Synthese van diketopiperazines als inhibitoren van histon deacetylase. (Gunther Roesems)

 

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B I B L I O G R A F I E

 

[1] A. Geerts, D. Tourwé: Suppression of hepatic stellate cell-myofibroblast transition by histon deacetylase inhibitors: implications for development of antifibrogenic drugs. Laboratory for Cell Biology and Histology, Extracellular Matrix Research Group (ECMR), Faculty of Medicine and Pharmacy and Department of Organic Chemistry (ORGC), Faculty of Sciences

 

[2] E. ten Winkel, H. Aalders, D. Ernest, E. Mol, K. Scholte, L. Verhoeven, J. Vermeer: Elseviers Medische Encyclopedie; Elsevier (1986); p 263 - 264

 

[3] M.S. Finnin, J.R. Donigian, A. Cohen, V.M. Richon, R.A. Rifkind, P.A. Marks, R. Breslow, N.P. Pavietich: Structures of a histon deacetylase homologue bound to the TSA and SAHA inhibitors; Nature (1999); vol 401; p 188 - 192

 

[4] J. Van Hemel: Eindverslag: Synthese en biologische evaluatie van trichostatine A en analogen; IWT postdoctoraal onderzoeksmandaat (1999)

 

[5] Greenstein, Winitz: Chemistry of the amino acids; John Wiley and Sons (1961); vol 2; p 925-926

 

[6] L.A. Paquette: Encyclopedia of reagents for organic synthesis; John Wiley and Sons (1961); vol 1; p 304-306

 

[7] D.E. Nitecki, B. Halpern, J.W. Westly: A simple route to sterically pure diketopiperazines; Journal of Organic Chemistry (1968); vol 33; p 864-866

 

[8] S. Rajappa, M.V. Natekar: Piperazine-2,5-diones and related lactim ethers; Advances in Heterocyclic Chemistry (1993); vol 57; p 187 - 289

 

[9] S.N. Danthi, R.A. Hill: Synthesis of chirally pure 2,5-disubstituted diketopiperazines derived from trisubstituted phenylalanines; Journal of Heterocyclic Chemistry (1997); vol 34; p 835 - 844

 

[10] B.S. Furniss, A.J. Hannaford, P.W.G. Smith, A.R. Tatchell: Vogel’s textbook of practical organic chemistry; 5th edition; Longman (1989); p 763

 

[11] G.R. Krow, K.C. Cannon, J.T. Carey, Hong Ma, R. Raghavachari, S.W. Szczepanski: Competitive [4+2] cycloaddition versus [1, 5] sigmatropy in a cycloheptatriene. An efficient route to 3-Azatricyclo[5.3.1.04,10]undeca-5,8-diene;.Journal of Organic Chemistry (1988), vol 53, p2665 - 2669

 

[12] K.J. Lee, D.H. Kim: Design of mechanism-based carboxypeptidase A inactivators on the basis of the X-ray crystal structure and catalytic reaction pathway; Bioorganic & Medicinal Chemistry (1998); vol 6; p 1613 - 1622

 

[13] F.A. Carey, R.J. Sundberg: Advanced organic chemistry; 3th edition; Plenum Press (1990); part B; p 145

 

[14] B.S. Furniss, A.J. Hannaford, P.W.G. Smith, A.R. Tatchell: Vogel’s textbook of practical organic chemistry; 5th edition; Longman (1989); p 917

 

[15] K. Ichimori, D.J. Stuehr, R.N. Atkinson, S.B. King: Synthesis and evaluation of new sulfur containing L-arginine-derived inhibitors of nitric oxide synthase; Journal of Medicinal Chemistry (1999); vol 42; p 1842 - 1848

 

[16] J.A.W. Kruijtzer, D.J. Lefeber, R.M.J. Liskamp: Approaches to the synthesis of ureapeptoid peptidomimetics; Tetrahedron Letters (1997); vol 38; p 5335 - 5338

 

[17] D. Nagarathnam, S.W. Miao, B. Lagu, G. Chiu, J. Fang, T.G.M. Dhar, J. Zhang, S. Tyagarajan, M.R. Marzabadi, F. Zhang, W.C. Wong, W. Sun, D. Tian, J.M. Wetzel, C. Forray, R.S.L. Chang, T.P. Broten, R.W. Ransom, T.W. Schorn, T.B. Chen, S. O’Malley, P. Kling, K. Schneck, R. Bendesky, C.M. Harrell, K.P. Vyas, C. Gluchowski: Design and synthesis of novel a1a adrenoceptor-selective antagonists. Structure – activity relationship in dihydropyrimidinones; Journal of Medicinal Chemistry (1999); vol 42; p 4764 – 4777

 

[18] L. Lapatsanis, G. Milias, K. Froussios, M. Kolovos: Synthesis of N-2,2,2-(Trichloro-ethoxycarbonyl)-L-amino acids and N-(9-Fluorenylmethoxycarbonyl)-L-amino acids involving succinimidoxy anion as a leaving group in amino acid protection; Synthesis (1983); p 671 – 673

 

[19] B.S. Furniss, A.J. Hannaford, P.W.G. Smith, A.R. Tatchell: Vogel’s textbook of practical organic chemistry; 5th edition; Longman; p 1384

 

[20] Fluka: Laboratory chemicals and analytical reagents

 

[21] K. Wuthrich: NMR of proteins and nucleic acids; John Wiley and Sons (1986); p 17

 

 

A F K O R T I N G E N

 

Boc:  t-butoxycarbonyl

bs: breed singlet

Bzl: benzyl

COSY: homonucleaire correlatie spectroscopie

d: doublet

dd: dubbel doublet

DiPEA: diisopropylethylamine

DMAP: dimethylaminopyridine

DMF: dimethylformamide

DNA: desoxyribonucleïnezuur

eq.: equivalent

ES: electrospray

HPLC: High Pressure Liquid Chromatography

IR: infrarood spectroscopy

kt: kamertemperatuur

LC / MS: Liquid Chromatography / Mass Spectrometry

Lys: lysine

M: massief

m: multiplet

Me: methyl

MS: massaspectrometrie

m/z: massa/lading

NMR: Nuclear Magnetic Resonance

ppm: parts per million

Ph: fenyl

Phe: fenylalanine

psi: 1 bar = 14.5 psi

Rf: ratio to the front

Rt: retentietijd

 

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