Propanolol complexes

Milk fat globule membrane (MFGM) emulsion was shown to enhance the absorption of epidermal growth factor (EGF) from the intestine, especially to intestinal lymph. The oral bioavailability of propanolol was shown to increase when administered in oleic acid and other lipid media. It is thought that the oleic acid forms an ion-pair with the drag and the entire complex is incorporated into chylomicrons. A further factor in the absorption enhancing effects may be that oleic acid per se stimulates chylomicron production. 

In epoxidation reactions allyl alcohol can act as a prochiral alkene. Enantio-merically pure glycidol isomers (see Table 1.1) may be used to make S-propanolol 9.61, a drug for heart disease and hypertension. The mechanistic details of the epoxidation reaction with V5+ and Mo6+ complexes as catalysts were discussed in Section 8.6. The basic mechanism of epoxidation reaction, the transfer of an oxygen atom from f-butyl hydroperoxide to the alkene functionality, remains the same. 

Asymmetric nitroaldol condensation, reaction 9.10, has been used to make an intermediate for the drug S-propanolol 9.61. The condensation reaction is catalyzed by the chiral heterobimetallic binaphthol complex 9.12 with high (>90%) enantioselectivity. 

A NMR study on the formation of diastereoisomeric inclusion complexes between fluorinated amino acid derivatives and a-CD in 10% D2O solution shows that the chemical shifts of the D-amino acid derivatives included by a-CD are upheld from those of their L analogues [77]. The shift difference between the diastereoisomers formed with D and L enantiomers can be used for chiral analysis and optical purity determinations. For example, the interaction of -CD with propanolol hydrochloride produces diastereomeric pairs. The protons of the antipode give NMR signals which differ in chemical shifts in D2O solution at 400 MHz. The intensity of the resonance signals for each diastereoisomer has been used for optical purity determination. By adding racemate to pure (—) isomer, this technique is able to measure optical purity of propanolol hydrochloride in water down to the level of 1%. 

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