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Volumn 57, Issue 9, 2009, Pages 920-936

Synthesis and biological activity of enantiomeric pairs of 5-(alk-2-enyl)thiolactomycin and 5-[(E)-cycloalk-2-enylidenemethyl] thiolactomycin congeners

Author keywords

5 (alk 2 enyl) thiolactomycin; 5 (E) cycloalk 2 enylidenemethyl thiolactomycin; Thiolactomycin; Type I fatty acid synthase inhibitor

Indexed keywords

5 (ALK 2 ENYL)THIOLACTOMYCIN; 5 [CYCLOALK 2 ENYLIDENE METHYL]THIOLACTOMYCIN; FATTY ACID SYNTHASE INHIBITOR; THIOLACTOMYCIN; UNCLASSIFIED DRUG;

EID: 70349182343     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.57.920     Document Type: Article
Times cited : (5)

References (43)
  • 28
    • 70349174412 scopus 로고    scopus 로고
    • note
    • In addition to 5a-c, 6a-c and their enantiomers (ent-5a-c, ent-6a-c), 5-[(E)-cyclopent-2-enylidenemethyl]-TLM, its 3-demethyl congener and their enantiomers (5d, 6d, ent-5d, ent-6d) were designed and their synthesis was attempted following the same synthetic scheme shown in Chart 2. Although the scheme proceeded smoothly to the stage of 20 (n=0), aldehyde 21 (n=0) derived from 20 (n=0) was found to be very unstable, probably due to facile isomerization to the cyclopentadiene derivative and the subsequent intramolecular Diels-Alder reaction (Ohata K. and Terashima S., unpublished results).
  • 31
    • 70349191168 scopus 로고    scopus 로고
    • note
    • 1H-NMR spectrum, the two olefinic protons of 11b showed larger chemical shifts than 24b. The same relationships were also observed for the chemical shift values of 11a, c-f and 24a, c-f.
  • 36
    • 70349169918 scopus 로고    scopus 로고
    • note
    • In the absence of HMPA, the deconjugative asymmetric α- sulfenylation of 19a did not take place at all.
  • 37
    • 70349178981 scopus 로고    scopus 로고
    • note
    • 1H-NMR spectrum and/or HPLC analysis are as follows: 19/26/27; 12 : 2 : 1 for 19a/26a/27a; 14 : 1 : 4 for 19b/26b/27b; 12 : 1 : 1 for 19c/26c/27c.
  • 38
    • 70349188047 scopus 로고    scopus 로고
    • note
    • 3): 5.44 ppm [(Me)(SR)C-CH=C] for 19a; 5.50 ppm [(Me)(SR)C-CH=C] for the (S)-diastereomer of 19a (26a); 5.56 ppm [(Me)(SR)C-CH=C] for 19b; 5.62 ppm [(Me)(SR)C-CH=C] for the (S)-diastereomer of 19b (26b); 5.64 ppm [(Me)(SR)C-CH=C] for 19c; 5.72 ppm [(Me)(SR)C-CH=C] for the (S)-diastereomer of 19c (26c); 5.72 ppm [(Me)(SR)C-CH=C] for the synthetic intermediate of 1; 5.77 ppm [(Me)(SR)C-CH=C] for the (S)-diastereomer of the synthetic intermediate of 1.
  • 39
    • 70349175867 scopus 로고    scopus 로고
    • note
    • The enantiomeric exesses of 3a-f, ent-3a-f, 4a-f, ent-4a-f, 5a-c, ent-5a-c, 6a-c and ent-6a-c were shown in Table 3 and in Experimental.
  • 40
    • 70349183511 scopus 로고    scopus 로고
    • note
    • Determination of MICs by agar dilution methods was performed according to the guideline M7-A6 of the Clinical and Laboratory Standards Institute (2003).
  • 42
    • 70349171369 scopus 로고    scopus 로고
    • note
    • Formation of two types of the by-products corresponding to 24b and 25b was observed, similar to the case described for the preparation of 11b, 24b and 25b from 9b.
  • 43
    • 70349163698 scopus 로고    scopus 로고
    • note
    • D α values for those compounds were not included in this report. At present, the reason for the observed inconsistency is unclear.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.