Adrenergic receptors belong to the seven transmembrane spanning, G-protein-coupled receptor super family, which mediate the actions of the endogenous catecholamines, adrenaline and noradrenaline (also known as epinephrine and norepinephrine). Adrenergic receptors are involved in several disease states such as hypertension, cardiac dysfunction, diabetes, glaucoma, depression, impotence and lower urinary tract disorders. This makes adrenergic receptors a valuable therapeutic target for the treatment of various disorders. Adrenergic receptors are broadly categorised into alpha(1)-, alpha(2)- and beta-subtypes. Of these, alpha(1)-adrenoceptors, located in both central and peripheral nervous systems, are of great therapeutic relevance because of their important role in the contraction of smooth muscle tissue, especially in the cardiovascular system and lower urinary tract. The alpha(1)-adrenoceptor subtype has been further divided into alpha(1A), alpha(1B) and alpha(1D) and ligands acting at these subtypes have therapeutic potential in the treatment of hypertension, stress urinary incontinence (SUI), benign prostatic hyperplasia (BPH) and lower urinary tract symptoms (LUTS). This review summarises the patent literature from 2001 to early 2005 on the development of selective ligands of the alpha(1)-adrenoceptor and its subtypes.

3-O-Allylcarbohydrate nitrone cycloaddition (3-OACNC) furnished pyran and oxepane derivatives from 3-O-allyl hexose N-benzyl nitrones and 3-O-allyl furanoside-5-aldehyde N-benzyl/methyl nitrones. The regioselectivity of 3-OACNC was found to depend on the following factors (a) the structural nature of the nitrone (b) substitution and stereochemistry at 3-C of the carbohydrate backbone (c) substitution at the terminus of the O-allyl moiety. Oxepanes or pyrans obtained from a particular set of a hexose nitrone and the corresponding furanoside nitrone were converted to enantiomeric cyclic ethers through degradation. A mixture of an oxepane and a pyran was formed in the intramolecular oxime olefin cycloaddition (IOOC) of a 3-O-allylcarbohydrate derived oxime.

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A novel strategy was developed by which chiral oxepinopyran and oxepinooxepane derivatives were synthesised from 1,2-isopropylidene furanoside fused pyran and oxepane derivatives by the cycloaddition of 4-O-allyl nitrone or nitrile oxide species generated from the furanoside ring.

Chiral nonracemic pyranocyclohexanes 7 and 8 and oxepanocyclohexane 11 and 12 were obtained from a single 1,2-isopropylidene-3-O-cyclohesenyl carbohydrate aldehyde 4 via intramolecular nitrile oxide cycloaddition. and were converted to 2-(2'-tetrahydrofuryl)pyran 28, which incorporates the lasalocid skeleton. and the related oxepane derivative 32 respectively, through modification of the furanoside ring by applying 2-O-allyl carbohydrate nitrone cycloaddition: (C) 1999 Elsevier Science Ltd. All rights reserved.

A useful synthesis of enantiomerically pure pyrano- and oxepanoisoxazole derivatives by the application of intramolecular cycloaddition of 3-O-alkynyl carbohydrate nitrile oxides is de scribed. One of the isoxazole derivatives was transformed to a furylpyran system having the lasalocid A skeleton using 2-O-allyl carbohydrate nitrone cycloaddition.