A theoretical and experimental study on the molecular and electronic structures of artemisinin and related drug molecules

Chemical Physics

Volumn 335, Issue 2-3, 2007, Pages 141-154

  Galasso, V ^a   Kovac B ^b   Modelli, A ^c  

^a UNIVERSITY OF TRIESTE   (Italy)

^b RUDER BO KOVI INSTITUTE   (Croatia)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Ab initio and DFT calculations; Artemisinin; Geometric and electronic structures; NMR chemical shifts and coupling constants; Photoelectron and electron transmission spectra; Vibrational frequencies

Indexed keywords

EID: 34249944078     PISSN: 03010104     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphys.2007.04.008     Document Type: Article

References (91)

1. World Health Organization. Trans. R. Soc. Trop. Med. Hyg. 94 Suppl. 1 (2000) 36
2. Meschnick S.R., Taylor T.E., and Kamchonwongpaisan S. Microbiol. Rev. 60 (1996) 301
3. Robert A., Benoit-Vical F., and Meunier B. Coord. Chem. Rev. 249 (2005) 1927
4. Wu W.-M., Wu Y., Wu Y.-L., Yao Z.-J., Zhou C.-M., Li Y., and Shan F. J. Am. Chem. Soc. 120 (1998) 3316
5. O'Neill P.M., Miller A., Bishop L.P.D., Hindley S., Maggs J.L., Ward S.A., Roberts S.M., Scheinmann F., Stachulski A.V., Posner G.H., and Park B.K. J. Med. Chem. 44 (2001) 58
6. Alberti A., Macciantelli D., and Marconi G. Res. Chem. Intermed. 30 (2004) 615
7. Arantes C., de Araujo M.T., Taranto A.G., and Carneiro J.W.d.M. Int. J. Quantum Chem. 103 (2005) 749
8. Drew M.G.B., Metcalfe J., and Ismail F.M.D. J. Mol. Struct. Theochem. 756 (2005) 87
9. Tonmunphean S., Parasuk V., and Kokpol S. Bioorg. Med. Chem. 14 (2006) 2082
10. Posner G.H., and Oh C.H. J. Am. Chem. Soc. 114 (1992) 8328
11. Becke A.D. J. Chem. Phys. 98 (1993) 5648
12. Frisch M.J., et al. Gaussian 03, Revision D.01 (2004), Gaussian Inc., Wallingford, CT
13. Wilson E.B., Decius J.C., and Cross P.C. Molecular Vibrations (1945), McGraw-Hill, New York
14. Rauhut G., and Pulay P. J. Phys. Chem. 99 (1995) 3093
15. Pipek J., and Mezey P.G. J. Chem. Phys. 90 (1989) 4916
16. Keith T.A., and Bader R.F.W. Chem. Phys. Lett. 210 (1993) 223
17. Dunning Jr. T.H. J. Chem. Phys. 53 (1970) 2823
18. Ramsey N.F. Phys. Rev. 91 (1953) 303
19. Cederbaum L.S. J. Phys. B 8 (1975) 290
20. Klasinc L., Kovač B., and Ruščić B. Kem. Ind. (Zagreb) 10 (1974) 569
21. Sanche L., and Schulz G.J. Phys. Rev. A 5 (1972) 1672
22. Modelli A., Jones D., and Distefano G. Chem. Phys. Lett. 86 (1982) 434
23. Johnston A.R., and Burrow P.D. J. Electron Spectrosc. Relat. Phenom. 25 (1982) 119
24. Hendrickson J.B. J. Org. Chem. 29 (1964) 991
25. Hendrickson J.B. J. Am. Chem. Soc. 89 (1967) 7036
26. Geremia S., Vicentini L., and Calligaris M. Inorg. Chem. 37 (1998) 4094
27. Luo X.D., Yeh H.J.C., Brossi A., Flippen-Anderson J.L., and Gilardi R. Helv. Chim. Acta 67 (1984) 1515
28. Lisgarten J.N., Potter B.S., Bantuzeko C., and Palmer R.A. J. Chem. Crystall. 28 (1998) 539
29. Jefford C.W., Burger U., Millasson-Schmidt P., Bernardinelli G., Robinson B.L., and Peters W. Helv. Chim. Acta 83 (2000) 1239
30. Haynes R.K., Chan H.-W., Cheung M.-K., Lam W.-L., Soo M.-K., Tsang H.-W., Voerste A., and Williams I.D. Eur. J. Org. Chem. (2002) 113
31. Avery M.A., Fan P., Karle J.M., Bonk J.D., Miller R., and Goins D.K. J. Med. Chem. 39 (1996) 1885
32. Haynes R.K., Chan H.-W., Cheung M.-K., Chung S.T., Lam W.-L., Tsang H.-W., Voerste A., and Williams I.D. Eur. J. Org. Chem. (2003) 2098
33. Barone V., Cossi M., and Tomasi J. J. Chem. Phys. 107 (1997) 3210
34. Christen D., Mack H.-G., and Oberhammer H. Tetrahedron 44 (1988) 7363
35. Kosnikov A.Yu., Antonovsky V.L., Lindeman S.V., Antipin M.Yu., Struchkov Yu.T., Turovskii N.A., and Zyat'kov I.P. Teor. Eksp. Khim. 25 (1989) 82
36. Xu X., Huang D., Zhu J., and Zhou W. Huaxue Xuebao 40 (1982) 1081
37. Fang Y., Zhu Z., and He D. Huaxue Xuebao 42 (1984) 1312
38. Koutsoupokis C., Gialou I., Pavlidou E., Kapetanaki S., and Varotsis C. Arkivoc (2002) 62
39. Mohnhaupt M., Hagemann H., Perler J.-P., Bill H., Boukouvalas J., Rossier J.-C., and Jefford C.W. Helv. Chim. Acta 71 (1988) 992
40. Gu J.-D., Chen K.-X., Jiang H.-L., Zhu W.-L., Chen J.-Z., and Ji R.-Y. Chem. Phys. Lett. 277 (1997) 234
41. Gu J., Chen K., Jiang H., and Ji R. J. Mol. Struct. Theochem 459 (1999) 103
42. Overend J., and Scherer J.R. J. Chem. Phys. 32 (1960) 1289
43. Christe K.O. Spectrochim. Acta 27A (1971) 463
44. Butwill Bell M.E., and Laane J. Spectrochim. Acta 28A (1972) 2239
45. Hawkins N., Kohlmiller C.K., and Andrews L. J. Phys. Chem. 86 (1982) 3154
46. Zhongshan W., Nakashima T.T., Kopecky K.R., and Molina J. Can. J. Chem. 63 (1985) 3070
47. Pathak A.K., Jain D.C., and Sharma R.P. Indian J. Chem. 34B (1995) 992
48. El-Feraly F.S., El-Sherei M.M., Hufford C.D., Croom E.M., and Mahier T.J. Spectrosc. Lett. 18 (1985) 843
49. Hufford C.D., and Elsohly H.N. Spectrosc. Lett. 20 (1987) 439
50. Brossi A., Venugopalan B., Dominguez Gerpe L., Yeh H.J.C., Flippen-Anderson J.L., Buchs P., Luo X.D., Milhous W., and Peters W. J. Med. Chem. 31 (1988) 645
51. Butler A.R., Conforti L., Hulme P., Renton L.M., and Rutherford T.J. J. Chem. Soc. Perkin II (1999) 2089
52. Sy L.-K., and Brown G.D. J. Chem. Soc. Perkin I (2001) 2421
53. Lee C.-H., Hong H., Shin J., Jung M., Shin I., Yoon J., and Lee W. Biochem. Biophys. Res. Commun. 274 (2000) 359
54. Avery M.A., Fan P., Karle J.M., Miller R., and Goins K. Tetrahedron Lett. 36 (1995) 3965
55. Abraham R.J., Warne M.A., and Griffiths L. J. Chem. Soc. Perkin II (1998) 1751
56. Pothier N., Rowan D.D., Deslongchamps P., and Saunders J.K. Can. J. Chem. 59 (1981) 1132
57. Gil V.M.S., and von Philipsborn W. Magn. Reson. Chem. 27 (1989) 409
58. Barfield M., and Smith W.B. J. Am. Chem. Soc. 114 (1992) 1574
59. Barfield M., and Smith W.B. Magn. Reson. Chem. 31 (1993) 696
60. Barfield M., and Smith W.B. Magn. Reson. Chem. 34 (1996) 740
61. San-Fabian J., Guilleme J., Diez E., Lazzeretti P., Malagoli M., Zanasi R., Esteban A.L., and Mora F. Mol. Phys. 82 (1994) 913
62. Cuevas G., Jauristi E., and Vela A. J. Phys. Chem. A 103 (1999) 932
63. Cuevas G., and Juaristi E. J. Am. Chem. Soc. 124 (2002) 13088
64. Martínez-Mayorga K., Jauristi E., and Cuevas G. J. Org. Chem. 69 (2004) 7266
65. Bock K., and Wiebe L. Acta Chem. Scand. 27 (1973) 2676
66. Novak I., and Kovač B. J. Org. Chem. 68 (2003) 5777
67. Deleuze M.S. J. Chem. Phys. 116 (2002) 7012
68. Deleuze M.S. J. Phys. Chem. A 108 (2004) 9244
69. Deleuze M.S. Chem. Phys. 329 (2006) 22
70. Knippenberg S., François J.-P., and Deleuze M.S. J. Comput. Chem. 27 (2006) 1703
71. Kimura K., and Osafune K. Bull. Chem. Soc. Jpn. 48 (1975) 2421
72. Brown R.S., and Marcinko R.W. J. Am. Chem. Soc. 100 (1978) 5584
73. Brown R.S. Can. J. Chem. 53 (1975) 3439
74. Coughlin D.J., Brown R.S., and Salomon R.G. J. Am. Chem. Soc. 101 (1979) 1533
75. Rademacher P., and Elling W. Liebigs Ann. Chem. 10 (1979) 1473
76. Böhm M.C., Gleiter R., Adam W., and Narita N. Z. Naturforsch. 38b (1983) 501
77. Gleiter R., Schang P., Adam W., Eggelte H.J., Erden I., and Bloodworth A.J. J. Electron Spectrosc. Relat. Phenom. 19 (1980) 223
78. Schulz G.J. Rev. Mod. Phys. 45 (1973) 378 423
79. Staley S.S., and Strnad J.T. J. Phys. Chem. 98 (1994) 116
80. Chao J.S.-Y., Falcetta M.F., and Jordan K.D. J. Chem. Phys. 93 (1990) 1125
81. Burrow P.D., Howard A.E., Johnston A.R., and Jordan K.D. J. Phys. Chem. 96 (1992) 7570
82. Venuti M., and Modelli A. J. Chem. Phys. 113 (2000) 2159
83. Modelli A., Hajgató B., Nixon J.F., and Nyulászi L. J. Phys. Chem. A 108 (2004) 7440
84. Aflatooni K., Gallup G.A., and Burrow P.D. J. Phys. Chem. A 104 (2000) 7359
85. Modelli A., and Szepes L. Chem. Phys. 286 (2003) 165
86. Modelli A. Trends Chem. Phys. (Res. Trends) 6 (1997) 57
87. Modelli A., Distefano G., and Jones D. Chem. Phys. 73 (1982) 395
88. Howard A.E., and Staley S.W. ACS Symp. Ser. 263 (1984) 183
89. Modelli A., Jones D., Distefano G., and Tronc M. Chem. Phys. Lett. 181 (1981) 361
90. Modelli A., Jones D., Favaretto L., and Distefano G. Organometallics 15 (1996) 380
91. Cumming J.N., Ploypradith P., and Posner G.H. Adv. Pharmacol. (San Diego) 37 (1997) 253