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Volumn 73, Issue 12, 2008, Pages 4362-4369

Expedient synthesis of N-methyl tubulysin analogues with high cytotoxicity

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; ALKYLATION; AMIDES; AMINATION; AMINES; AMINO ACIDS; BIOLOGICAL MATERIALS; CHEMICAL REACTIONS; HEALTH; HYDROCARBONS; ORGANIC ACIDS; ORGANIC COMPOUNDS; STEREOCHEMISTRY; STEREOSELECTIVITY;

EID: 45249085481     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800384x     Document Type: Article
Times cited : (61)

References (55)
  • 13
    • 45249115525 scopus 로고    scopus 로고
    • Reference 4 originally reported the total synthesis of naturally occurring tubulysins U and V, but was actually the synthesis of epimeric compounds. Correction: Dömling, A.; Beck, B.; Eichelberger, U.; Sakamuri, S.; Menon, S.; Chen, Q.-Z.; Lu, Y.; Wessjohann, L. A. Angew. Chem., Int. Ed. 2007, 46, 2337-2348.
    • Reference 4 originally reported the total synthesis of naturally occurring tubulysins U and V, but was actually the synthesis of epimeric compounds. Correction: Dömling, A.; Beck, B.; Eichelberger, U.; Sakamuri, S.; Menon, S.; Chen, Q.-Z.; Lu, Y.; Wessjohann, L. A. Angew. Chem., Int. Ed. 2007, 46, 2337-2348.
  • 17
    • 45249103348 scopus 로고    scopus 로고
    • Other cancer cell lines such as human cervix carcinoma KB-3-1 (DSMZ ACC 158) and mouse fibroblast L929 (DSMZ ACC 2) also showed comparable biological activities.
    • Other cancer cell lines such as human cervix carcinoma KB-3-1 (DSMZ ACC 158) and mouse fibroblast L929 (DSMZ ACC 2) also showed comparable biological activities.
  • 18
    • 45249107822 scopus 로고    scopus 로고
    • For an alternative synthesis of 2, see ref 7
    • For an alternative synthesis of 2, see ref 7.
  • 24
    • 45249118453 scopus 로고    scopus 로고
    • Prepared as described in ref 12 in three steps from phenylacetaldehyde
    • Prepared as described in ref 12 in three steps from phenylacetaldehyde.
  • 42
    • 0025155117 scopus 로고    scopus 로고
    • For examples of borohydride reduction of 1,3-N-alkyl- tetrahydrooxazines, see: (a) Kirst, H. A, Wind, J. A, Leeds, J. P, Willard, K. E, Debono, M, Bonjouklian, R, Greene, J. M, Sullivan, K. A, Paschal, J. W, Deeter, J. B, Jones, N. D, Ott, J. L, Felty-Duckworth, A. M, Counter, F. T. J. Med. Chem. 1990, 33, 3086-3094
    • For examples of borohydride reduction of 1,3-N-alkyl- tetrahydrooxazines, see: (a) Kirst, H. A.; Wind, J. A.; Leeds, J. P.; Willard, K. E.; Debono, M.; Bonjouklian, R.; Greene, J. M.; Sullivan, K. A.; Paschal, J. W.; Deeter, J. B.; Jones, N. D.; Ott, J. L.; Felty-Duckworth, A. M.; Counter, F. T. J. Med. Chem. 1990, 33, 3086-3094.
  • 47
    • 45249093277 scopus 로고    scopus 로고
    • To our knowledge no examples exist of reducing 1,3-N-acyl-, 1,3-N-sulfonyl-, or 1,3-N-sulfinyl-tetrahydrooxazines to the corresponding 1,3-amino alcohol. For examples with 1,2-N-acyl- oxazolidines, see refs 25f, i, and 25j, as well as: (a) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Chem. Commun. 1999, 4, 317-318.
    • To our knowledge no examples exist of reducing 1,3-N-acyl-, 1,3-N-sulfonyl-, or 1,3-N-sulfinyl-tetrahydrooxazines to the corresponding 1,3-amino alcohol. For examples with 1,2-N-acyl- oxazolidines, see refs 25f, i, and 25j, as well as: (a) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Chem. Commun. 1999, 4, 317-318.
  • 54
    • 0031047509 scopus 로고    scopus 로고
    • Facile O- to N-acyl transfer has been reported, most notably in the N-methyl-1,2-amino alcohol pseudoephedrine series. See ref 29 and: (a) Myers, A. G, Gleason, J. L, Yoon, T, Kung, D. W J. Am. Chem. Soc. 1997, 119, 656-673
    • Facile O- to N-acyl transfer has been reported, most notably in the N-methyl-1,2-amino alcohol pseudoephedrine series. See ref 29 and: (a) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W J. Am. Chem. Soc. 1997, 119, 656-673.
  • 55
    • 45249115968 scopus 로고    scopus 로고
    • Due to the unprotected carboxylic acid present in 22, PFP-ester activation was used in preference to carbodiimide coupling procedures that would cause oligomerization.
    • Due to the unprotected carboxylic acid present in 22, PFP-ester activation was used in preference to carbodiimide coupling procedures that would cause oligomerization.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.