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Volumn , Issue 17, 2007, Pages 2756-2758

Enantioselective total synthesis of (-)-dibromophakellstatin

Author keywords

Hydroxyproline; Imidazolidinone; Marine natural products; N oxycarbamates; Pyrrole imidazole alkaloids

Indexed keywords

ANTINEOPLASTIC AGENT; DIBROMOPHAKELLSTATIN; DIPYRROLOPYRAZINONE; IMIDAZOLIDINONE; IMIDAZOLINE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 35648950535     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-986664     Document Type: Article
Times cited : (23)

References (25)
  • 5
    • 33846047483 scopus 로고    scopus 로고
    • 50 of 0.7 μM against the glioblastoma cancer cell line CNXF 498NL, while (+)-1 was inactive. See: Zöllinger, M.; Kelter, G.; Fiebig, H.-H.; Lindel, T. Bioorg. Med. Chem. Lett. 2007, 17, 346.
    • 50 of 0.7 μM against the glioblastoma cancer cell line CNXF 498NL, while (+)-1 was inactive. See: Zöllinger, M.; Kelter, G.; Fiebig, H.-H.; Lindel, T. Bioorg. Med. Chem. Lett. 2007, 17, 346.
  • 13
    • 0015857556 scopus 로고    scopus 로고
    • Compound 4 can be obtained by alkaline hydrolysis of the corresponding trichloromethylketone. See: Bailey, D. M.; Johnson, R. E. J. Med. Chem. 1973, 16, 1300.
    • Compound 4 can be obtained by alkaline hydrolysis of the corresponding trichloromethylketone. See: Bailey, D. M.; Johnson, R. E. J. Med. Chem. 1973, 16, 1300.
  • 14
    • 35649006888 scopus 로고    scopus 로고
    • CCDC-623847 (12) and CCDC-623846 (15) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: +44 (1223)336033; or deposit@ccdc.cam.ac.uk].
    • CCDC-623847 (12) and CCDC-623846 (15) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: +44 (1223)336033; or deposit@ccdc.cam.ac.uk].
  • 21
    • 35648981108 scopus 로고    scopus 로고
    • Compound, )-16: [α]D25 +46.1 (c 1.2 mg/10.0 mL, MeOH, TLC (silica, EtOAc, Rf, 0.83. 1H NMR (600 MHz, CDCl3, δ, 1.40 (t, 3 H, 3J, 7.1 Hz, OCH2CH3, 2.42 (s, 3 H, ArCH3, 2.90-3.00 (m, 2 H, CCH2, 3.63 (dd, 1 H, 2J, 11.7 Hz, 3J, 9.9 Hz, NCHH, 4.12-4.18 (m, 1 H, CHBr, 4.42 (dq, 1 H, 2J, 11.5 Hz, 3J, 7.1 Hz, OCHH, 4.44 (dq, 1 H, 2J, 11.5 Hz, 3J, 7.1 Hz, OCHH, 4.53 (dd, 1 H, 2J, 11.7 Hz, 3J, 7.5 Hz, NCHH, 6.05 (s, 1 H, NCHN, 6.36 (dd, 1 H, 3J, 3.6, 3.1 Hz, CHCHCHN, 6.87 (dd, 1 H, 3J, 2.7 Hz, 4J, 1.6 Hz, CHCHCHN, 7.07 dd, 1 H, 3J, 3.9 Hz, 4
    • 7S + H]: 553.0393; found: 553.0375.
  • 22
    • 35648988025 scopus 로고    scopus 로고
    • 2 has rarely been reported: (a) Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485.
    • 2 has rarely been reported: (a) Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485.
  • 24
    • 35649004440 scopus 로고    scopus 로고
    • Compound 17 had also been obtained as the (+)-enantiomer by Romo (ref. 5) and as the racemate by Austin (ref. 9).
    • Compound 17 had also been obtained as the (+)-enantiomer by Romo (ref. 5) and as the racemate by Austin (ref. 9).
  • 25
    • 35649017706 scopus 로고    scopus 로고
    • Compound, )-1: [α]D20 -75.7 (c 0.14 mg/mL, MeOH, TLC (silica, MeOH-CHCl3, 1:9, R f, 0.52. 1H NMR (600 MHz, DMSO-d6, δ, 1.95-2.00 (m, 1 H, NCHHCHH, 2.08-2.15 (m, 2 H, NCHHCHHCHH, 2.27-2.33 (m, 1 H, NCHHCHHCHH, 3.40-3.45 (m, 1 H, NCHH, 3.54-3.57 (m, 1 H, NCHH, 5.98 (s, 1 H, NCHN, 6.91 (s, 1 H, CBrCH, 7.97 (s, 1 H, NH, 8.26 (s, 1 H, NH, 13C NMR (150 MHz, DMSO-d6, δ, 18.8 (NCH2CH 2, 39.7 (CCH2, 44.1 (NCH2, 68.6 (NCHN, 78.9 (CCH2, 101.0 (CBrCH, 105.5 (NCBr, 113.7 (CBrCH, 125.3 (CBrCHC, 154.0 [N(CO)N, 157.8 [N(CO, MS (ESI, FTMS, m/z, 389/391/393 (40.9/100/39.1, M, H, CD (MeOH, λmax Δε, 260 nm, 1.1, tr, sh, 233, 2
    • +]: 388.9249; found: 388.9255.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.