2,4-Diamino-6-methylpyrimidines having saturated straight-chain alkyl groups (C3, Cs-C8, Ciq) in the 5 position were less potent growth inhibitors (IDS0 1.1 to 53 µ ) of mouse mammary adenocarcinoma cells (TA3) in vitro than 2,4-diamino-5-( 1 -adamantyl)-6-methylpyrimidine (DAMP) (15a) (IDso6.0 M).The IDS0 values for another series of 2,4-diamino-6-methylpyrimidines having increasingly bulky 5 sub-
Salts of 4-hydroxypyrimidine and several 2-substituted 4-hydroxypyrimidines were treated with alkyl halides under a variety of reaction conditions. In cation-solvating media, methylation occurred mainly at N-3. Increased N-l methylation was observed in hydrogen-bonding solvents and solvents of lower dielectric constant. Studies in dimethylf ormamide revealed significant steric influences. When the alkyl halide was varied from methyl to ethyl to isopropyl or when the group on the 2 position was varied from hydrogen to methyl to ethyl, alkylation at oxygen increased at the expense of alkylation at N-3. 2-Trifluoromethyl-4-hydroxypyrimidine in dimethylf ormamide reacted with alkyl halides to give mainly 4-alkoxy-2-trifluoromethylpyrimidines.
norepinephrine is reproduced in Figure 3 and the complete results of this study are shown in Table II.Biogenic Amine Analysis.-Biogenic amine analyses were performed 3 hr after the ip injection of MT or IpT (1 mmole/kg) and the results compared with those of saline, a-MPT, and a-MMT(1 mmole/kg) treated groups. Brain and heart from decapitated (guillotine) male Wistar rats (200 g) were placed on Dry Ice immediately after excision and stored at -15°until assayed.At that time the tissues were homogenized in acidified n-BuOH, serotonin was measured fluorometrically as the o-phthaldialdehyde condensation product according to a modification of the method of Maickel.®3 Dopamine and NE were assayed by measuring fluorescence after I, oxidn by modification of the method of Chang.®4 Table III lists these results.
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