Arabia

    Muhammad Nadeem Arshad & Abdullah M. Asiri

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  1. Muhammad Danish
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  2. Arusa Akhtar
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  3. Muhammad Ashfaq
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  4. Muhammad Nadeem Arshad
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  5. Abdullah M. Asiri
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Correspondence to Arusa Akhtar.

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Danish, M., Akhtar, A., Ashfaq, M. et al. Synthesis Crystal Structure and Spectral Properties of New Sulfonamides. J Chem Crystallogr 51, 543–552 (2021). https://doi.org/10.1007/s10870-021-00878-1

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