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Johangirian et al recently reported the synthesis of fatty hydroxamic acid derivatives using lipozyme TL 1M catalyst at biphasic medium.


The mixtures were shaken at rpm and 39 in a water bath shaker for 72 h. The product was separated from the reaction mixture as follows: First, the enzyme was filtered.


The filtrate was then transferred into HP Compaq nx9500A Notebook Conexant Audio EQ separation funnel for separation of aqueous phase from organic phase. Finally, the product was extracted from the unreacted oil using absolute methanol 20 mL and then recovered by rotatory evaporation. The percentage of conversion at every experiment was calculated as follows: B amount of theoretical fatty hydroxamic acid derivatives assuming all of the fatty acids in the oil were converted to fatty hydroxamic acid derivative. Given the proportion of fatty acid in the oil, only the derivative of myristic, lauric acid and oleic acid was formulated.

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Formulation of methyl lauro hydroxamic acid ; methyl myristo hydroxamic acidmethyl oleo hydroxamic acid Scheme 30Formulation of isopropyl laureo hydroxamic acidisopropyl myristo hydroxamic acidisopropyl oleo hydroxamic acid Scheme 31Formulation of benzyl laureo hydroxamic acidbenzyl myristo hydroxamic acidbenzyl oleo hydroxamic acid Scheme Synthesis of Cardiovascular HydroxamatesCardiovascular hydroxamate belongs to matrix metalloproteinase MMP inhibitors. The expression HP Compaq nx9500A Notebook Conexant Audio EQ MMP is increased is increased in various pathological conditions like inflammatory conditions, metabolic bone disease.

Examples of disease are periodontitis, hepatitis, glomerulo nephritis, atherosclerosis etc. These groups of inhibitors contain a hydroxamate group that binds the zinc atom in the active site of MMP enzyme. It is basically used for the treatment of periodontitis. Other MMP inhibitors have exhibited serious side effects during preclinical trials.

This side effect has been linked to the insufficient selectivity. This new derivatives was achieved using series of alkylaryl and sulphonylaryl groups on the IDA basic scaffold. The synthesis is reported in scheme 33 and The HP Compaq nx9500A Notebook Conexant Audio EQ route for the preparation of the new compoundsand are reported in scheme 34 and For the preparation of compound and scheme 33, the first step involved the IDA N-coupling with the appropriate alkylaryl or sulphonylaryl halides R1X, to give the corresponding N-substituted IDA intermediates a-f, a-c. Depending on the intermediate type, different reaction conditions have been used, namely, a homogenous phase for compounds a-f and Schotten-Baumann conditions for compounds a-c.

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The second step consisted of the condensation of one carboxylic group of the N-substituted IDA with hydroxylamine, upon previous activation of that group with ethyl chloroformate ECF in the presence of N-methyl morpholine. For the preparation of some compounds, the hydroxylamine was O-alkyl protected alkyl benzyl for compounds cf1, a1and b1, and alkyl 2,4-dimethoxybenzyl DMB for compounds c1 and d1, here, the alphabets with prime refers to the respective intermediates containing a carboxylic acid and an O-protected hydroxamic acids whenever it exists and the HP Compaq nx9500A Notebook Conexant Audio EQ alphabet refers to the dicarboxylic acid intermediates. The DMB O-protection was selected to avoid the undesirable removal of N-alkyl substituents by catalytic hydrogenolysis with palladium, the usual method for O-benzyl de-protection. The O-DMB protected hydroxylamine was prepared by amination of the dimethoxy benzyl alcohol according to the literature.

Compound was prepared by first, monoamidation of the N-benzyl imino diacetic anhydride with 3- 4-phenyl piperazinyl propylamide, scheme 34, followed by condensation of the second carboxylic group with hydroxylamine in the presence of ECF and N-methylmorpholine NMM ; 3- 4-phenyl piperazinyl propylamide was prepared by standard methods Scheme 33Synthesis of compounds s and s: However, their sulphonamide analogues showed high inhibitory potency against the MMPs screened with IC50 values in the nano molar range, thus a comparable or improved potency in comparison with reference drug CGS A. The introduction of bulky aromatic groups on the sulphonamide namely on the para position of the benzene sulphonamide moiety such as the rigid biphenyl sulphonamide b or the more flexible and adaptable p-phenoxy benzene sulphonamide c showed a considerable improvement in their inhibitory potential.

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Synthesis of CipemastatScheme 35Broadhurst et al reported the synthesis of cipemastat using chiral hydroxyl acid The first step was protection of the chiral hydroxyl acid as its benzyl ester The hydroxyl group of compound was then activated towards displacement by conversion to its triflate Reaction of the triflate with the anion from unsymmetrical malonate leads to trimester Treatment of with formaldehyde leads to a carbinol HP Compaq nx9500A Notebook Conexant Audio EQ addition to the free amino group on the imidazole dione. The hydroxyl group was then converted to the bromo derivative with phosphorus tribromide. Catalytic hydrogenation of leads to the formation of the corresponding ester-diacid by loss of the benzyl protection groups on two of the esters.

Heating in the presence of N-methyl morpholine causes the free acid on the carbon bearing the t-butyl ester to decarboxylate to compound The desired stereoisomer predominates, in effect reflecting the selectivity of alkylation step caused by the presence of the HP Compaq nx9500A Notebook Conexant Audio EQ adjacent chiral center. The free carboxylic acid is condensed with piperidine to form The remaining ester was then hydrolyzed in acid to afford the acid Reaction of with O-benzyl hydroxylamine followed by hydrogenolysis of the benzyl group then led to the hydroxamic acid. Thus, the collagenase inhibitor cipemastat was obtained. Synthesis of Bifunctional Metalloproteinase InhibitorsThe preparation of all the compounds started from an amino acid or its ester derivative as reported by Marques et al.

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