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Synthesis and Antibacterial Activity of New 3-Benzylspiro[benzo[h]quinazoline-5,1′-cycloheptan]-4(6H)-one Derivatives

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Abstract

The condensation of 3-benzyl-2-sulfanylidene-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1′-cyclo­heptan]-4(6H)-one with 5,5-dialkyl-2-(chloromethyl)benzo[h]quinazolines gave bis-benzo[h]quinazoline compounds in which the spiro[benzo[h]quinazoline-5,1′-cycloheptane] fragment is linked through the 2-position to another benzo[h]quinazoline moiety via a SCH2 spacer. 3-Benzyl-2-sulfanylidene-2,3-dihydro-1H-spiro­[benzo[h]quinazoline-5,1′-cycloheptan]-4(6H)-one reacted under similar conditions with methylene iodide to produce 2,2′-[methylenebis(sulfanediyl)]bis{3-benzyl-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptan]-4(6H)-one}. The initial benzo[h]quinazoline was converted to 2-hydrazinyl derivative which underwent elimination of the hydrazine moiety by the action of alkali with the formation of 3-benzyl-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptan]-4(6H)-one. The 2-hydrazinyl derivative was used to obtain the corresponding phenylhydrazone, thiosemicarbazide, and 4-benzyl-4H-spiro[benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1′-cycloheptanone]-5(7H)-one. The alkylation of 4-benzyl-1-sulfanyl-4H-spiro[benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1′-cycloheptan]-5(7H)-one with alkyl halides afforded the corresponding 1-alkylsulfanyl derivatives. The synthe­sized compounds were tested for antibacterial activity.

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Funding

This study was financially supported by the Science Committee of Republic of Armenia (project no. 21AA-1D002).

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Authors and Affiliations

  1. Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, 0014, Yerevan, Armenia

    A. I. Markosyan, A. S. Ayvazyan, S. A. Gabrielyan, S. S. Mamyan & R. E. Muradyan

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  1. A. I. Markosyan
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  2. A. S. Ayvazyan
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  3. S. A. Gabrielyan
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  4. S. S. Mamyan
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  5. R. E. Muradyan
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Correspondence to A. I. Markosyan.

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Markosyan, A.I., Ayvazyan, A.S., Gabrielyan, S.A. et al. Synthesis and Antibacterial Activity of New 3-Benzylspiro[benzo[h]quinazoline-5,1′-cycloheptan]-4(6H)-one Derivatives. Russ J Org Chem 60, 415–422 (2024). https://doi.org/10.1134/S1070428024030072

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