Arylaliphatic acids

Chiarini, A. Tartarini, A. Fini, A., pH-solubility relationship and partition coefficients for some anti-inflammatory arylaliphatic acids, Arch. Pharm. 317, 268-273 (1984). 

While some arylaliphatic acids are established as antiinflammatory agents, it is interesting to note that some arylketones share this activity. Fenbufen... 

Very strong cholinomimetic activity was found for 3-hydroxyquinuclidine esters with arylaliphatic acids. For example, 3-(a,a-diphenylpropionyloxy)quinuclidine (162) (which is known in the USSR as Aprolidine219-218 significantly exceeds the similar 2-diethylaminoethyl ester (163) (in the USSRAprophen) in its influence on the central and peripheral cholinergic systems.219... 

Table 5.12 Commercial products containing benzoic or arylaliphatic acid.

Solubility relationship and partition coefficients for some antiinflammatory arylaliphatic acids. 

The pKa values of some antiinflammatory arylaliphatic acids, including alclofenac and ibuprofen, were measured potentiometrically in dimethyl sulfoxide/water. The values were confirmed by assessing the solubility of the acids as a function of the pH of the aqueous solutions. In this way, the intrinsic partition coefficient in octanol/ water was defined."... 

Esters of 3-hydroxyquinuclidine with arylaliphatic acids, have proved by their central and peripheral cholinolytic activity to be more potent than related esters (diphenylpropionates, benzilates) of 2-diethylaminoethanol (Table 4) and 3-hydroxy-iV-methylpiperidine. 

Aceclidine being a tertiary amine was significantly more active than its quaternary salt (methiodide). Other regularities were noted in the acyl-choline-derivatives acetylcholine was 50 times as active as its tertiary analogue (/3-dimethylaminoethanolacetate) [217, 218]. One can observe similar relationships in the esters with arylaliphatic acids. 

The reaction of aliphatic, aromatic and arylaliphatic nitriles and dinitriles with formaldehyde, aliphatic and aromatic aldehydes in the presence of acids leads to the A,Af -alkylidene- and Af,AT -arylalkylidene-bis-amides 9a and has been known since 187634. 

Very well studied are arylaliphatic compounds ), especially those which have one double bond. By varying the ratio of carbonyl silane acid, the course of reaction can be immensely influenced. If the ratio is 1 1 10, only the double bond is hydrogenated ) whereas a mixture 1 3 10 hydrogenates both the double bond and the carbonyl function ). When this reducing combination is used in the former ratio, 3-benzoyl-butyric acid yields 4-phenyl-vaIeric acid (722), p.p -dinitrobenzophenone p,p -dinitrodiphenylmethane(123), l,6-diphenyl-hexane-l,6-di-one 1,6-diphenyl-hexane 124) and p-methoxybenzaldehyde p-methoxytoluene (725), respectively ). l,3-Diphenyl-l-propene-3-one gives (depending on the ratio ketone silane acid) 1,3-diphenyl-l-propanone (726) (1 1 10) and 1,3-diphenyI-propane (727) (1 3 10), respectively ). 

Glueck SM, Pirker M, Nest BM, Ueberbacher BT, Larissegger-Schnell B, Csar K, Hauer B, Stuermer R. Biocatalytic reaction of aliphatic, arylaliphatic, and aromatic a-hydroxycarboxylic acids. J Org Chem 2005 70 4028-4232. 

Hydrogenation of quinuclidon-3, or of its derivatives, to the corresponding alcohols followed by esterification gave 3-hydroxyquinuclidine esters with ahphatic, arylaliphatic and aromatic acids of great pharmacological interest [74, 79, 80, 106, 107]. 

The nitrilase NITl in A. thaliana, which was overproduced in E. coli, proved to have a wide S5mthetic use, its products being aliphatic and arylaliphatic carboxylic acids or amides depending on the structure of the substrate [81]. A similar nitrilase (ZmNIT2) was characterized in Zea mays (maize) [82]. This enzyme also... 

Furthermore, kinetic resolutions of arylaliphatic and acyclic ketones using BVMOs were also reported. Thus, Bornscheuer and co-workers could recently show that even enantiomerically pure (3-amino alcohols and (3-amino acids can be accessed by enzyme-catalyzed BVO of chiral (3-acetamido ketones. ... 

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