Physiologically Active Compounds. II. Hydrochlorides of Aminoesters of Substituted Benzilic and Glycolic Acids¹

Abstract

VOL. 23 tion presented here could be a useful supplement to the standard methods for determining absolute configuration.In all tables, unless otherwise specified, the rotations were measured in water. A solvent other than water is indicated by the following symbols appearing after the specific rotation value : A-acetonel C-chloroform, E-ethanol, M-methanol, Ppyridine. The epimeric pairs that do not conform to our predictions are underlined.Thirty-nine aminoester hydrochlorides of substituted benzilic and glycolic acids were synthesized. Two of these compounds appear to be more active in experimental animals than atropine in preventing mortality from an anticholinesterase compound and four of them exhibit the highest anticholinergic activity. One compound previously reported offers some advantage over three of these as an anticholinergic.

Pyrazolo[3,4-c]pyridazines as Novel and Selective Inhibitors of Cyclin-Dependent Kinases

“…The method utilized for the synthesis of pyrazolo[3,4- c ]pyridazines 1a − l is outlined in Scheme . The necessary 1,2-dicarbonyl compounds were commercially available ( 3a and 3f − l ) or easily prepared ( 3b − d ) following previously described methods. − Diketone 3e was described as a secondary product (10%) in the synthesis of ethyl 2-oxo-2-( p -trifluoromethylphenyl)acetate, by reaction of trifluoromethylphenyl bromide with diethyl oxalate in the presence of BuLi . We have found that with the use of equivalent amounts of reactants and a high excess of base, the yield of the desired diketone can be increased to 25%.…”

“…From 4,4′-diphenylbenzil 10 (1.34 g, 3.70 mmol) in DMF (15 mL) and cyanoacetohydrazide (0.73 mg, 7.37 mmol) in DMF (6 mL) was obtained 5g (786 mg, 50%) as a yellow solid, mp >300 °C (dioxane).…”

Reactions of ceric ammonium nitrate: I. with substituted cycloheptatrienes, II. with diazoalkanes, III. with sodium azide and olefins

“…The ether layer was separated, washed with water and saturated sodium bicarbonate solution, dried (MgS04), and the ether was removed in vacuo.The 2-phenylbenzyl alcohol was oxidized to 2-phenylbenzaldehyde using the procedure of Trahanovsky (58). The product was a thick liquid(41); nmr (CDCI3) 6 9.91 (s, 1, PhPhCHO), 7.PhPhCHO).m-PhenylbenzaldehydeTo a Grignard prepared from 0.01 moles of magnesium and 0.01 moles of 3-bromobiphenyl (K & K Laboratories, purified by distillation, bp 138-142 (15 mm)) in 25 ml of ether was added 0.01 moles of N-methylformaline at 0° using the method of Buehler(42). Each drop caused vigorous boiling and a copious white precipitate was obtained.…”