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Synthesis and Antibacterial Activity of 1-Aryl-3-(4-methoxyphenyl)-3-(4-fluorophenyl)propanamides and Propanoates

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Abstract

N-Acylation of some primary alkyl-, aryl-, and heterocyclic amines with 3-(4-methoxyphenyl)-3-(4-fluorophenyl)propanoic acid chloride gave propanamide derivatives. The reaction of the above acid chloride with N,N-dimethylpropane-1,3-diamine and the subsequent action of an ethereal solution of methyl iodide affords 3-{[3-(4-methoxyphenyl)-3-(4-fluorophenyl)propanoyl]amino}-N,N,N-trimethylpropane-1-aminium iodide. O-Acylated compounds—(1,3-benzothiazol-2-yl)methyl and 2-dimethylaminoalkyl 3-(4-methoxyphenyl)-3-(4-fluorophenyl)propanoates—were obtained by heating a mixture of the corresponding compounds with 3-(4-methoxyphenyl)-3-(4-fluorophenyl)propionic acid anhydride. Their subsequent treatment with an ethereal solution of methyl iodide leads to the corresponding N,N,N-trimethylalkane-1-aminium iodides. Antibacterial activity of the synthesized compounds was studied.

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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, 0014, Yerevan, Armenia

    A. U. Isakhanyan, N. Z. Akopyan, Z. A. Ovasyan, N. S. Arutyunyan, H. M. Stepanyan, J. A. Avakimyan & G. A. Panosyan

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  1. A. U. Isakhanyan
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  2. N. Z. Akopyan
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  3. Z. A. Ovasyan
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  4. N. S. Arutyunyan
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  5. H. M. Stepanyan
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  6. J. A. Avakimyan
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  7. G. A. Panosyan
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Correspondence to A. U. Isakhanyan.

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Isakhanyan, A.U., Akopyan, N.Z., Ovasyan, Z.A. et al. Synthesis and Antibacterial Activity of 1-Aryl-3-(4-methoxyphenyl)-3-(4-fluorophenyl)propanamides and Propanoates. Russ J Gen Chem 92, 932–936 (2022). https://doi.org/10.1134/S1070363222060020

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  • DOI: https://doi.org/10.1134/S1070363222060020

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