Salicylhydroxamic acid

The complexes formed from salicylhydroxamic acid and acetylsalicylhydroxamic acid (104) with zinc show loss of one ligand proton and loss of two ligand protons respectively. The zinc complex of the acetyl derivative appears to show coordination via the deprotonated amide and phenolate oxygen of the ligand. IR studies are presented.849... 

Typically, the boronic acid group is part of an aminophenyl boronic acid derivative, and this group has been used for bioconjugation and affinity chromatography purposes (Burnett et al., 1980 O Shannessy and Quarles, 1987). A common partner for a phenyl boronic acid group in bioconjugation is the salicylhydroxamic acid (SHA) group (Chapter 17, Section 3) (Reaction 59). 

Stolowitz, M.L., Ahlem, C., Hughes, K.A., Kaiser, R.J., Kesicki, E.A., Li, G., Lund, K.P., Torkelson, S.M., and Wiley, J.P. (2001) Phenylboronic acid-salicylhydroxamic acid bioconjugates. 1. A novel boronic acid complex for protein immobilization. Bioconjugate Chem. 12, 229-239. 

Although the synthesis of 3-isoxazolols from P-keto esters and hydroxylamine suffers from the formation of 5-isoxazolones as major products, treatment of acyl chlorides with Meldrum s acid 4 followed by aminolysis gave rise to p-keto hydroxamic acids 6 that cyclised to the corresponding 5-substituted 3-isoxazolols 7 without formation of any byproduct <00JOC1003>. Cyclisation of N-substituted salicylhydroxamic acids 9 under... 

Additionally, the myeloperoxidase system even regulates the duration of the respiratory burst because neutrophils from patients with myeloperoxidase deficiency (see 8.3) generate more reactive oxidants than control cells. Also, when myeloperoxidase is inhibited with a specific antibody or a specific inhibitor such as salicylhydroxamic acid, the duration of the respiratory burst, but not the maximal rate of oxidant production, is extended. This indicates that a product of the myeloperoxidase system inhibits the NADPH oxidase and so self-regulates reactive oxidant production during inflammation. 

The molecular species responsible for luminol and lucigenin chemiluminescence are not fully defined. Clearly, luminol chemiluminescence requires the combined activities of both the NADPH oxidase and myeloperoxidase inhibitors of either enzyme (e.g. diphenylene iodonium for the oxidase and salicylhydroxamic acid for myeloperoxidase) completely prevent luminol... 

DFT calculations were also used to study the NMR spectra of salicylhydroxamic acid in DMSO-dg solutions. Best fit with experimental results was observed for association with two solvent molecules. Assignments could be made for the specific structure formed in solution. Similar studies were made on other types of hydroxamic acids . 

S glycerol 3-phosphate -I- D-fructose <1> (<1> less effectiv than glucose, reaction with living Trypanosoma brucei in presence of salicylhydroxamic acid [1]) (Reversibility <1> [1]) [1]... 

Salicylhydroxamic acid [89-73-6] M 153.1, m 179-180°(dec). Crystd from acetic acid. 

A large volume of work64 has been published on the determination of stability constants for complexes of hydroxamic acids, e.g. acetohydroxamic acid.65 The stability of 3d transition metal ions (Mn2+ to Zn2+) with salicylhydroxamic and 5-methyl-, 5-chloro-, 5-bromo-, 5-nitro-, 4-chloro-, 4-bromo- and 3-chloro-salicylhydroxamic acids,66 as well as with methyltolylbenzohydroxamic acid,67 has been studied potentiometrically. Stability constants of iron(III) with a number of hydroxamic acids have been determined by redox potential studies.68... 

Catecholases and laccases may be differentiated by the use of substrate specificity tests and selective specific inhibitors (Walker and McCallion, 1980 Ferrar and Walker, 1996 Table C4.1.1). Salicylhydroxamic acid (SHAM), PVP, and/or cinnamic acids (cinnamic, p-coumaric, or ferulic) are probably the best choice for catecholase inhibitors, whereas cetyltrimethylammonium bromide (CETAB) has been found to inhibit most laccases. 

CETAB, cetyltrimethylammoniuin bromide SHAM, salicylhydroxamic acid. 

Allan, A.C. and Walker, J.R.L. 1988. The selective inhibition of catechol oxidases by salicylhydroxamic acid. Phytochemistry 27 3075-3076. 

SD standard deviation SDE simultaneous distillation extraction SDS sodium dodecyl sulfate SFC solid fat content SFI solid fat index SHAM salicylhydroxamic acid SIM selected ion monitoring SNIF-NMR site-specific natural isotope fractionation measured by nuclear magnetic resonance spectroscopy SP-HPLC straight-phase high-performance liquid chromatography... 

Glycolytic enzymes Kinetoplastida Glycerol plus salicylhydroxamic acid and suramin... 

A successful synthesis of 3-hydroxyindoxazene (28) starts from salicylhydroxamic acid (29), which gives a cyclic mixed anhydride (30) with thionyl chloride 30 is converted into the indoxazene with triethylamine.48... 

These various structures together with the conserved structures around the 5-edge heme suggests a common pattern of binding between class III peroxidases and aromatic substrates. Such common aromatic contacts have also been observed in the complexes between class II peroxidase ARP and BHA, and salicylhydroxamic acid, respectively. ... 

Fractions prepared from September, October, and November fruit were almost completely inhibited by 1 mM KCN, but preparations from December and January fruit were inhibited 65 to 70%. The KCN-insensitive respiration was inhibited 65 to 70% by salicylhydroxamic acid (SHAM). The SHAM-sensitive oxidase, or alternative oxidase, accounted for about 22% of the total, and residual oxidase (activity in presence of KCN + SHAM) about 10% in mitochondria from mature tissue. 

A group of less sensitive Ti determination methods have been based on hydroxylamine derivatives, such as BPHA (formula 55.1) [46], benzohydroxamic acid [47,48], salicylhydroxamic acid (extraction into TOA-CCI4 S = 1.2-lO at 370 nm) [47,49,50]. 

In the group of hydroxamic acids used for determining vanadium are benzohydroxamic acid [37], iV-salicylhydroxamic acid [37,38], A-benzylbenzohydroxamic acid [39], phenylbenzohydroxamic acid [40], A-benzyl-2-naphthohydroxamic acid [41], and 5-bromosalicylhydroxamic acid [42,43]. 

A combination of salicylhydroxamic acid (SHAM) and glycerol, although capable of destroying bloodstream trypanosomiasis, is less effective against infections involving the central nervous system. 

The reaction of thionyl chloride with salicylhydroxamic acids (22 R2 = H) has been developed as a general synthetic method for 3-hydroxy-indoxazenes.1,23 An improvement of this two-stage process is claimed by treating the hydroxamic acids with carbonyl diimidazole in boiling tetra-hydrofuran followed by acidification.24... 

The action of cold thionyl chloride on salicylhydroxamic acids, and on o-hydroxyaldoximes and -ketoximes, is a versatile synthetic route to 3-hydroxy-, 3-unsubstituted, and 3-alkylindoxazenes.26... 

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