PANTOTHENIC ACID 629 



with Plasmodium lophurae lengthened the survival period of the para- 

 sites. 63 



The condensation product of DL-pantolactone and DL-a-phenyltaurine 

 does not appreciably affect the growth of Lactobacillus arabinosus. G0 



DL-N-Pantoyl-/?-mercaptoethylamine and the corresponding disulfide 

 have been found to be approximately as active as pantoyltaurine in pre- 

 venting the utilization of pantothenic acid by Lactobacillus arabinosus. 

 Di(N-pantoyl-/?-aminoethyl) sulfide and the corresponding sulfoxide 



Table 26. Pantoyltaurine and Related Inhibitory Analogues of Pantothenic Acid. 



Formula Name References 



R°-NH-CH 2 -CH 2 -S0 2 -OH DL-N-Pantoyltaurine 15 ^ «. «• 46 



D-N-Pantoyltaurine 44, 45 



L-N-Pantoyltaurine **• ** 



R-NH-CH 2 -CH 2 -S0 2 -NH 2 DL-N-Pantoyltauramide 1B - 46 



D-N-Pantoyltauramide 88 ' 89 

 R-NH-CH 2 -CH(C 6 H 6 )-S0 2 -OH c N-Pantoyl-^-amino-a-phenylethane- 



sulfonic acid 60 



R-NH-CH 2 -CH 2 -S0 2 -N(Ri)(R 2 ) Substituted Pantoyltauramides Table 27 



R-NH-CH 2 -CH 2 -SH DL-N-Pantoyl-/3-mercaptoethylamine 59 



(R-NH-CH 2 -CH 2 ) 2 -S 2 Di(N-Pantoyl-jS-aminoethyl) disulfide 6 " 



(R-NH-CH 2 -CH 2 ) 2 S Di(N-Pantoyl-/3-aminoethyl) sulfide 11 59 



(R-NH-CH 2 -CH 2 ) 2 SO Di(N-Pantoyl-/3-aminoethyl) sulfoxide" B9 



(R-NH-CH 2 -CH 2 ) 2 S0 2 Di(N-Pantoyl-/3-aminoethyl) sulfone* 69 



R-NH-CH 2 -CH 2 -S-C 6 H 6 D-(N-Pantoyl-/3-aminoethyl) phenyl 



sulfide 61 

 R-NH-CH 2 -CH 2 -SO-C 6 H 6 D-(N-Pantoyl-/3-aminoethyl) phenyl 



sulfoxide 61 

 R-NH-CH 2 -CH 2 -S0 2 -C 6 H B D~(N-Pantoyl-/3-aminoethyl) phenyl 



sulfone 61 



R-NH-CH 2 -CH 2 -S-C 6 H 4 C1 D-(N-Pantoyl-/3-aminoethyl) p-chloro- 61 



phenyl sulfide 

 R-NH-CH 2 -CH 2 -S0 2 -C 6 H 4 -CH 3 DL-(N-Pantoyl-/3-aminoethyl) p-tolyl 



sulfone 62 

 R-NH-CH 2 -CH 2 -S0 2 -C 6 H 4 -NH 2 Di^(N-Pantoyl-/3-aminoethyl) p- 



aminophenyl sulfone 62 

 R-NH-CH 2 -CH 2 -S0 2 -C 6 H4-OCH 3 DL-(N-Pantoyl-/3-aminoethyl) p- 



methoxyphenyl sulfone 62 



« R represents the pantoyl group, H0CH2-C(CH 3 )2-CH0H-C0-. 

 *> A crystalline compound, one of the two diastereoisomers. 

 c Presumably a mixture of diastereoisomers. 



and sulfone were reported to be less effective than pantoyltaurine 

 in inhibiting the growth of Lactobacillus arabinosus. In vivo tests indi- 

 cated that these compounds were less effective than pantoyltaurine in 

 preventing streptococcal infections in rats. 



D(N-Pantoyl-/?-aminoethyl) phenyl sulfide, the corresponding sulfoxide 

 and sulfone, and the corresponding p-chlorophenyl sulfide have been pre- 

 pared 64 and tested for antimalarial activity G1 in chicks infected with 

 Plasmodium gallinaceum. The quinine equivalents obtained for the sup- 

 pressive action were 0.8, 1.5, 1.0 and 1.0, respectively. 



The phenyl sulfide and sulfoxide have also been found to be effective 

 against Trichomonas vaginalis with inhibition indices of 3.1 and 140 r 



