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Հայաստանի քիմիական հանդես =Chemical Journal of Armenia
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Н. П. Григорян ; Р. В. Пароникян ; Г. М. Степанян
Contributor(s):
Պատ․ խմբ․՝ Ա․ Լ․ Մնջոյան (1957-1962) ; Գլխ․ խմբ․՝ Գ․ Տ․ Թադևոսյան (1962-1973) ; Մ․ Հ․ Ինճիկյան (1974-1976)
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Գրիգորյան Ն. Պ. ; Պարոնիկյան Ռ. Վ. ; Ստեփանյան Հ. Մ. ; Grigoryan N. P. ; Paronikyan R. V. ; Stepanyan G. M.
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Abstract:
На базе этилового эфира 4'-амино-5',8'-диметил-1'Н-спиро[циклопентан-1,2'-нафталин]-3'-карбоновой кислоты разработан метод синтеза 2-меркапто-3-бензил-7,10-диметил-3H-спи-ро[бензо[h] хиназолин-5,1'-циклопентан]-4(6H)-она. Взаимодействием последнего с различны-ми алкил(бензил) галогенидами синтезирован новый ряд бензо[h] хиназолинов, содержащих в третьем положении бензильную группу, а в бензольном кольце–метильные заместители. 4'-Ամինո-5',8'-դիմեթիլ-1'Н-սպիրո[ցիկլոպենտան-1,2'-նավթալին]-3'-կարբոնաթթվի էթիլ էսթերի հիման վրա մշակվել է 2-մերկապտո-3-բենզիլ-7,10-դիմեթիլ-3H-սպիրո[բենզո[h] խինազոլին-5,1'-ցիկլոպենտան]-4(6H)-ոնի սինթեզի եղանակ: Ստացված նյութի փոխազդեցությամբ տարբեր ալկիլ(բենզիլ)հալոգենիդների հետ սինթեզվել են նոր բենզո[h] խինազոլիններ, որոնք երրորդ դիրքում պարունակում են բենզիլ խումբ, իսկ բենզոլային օղակում` մեթիլ տեղակալիչներ: Literature data show that the derivatives of spirobenzo[h]quinazolines possess antitumor and psychotropic properties; therefore obtaining new functional and heterocyclic derivatives on their basis is of interest. It was expedient to synthesize similar spirobenzo[h] quinazoline compound - 2-mercapto-3-benzyl-7,10-dimethyl-3H-spirobenzo[h]quinazoline-5,1'-cyclopentan] -4(6H)-one containing a benzyl group at position 3 and a cyclopentane moiety and to carry out a series of transformations based thereon. To achieve this goal, we propose an effective method for the synthesis of the key compound - β-amino ester of dihydronaphthalene series. This amino ester serves as the basis for the synthesis of dihydrobenzo[h]quinazolines spiroassociated with cyclopentane. Synthesis of ethyl ester of 4'-amino-5',8'-dimethyl-1'H-spiro[cyclopen- tane-1,2'-naphthalene] -3'-carboxylic acid was done by cyclizing (under the action of sulfuric acid) ethyl ester of [1-(2,5-dimethyl) benzylcyclopentyl]cyanoacetic acid obtained by reacting 2,5-dimethylbenzylmagnezium cհloride with 2-cyano-2-cyclo-pentylideneacetic ester. On the basis of ethyl ester of 4'-amino-5',8'-dimethyl-1'H-spiro[cyclopentane-1,2'-naphthalene] -3'-carboxylic acid a method for the synthesis of 2-mercapto-3-benzyl-7,10-dimetyl-3H-spiro[benzo[h] quinazoiline-5,1'-cyclopentan] -4(6H) -one was developed. By reaction of the latter with a variety of alkyl(benzyl) halides, a new series of benzo[h]quinazolines containing a benzyl group at the third position and methyl substituents in the benzene ring were synthesized. In order to obtain new heterocyclic systems containing spirobenzo[h] quinazoline fragment, 4'-amino-5',8'-dimethyl-1'H-spiro[cyclopentane-1,2'-naphthalene]-3'-carboxylic acid interacted with benzylisothio-cyanate. It should be note d that the benzylisothiocyanate is formed using thioureido compounds, alkaline hydrolysis of which results in 2-mercapto-3-benzyl-7,10-dimethyl-3H-spiro[benzo[h]quinazoline-5,1'-cyclopentan] -4(6H)-one, with benzylisothiocyanate under heating for 18 hours. Intramolecular cyclization takes place to give 2-mercapto-3-benzyl-7,10-dimethyl-3H-spirobenzo[h] quinazoline -5,1'-cyclopentan] -4(6H)-one. This is apparently due to the intramolecular proton transfer to a carbonyl group while splitting off ethanol under prolonged heating. Studies have shown that compounds 8 and 13 exhibit pronounced activity against staphylococci and dysеntery bacillus, inhibiting their growth in the zone of 18-19 mm diameter. Compounds 5i and 5d are almost devoid of activity, and the rest ones have weak effect on the afore-mentioned strains (d = 10-14 mm). In respect of Escherichia coli (Esherichia Coli 0-55) weak activity show only compounds 8, 10, 11 and 13 (d = 10-12 mm).
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Երևան
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ՀՀ ԳԱԱ Հիմնարար գիտական գրադարան