User:Friday01/Heterocyclic and Aromatic Thiourea Derivatives

Heterocyclic and aromatic thiourea compounds characterized by a thiourea group with an alkyl substituted phenyl or heterocyclic group attached to one of the two Nitrogen groups. These groups can be used as organocatylists for Michael additions of malonate derivatves to trans-B-nitrostyrene, as well as a new class of anti-allergenic agents. --Friday01 (talk) 22:08, 17 December 2010 (UTC https://gw.innocentive.com/projectImages/12796533709780heterocyclic-thioure-lgLarge.gif

Synthesis of thiourea derivatives

Thiourea derivatives of Tröger's base have been synthesized an evaluated, both in racemic and enantiomerically pure form, as organocatalysts for the Michael's addition of malonite derivatives to trans-beta-nitrostyrene. Using Tröger's base with attached tertiary amines, a chemical reaction was proposed that converted the tertiary amines into thiourea derivatives. Using Ar-N=C=S in THF as reagents, Tröger's base is converted into a racemic catalytic thiourea derivatives. Based on the complementarities of the tertiary amine and the thiourea derivatie, a bifunctional catalytic mechanism has been proposed. The result of these addition reactions were found to be highly dependent on the pKa of the malonate nubleophiles used.

Clinical use

Heterocyclic thiourea compounds have been synthesized as a new class of anti-allergenic agents. Recent studies have also examined the use of these compounds for their in-vitro effects on the IgE/FcE RI receptor mediated mast cell leukotriene release. Mast cell derived leukotrienes play a vital role in the pathophysiology of allergy and asthma. Various analogues of indolyl, naphthyl, and phenylethyl substituted halopyridyl, thiazolyl and benzothiazolyl thioureas have been examined for their in vitro effects on the high affinity IgE receptor RI-mediated mast cell leukotriene release. N-[1[(1-naphthyl)ethyl}-N-[2-(ethyl-4acetylthiazolyl]thiourea and N-[1-(1R)-naphthylethyl]-N-[2-(5-methylpyridyl)]thiourea have been identified as the most active compounds for this effect.

By releasing chemical mediators, such as the pro-inflammatory leukotrienes (LTs), mast cells parcipitate in the pathophysiology of allergy and asthma. These thiourea compounds can bind to the IgE receptor and inhibit the symptoms associated with allergy and asthma attacks. Further study into the clinical use of these derivatives can provide a much more useful anti-allergy medicine in the future.