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Several sulfur-containing derivatives of pyridine 1-oxide and quinoline 1-oxide were prepared for evaluation as antibacterial and antifungal agents. Both 2-thiocyano-and 4-nitro-2-thiocyano-pyridine 1-oxide were obtained by displacement reactions on the appropriate bromide 1-oxides. Anomalous reaction behaviour was encountered in all attempts to convert 3or 4-bromopyridine 1-oxides and 3-bromoquinoline 1-oxide to the corresponding thiocyanates. 3-Bromopyridine 1-oxide and 3-bromoquinoline 1-oxide were found to add in the normal fashion to thiourea with the formation of the corresponding thiuronium bromides. 4-Thiocyanopyridine 1-oxide but not 3-thiocyanopyridine 1-oxide was obtained in very low yield by a Sandmeyer reaction. Treatment of picolinonitrile 1-oxide with ammonia and hydrogen sulfide gave thiopicolinamide 1-oxide. Only those of our compounds which bore a sulfur-containing group at position 2 of the pyridine 1-oxide ring system, wherein the sulfur atom was contiguous to the pyridine ring, showed outstanding antimicrobic activity.

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Alkylation of several arylmalonates with chloroalkylcyanides gave cyanoalkylmalonates (4) which were hydrogenated to aminoalkylmalonates (5). The latter were hydrolyzed to a-aryl-7-aminobutyric acids (6) which in turn were converted to ethyl esters (7). Preliminary pharmacological data demonstrate that 5, 6, and 7 are weak central stimulants.The possibility that 7-amino butyric acid (GABA) may participate in the control of neurophysiological ac-tivity1 provided a biological rationale for the synthesis of a number of its homologs and analogs for biological evaluation.2-4 The program on the synthesis of GABA homologs in these laboratories encompassed the synthesis of a-aryl-/3-alanines (1), a-aryI-7-aminobutyric acids (2), and the related esters. Our findings on the R1-R2' CHCOOH CH2NH2R+C1~R 1 R2 2 CHCOOH CH(R3)CH2NH3+Cr