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Synthesis and Antitumor and Antibacterial Activity of Novel Dihydronaphthaline and Dihydrobenzo[H]Quinazoline Derivatives

  • A. I. MarkosyanEmail author
  • K. K. Airapetyan
  • S. A. Gabrielyan
  • S. S. Mamyan
  • V. Z. Shirinyan
  • A. V. Zakharov
  • F. G. Arsenyan
  • Dzh. A. Avakimyan
  • G. M. Stepanyan
Article
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A method for the synthesis of 1-amino-3,3-dimethyl-3,4-dihydronaphthaline-2-carbonitrile (β-aminonitrile) was developed and used to synthesize Schiff bases, thioureide and chloracetamide derivatives. This latter was cyclized to 5,5-dimethyl-2-chloromethyl-5,6-dihydrobenzo[h]quinazoline-4(3H)-one, which was used to synthesize a series of 2-sulfanylmethyl and 2-aminomethyl derivatives. 2-Chloromethylbenzo[h]quinazoline in the presence of a base was found to form condensed heterocyclic compounds with seven rings: 1,1,11,11-tetramethyl-1,2,11,12-tetrahydropyrazino[2,1-b:5,4-b′]di(benzo[h]quinazoline)-10,16(8H,18H)-di one. The antitumor properties of the compounds synthesized here were studied in an ascites carcinoma model and the antibacterial properties were studied using the agar diffusion method.

Keywords

cyclization aminonitrile benzo[h]quinazoline; antitumor and antibacterial activity 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • A. I. Markosyan
    • 1
    Email author
  • K. K. Airapetyan
    • 1
  • S. A. Gabrielyan
    • 1
  • S. S. Mamyan
    • 1
  • V. Z. Shirinyan
    • 2
  • A. V. Zakharov
    • 2
  • F. G. Arsenyan
    • 1
  • Dzh. A. Avakimyan
    • 1
  • G. M. Stepanyan
    • 1
  1. 1.A. L. Mndzhoyan Institute of Fine Organic Chemistry, Scientific-Technological Center for Organic and Pharmaceutical ChemistryNational Academy of Sciences of the Republic of ArmeniaErevanArmenia
  2. 2.N. D. Zelinskii Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia

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