- Synthesis and configurational assignment of some novel bicyclic sulphamidites and sulphamidates
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(S)-Prolinol and 2(RS)-piperidine-methanol each react with thionyl chloride to give a pair of diastereoisomeric bicyclic sulphamidites which differ only in their configuration at sulphur. By contrast 2(RS)-pyrrolidine-ethanol and 2(RS)-piperidine-ethanol each react with thionyl chloride to give single diastereoisomeric products. The configurations of these bicyclic sulphamidites, and the sulphamidates derived from them, have been determined.
- Lowe,Reed
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- The direct synthesis of the cyclic sulphamidate of (S)-prolinol: Simultaneous N-protection and activation towards nucleophilic displacement of oxygen
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The preparation of the cyclic sulphamidate of (S)-prolinol has been achieved by reaction with sulphuryl chloride at low temperature. This material has been shown to be susceptible to acid catalysed nucleophilic attack to furnish 2-(N,N-dialkylamino)methyl- and 2-(methoxymethyl)pyrrolidines after hydrolysis of the intermediate sulphamic acid derivatives.
- Alker,Doyle,Harwood,McGregor
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- Discovery of N-Substituted 3-Amino-4-(3-boronopropyl)pyrrolidine-3-carboxylic Acids as Highly Potent Third-Generation Inhibitors of Human Arginase i and II
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Recent efforts to identify new highly potent arginase inhibitors have resulted in the discovery of a novel family of (3R,4S)-3-amino-4-(3-boronopropyl)pyrrolidine-3-carboxylic acid analogues with up to a 1000-fold increase in potency relative to the current standards, 2-amino-6-boronohexanoic acid (ABH) and N-hydroxy-nor-l-arginine (nor-NOHA). The lead candidate, with an N-2-amino-3-phenylpropyl substituent (NED-3238), example 43, inhibits arginase I and II with IC50 values of 1.3 and 8.1 nM, respectively. Herein, we report the design, synthesis, and structure-activity relationships for this novel series of inhibitors, along with X-ray crystallographic data for selected examples bound to human arginase II.
- Van Zandt, Michael C.,Jagdmann, G. Erik,Whitehouse, Darren L.,Ji, Minkoo,Savoy, Jennifer,Potapova, Olga,Cousido-Siah, Alexandra,Mitschler, Andre,Howard, Eduardo I.,Pyle, Anna Marie,Podjarny, Alberto D.
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p. 8164 - 8177
(2019/10/02)
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- METHODS FOR WOUND HEALING AND SCAR PREVENTION
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The present invention is related to a compound of formula (I) or a pharmaceutically acceptable salt or ester thereof. The present invention is further related to a method of healing and/or inhibiting formation of scar tissue in an external wound of a subj
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Paragraph 0070; 0071; 0072
(2017/09/29)
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- Discovery and optimisation of 1-acyl-2-benzylpyrrolidines as potent dual orexin receptor antagonists
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Starting from a thienopiperidine lead compound with high intrinsic clearance in rat and human liver microsomes and low aqueous solubility, a novel series of 1-acyl-2-benzylpyrrolidines were discovered as potent and competitive dual orexin receptor antagon
- Williams, Jodi T.,Gatfield, John,Roch, Catherine,Treiber, Alexander,Jenck, Francois,Bolli, Martin H.,Brotschi, Christine,Sifferlen, Thierry,Heidmann, Bibia,Boss, Christoph
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supporting information
p. 1054 - 1064
(2015/06/25)
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- Insights into the mechanism for gold catalysis: Behaviour of gold(i) amide complexes in solution
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We report the synthesis and activity of new mononuclear and dinuclear gold amide complexes 1-7. The dinuclear complexes 6b and 7 were characterised by single crystal X-ray analysis. We also report solution NMR and freezing point depression experiments to rationalise their behaviour in solution and question the de-ligation process invoked in gold catalysis.
- Bobin, Mariusz,Day, Iain J.,Roe, Stephen M.,Viseux, Eddy M. E.
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p. 6592 - 6602
(2013/07/26)
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- A [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: A formal synthesis of (S)-coniine from l-norvaline
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Regioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding δ-amino-α,β-unsaturated esters after acidic hydrolysis. Hydrogenation of the unsaturated esters and subsequent thermal cyclization afforded the related alkyl substituted piperidine-2-ones. This approach represents a novel [3+3] cyclization strategy for the asymmetric synthesis of alkyl substituted piperidin-2-ones. Efficiency of the cyclization process is illustrated by a formal asymmetric synthesis of (S)-coniine from l-norvaline.
- Karanfil, Abdullah,Balta, Berrin,Eskici, Mustafa
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p. 10218 - 10229,12
(2020/09/02)
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- Imidazolinium sulfonate and sulfamate zwitterions as chiral solvating agents for enantiomeric excess calculations
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The synthesis of enantiopure unsymmetrical N-heterocyclic based zwitterions incorporating imidazolinium and alkylsulfonate or sulfamate groups is described. The desired compounds were prepared in good yields from 1,3-propanesultone or cyclic sulfamidates
- Tabassum, Sobia,Gilani, Mazhar Amjad,Wilhelm, Rene
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experimental part
p. 1632 - 1639
(2012/01/04)
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- Novel Microbiocides
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Compounds of Formula (I), in which the substituents are as defined in claim 1, are suitable for use as microbiocides.
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Page/Page column 31-32
(2010/01/12)
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- 7-Azaindole derivatives as potential partial nicotinic agonists
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We have investigated a series of 7-azaindoles as potential partial agonists of the α4β2 nicotinic acetylcholine receptor (nAChR). Three series of 7-azaindole derivatives have been synthesized and evaluated for rat brain neuronal nicotinic receptor affinity and functional activity. Compound (+)-51 exhibited the most potent nAChR binding (Ki = 10 nM). Compound 30A demonstrated both moderate binding affinity and partial agonist potency, thus representing a promising lead for the indications of cognition and smoking cessation.
- Stoit, Axel R.,den Hartog, Arnold P.,Mons, Harry,van Schaik, Sjoerd,Barkhuijsen, Nynke,Stroomer, Cees,Coolen, Hein K.A.C.,Reinders, Jan Hendrik,Adolfs, Tiny J.P.,van der Neut, Martina,Keizer, Hiskias,Kruse, Chris G.
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p. 188 - 193
(2008/12/23)
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- Combinatorial synthesis of functionalized chiral and doubly chiral ionic liquids and their applications as asymmetric covalent/non-covalent bifunctional organocatalysts
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A facile combinatorial strategy was developed for the construction of libraries of functionalized chiral ionic liquids (FCILs) including doubly chiral ionic liquids and bis-functional chiral ionic liquids. These FCIL libraries have the potential to be use
- Zhang, Long,Luo, Sanzhong,Mi, Xueling,Liu, Song,Qiao, Yupu,Xu, Hui,Cheng, Jin-Pei
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supporting information; experimental part
p. 567 - 576
(2008/10/09)
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- 1,2-Cyclic sulfamidates as versatile precursors to thiomorpholines and piperazines
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(Matrix presented) 1,2-Cyclic sulfamidates undergo regiospecific nucleophilic displacement with either methyl thioglycolate or α-amino esters, followed by lactamization (thermal, base-mediated, or cyanide-catalyzed), to give thiomorpholin-3-ones and piper
- Williams, Andrew J.,Chakthong, Suda,Gray, Diane,Lawrence, Ron M.,Gallagher, Timothy
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p. 811 - 814
(2007/10/03)
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- Process for preparing cyclic amines and intermediate products thereof
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A process for preparing a cyclic amine of Formula I STR1 in which R1 is phenyl, optionally substituted by 1 to 3 lower alkoxy groups; R2, R3 and R4 are independently hydrogen or lower alkyl; and n is 1 or 2, comprises (1) converting an aminoalcohol of Formula III STR2 to a dioxooxathiazolidine of Formula II STR3 in which R2, R3, R4 and n are as defined above; and (2) reacting the dioxooxathiazolidine of Formula II with an organometallic nucleophile, R1 M*, wherein R1 is as defined above, and hydrolyzing the resulting sulfamate salt.
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