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Volumn 11, Issue 14, 2009, Pages 2976-2979

New S-adenosyl-L-methionine analogues: Synthesis and reactivity studies

Author keywords

[No Author keywords available]

Indexed keywords

5' N CHLOROETHYLAMINO 5' DEOXYADENOSINE; 5'-N-CHLOROETHYLAMINO-5'-DEOXYADENOSINE; AZIRIDINE DERIVATIVE; DEOXYADENOSINE DERIVATIVE; DRUG DERIVATIVE; S ADENOSYLMETHIONINE;

EID: 67650308454     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9009859     Document Type: Article
Times cited : (26)

References (32)
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    • (b) Dalhaff, C., Weinhold, E. In Modified Nucleosides; Herdewijn, P., Ed.; Wiley-VCH: Weinheim, Germany, 2008; pp 223-247.
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    • Dalhaff, C.1    Weinhold, E.2
  • 6
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    • For selected references, see: (a) Borchardt, R. T.; Wu, Y. S.; Huber, J. A; Wycpalek, A. F. J. Med. Chem. 1976, 19, 1104-1110.
    • For selected references, see: (a) Borchardt, R. T.; Wu, Y. S.; Huber, J. A; Wycpalek, A. F. J. Med. Chem. 1976, 19, 1104-1110.
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    • 0035233367 scopus 로고    scopus 로고
    • For a review on the elucidation of biological pathways using chemical probes, see
    • For a review on the elucidation of biological pathways using chemical probes, see: Shogren-Knaak, M. A.; Alaimo, P. J.; Shokat, K. M. Annu. Rev Cell Dev. Biol. 2001, 17, 405-433.
    • (2001) Annu. Rev Cell Dev. Biol , vol.17 , pp. 405-433
    • Shogren-Knaak, M.A.1    Alaimo, P.J.2    Shokat, K.M.3
  • 21
    • 22244453371 scopus 로고    scopus 로고
    • Note that there has been an investigation with respect to the in situ formation of the aziridine by Rajski et al, however, this was just a preliminary investigation and did not lead to the determination of a halflife: Petersen, S. G, Rajski, S. R. J. Org. Chem. 2005, 70, 5833-5839
    • Note that there has been an investigation with respect to the in situ formation of the aziridine by Rajski et al.; however, this was just a preliminary investigation and did not lead to the determination of a halflife: Petersen, S. G.; Rajski, S. R. J. Org. Chem. 2005, 70, 5833-5839.
  • 22
    • 0025023154 scopus 로고    scopus 로고
    • Jenkins, T. C.; Naylor, M. A.; O'Neill, P.; Threadgill, M. D.; Cole, S.; Stratford, I. J.; Adams, G. E.; Fielden, E. M.; Suto, M. J.; Stier, M. A J. Med. Chem. 1990, 33, 2603-2610.
    • Jenkins, T. C.; Naylor, M. A.; O'Neill, P.; Threadgill, M. D.; Cole, S.; Stratford, I. J.; Adams, G. E.; Fielden, E. M.; Suto, M. J.; Stier, M. A J. Med. Chem. 1990, 33, 2603-2610.
  • 23
    • 0011763757 scopus 로고    scopus 로고
    • For a review on reductive aminations, see
    • For a review on reductive aminations, see: Baxter, E.; Reitz, A. B. Org. Reactions 2002, 59, 1-714.
    • (2002) Org. Reactions , vol.59 , pp. 1-714
    • Baxter, E.1    Reitz, A.B.2
  • 24
    • 67650315707 scopus 로고    scopus 로고
    • Note that 2',3'-O-isopropylideneadenosine is also commercially available, i.e., from Sigma-Aldrich.
    • Note that 2',3'-O-isopropylideneadenosine is also commercially available, i.e., from Sigma-Aldrich.
  • 25
    • 67650312849 scopus 로고    scopus 로고
    • Kinetic studies involving N-chloromustards bearing a second nitrogen substituent are ongoing and will be reported in due course.
    • Kinetic studies involving N-chloromustards bearing a second nitrogen substituent are ongoing and will be reported in due course.
  • 26
    • 0036007052 scopus 로고    scopus 로고
    • For a review on photolabile protecting groups, see
    • For a review on photolabile protecting groups, see: Bochet, C. G. J. Chem. Soc., Perkin Trans. 1 2002, 125-142.
    • (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 125-142
    • Bochet, C.G.1
  • 29
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    • The intramolecular cyclization product results of an attack of N-9 on the 5'-carbon to form a tetracyclic salt; see: (a) Liu, F.; Austin, D. J. J. Org. Chem. 2001, 66, 8643-8645.
    • The intramolecular cyclization product results of an attack of N-9 on the 5'-carbon to form a tetracyclic salt; see: (a) Liu, F.; Austin, D. J. J. Org. Chem. 2001, 66, 8643-8645.
  • 32
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    • It should be noted that this yield is that after a double purification by column chromatography. The overall yield can be increased by submitting the crude product directly to the next step
    • It should be noted that this yield is that after a double purification by column chromatography. The overall yield can be increased by submitting the crude product directly to the next step.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.