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Synthesis, Some Transformations, and Biological Properties of 3-Phenethyl-2-Thioxo-2,3-Dihydro-1H-spiro[Benzo[H]Quinazoline-5,1′-Cycloheptane]-4(6H)-Ones

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Pharmaceutical Chemistry Journal Aims and scope

The reaction of ethyl 4′-amino-1′H-spiro[cycloheptane-1, 2′-naphthalene]-3′-carboxylate with phenethylisothiocyanate followed by cyclization of the intermediate thiourea synthesized 3-phenethyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-4(6H)-one (2-thioxobenzo[h]quinazoline), which was alkylated in the presence of alkali into 2-alkylthio-substituted 3-phenethyl-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-4(6H)-ones. 2-Thioxobenzo[h]quinazoline was converted to 2-hydrazinyl-3-phenethyl-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptane]-4(6H)-one, condensation of which with carbon disulfide resulted in 1-mercapto-4-phenethyl-4H-spiro[benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1′-cycloheptane]- 5(7H)-one. A study of the antitumor properties of the synthesized compounds showed that some of them were active (37 – 66%) against sarcoma 180. The synthesized compounds possessed weak bacteriostatic activity against Gram-positive (St. aureus 209 P and 1) and Gram-negative microorganisms (Sh. flexneri 6858 and E. coli 0 – 55).

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Authors and Affiliations

  1. Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 26 Prosp. Azatutyan, 0014, Yerevan, Armenia

    A. I. Markosyan, A. S. Ayvazyan, S. A. Gabrielyan, S. S. Mamyan, J. A. Avakimyan & L. A. Martirosyan

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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. J. A. Avakimyan
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  6. L. A. Martirosyan
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Correspondence to A. I. Markosyan.

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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 56, No. 10, pp. 17 – 22, October, 2022.

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Markosyan, A.I., Ayvazyan, A.S., Gabrielyan, S.A. et al. Synthesis, Some Transformations, and Biological Properties of 3-Phenethyl-2-Thioxo-2,3-Dihydro-1H-spiro[Benzo[H]Quinazoline-5,1′-Cycloheptane]-4(6H)-Ones. Pharm Chem J 56, 1321–1326 (2023). https://doi.org/10.1007/s11094-023-02792-6

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  • DOI: https://doi.org/10.1007/s11094-023-02792-6

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