112091-17-5Relevant academic research and scientific papers
Regioselective C-2 and C-6 substitution of (S)-nicotine and nicotine derivatives
Fevrier, Florence C.,Smith, Emilie D.,Comins, Daniel L.
, p. 5457 - 5460 (2005)
(Chemical Equation Presented) Regioselective deprotonations of (S)-nicotine and derivatives at the C-2 and C-6 positions of the pyridine ring were performed in good to excellent yields. These methodologies allow the direct introduction of a plethora of fu
Synthesis of nornicotine, nicotine and other functionalised derivatives using solid-supported reagents and scavengers
Baxendale, Ian R.,Brusotti, Gloria,Matsuoka, Masato,Ley, Steven V.
, p. 143 - 154 (2002)
The sequential use of solid-supported reagents and scavengers has led to an efficient synthesis of the natural products nornicotine 1, nicotine 2 and further fuctionalised derivatives. Also reported is a diastereoselective route to both enantiomers of nicotine 2.
6-Pyridylnicotine and bis-6,6'-nicotine - new chiral 2,2'-bipyridines
Schmidt, Boris,Neitemeier, Vera
, p. 42 - 44 (1998)
Starting from (-)-nicotine, two new 2,2'-bipyridine ligands 6 and 7 with chiral pyrrolidine side chains have been synthesized. The stoichiometric complexation by palladium(II) or mercury(II) ions gives the bipyridyl complexes 8 and 9.
A five-step synthesis of (S)-macrostomine from (S)-nicotine
Enamorado, Monica F.,Ondachi, Pauline W.,Comins, Daniel L.
, p. 4513 - 4515 (2010)
A concise synthesis of (S)-macrostomine has been accomplished in five steps from natural nicotine in 19% overall yield via a pyridyne Diels - Alder cycloaddition reaction as the key step. A Kumada cross-coupling reaction on a 1-chloroisoquinoline intermediate provided the natural product.
Novel and potent 6-chloro-3-pyridinyl ligands for the α4β2 neuronal nicotinic acetylcholine receptor
Latli, Bachir,D'Amour, Kevin,Casida, John E.
, p. 2227 - 2234 (1999)
1-[(6-Chloro-3-pyridinyl)methyl]-2-imidazolidine (1), the N-desnitro metabolite of the major insecticide imidacloprid, is known to have similar potency to that of (-)-nicotine as an inhibitor of [3H](-)-nicotine binding at the rat recombinant α4β2 neuronal nicotinic acetylcholine receptor (nAChR); IC50 values in the present study are 3.8 nM for (-)-nicotine, 6.0 nM for 1, and 155 nM for imidacloprid. Synthesis of new analogues of 1, modified only in the heterocyclic moiety (five-, six-, or seven-membered rings with NH, S, O, and CH2 substituents), gave compounds varying from 4- fold higher potency (2-iminothiazole analogue 10) to > 6000-fold less active than (-)-nicotine. Other potent N-[(6-chloro-3-pyridinyl)methyl] compounds are those in which the heterocyclic imine is replaced with pyrrolidine (19) (IC50 9 nM) or trimethylammonium (22) (IC50 18 nM). A novel conversion of (-)-nicotine to its 6-chloro analogue increased the potency 2-fold. These 6- chloro-3-pyridinyl compounds are of interest as novel nAChR probes and potential metabolites of candidate insecticides.
CONJUGATES FOR PREVENTION OR TREATMENT OF NICOTINE ADDICTION
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Paragraph 0136; 0137, (2016/10/09)
PROBLEM TO BE SOLVED: To provide nicotine-derived haptens, nicotine-derived hapten-carrier conjugates, and vaccine compositions containing the conjugates, which are useful for enhancing smoking quit rates or reducing smoking relapse rates in smoking cessa
INHIBITORS OF BRUTON'S TYROSINE KINASE
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Page/Page column 62; 63, (2013/03/26)
This application discloses compounds according to generic Formula I: wherein the variables are defined as described herein, and which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with
Inhibitors of Bruton's Tyrosine Kinase
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Page/Page column 82, (2012/03/08)
This application discloses 6-(2-Hydroxymethyl-phenyl)-2-methyl-2H-pyridazin-3-one derivatives according to generic Formula I: wherein, variables X, R, and Y4, are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are further useful to treat inflammatory and auto immune diseases associated with aberrant B-cell proliferation, such as rheumatoid arthritis. Also disclosed are compositions containing compounds of Formula I and at least one carrier, diluent or excipient.
CONJUGATES FOR THE PREVENTION OR TREATMENT OF NICOTINE ADDICTION
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, (2011/12/14)
The present invention relates in part to nicotine-derived hapten-carrier conjugates of the formula (III): wherein m, n, W, -(spacer)-, X* and Y are as defined in the description. In certain embodiments, said nicotine-derived hapten-carrier conjugates can
Hydroxyarylketones via Ring-Opening of lactones with aryllithium reagents: An expedient synthesis of ( )-anabasamine
Miao, Lei,Dimaggio, Stassi C.,Trudell, Mark L.
experimental part, p. 91 - 97 (2010/06/14)
The regioselective ring-opening of lactones (δ-valerolactone and γ-butyrolactone) with aryllithium reagents is reported for the construction of a series of δ-hydroxy aryl ketones and γ-hydroxy aryl ketones. Application of this method for the expeditious syntheses of ( )-anabasamine and its nicotine-related analogue are also described.
