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Volumn 63, Issue 6, 1998, Pages 1961-1973

Macrocyclic bisindolylmaleimides: Synthesis by inter- and intramolecular alkylation

Author keywords

[No Author keywords available]

Indexed keywords

BISINDOLYLMALEIMIDE; PROTEIN KINASE C INHIBITOR;

EID: 0032549529     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971980h     Document Type: Article
Times cited : (38)

References (53)
  • 1
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    • Diabetes Control and Complication Trial Research Group. N. Engl. J. Med. 1993, 329, 977.
    • (1993) N. Engl. J. Med. , vol.329 , pp. 977
  • 11
    • 0029087513 scopus 로고    scopus 로고
    • ref 4
    • For preliminary communications, see: (a) Jirousek, M. R.; Gillig, J. R.; Neel, D. A.; Rito, C. J.; O'Bannon, D.; Heath, W. F.; McDonald, J. H. III.; Faul, M. M.; Winneroski, L. L.; Melikian-Badalian, A.; Baevsky, M.; Ballas, L. M.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2093. (b) ref 4.
  • 22
    • 7144263367 scopus 로고    scopus 로고
    • note
    • (R)-(+)-Glycidol (16.) was purchased in 89% enantioselectivity from Diasco.
  • 23
    • 7144266623 scopus 로고    scopus 로고
    • note
    • (R)-1-Chloro-2,3-propanediol (21) was purchased in >98% enantioselectivity from Diasco.
  • 41
    • 7144249507 scopus 로고    scopus 로고
    • note
    • On large scale yield of 7 by crystallization from DMF/acetonitrile varied from 55 to 68%.
  • 45
    • 7144224180 scopus 로고    scopus 로고
    • note
    • Neutralization with strong acid was unsuccessful due to competitive detritylation.
  • 47
    • 7144267560 scopus 로고
    • A number of methods to deprotect imide nitrogens have been reported: (a) PMB (i) Akiyama, T.; Kumegawa, M.; Takesue, Y.; Nishimoto, H.; Ozaki, S. Chemistry Lett. 1990, 339. (ii) Van Aerschot, A.; Jie, L.; Herdewijn, P. Tetrahedron Lett. 1991, 32, 1905. (b) BOM: Link, J. T.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 552.
    • (1990) Chemistry Lett. , pp. 339
    • Akiyama, T.1    Kumegawa, M.2    Takesue, Y.3    Nishimoto, H.4    Ozaki, S.5
  • 48
    • 0025974997 scopus 로고
    • A number of methods to deprotect imide nitrogens have been reported: (a) PMB (i) Akiyama, T.; Kumegawa, M.; Takesue, Y.; Nishimoto, H.; Ozaki, S. Chemistry Lett. 1990, 339. (ii) Van Aerschot, A.; Jie, L.; Herdewijn, P. Tetrahedron Lett. 1991, 32, 1905. (b) BOM: Link, J. T.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 552.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 1905
    • Van Aerschot, A.1    Jie, L.2    Herdewijn, P.3
  • 49
    • 0028789416 scopus 로고
    • A number of methods to deprotect imide nitrogens have been reported: (a) PMB (i) Akiyama, T.; Kumegawa, M.; Takesue, Y.; Nishimoto, H.; Ozaki, S. Chemistry Lett. 1990, 339. (ii) Van Aerschot, A.; Jie, L.; Herdewijn, P. Tetrahedron Lett. 1991, 32, 1905. (b) BOM: Link, J. T.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 552.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 552
    • Link, J.T.1    Raghavan, S.2    Danishefsky, S.J.3
  • 50
    • 7144236591 scopus 로고    scopus 로고
    • note
    • -1, indicating that no cyclic imide was present.
  • 51
    • 85099487569 scopus 로고    scopus 로고
    • note
    • R = 8.0 min.
  • 52
    • 85099487796 scopus 로고    scopus 로고
    • note
    • R = 19.9 min.
  • 53
    • 85099487480 scopus 로고    scopus 로고
    • note
    • R = 22.7 min.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.