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Volumn 65, Issue 12, 2002, Pages 1809-1814

Semisynthesis of new sarcophine derivatives with chemopreventive activity

Author keywords

[No Author keywords available]

Indexed keywords

7,8 EPOXY 1,3,11 CEMBRATRIENE 16 DIOL 20 CARBOXYALDEHYDE; 7,8 EPOXY 1,3,11 CEMBRATRIENE 16 TRIOL; 7,8 EPOXY 13 OXO 1,3,11 CEMBRATRIENE 16 DIOL; ANTINEOPLASTIC AGENT; EPSTEIN BARR VIRUS ANTIGEN; LACTONE; SARCOPHINE; SARCOPHYTOL A; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0036924149     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np020221d     Document Type: Article
Times cited : (44)

References (26)
  • 4
  • 10
    • 0013490547 scopus 로고
    • Japanese Patent 81 61317 and 81 61318 to Mitsubishi Kasei Corporation
    • Japanese Patent 81 61317 and 81 61318 to Mitsubishi Kasei Corporation; Chem. Abstr. 1981, 95, 169547 and 169548.
    • (1981) Chem. Abstr. , vol.95 , pp. 169547
  • 14
    • 12244303328 scopus 로고    scopus 로고
    • note
    • 2 workstation (Silicon Graphics, Inc., CA). The geometry of sarcophine (3) was initially constructed by reference to its X-ray data reported in ref 11. This geometry was then optimized at the PM3 to obtain the most stable conformation of 3. The geometries of 13-hydroxysarcophines were constructed on the basis of this conformation and then optimized at the PM3.
  • 15
    • 12244291574 scopus 로고    scopus 로고
    • note
    • The obtained PM3 geometries of 13-hydroxysarcophines show that the distance between H-13 and H-2β is 2.35 A in the S-configuration, while it is 4.04 Å in the R-configuration and that the dihedral angles between H-13 and H-14 are -84.1° and 158.8° in the S-configuration, while they are 50.5° and 165.2° in the R-configuration.
  • 16
    • 12244306567 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum, the ratio for the formation of 7a/7b is 75:25.
  • 18
    • 0004124913 scopus 로고    scopus 로고
    • Wavefunction, Inc.: CA
    • All geometries were initially constructed on the basis of the most stable conformation of 3 and then subjected to optimization for the intermediates (8 and 9) or to search for the transition state (TS) at the PM3. All energies were calculated using the PM3 geometries at the pBP/DN* level. Energetic results for numerical basis sets DN* have been reported to be similar to those for Gaussian basis sets 6-31G*. See: Hehre, W. J.; Yu, J.; Kluzinger, P. E.; Lou, L. In A Brief Guide to Molecular Mechanics and Quantum Chemical Calculations; Wavefunction, Inc.: CA, 1998; p 28.
    • (1998) A Brief Guide to Molecular Mechanics and Quantum Chemical Calculations , pp. 28
    • Hehre, W.J.1    Yu, J.2    Kluzinger, P.E.3    Lou, L.4
  • 19
    • 12244311543 scopus 로고    scopus 로고
    • note
    • Conformational analysis was carried out using the Osawa method in conjunction with MMFF94 molecular mechanics starting from the most stable conformation of 3.
  • 20
    • 12244300594 scopus 로고    scopus 로고
    • note
    • The conformers B and C are 6 kcal/mol higher in potential energy than the conformer A, the global minimum conformer. These energies were calculated at the pBP/DN* after the PM3 geometry optimization of conformers, generated by use of the conformational analysis.
  • 21
    • 12244271114 scopus 로고    scopus 로고
    • note
    • The HOMO energies of the conformer A, B, and C are respectively -0.221, -0.220, and -0.222 hartrees at the pBP/DN* level.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.