No abstract

Suspensions of Pseudomonas grown on phenylacetic acid oxidized 3,4-dihydroxy-phenylacetic acid to δ-carboxymethyl-α-hydroxymuconic semialdehyde. The compound was characterized by conversion to 2,5-pyridine dicarboxylic acid. The results show that cleavage of the aromatic ring occurs between carbons 2 and 3. δ-Carboxymethyl-α-hydroxymuconic semialdehyde is relatively unstable. Maximum absorption of the compound is obtained in acid at 318 mμ and in alkali at 380 mμ. The ratio of optical densities (380/318) is 1.8. In 2% sodium carbonate solution the molar extinction coefficient at 380 mμ is 2.7 × 104. Other chemical properties of the cleavage product are described.

14) Two Pyrex tubes, the first containing l a and the second containing l b , in equimolar amount, and both containing equimolar amounts of sensitizer (benzophenone), were irradiated in a merry-goround apparatus to ensure equal absorption of light, then analyzed for the amount of 3 and 4 produced. The low yield of the products and their instability to the reaction conditions limit the accuracy of this experiment.

Methoxybromination of 4,5‐dihydro‐2‐methylfuran (4), followed by treatment of the resulting bromoketal 5 with hot formamide, gave 4‐(2‐hydroxyethyl)‐5‐methyl‐1H‐imidazole (3) in 25% yield. This method provides easy access to the selective H2‐agonist 4‐methylhistamine (1) via the chloromethyl intermediate 2.

A series of para-substituted N-(beta-styryl)formamides, analogues of tuberin (4a), has been prepared and assayed for antibacterial activity. The methylthio, ethoxy, and methyl analogues 4e, 4j, and 4t were about twice as active as tuberin against Mycobacterium phlei. Although tuberin lacks activity against Staphylococcus aureus, several of the analogues described were found to inhibit this organism. The phenyl group of tuberin is not a prerequisite for activity since analogues based on naphthyl or ferrocenyl groups were also active. A quantitative structure-activity relationship further implied that an aromatic group need not be present, suggesting the synthesis of the cyclohexyl and n-amyl analogues which were found to possess high activity.