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Abstract: A comprehensive review of pharmacological and medical aspects of the muscarinic class of acetylcholine agonists and antagonists is presented. The therapeutic benefits of achieving receptor subtype selectivity are outlined and applications in the treatment of Alzheimer’s disease are discussed. A selection of chemical routes are described, which illustrate contemporary methodology for the synthesis of chiral medicinal compounds (asymmetric synthesis, chiral pool, enzymes). Routes to bicyclic intrannular amines and intramolecular Diels-Alder reactions are highlighted.

Abstract: 7-(1-Acetoxymethylidene)benzonorbornadiene 3, prepared in one step by the addition of benzyne to 6-acetoxyfulvene 2, is hydrolysed in acid solution to form a 3:2-epimeric mixture of syn- and anti- 7-formylbenzonorbornadienes 4 and 5, respectively; the corresponding 7-hydroxymethylbenzonorbornadienes 6 and 9 were produced by reduction of the formyl isomers with sodium borohydride.

Abstract: Synthesis of the title compound,1-(2'-O-methyl-ß-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ß-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies.

Abstract: The ZnBr₂ complex of the title compound has been studied by both structural and theoretical methods. Similar reactivities have been observed for the nitrone alone and the complex in 1,3-dipolar cycloadditions and nucleophilic additions.

Abstract: Association constants of complexes of a new class of cyclodextrin alkyl derivatives - randomly susbstituted tert-butyl derivatives (TB-CDs) with complete set of mono-halobenzoic acids and acridine derivatives were measured using capillary electrophoresis and compared with association constants of natural cyclodextrins. In most cases the association constants of natural cyclodextrin and its corresponding tert-butyl derivative were comparable. Strong dependence of association constants on actual cyclodextrin concentration was observed for complexes of tert-butyl-α-cyclodextrin with acridine derivatives. Significant increase of the association constant occurred below the critical micelle concentration of the cyclodextrin derivative, while an increase above this value was less significant.

Abstract: Methods for the synthesis of N¹, N⁸-bis(9-acridinyl)-N⁴-(4-hydroxybenzyl)-spermidine and N¹, N⁷-(hydroxybenzyl)-bis-(3-aminopropyl)amine were investigated. Thus monocyanoethylation of 4-methoxybenzylamine followed by treatment with 4-chlorobutyronitrile gave the dinitrile N-(2-cyanoethyl)-N-(3-cyanopropyl)-4-methoxybenzylamine. Subsequent in situ reduction with lithium aluminium hydride gave the corresponding diamine. Biscyanoethylation of 4-methoxybenzylamine with 2 mole of acrylonitrile followed by reduction yielded the diamine N, N-bis-(3-aminopropyl)-4-methoxybenzylamine. Both diamines reacted smoothly with 9-methoxyacridine to give the bis-(9-acridinyl) compounds 11 and 15 but with 4,5-dimethyl-9-methoxyacridine, the bis compound 16 was produced in only low yields. Demethylation of the dinitriles by a variety of approaches all failed to give the corresponding hydroxybenzyl derivatives. These studies yielded useful methylated tyrosine derivatives which could also be iodinated. This study has been useful for elucidating chemical methods needed for the synthesis of the desired tyrosine-based bis acridine compound and for alerting us to the need to synthesise a more labile protected tyrosine intermediate which will be easily deprotected to afford the desired tyrosine-based bis acridine compound.

Abstract: The cyclic hydroboration of 2,7-dimethyl-2,6-octadiene (6) was studied. It was found that the stereochemical outcome of the reaction was dependent upon the solvent, temperature, time and the nature of the borane reagent. Pure racemic trans-2,5-diisopropylborolane (14) was isolated following selective complexation of the cis-2,5-diisopropylborolane (15) with 1-(2-hydroxyethyl)-pyrrolidine.

Abstract: N-Bromosulphonamides, synthesized via direct bromination of sulphonamides, react with several types of arene substrates in the presence of KSCN to afford aryl thiocyanates. The method appears to be generally applicable to benzenoid substrates with a wide range of substituents, such as N,N-dimethylaniline, p-xylene, anisole, mesitylene and cumene.

Abstract: The Cu-catalyzed intramolecular CH insertion of phenyliodonium ylide 5b has been investigated at 0° C in the presence of several chiral ligands. Enantioselectivities vary in the range of 38–72 %, and are higher than those resulting from reaction of the diazo compound 5c at 65° C. The results are consistent with a carbenoid mechanism for Cu-catalyzed decomposition of phenyliodonium ylides.

Abstract: A number of novel triazinoquinazolinones (5b,c and 8), triazepinoquinazolinones(5a, 6b, 7 and 9) and triazocinoquinazolinones (6a and 10) were obtained via nucleophilic interaction of 3-aminoquinazolinone derivatives 3 with different reagents.

Abstract: Both pyrophosphoryl chloride and phosphorus oxychloride react with aryl aliphatic acids to form mixed anhydrides which undergo intramolecular acylation to afford cyclic ketones without the addition of a Friedel-Crafts catalyst. Aryl and aroylbenzoic acids could be cyclized to the corresponding anthrones and anthraquinones respectively.