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Issue
Korean Journal of Chemical Engineering,
Vol.32, No.6, 1142-1150, 2015
Green synthesis, biochemical and quantum chemical studies of steroidal oximes
Alam M, Lee DU
Microwave-assisted condensation of steroidal ketones with hydroxylamine under solvent-free condition in presence of basic alumina as solid support yielded the title compounds. The compounds were subjected for their in vitro antimicrobial against a set of pathogenic bacteria and fungi. The 3β-chloro-5α-cholestan-6-one oxime (6) showed highest antimicrobial activity. Steroidal oximes were also screened for their in vitro anthelmintic activity against earthworms. Chloro compound was found to be a more potent anthelmintic agent when compared with albendazole. The in silico docking technique has been applied to ascertain the potential binding sites of the compounds with the pathogenic receptor. The binding modes of a representative compound 6 were accessed on the basis of molecular docking studies. Moreover the structure.antimicrobial activity relationships were studied using some physicochemical and quantum-chemical parameters with GAMESS interface as well as WebMO Job Manager by DFT at B3LYP/6-31G & STO-3G level of theory.
Keywords: Solid State Synthesis; Steroidal Ketone; Antimicrobial; in silico Analysis; Quantum Chemical Analysis
[References]
  1. Kassa J, Kuca K, Karasova J, Musilek K, Mini-Rev. Med. Chem., 8, 1134, 2008
  2. Kuryanov VO, Chupakhina TA, Shapovalova AA, Katsev AM, Chirva VY, Russ. J. Bioorg. Chem., 37, 231, 2011
  3. Worek F, Thiermann H, Strategies for the development of effective broad spectrum oximes, In defence against the effects of chemical hazards, Toxicology, Diagnosis and Medical Countermeasures (pp. 30-1-30-6). Meeting Proceedings RTO-MP-HFM-149, Paper 30. Neuilly-sur-Seine, France: RTO.
  4. Cuia J, Fana L, Huanga L, Liub H, Zhou A, Steroids, 74, 62, 2009
  5. Cuia JG, Fana L, Huanga Y, Xinb Y, Zhou A, Steroids, 74, 989, 2009
  6. Krstic MS, Bjelakovic MS, Zizak Z, Pavlovic MD, Juranic ZD, Pavlovic VD, Steroids, 72, 406, 2007
  7. Huang Y, Cui J, Zheng Q, Zeng C, Chen Q, Zhou A, Steroids, 77, 829, 2012
  8. Jindal DP, Chattopadhaya R, Guleria S, Gupta R, J. Med. Chem., 38, 1025, 2003
  9. Bansal R, Guleria S, Ries C, Hartmann RW, Arch. Pharm., 343, 377, 2010
  10. Sikharulidze MI, Nadaraia N, Kakhabrishvili ML, Barbakadze NN, Mulkidzhanyan KG, Chem. Nat. Compd., 46, 493, 2010
  11. Horii Y, Otsuka Y, Tateishi M, Makimura S, Kusano K, J. Vet. Med. Sci., 60, 271, 1998
  12. Cantrall EW, Littell R, Stolar SM, Cekleniak WP, Albers HJ, Gordon S, Bernstein S, Steroids, 1, 173, 1963
  13. Kovganko NV, Sokolov SN, Chernov YG, Kashkan ZN, Survilo VL, Chem. Nat. Compd., 46, 750, 2010
  14. Dubey S, Jindal DP, Piplani P, Ind. J. Chem., 44B, 2126, 2005
  15. Pokhrel M, Ma E, Molecules, 16, 9868, 2011
  16. Iranpoor N, Firouzabadi H, Aghapour G, Synth. Commun., 32, 2535, 2002
  17. Donaruma LG, Helst WZ, Org. React., 11, 1, 1960
  18. Smith PAS, Robertson JE, J. Am. Chem. Soc., 84, 1197, 1962
  19. Buehler EJ, Org. Chem., 33, 261, 1967
  20. Schoenewaldt EF, Kinnel RB, Davis P, J. Org. Chem., 33, 4270, 1968
  21. Chiang YH, J. Org. Chem., 36, 2146, 1971
  22. Liu KC, Shelton BR, Howe RK, J. Org. Chem., 45, 3916, 1980
  23. Hajipour AR, Mahboubghah N, J. Chem. Res.(S), 122, 1998
  24. Dave PR, Forshar F, J. Org. Chem., 61, 8897, 1996
  25. Whitesell JK, Whitesell MA, Synthesis, 517, 1983
  26. Shinada T, Yoshihara K, Tetrahedron Lett., 37, 6701, 1995
  27. Ley JP, Bertram HJ, Bioorgan. Med. Chem., 9, 1879, 2001
  28. Shen C, Sigman DS, Arch. Biochem. Biophys., 286, 596, 1991
  29. Finar IL, Lord GH, J. Chem. Soc., 3314, 1957
  30. Li JT, Li XL, Li TS, Sonochem., 13, 200, 2006
  31. Guo JJ, Jin TS, Zhang SL, Li TS, Green Chem., 3, 193, 2001
  32. Sharghi H, Sarvari MH, J. Chem. Res.(S), 24, 2000
  33. Niknam K, Karimi B, Kiasat AR, Bull. Korean Chem. Soc., 26, 975, 2005
  34. Eshghi H, Alizadeh MH, Davamdar E, J. Korean Chem. Soc., 52, 52, 2008
  35. Damljanovic I, Vukicevic M, Vukicevic RD, Monatsh. fur Chem., 137, 301, 2006
  36. Xia JJ, Wang GW, Molecules, 12, 231, 2007
  37. Zang H, Wang M, Cheng BW, Song J, Sonochem., 16, 301, 2009
  38. Kidwai M, Dave B, Bhushan KR, Chem. Papers, 54, 231, 2000
  39. Kidwai M, Bhushan KR, Sapra P, Saxena RK, Gupta R, Bioorg. Med. Chem., 8, 69, 2000
  40. Kidwai M, Pure Appl. Chem., 73, 147, 2001
  41. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ, Adv. Drug Deliv. Rev., 23, 4, 1997
  42. Jones DN, Lewis JR, Shoppee CW, Summers GHR, J. Chem. Soc., 2876, 1955
  43. Shoppee CW, Jenkins RH, Summers GHR, J. Chem. Soc., 1657, 1958
  44. Dodson RM, Riegel B, J. Org. Chem., 13, 424, 1948
  45. Windaus A, Dalmer O, Ber., 52, 162, 1919
  46. Jones DN, Lewis JR, Shoppee CW, Summers GHR, J. Chem. Soc., 2876, 1955
  47. Suginome H, Takahashi H, Bull. Chem. Soc. Jpn., 48, 576, 1975
  48. Anagnostopoulos CE, Fieser LF, J. Am. Chem. Soc., 76, 532, 1954
  49. Barnett J, Ryman BR, Smith F, J. Chem. Soc., 527, 1946
  50. Knof L, Justus Liebigs Ann. Chem., 642, 194, 1961
  51. Shafiullah, Ansari MR, Husain S, Bull. Chem. Soc. Jpn., 60, 3411, 1987
  52. Ford EG, Chakravorty P, Wallis ES, J. Am. Chem. Soc., 60, 413, 1938
  53. Duddeck H, Frelek J, Kriiger C, Snatzke G, Szezepek WJ, Wagner P, Werner S, Tetrahedron: Asymmetry, 3, 613, 1992
  54. Galani I, Kontopidou F, Souli M, Rekatsina PD, Koratzanis E, Deliolanis J, Giamarellou H, Int. J. Antimicrob. Agents, 31, 434, 2008
  55. Bauer AW, Kirby WMM, Sherris JC, Turk M, Am. J. Clin. Pathol., 45, 493, 1966
  56. NCCLS - Clinical laboratory standards institute method for antifungal disk diffusion susceptibility testing of yeasts, Proposed Guideline- M. 44A, 23 (2004).
  57. Ajaiyeoba EP, Onocha PA, Olarenwaju OT, Pharm. Biol., 39, 217, 2001
  58. Accelrys Software Inc., Discovery Studio Modeling Environment, Release 3.1. (2011).
  59. Thomsen R, Christensen MH, J. Med. Chem., 11, 3315, 2006
  60. Wolber G, Dornhofer AA, Langer T, J. Comput. Aided Mol. Des., 20, 773, 2007
  61. Yang JM, Chen CC, Proteins, 55, 288, 2004
  62. Alam MS, Liu L, Lee YE, Lee DU, Chem. Pharm. Bull., 59, 568, 2011
  63. Sharma K, Mishra SB, Mishra AK, Helv. Chim. Acta, 94, 2256, 2011
  64. Ertl P, Rohde B, Selzer P, J. Med. Chem., 43, 3714, 2000
  65. Uzzoman S, Khanam H, Mashrai A, Mabkhot YN, Husain A, Acta Cryst., E68, o3037, 2012
  66. Ketuly KA, Hadi AHA, Ng SW, Tiekink ERT, Acta Cryst., E67, o773, 2011
  67. Wallace AC, Laskowski RA, Thornton JM, Prot. Eng., 8, 127, 1995
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