메뉴 건너뛰기




Volumn 40, Issue 1, 2010, Pages 144-150

Synthesis of arcyriarubin a and arcyriaflavin a via cross-coupling of indolylboronic acid with dibromomaleimides

Author keywords

Arcyriaflavin A; Arcyriarubin A; Indolocarbazoles; Suzuki coupling

Indexed keywords

ARCYRIAFLAVIN A; ARCYRIARUBIN A; BISINDOLYLMALEIMIDE; BORONIC ACID DERIVATIVE; DIBROMOMALEIMIDE DERIVATIVE; INDOLE; INDOLE DERIVATIVE; MALEIMIDE DERIVATIVE; NATURAL PRODUCT; PALLADIUM; STAUROSPORINE; UNCLASSIFIED DRUG;

EID: 72049108357     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902962878     Document Type: Article
Times cited : (22)

References (28)
  • 1
    • 0017395981 scopus 로고
    • A new alkaloid AM-2282 of streptomyces origin taxonomy, fermentation, isolation and preliminary characterization
    • Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsuchiya, H.; Takahashi, Y.; Masuma, R. A new alkaloid AM-2282 of streptomyces origin taxonomy, fermentation, isolation and preliminary characterization. J. Antibiot. 1977, 30, 275.
    • (1977) J. Antibiot. , vol.30 , pp. 275
    • Omura, S.1    Iwai, Y.2    Hirano, A.3    Nakagawa, A.4    Awaya, J.5    Tsuchiya, H.6    Takahashi, Y.7    Masuma, R.8
  • 2
    • 33751335837 scopus 로고    scopus 로고
    • Indolocarbazole natural products: Occurrence, biosynthesis, and biological activity
    • (a) Sanchez, C.; Mendez, C.; Salas, J. A. Indolocarbazole natural products: Occurrence, biosynthesis, and biological activity. Nat. Prod. Rep. 2006, 23, 1007-1045;
    • (2006) Nat. Prod. Rep. , vol.23 , pp. 1007-1045
    • Sanchez, C.1    Mendez, C.2    Salas, J.A.3
  • 3
    • 0033755667 scopus 로고    scopus 로고
    • Recent developments of rebeccamycin analogues as topoisomerase i inhibitors and antitumor agents
    • (b) Prudhomme, M. Recent developments of rebeccamycin analogues as topoisomerase I inhibitors and antitumor agents. Curr. Med. Chem. 2000, 7, 1189-1212;
    • (2000) Curr. Med. Chem. , vol.7 , pp. 1189-1212
    • Prudhomme, M.1
  • 4
    • 0037294445 scopus 로고    scopus 로고
    • Rebeccamycin analogues as anti-cancer agents
    • (c) Prudhomme, M. Rebeccamycin analogues as anti-cancer agents. Eur. J. Med.Chem. 2003, 38, 123-140.
    • (2003) Eur. J. Med.Chem. , vol.38 , pp. 123-140
    • Prudhomme, M.1
  • 5
    • 0022914385 scopus 로고
    • Staurosporine a potent platelet aggregation inhibitor from a streptomyces species
    • (a) Oka, S.; Kodama, M.; Takada, H.; Tomizuka, N.; Suzuki, H. Staurosporine, a potent platelet aggregation inhibitor from a streptomyces species. Agric. Biol. Chem. 1986, 50, 2723;
    • (1986) Agric. Biol. Chem. , vol.50 , pp. 2723
    • Oka, S.1    Kodama, M.2    Takada, H.3    Tomizuka, N.4    Suzuki, H.5
  • 6
    • 0000155010 scopus 로고
    • Antibiotic AM-2282
    • Japan Kokai 7873501, 1978
    • (b) Omura, S.; Iwai, Y.; Hirano, A. Antibiotic AM-2282. Japan Kokai 7873501, 1978. Chem Abstr. 1978, 89, 178086h;
    • (1978) Chem Abstr. , vol.89
    • Omura, S.1    Iwai, Y.2    Hirano, A.3
  • 8
    • 0001562678 scopus 로고
    • Chem Abstr. 1978, 89, 58348y;
    • (1978) Chem Abstr. , vol.89
  • 10
    • 17844399025 scopus 로고    scopus 로고
    • Natural products to drugs: Natural product derived compounds in clinical trials
    • (a) Butler, M. S. Natural products to drugs: Natural product derived compounds in clinical trials. Nat. Prod. Rep. 2005, 22, 162-195.
    • (2005) Nat. Prod. Rep. , vol.22 , pp. 162-195
    • Butler, M.S.1
  • 11
    • 10244241837 scopus 로고    scopus 로고
    • Phase i clinical trial of CEP-2563 dihydrochloride, a receptor tyrosine kinase inhibitor, in patients with refractory solid tumors
    • (b) Undevia, S. D.; Vogelzang, N. J.; Mauer, A. M.; Janischm, L.; Mani, S.; Ratain, M. J. Phase I clinical trial of CEP-2563 dihydrochloride, a receptor tyrosine kinase inhibitor, in patients with refractory solid tumors. Invest. New Drugs 2004, 22, 449-458;
    • (2004) Invest. New Drugs , vol.22 , pp. 449-458
    • Undevia, S.D.1    Vogelzang, N.J.2    Mauer, A.M.3    Janischm, L.4    Mani, S.5    Ratain, M.J.6
  • 13
    • 26944481508 scopus 로고    scopus 로고
    • Becatecarin (helsinn)
    • (d) Rewcastle, G. W. Becatecarin (helsinn). Drugs 2005, 8, 838-847;
    • (2005) Drugs , vol.8 , pp. 838-847
    • Rewcastle, G.W.1
  • 16
    • 0028068651 scopus 로고
    • Staurosporine aglycone (k252-c) and arcyriaflavin A from the marine ascidian Eudistoma sp
    • Horton, P. A.; Lougley, R. E.; McConnell, O. J.; Ballas, L. M. Staurosporine aglycone (k252-c) and arcyriaflavin A from the marine ascidian Eudistoma sp. Birk. Ver. Basel. 1994, 843-845.
    • (1994) Birk. Ver. Basel. , pp. 843-845
    • Horton, P.A.1    Lougley, R.E.2    McConnell, O.J.3    Ballas, L.M.4
  • 17
    • 0028789416 scopus 로고
    • First total synthesis of staurosporine and ent-staurosporine
    • (a) Link, J. T.; Raghavan, S.; Danishefsky, S. J. First total synthesis of staurosporine and ent-staurosporine. J. Am. Chem. Soc. 1995, 117, 552-553;
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 552-553
    • Link, J.T.1    Raghavan, S.2    Danishefsky, S.J.3
  • 19
    • 0023201991 scopus 로고
    • Coupling of indoleacetic acid trianion or methyl indoleacetic acid dianion: A biomimetic approach to indolocarbazole alkaloids
    • (c) Bergaman, J.; Pelcman, B. Coupling of indoleacetic acid trianion or methyl indoleacetic acid dianion: A biomimetic approach to indolocarbazole alkaloids. Tetrahedron Lett. 1987, 28, 4441-4444;
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4441-4444
    • Bergaman, J.1    Pelcman, B.2
  • 21
    • 33750350236 scopus 로고    scopus 로고
    • A practical method for the synthesis of indolylaryl-and bisindolylmaleimides
    • (e) Roy, S.; Gribble, G. W. A practical method for the synthesis of indolylaryl-and bisindolylmaleimides. Org. Lett. 2006, 8, 4975-4977;
    • (2006) Org. Lett. , vol.8 , pp. 4975-4977
    • Roy, S.1    Gribble, G.W.2
  • 22
    • 0024503059 scopus 로고
    • Synthesis of indolo[2,3-a]pyrrolo[3,4-c]carbazoles by double Fischer indolizations
    • (f) Bergman, J.; Pelcman, B. Synthesis of indolo[2,3-a]pyrrolo[3,4-c] carbazoles by double Fischer indolizations. J. Org. Chem. 1989, 54, 824-828;
    • (1989) J. Org. Chem. , vol.54 , pp. 824-828
    • Bergman, J.1    Pelcman, B.2
  • 23
    • 0001186193 scopus 로고    scopus 로고
    • A new, efficient method for the synthesis of bisindolylmaleimides
    • (g) Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. A new, efficient method for the synthesis of bisindolylmaleimides. J. Org. Chem. 1998, 63, 6053-6058;
    • (1998) J. Org. Chem. , vol.63 , pp. 6053-6058
    • Faul, M.M.1    Winneroski, L.L.2    Krumrich, C.A.3
  • 24
    • 49249118744 scopus 로고    scopus 로고
    • Recent progress in the chemistry and applications of indolocarbazoles
    • (h) Janosik, T.; Wahlstroem, N.; Bergman, J. Recent progress in the chemistry and applications of indolocarbazoles. Tetrahedron 2008, 64, 9159-9180.
    • (2008) Tetrahedron , vol.64 , pp. 9159-9180
    • Janosik, T.1    Wahlstroem, N.2    Bergman, J.3
  • 25
    • 0037032310 scopus 로고    scopus 로고
    • The first total synthesis of dragmacidin D
    • Garg, N. K.; Sarpong, R.; Stoltz, B. M. The first total synthesis of dragmacidin D. J. Am. Chem. Soc. 2002, 124, 13179-13184.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 13179-13184
    • Garg, N.K.1    Sarpong, R.2    Stoltz, B.M.3
  • 26
    • 0000794582 scopus 로고
    • Metalated hetercoclcles in the synthesis of ellipticine analogs. A new route to the 10H-pyrido[2,3-b]carbazole ring system
    • Gribble, G. W.; Fletcher, G. L.; Ketcha, D. M.; Rajopadhye, M. Metalated hetercoclcles in the synthesis of ellipticine analogs. A new route to the 10H-pyrido[2,3-b]carbazole ring system. J. Org. Chem. 1989, 54, 3267.
    • (1989) J. Org. Chem. , vol.54 , pp. 3267
    • Gribble, G.W.1    Fletcher, G.L.2    Ketcha, D.M.3    Rajopadhye, M.4
  • 27
    • 0025127244 scopus 로고
    • A mild conversion of maleic anhydrides into maleimides
    • Davis, P. D.; Bit, R. A. A mild conversion of maleic anhydrides into maleimides. Tetrahedron Lett. 1990, 31, 5201-5204.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 5201-5204
    • Davis, P.D.1    Bit, R.A.2
  • 28
    • 0027729427 scopus 로고
    • Oxidative cyclisations with palladium acetate: A short synthesis of staurosporine aglycone
    • Harris, W.; Hill, C. H.; Keech, E.; Malsher, P. Oxidative cyclisations with palladium acetate: A short synthesis of staurosporine aglycone. Tetrahedron Lett. 1993, 34, 8361-8364.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 8361-8364
    • Harris, W.1    Hill, C.H.2    Keech, E.3    Malsher, P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.