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Volumn 121, Issue 39, 1999, Pages 9073-9087

Synthesis and preliminary evaluation of a library of polycyclic small molecules for use in chemical genetic assays

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; DISCODERMOLIDE; NATURAL PRODUCT; PACLITAXEL; RAPAMYCIN; SHIKIMIC ACID; TRAPOXIN; UNCLASSIFIED DRUG;

EID: 0032879750     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992144n     Document Type: Article
Times cited : (162)

References (107)
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    • note
    • Tamura et al. propose reaction of the Z-nitrone via an exo transition state. However, orbital overlap appears to be more favorable in the reaction of the E-nitrone via an endo transition state as indicated in Scheme 1.
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    • note
    • All resin-bound products were photocleaved and analyzed by standard techniques (TLC, HPLC, NMR, MS).
  • 36
    • 0345248489 scopus 로고    scopus 로고
    • note
    • Abbreviations not cited in text: DMF = N,N-dimethylformamide, DMA = N,N-dimethylacetamide, NMP = N-methylpyrrolidinone, PyBroP = bromotripyrrolidinophosphonium hexafluorophosphate, HATU = N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N- methylmethan-aminium hexafluorophosphate, PyBOP = benzotriazol-1-yloxytripyrroli-dinophosphonium hexafluorophosphate, TFFH = N,N,N′,N′-tetramethylfluoroformamidinium hexafluorophosphate, DIPC = 1,3-diisopropylcarbodiimide, CDI = 1,1′-carbonyldiimidazole, DIPEA = N,N-diisopropylethylamine, DMAP = 4-(dimethylamino)pyridine, cod = 1,5-cyclooctadiene, DPPF = 1,1′-bis(diphenylphosphino)ferrocene, DBN = 1,5-diazabicyclo[4.3.0]non-5-ene, LC-MS = tandem high-pressure liquid chromatography-mass spectrometry, HR-FAB-MS = high-resolution fast atom bombardment mass spectrometry, HR-TOF-ESI-MS = high-resolution time-of-flight electrospray induction mass spectrometry, EC-GC = electron capture detection gas chromatography.
  • 37
    • 0345680152 scopus 로고    scopus 로고
    • note
    • The term "building block" is preferred over the commonly used term "monomer" since the products are non-oligomeric.
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    • 0000633011 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Permangon Press: Oxford
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    • Heck, R.F.1
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    • note
    • 3-Bn, 69% side reaction; R = 4-I-Bn, 59%; R = 4-Cl-Bn, 32%; R = Bn, 24%; R = 4-tBu-Bn, 13%; R = 3-I-Bn, 46%; R = 2-I-Bn, 31%.) Replacement of the ω-aminocaproic acid spacer with glycine or removal of the spacer altogether actually decreases the amount of 10 formed. (For 12, R = 4-I-Bn: Aca spacer, 59% side reaction; Gly spacer, 36%; no spacer 29%.) Interestingly, substitution at the benzylic carbon eliminates the side reaction altogether (for 12, R = 4-I-α-Me-Bn, 0% side reaction). Moreover, solution-phase aminolysis of the tetracycle below results in no side reaction. Control experiments verified that the side reaction is not caused by photocleavage. (illustration presented)
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    • note
    • Aminolysis in the presence of sodium cyanide in MeOH, sodium hydride in DMA, sodium methoxide in benzene, ferric chloride in MeOH, lithium chloride in MeOH, and lithium hydroxide in MeOH all appeared to result in degradation of the linker. Aminolysis in the presence of the Otera organotin catalyst in toluene did not reduce the amount of epoxycyclohexenol recovered.
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    • Wiley & Sons: New York, Collect.
    • Kamm, O. Organic Syntheses; Wiley & Sons: New York, 1941; Collect. Vol. I, pp 445-447.
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    • 2; and (7) esterification with the Otera organotin catalyst.
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    • Despite considerable efforts to understand this vexing side reaction, both its exact mechanism and a rationalization of the ameliorating effects of alkynylbenzyl substituents remain mysterious to us.
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    • The 1996-1997 Aldrich Structure Index lists 24 applicable salicyl aldehydes
    • The 1996-1997 Aldrich Structure Index lists 24 applicable salicyl aldehydes.
  • 83
    • 0345248471 scopus 로고    scopus 로고
    • note
    • The 1996-1997 Aldrich Structure Index lists 54 applicable symmetrical anhydrides compared to over 1000 carboxylic acids.
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    • Certain acid-sensitive products were also analyzed by TLC and FABMS
    • Certain acid-sensitive products were also analyzed by TLC and FABMS.
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    • note
    • n = X, where X represents all eight building blocks at a given position.
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    • Based upon previous results, a 50% yield was assumed
    • Based upon previous results, a 50% yield was assumed.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.