M. D. Mashkovskii

Synthesis and psychotropic activity of pyrazidole analogs

30. West German Patent No. 2207298 (1973); Chem. Abstr., 78, 148974h (1973). 31. West German Patent No. 2226668 (1974); Chem. Abstr., 9 80, 194171z (1974). 32. U. S. Patent No. 3793455 (1974); Chem. Abstr., 80, i12665d (1974). 33. S. Tomizawa, N. Suguro, and M. Kagoshima, Oyo Yakuri, 16, 671-682 (1978); Chem. Abstr., 90, 162125c (1979). 34. T.IK~ Gar and V. F. Mironov, The BiDlogical Activity of Germanium Componnds [in Russian], NIITEKhlM, Moscow (1982), p. 26. 35. E. Lukevits, S. Germane, O. A. Pudova, et al., Khim.-farm. Zh., No. i0, 52-57 (1979). 36. V. F. Mironov, N. Yu. Khromova, and T. K. Gar, Zh. Obshch. Khim., 5__1, No. 4, 954-955 (1981). 37. T. K. Gar, N. Yu. Khromova, N. V. Sonina, et al., Zh. Obshch. Khim., 49, No. 7, 15161522 (1979). 9 38. T. K. Gar, N. Yu. Khromova, V. N. Nosova, et al., Zh. Obshch. Khim., 50, No. 8, 17641767 (1980). 39. V. I. Shiryaev,~ E. M. Stepina, T. G. Basanina, et al., Zh. Obshch. Khim., 51, No. 8, 18191823 (1981). 40. V. F. Miro~ov, E. M. Berliner, and T. K. Gar, Zh. Obshch. Khim., 37, No. 4, 962 (1967). 41. R. E. H~tton, J. W. Burley, and V. Oakes, J. Organomet. 9 156, 369 (1978). 42. N. V. Alekseev, S. N. Gurkova, A. I. Gusev, et al., Zh. Obshch. Khim,, 52, No. 9, 2136 (1982).

Synthesis and pharmacological activity of derivatives of pyrano- and pyrido-[3,2]carbazoles

The intramolecular cyclization of diaminodienyl diketones la, b has been previously used [i~ 2] to synthesize coumarin derivatives IIa, b, the reaction of which with ammonium acetate gave substituted carbostyrils IIIa, b. The alkylation of the Na salts of the latter with benzyl chloride and N,N-dimethylaminoethyl chloride proceeds at the ring nitrogen atom to give N-alkylcarbostyrils IIIc-e. The compounds that were synthesized by this method contain a carbonyl function in their structure; this ensures the possibility of their use in the Fischer reaction to obtain four-ring indole-containing systems that are of interest for the investigation of their psychotropic activity.

Derivatives of pyrazino- and piperazino[1,2-a]indole

The piperazino[1,2-a]indole derivatives (XVII-XIX) were obtained on reduction of XI~ XIH, and XV with sodium in boiling alcohol. Additionally, XVII and XVIII could be prepared by hydrogenating the pyrazino[1,2-a]indole derivatives over Raney nickel catalyst at a pressure of 60-70 atm and a temperature of 50 ~ An attempt to carry out the catalytic hydrogenation of the pyrazine ring at elevated pressure in compounds which contained a chlorine atom in the molecule (XII, XIV) led to the formation of piperazino[1,2-a]indole (XX), which does not contain substituents in the benzene ring of the molecule; that is, hydrogenolysis of the chlorine atom takes place in this reaction along with reduction of the pyrazine ring.

Synthesis of derivatives of 1-methylamino-9-methyl-l,2, 3,4-tetrahydrocarbazole, analogs of the preparation pyrazidole

Pyraz ido le , the hydrochlor ide of 1 , 1 0 t r i m e t h y l e n e 8 m e t h y l 1 ,2 ,3 ,4te t rahydropyrazino[1,2a] indole , belongs to a group of new highly effect ive an t idepress ive p repa ra t ions [1]. In this connection the synthes is of analogs of the p repa ra t ion pyraz idole , among them compounds with a broken p iperaz ine r ing, is of in teres t . These invest igat ions were also c a r r i e d out to c la r i fy the s t ruc tu ra l e lements of the molecule of the p repa ra t ion pyraz ido le r e spons ib l e for the biological act ivi ty.

Antiserotonin and antihistaminic properties of derivatives of 2-methyl-3-ethoxycarbonyl-4-dialkylaminomethyl-5-hydroxyindole

An investigation has been made of derivatives of the 4-dialkylaminoalkyl-5-hydroxyindoles obtained from the corresponding 5-hydroxyindoles by the action of bis(dimethylamino) methane and bis(diethylamino) methane. It has been found that the derivatives of 4-dialkylaminoalkyl-5-hydroxyindoles possess ananti-serotonin action. In experiments on animals, compounds IV–VI and VIII with a dimethylaminomethyl substituent in position 4 and o-tolyl, p-anisyl, p-tolyl, and m-chlorophenyl substituents on the nitrogen of the indole ring, respectively, proved to be the most active. The compounds studied did not exhibit antihistaminic activity.