SU772099A1 - 2-diazo-1-adamantyl-5-phenyl-1,3,5-pentanetrione exhibiting antispasmotic activity - Google Patents

Description

This invention relates to a novel biologically active chemical compound derived from adamantane.

namely, to 2-diazo-l-adamant fl-phenml-1, 3.5 t1 antantrione of formula

showing anticonvulsant activity.

Its preparation is carried out by the interaction of 5 phenyl-2,3-furandione with ada37 with mantanoyl diazomethane in inert medium temperature solvent 7b-80 C for 1 hour, followed by isolation of the target product by known methods. The synthesized compound is a yellow crystalline product, insoluble in water and alcohol, but well soluble in chloroform and acetone. Its structure is confirmed by elemental analysis data, IR and PMR spectroscopy. In plant thieves is in the enol form. Example. 2-Diazo-1-ad4mantil-5-phenyl-1,3,5 pentantrione. To a solution of 2.04 g (0.01 mol) of adamantanoyl-1-diazometaia in 1.7 g of carbon tetrachloride is added 1.74 g (0 , 01 mole) 5-phenyl 2,3-furandione. The mixture is boiled for 1.5-2 hours until the evolution of gas ceases and the solvent is removed, the oily residue crystallizes upon treatment with hexane. The product is recrystallized from methanol-CC1d (2: 1), m.p. 103-5 seconds. Yield 2.48 g. C, 71.93; H 6.29; Found,% N, 8.20. C. C 72.02; H 6.28; Calculated, jN 7.93 .. IR spectrum, l), cm, CC1. 4. 157 1612; 1652, 2118. PMR spectrum, S MD, CCL: Ad 1.78, Ar 7.48; CH 7.18; OH 15.15.

Anticonvulsant activity and acute toxicity in comparison with chloraconone and hexamidine. For comparison, the known anticonvulsant drugs hexamidine, chloracon and adamantoyl diazomethane were selected (see table). In biological tests, it was revealed that 2-diazo-1-adamantyl-5-phenyl-1, 3) 5-pentantrion at a dose of 140 mg / kg (116-168) has an anticonvulsant effect and is slightly inferior to hexamidine, in which ED has em 00 (79-103) mg / kg, and chloracon, the ED j-fjKOToporo is 100 (86-119) mg / kg. The maximum manifestation of anticonvulsant activity is the same as that of chloracones, i.e. the peak of action is 15 minutes, which is much faster than hexamidine, the peak of which occurs after 4 hours. A study of the acute toxicity of 2-diazo-1-adamantyl-5-phenyl-1,3,5 pentantrione showed that its LD is 1070 (870-131b) mg / kg in the intraperitoneal route of administration, i.e. it is 2 times less toxic than chloracon, the LD of which is 650 mg / kg, and Zraza is less toxic than hexamidine, the LD of which is 340 mg / kg. Accordingly, the index of conditional pharmacological latitude (EFS) of 2-diazo-1-adamantyl-5-phenyl 1, 3.5 pentantrione is 7.6 and higher than that of the chloracon, whose EFS is 6.5, and 2 times higher than hexamidine, UFSH which is 3.7.

2-Liazo-1-adamantylrtUj-. / -adamanty -5-phenyl -1,3,5140 1070

7,6

15 (116-168) 870-1316

-pantrion

CHg-BH-C-CHg-CHCl Chloracon

650

6.5

100

Claims (1)

(84-119) 586-722 Claims of the invention 2-Diazo-1-adamantyl-5-phenyl-1,3,5 .4 oib-pantanetrione of the formula CIS A continuation of the table showing anticonvulsant activity Sources of information taken into account during the examinations 1. Chemical and pharmaceutical well., 197, № 7. p. 6-8.