New Anti-Infective Preparations of Naphthyloxypropargylpiperidine Series

  • F. M. Sadyrbayeva Kazakh-British Technical University, 106 Ualikhanov str., 050010, Almaty, Kazakhstan
  • G. S. Akhmetova JSC “Institute of Chemical Sciences named after A.B. Becturov”, 106 Ualikhanov str., 050010, Almaty, Kazakhstan
  • K. D. Praliyev JSC “Institute of Chemical Sciences named after A.B. Becturov”, 106 Ualikhanov str., 050010, Almaty, Kazakhstan
  • H. Osman University Science Malaysia, School of Chemical Sciences, Penang, 11800 Gelugor, Malaysia
  • N. V. Korotetskaya Scientific Center of Antimicrobial Preparations JSC, 84 Auezov str. 84, 050008 Almaty, Kazakhstan
Keywords: piperidin, naphthyloxypropargylic piperidols, cyclopropane, antimicrobial activity

Abstract

1-Alkyl-4-(3-naphthyloxyprop-1-ynyl)piperidine-4-ols have been obtained by the condensation of 1-alkyl-pipieridin-4-ones with 1- and 2-naphthoxypropines by the Favorsky method in absolute diethylether, in the presence of powered technical KОН, under atmospheric pressure. Acylation of tertiary naphthoxypropynyl piperidols by cyclopropanecarbonylchloride has been carried out in order to introduce a cyclopropanecarbonyl fragment into the structures of naphthoxypropargylpiperidines. The obtained esters of cyclopropanecarboxylic acid represent crystalline substances with the definite melting temperature, very soluble in water, ethanol, acetone. The composition and structure of the synthesized compounds have been confirmed by the data of elemental analysis, IR-spectroscopy, NMR-spectroscopy, the identity has been confirmed by thin-layer chromatography. The compounds under the code AIP (anti-infective preparation) have been studied for an antimicrobial activity in relation to museum microbial strains. The effects of these preparations have been assessed in vitro in relation to Bacillus subtilis ATCC 6633, Escherichia coli ATCC 25922, Salmonella enterica ATCC 14028 and Staphylococcus aureus ATCC 6538- P. It has been found that the compounds AIP-30 and AIP-31 possess an antimicrobial activity in relation to all strains of microorganisms, engaged in the experiment. AIP- 30 and AIP-31 have antimicrobial effects to different extents, AIP-30 has displayed the highest activity in relation to the museum strain Bacillus subtilis ATCC 6633 in the concentration of 250 μg/ml. It has been established that AIP-32 displays a selective antimicrobial activity towards one type, and AIP-33 ‒ towards two types of the museum strains, engaged in the experiment.

 

References

[1]. L. Bryan, Antimicrobial drug resistance. / L. Bryan. – Orlando: Academic press, 1984. – 450 p.

[2]. G. Regev-Yochay, M. Raz, R. Dagan, H. Roizin, B. Morag, Sh. Hetman, S. Ringel, N. Ben-Israel, M. Varon, E. Somekh, E. Rubinstein, Clinical Infectious Diseases 3 (1) (2011) 33‒41. Crossref

[3]. Antimicrobial resistance surveillance in Europe 2012. Annual Report of the European Antimicrobial Resistance Surveillance Network (EARS-Net). European Centre for Disease Prevention and Control.: – Introduced 2013, Stockholm, 208 p. Crossref

[4]. K.D. Praliyev. С- and N- substituted mono- and bicyclic piperidines: synthesis, stereochemistry, transformations and properties. Materialy Pervoj Mezhdunarodnoj konferencii "Himija i biologicheskaja aktivnost' azotistyh geterociklov i alkaloidov" [Materials of the First International Conference "Chemistry and Biological Activity of Nitrous Heterocycles and Alkaloids"]. Moscow, Russia. (in Russian) 2001, p. 130‒138 (in Russian).

[5]. K.D. Praliyev, V.K. Yu, I.A. Poplavskaya. The directed synthesis of new pharmacologically active substances in the series of 4-ethinyl- 4-hydroxypiperidine derivatives. Materialy Pervoj Mezhdunarodnoj konferencii "Himija i biologicheskaja aktivnost' azotistyh geterociklov i alkaloidov" [Materials of the First International Conference "Chemistry and Biological Activity of Nitrous Heterocycles and Alkaloids"]. Moscow, Russia. (in Russian) 2001, p. 484‒489 (in Russian).

[6]. E.A. Babayan. “Procidol” – an organic domestic synthetic analgesic of central action. Novye lekarstvennye preparaty [New drugs] 7 (2006) 3‒6 (in Russian).

[7]. G.S. Akhmetova, V.K. Yu, K.D. Praliyev, N.M. Pominova, Ye.A. Severova. Synthesis and pharmacological activity of some N-aryl-ethyl-4,4-disubstituted piperidines. Izvestija ministerstva obrazovanija i nauki Respubliki Kazahstan (serija khimicheskaja) [Proceedings of the Ministry of Education and Science of the Republic of Kazakhstan (chemical series)] 3 (2001) 53‒65 (in Russian).

[8]. G.S. Akhmetova, A.K. Amantayeva, V.K. Yu, K.D. Praliyev, L.M. Moisseyeva, M.S. Lukiyanova, A.A. Koltunova, Ye.I. Voronina. Synthesis and pharmacological properties of the new homolog of the native original analgesic drug prosidol. Izvestija Tomskogo politehnicheskogo universiteta [Proceedings of Tomsk Polytechnic University] 3 (317) (2010) 140‒143. (in Russian).

[9]. V. Yu, K. Praliyev, A. Nagimova, A. Zazybin, Tetrahedron Lett. 56 (2015) 1631‒1634.
Crossref

[10]. V.I. Kozlovskiy, K.D. Praliyev, V.V. Goncharuk, L.B. Zavodnik, G.S. Akhmetova, T.K. Iskakova, V.K. Yu, Analgesic activity of the original substances of the piperidine series: an experimental study on the model of thermal stimulation, Zhurnal Grodnenskogo gosudarstvennogo medicinskogo universiteta [Journal of Grodno State Medical University, Belarus] 3 (2014) 38‒41. (in Russian).

[11]. G.S. Akhmetova, F.M. Sadyrbayeva, V.K. Yu, K.D. Praliyev, O.T. Zhilkibayev, G.M. Pichkhadze, S.R. Nassyrova, Sh.O. Imashova, M.K. Amirkulova. Piperidine-containing cyclopropanecarboxylic acid derivatives ‒ potential PEAs, Khimicheskij zhurnal Kazahstana [Chemical Journal of Kazakhstan], 1 (2012) 118‒127 (in Russian).

[12]. F.M. Sadyrbayeva, S.I. Ospanova, U.B. Issayeva, G.S. Akhmetova, V.K. Yu, K.D. Praliyev. Amides of cyclopropanecarboxylic acid – potential biologically active substances, Klaster konferencij po organicheskoj khimii OrgHim-2013 [Cluster of conferences on organic chemistry OrgChim-2013] St. Petersburg, Russia, June 17-21. (in Russian) p. 248‒249 (in Russian).

[13]. K. Ajar Kumar, International Journal of Pharmacy and Pharmaceutical Sciences 5 (1) (2013) 467‒472.

[14]. Guidance for experimental (pre-clinical) study of new pharmacological substances, the RF Ministry of Health»], «IIA Remedium», Moscow, 2000, 679 p. (in Russian).

[15]. Pre-clinic tests of medicinal preparations (Methodological recommendations). The Republic of Kazakhstan State Pharm. Committee, Almaty, Kazakhstan. 1997, 22 p. (in Russian).

[16]. N.S. Yegorov. Rukovodstvo k prakticheskim zanjatijam po mikrobiologii [A guide to practical lessons in microbiology Guidance for practical training in microbiology]. Moscow State University, Moscow, Russia. (in Russian) 1995, p. 224. (in Russian).

[17]. J. Jolt, N. Crieg, P. Smith, J. Staily, S. Williams. Opredelitel' bakterij Berdzhi [The Berji bacteria determinant] In 2 volumes. v.1: Translated from English. Mir, Moscow, USSR. (in Russian) 1997. – p. 432.

[18]. CLSI M07-A9 Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. Approved Standard – Ninth Edition. - 2012.- v.32.- No.2.- p.88.

[19]. M.T. Omirzak, R.Sh. Erkassov, B.G. Sukhov, T.V. Ganyenko. “Synthesis, structure, and growth-promoting activity of 1-alkyl-4-(3- naphthyloxyprop-1-ynyl)piperidine-4-ols”, Russian Chem. Bull., Int. Edition, 62 (11) (2013) 2442‒2444. . Crossref

[20]. K.D. Praliyev, M.Ye. Kulmanov, A.I. Ilyin, F.M. Sadyrbayeva, G.S. Akhmetova, V.K. Yu, U.B. Issayeva, N.V. Leonova et al. [Hydrochloride of 1-methyl-4-[3-(naphth-1-yloxy)prop-1-in- 1-yl]-4-cyclopropanecarbonyloxypiperidine (AIP-30), possessing an antimicrobial activity]. RK Innovative Patent No. 29020. Published in Bulletin No.10, dated 15.10.14. (in Russian).

[21]. K.D. Praliyev, M.Ye. Kulmanov, A.I. Ilyin, F.M. Sadyrbayeva, G.S. Akhmetova, V.K. Yu, U.B. Issayeva., N.V. Leonova et al. Hydrochloride of 1-methyl-4-[3-(naphth-2-yloxy)prop-1-in- 1-yl]-4-cyclopropanecarbonyloxypiperidine (AIP-31), possessing an antimicrobial activity. RK Innovative Patent No.29021. Published in Bulletin No.10, dated 15.10.14. (in Russian).

[22]. K.D. Praliyev, M.Ye. Kulmanov, A.I. Ilyin, F.M. Sadyrbayeva, G.S. Akhmetova, V.K. Yu, U.B. Issayeva, N.V. Leonova et al. Hydrochloride of 1-propyl-4-[3-(naphth-1-yloxy)prop-1-in- 1-yl]-4-cyclopropanecarbonyloxypiperidine (AIP-32), possessing an antimicrobial activity. RK Innovative Patent No.29022. Published in Bulletin No.10, dated 15.10.14. (in Russian).

[23]. K.D. Praliyev, M.Ye. Kulmanov, A.I. Ilyin, F.M. Sadyrbayeva, G.S. Akhmetova, V.K. Yu, U.B. Issayeva, N.V. Leonova et al. Hydrochloride of 1-propyl-4-[3-(naphth-2-yloxy)prop-1-in- 1-yl]-4-cyclopropanecarbonyloxypiperidine (AIP-33), possessing an antimicrobial activity. RK Innovative Patent No.29023. Published in Bulletin No.10, dated 15.10.14. (in Russian).
Published
2017-06-30
How to Cite
[1]
F. Sadyrbayeva, G. Akhmetova, K. Praliyev, H. Osman, and N. Korotetskaya, “New Anti-Infective Preparations of Naphthyloxypropargylpiperidine Series”, Eurasian Chem. Tech. J., vol. 19, no. 2, pp. 183-190, Jun. 2017.
Section
Articles