insérer le précurseur de la chaîne butyroyle au niveau de la fonction ester en position 5. L'insertion du bras espaceur sur la position 2 dépendra de la nature du groupe R 1 . Ainsi, si R 1 est du type alkyle comme un méthyle, on peut imaginer la fonctionnalisation de celui-ci en utilisant une base 92 afin de former le carbanion qui pourrait réagir avec un électrophile, Si R' est un halogène, 74abfgh,93 dans ce cas on pourrait envisager la fonctionnalisation par une réaction de substitution nucléophile ,
Chim. Pays-Bas, p.854, 1938. ,
AHF NCI Collection, Nitrosamines in Cigarette Smoke, pp.8790-8796, 1981. ,
Estimates of global mortality attributable to smoking in, Lancet, vol.3626, pp.847-852, 2000. ,
The Tobacco Atlas. World Health Organization ,
Molecular and Cellular Aspects of Nicotine Abuse, Neuron, vol.16, issue.5, pp.905-908, 1996. ,
DOI : 10.1016/S0896-6273(00)80112-9
Acetylcholine receptors containing the ?2 subunit are involved in the reinforcing properties of nicotine, Nature, vol.3919, pp.173-177, 1998. ,
Nicotine activation of ?4 * receptors sufficient for reward, tolerance, and sensitization, Sciences, vol.306, pp.1029-1032, 2004. ,
Basic Neurochemistry: Molecular, Cellular and Medical Aspects, Sixth Edition. GABA Receptor Physiology and Pharmacology ,
Neuronal nicotinic receptors: from protein structure to function, FEBS Letters, vol.15, issue.3, pp.118-125, 2001. ,
DOI : 10.1073/pnas.89.20.9949
Refined Structure of the Nicotinic Acetylcholine Receptor at 4?? Resolution, Journal of Molecular Biology, vol.346, issue.4, 2005. ,
DOI : 10.1016/j.jmb.2004.12.031
Crystal structure of a Cbtx-AChBP complex reveals essential interactions between snake alpha-neurotoxins and nicotinic receptors, Embo. J, pp.1512-1522, 2005. ,
URL : https://hal.archives-ouvertes.fr/hal-00021395
Irreversible inhibition of monoamine oxidase by some components of cigarette smoke, Life Sciences, vol.41, issue.6, pp.675-82, 1987. ,
DOI : 10.1016/0024-3205(87)90446-2
Pharmacotherapy for Nicotine Dependence, CA: A Cancer Journal for Clinicians, vol.55, issue.5, pp.281-299, 2005. ,
DOI : 10.3322/canjclin.55.5.281
Varenicline: an ?4?2 nicotinic receptor partial agonist for smoking cessation, J. Med. Chem, vol.48, pp.3474-3477, 2005. ,
Nicotine Vaccine Moves Toward Clinical Trials, National Institute on Drug Abuse, 2000. ,
DOI : 10.1037/e313322004-001
Safety and immunogenicity of a nicotine conjugate vaccine in current smokers, Clinical Pharmacology & Therapeutics, vol.78, issue.5, pp.456-467, 2005. ,
A therapeutic vaccine for nicotine dependence: preclinical efficacy, and Phase I safety and immunogenicity, European Journal of Immunology, vol.35, issue.7, pp.2031-2040, 2005. ,
Cancer statistics, 1999, Wingo Cancer statistics, pp.8-31, 1999. ,
DOI : 10.3322/canjclin.49.1.8
Fraumeni Cancers of the lung and pleura, Cancer Epidemiology and Prevention, pp.637-65, 1996. ,
Formation and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol enantiomers
in vitro
in mouse, rat and human tissues, Carcinogenesis, vol.21, issue.6, pp.1233-1238, 2000. ,
DOI : 10.1111/j.1432-1033.1996.0484z.x
Biotransformation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in freshly isolated human lung cells, Carcinogenesis, vol.20, issue.9, pp.1809-1818, 1999. ,
DOI : 10.1093/carcin/20.9.1809
Catalyzed Addition of Aldehydes to Activated Double Bonds?A New Synthetic Approach, Angewandte Chemie International Edition in English, vol.37, issue.11, pp.639-712, 1976. ,
DOI : 10.1002/cber.19761090218
(e) A. Lapworth, Chem. Int. Ed. Organic Syntheses, Coll. Journal of the Chemical Society Transactions, vol.45, issue.85, pp.1463-14679433, 1904. ,
6,6-Disubstituted hex-5-enoic acid derivatives as combined thromboxane A2 receptor antagonists and synthetase inhibitors, Journal of Medicinal Chemistry, vol.37, issue.1, pp.26-39, 1994. ,
DOI : 10.1021/jm00027a004
Cesium Effect:?? High Chemoselectivity in Direct N-Alkylation of Amines, The Journal of Organic Chemistry, vol.67, issue.3, pp.674-683, 2002. ,
DOI : 10.1021/jo010643c
-Alkylation for the Generally Efficient Synthesis of Secondary Amines, Organic Letters, vol.1, issue.12, pp.1893-1896, 1999. ,
DOI : 10.1021/ol9910417
Synthesis of [4-2H2]-, (4R)[4-2H1]- and (4S)[4-2H1]- 4-(methylnitrosamino)-1-(3'-pyridyl)-1-butanone, c-4 deuteriated isotopomers of the procarcinogen nnk, Tetrahedron, vol.46, issue.5, pp.1733-1745, 1990. ,
DOI : 10.1016/S0040-4020(01)81978-5
Ceric ammonium nitrate in the deprotection of tert-butoxycarbonyl group, Tetrahedron Letters, vol.37, issue.12, pp.2035-2038, 1996. ,
DOI : 10.1016/0040-4039(96)00211-0
Synthetic methods and reactions. 62. Transformations with chlorotrimethylsilane/sodium iodide, a convenient in situ iodotrimethylsilane reagent, The Journal of Organic Chemistry, vol.44, issue.8, pp.1247-1251, 1979. ,
DOI : 10.1021/jo01322a012
Synthetic methods and reactions. 112. Synthetic transformations with trichloromethylsilane/sodium iodide reagent, The Journal of Organic Chemistry, vol.48, issue.21, pp.3667-3672, 1983. ,
DOI : 10.1021/jo00169a010
The facile preparation of alkenyl metathesis synthons, Tetrahedron, vol.60, issue.48, pp.10943-10948, 2004. ,
DOI : 10.1016/j.tet.2004.09.021
(b) Patent, Shell, Chem. Chem.Abstr, vol.34, issue.59, pp.262-271, 1957. ,
(d) Patent, Basf, DE 1198340, Chem.Abstr, vol.63, issue.4, pp.2067-2074, 1963. ,
(b) Austrian Patent 121 246. (c) German Patents 513 293 (d) Swiss Patent 129 173, Chem. Ber, vol.58, issue.60, pp.681-766, 1925. ,
Substituted 2-Sulfonamido-5-aminopyridines. II, Journal of the American Chemical Society, vol.66, issue.9, p.1479, 1944. ,
DOI : 10.1021/ja01237a018
An HIV Reverse Transcriptase-Selective Nucleoside Chain Terminator, Journal of the American Chemical Society, vol.125, issue.3, pp.616-617, 2003. ,
DOI : 10.1021/ja020639y
Intramolekularer Synergismus als Erkl??rung f??r die erh??hte Fungitoxizit??t von halogenierten 8-Chinolinolen, Monatshefte f??r Chemie - Chemical Monthly, vol.125, issue.12, p.1303, 1995. ,
DOI : 10.1128/AAC.1.5.373
An efficient and selective method for the preparation of iodophenols, The Journal of Organic Chemistry, vol.55, issue.18, pp.5287-5291, 1990. ,
DOI : 10.1021/jo00305a026
Dendrimeric Pyridoxamine Enzyme Mimics, Journal of the American Chemical Society, vol.125, issue.40, pp.12110-12111, 2003. ,
DOI : 10.1021/ja0374473
Synthesis of functionalized 3-pyridyl methyl ketones, Journal of Heterocyclic Chemistry, vol.35, issue.3, pp.717-724, 1998. ,
DOI : 10.1002/jhet.5570350335
), Journal of Agricultural and Food Chemistry, vol.52, issue.23, pp.6944-6949, 2004. ,
DOI : 10.1021/jf049259h
Alkylations of Heterocyclic Ambident Anions II. Alkylation of 2-Pyridone Salts, The Journal of Organic Chemistry, vol.32, issue.12, pp.4040-4075, 1967. ,
DOI : 10.1021/jo01287a600
-Thiazolines from N-Acyl-2-aminoethanols, Journal of the American Chemical Society, vol.57, issue.6, pp.1079-1080, 1935. ,
DOI : 10.1021/ja01309a034
Organometallic ring-opening reactions of N-acyl and N-alkoxycarbonyl lactams. Synthesis of cyclic imines, The Journal of Organic Chemistry, vol.54, issue.1, pp.228-234, 1989. ,
DOI : 10.1021/jo00262a048
Probing the proposed phenyl-A region of the sigma-1 receptor, Bioorganic & Medicinal Chemistry, vol.10, issue.8, pp.2759-2765, 2002. ,
DOI : 10.1016/S0968-0896(02)00096-2
Effective lithiation of 3-bromopyridine: synthesis of 3-pyridine boronic acid and variously 3-substituted pyridines, Tetrahedron Letters, vol.43, issue.23, pp.4285-4287, 2002. ,
DOI : 10.1016/S0040-4039(02)00776-1
-1,2-Di(2-pyridyl)ethylene, The Journal of Organic Chemistry, vol.21, issue.12, p.1420, 1956. ,
DOI : 10.1021/jo01118a024
CARBANIONIC DISPLACEMENT REACTIONS AT PHOSPHORUS: DIETHYL (2-PYRIDY L)METHYLPHOSPHONATE SYNTHESIS, Phosphorus, Sulfur, and Silicon and the Related Elements, vol.30, issue.1, pp.209-218, 1950. ,
DOI : 10.1055/s-1994-25411
Pays-Bas, p.854, 1938. ,
(b) A. Reissert, Chem. Ber. Chem. Ber. Chem. Pharm. Bull. Bonnet, F. Mongin, F. Trecourt, G. Queguiner, P. Knochel Tetrahedron, vol.100, issue.36, pp.2394-1895, 1884. ,
(b) Okata, J. Med. Chem. Bl. Textile Res. Inst. Yokohama Chem.Abstr, vol.44, issue.82, pp.3141-3149, 1956. ,
(h) Patent, Rohm and Haas (i) Pogorzel'skaja, J. Org. Chem. Chem.Abstr. J.Org.Chem.USSR (Engl.Transl, vol.314, issue.5, pp.353-364, 1961. ,
-Acylbenzotriazoles:?? Neutral Acylating Reagents for the Preparation of Primary, Secondary, and Tertiary Amides, The Journal of Organic Chemistry, vol.65, issue.24, pp.8210-8213, 2000. ,
DOI : 10.1021/jo000792f
Synthesis of ??-Dicarbonyl Compounds Using 1-Acylbenzotriazoles as Regioselective C-Acylating Reagents, The Journal of Organic Chemistry, vol.65, issue.12, pp.3679-3682, 1980. ,
DOI : 10.1021/jo991878f
Chim. Pays-Bas, J. Chem. Soc. J. Am. Chem, vol.70, issue.67, p.222, 1895. ,
Notes- Some Nitropyridine Derivatives, The Journal of Organic Chemistry, vol.24, issue.7, p.1007, 1959. ,
DOI : 10.1021/jo01089a615
(b) Kabatschnik, Kaznel'son, Arch.Pharm. J. Chem. Soc. Perkin Trans. 2 Chem. Ber. J. Org. Chem. J. Am. Chem. Soc, vol.308136, issue.81, pp.363-397, 1935. ,
Protective Groups in Organic Synthesis, pp.433-435, 1999. ,
DOI : 10.1002/0471220574
Synthesis and ionophore properties of a series of new tetrapyrazolic macrocycles, Tetrahedron, vol.44, issue.1, pp.91-100, 1988. ,
DOI : 10.1016/S0040-4020(01)85096-1
Solid and solution phase syntheses of the 2-cyanopyrrolidide DPP-IV inhibitor NVP-DPP728, Tetrahedron, vol.58, issue.28, pp.5741-5746, 2002. ,
DOI : 10.1016/S0040-4020(02)00536-7
URL : https://hal.archives-ouvertes.fr/inserm-00110441
Direct coupling between ??-functionalized organolithium compounds and aryl and vinyl halides, Tetrahedron Letters, vol.33, issue.41, pp.6183-6186, 1992. ,
DOI : 10.1016/S0040-4039(00)60038-2