메뉴 건너뛰기




Volumn 76, Issue 2, 2011, Pages 512-522

Total synthesis of natural and non-natural δ 5,6δ 12,13-jatrophane diterpenes and their evaluation as MDR modulators

Author keywords

[No Author keywords available]

Indexed keywords

CANCER CHEMOTHERAPY; CARBONYL-ENE REACTIONS; DFT CALCULATION; DITERPENES; DOUBLE BONDS; JATROPHA; MULTIDRUG RESISTANCE; PENTADECANE; RING CLOSING METATHESIS; SUZUKI-MIYAURA CROSS-COUPLING; TOTAL SYNTHESIS;

EID: 78651520488     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1019738     Document Type: Article
Times cited : (49)

References (90)
  • 11
    • 67149090849 scopus 로고    scopus 로고
    • For the first total synthesis of a jatrophane diterpene from Euphorbia sp., see
    • For the first total synthesis of a jatrophane diterpene from Euphorbia sp., see: Schnabel, C.; Hiersemann, M. Org. Lett. 2009, 11, 2555-2558
    • (2009) Org. Lett. , vol.11 , pp. 2555-2558
    • Schnabel, C.1    Hiersemann, M.2
  • 18
    • 0035144033 scopus 로고    scopus 로고
    • This approach was inspired by chemistry previously reported from our laboratory; see
    • This approach was inspired by chemistry previously reported from our laboratory; see: Hiersemann, M. Eur. J. Org. Chem. 2001, 483-491
    • (2001) Eur. J. Org. Chem. , pp. 483-491
    • Hiersemann, M.1
  • 20
    • 78651481889 scopus 로고    scopus 로고
    • For computational details see the Supporting Information
    • For computational details see the Supporting Information.
  • 24
    • 33847317415 scopus 로고    scopus 로고
    • For computational studies on the intramolecular carbonyl-ene reaction of unsaturated aldehydes and ketones, see
    • For computational studies on the intramolecular carbonyl-ene reaction of unsaturated aldehydes and ketones, see: Sauer, E. L. O.; Hooper, J.; Woo, T.; Barriault, L. J. Am. Chem. Soc. 2007, 129, 2112-2119
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 2112-2119
    • Sauer, E.L.O.1    Hooper, J.2    Woo, T.3    Barriault, L.4
  • 29
    • 78651480998 scopus 로고    scopus 로고
    • B3LYP/6-31G(d) and M05-2X/6-31G(d) calculations provided unrealistic reaction free energies. See the Supporting Information for details
    • B3LYP/6-31G(d) and M05-2X/6-31G(d) calculations provided unrealistic reaction free energies. See the Supporting Information for details.
  • 30
    • 78651489746 scopus 로고    scopus 로고
    • See the Supporting Information for B3LYP and M05-2X values. Calculated interatomic distances are virtually insensitive to the size of the basis set; see the Supporting Information for 6-31+G(d,p) and 6-311++G(d,p) values
    • See the Supporting Information for B3LYP and M05-2X values. Calculated interatomic distances are virtually insensitive to the size of the basis set; see the Supporting Information for 6-31+G(d,p) and 6-311++G(d,p) values.
  • 31
    • 78651515107 scopus 로고    scopus 로고
    • Relative NBO atomic charges are virtually independent of the basis set size. See the Supporting Information for details
    • Relative NBO atomic charges are virtually independent of the basis set size. See the Supporting Information for details.
  • 34
    • 55949130058 scopus 로고    scopus 로고
    • For a recent example, see
    • For a recent example, see: Zhou, Y.; Murphy, P. V. Org. Lett. 2008, 10, 3777-3780
    • (2008) Org. Lett. , vol.10 , pp. 3777-3780
    • Zhou, Y.1    Murphy, P.V.2
  • 51
    • 4644275985 scopus 로고    scopus 로고
    • Knorr, R. Chem. Rev. 2004, 104, 3795-3850
    • (2004) Chem. Rev. , vol.104 , pp. 3795-3850
    • Knorr, R.1
  • 75
    • 0019806173 scopus 로고
    • For the first determination of the absolute configuration of a jatrophane diterpene by X-ray crystallography, see
    • For the first determination of the absolute configuration of a jatrophane diterpene by X-ray crystallography, see: Yamamura, S.; Kosemura, S.; Ohba, S.; Ito, M.; Saito, Y. Tetrahedron Lett. 1981, 22, 5315-5318
    • (1981) Tetrahedron Lett. , vol.22 , pp. 5315-5318
    • Yamamura, S.1    Kosemura, S.2    Ohba, S.3    Ito, M.4    Saito, Y.5
  • 84
    • 78651498086 scopus 로고    scopus 로고
    • ABCB1 transport activity was determined using the calcein-AM assay as described in the Supporting Information
    • ABCB1 transport activity was determined using the calcein-AM assay as described in the Supporting Information.
  • 85
    • 78651488914 scopus 로고    scopus 로고
    • See the Supporting Information for structural information on compounds labeled S
    • See the Supporting Information for structural information on compounds labeled S.
  • 86
    • 84855639464 scopus 로고    scopus 로고
    • The fluorescent dye Hoechst 33342 was used for detecting ABCG2 inhibition. 33 effected about 70% inhibition of Hoechst 33342 efflux at a concentration of 10 μmol/L
    • The fluorescent dye Hoechst 33342 was used for detecting ABCG2 inhibition. 33 effected about 70% inhibition of Hoechst 33342 efflux at a concentration of 10 μmol/L.
  • 87
    • 84855621969 scopus 로고    scopus 로고
    • A significant increase in the intracellular accumulation of calcein-AM was also detected in the presence of 10 μmol/L 34 and 35, but an effect of a similar order of magnitude could also be observed in wild-type cells lacking ABCB1. Accordingly, their effect on ABCB1 cannot be finally estimated
    • A significant increase in the intracellular accumulation of calcein-AM was also detected in the presence of 10 μmol/L 34 and 35, but an effect of a similar order of magnitude could also be observed in wild-type cells lacking ABCB1. Accordingly, their effect on ABCB1 cannot be finally estimated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.