Synthesis of novel pyridine-connected piperidine and 2H-thiopyran derivatives and their larvicidal, nematicidal, and antimicrobial activities

Authors

  • Idhayadhulla Akbar Research Department of Chemistry, Nehru Memorial College (Affiliated to Bharathidasan University), Puthanampatti -621007, Tiruchirappalli District, Tamil Nadu, South India. http://orcid.org/0000-0003-0309-6274
  • Anis Ahamed Prince Sultan Research Chair for Environment and Wildlife, Department of Botany & Microbiology, College of Sciences, King Saud University (KSU), Riyadh, Saudi Arabia
  • Ibrahim A. Arif Prince Sultan Research Chair for Environment and Wildlife, Department of Botany & Microbiology, College of Sciences, King Saud University (KSU), Riyadh, Saudi Arabia
  • Radhakrishnan Surendra Kumar Research Department of Chemistry, Nehru Memorial College (Affiliated to Bharathidasan University),Puthanampatti -621007, Tiruchirappalli District, Tamil Nadu, South India.
  • Keerthana Selva raj Research Department of Chemistry, Nehru Memorial College (Affiliated to Bharathidasan University),Puthanampatti -621007, Tiruchirappalli District, Tamil Nadu, South India.
  • Aseer Manilal Department of Medical Laboratory Sciences, College of Medicine and Health Sciences, Arba Minch University, Arba Minch, Ethiopia.

DOI:

https://doi.org/10.29356/jmcs.v62i4.472

Keywords:

Larvicidal activity, Nematicidal activity, Antimicrobial activity, Piperidine, 2H-thiopyran derivatives

Abstract

A series of novelpyridine-connected piperidine derivatives (2a-g) and pyridine-connected 2H-thiopyran derivatives (4a-g) were synthesized and screened for larvicidal, nematicidal, and antimicrobial activities. Compound 4e exhibited larvicidal activity against second instar larvae with an LD50 value of 0.8μg/mL. In addition, 4e exhibited high nematicidal activity, with an LD50 value of 3.2μg/mL.Compounds 2e (MIC: 4 μg/mL) and 2d (MIC: 4 μg/mL) exhibited high antibacterial activity against Klebsiella pneumoniae and Escherichia coli, respectively. Compounds 4b (MIC: 0.25 μg/mL) and 4f (MIC: 2 μg/mL) showed high antifungal activity against Candida albicans and Microsporum audouinii, respectively. Therefore, it can be suggested that compounds 2e, 2d, 4e, 4b, and 4f may be useful as lead molecules for the development of new classes ofdrugs with larvicidal,nematicidal,and antimicrobial activities.

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References

Nagano, R.; Adachi, Y.; Imamura, H.; Yamada, K.; Hashizume,

T.; Morishima, H. Antimicrob. Agents Chemother. 1999, 43,

-2503.

Chang Yong, H.; Young Kwan, K.; Jay Hyok, C.; Se Ho, K.;

Hoon, C.; Do Hyun, N. J. Med. Chem.1997, 40, 3584-3593.

Stefania, M.; Maddalena, R.; Piero, V.; Paolo, D.R. Farmaco

, 54, 411-415.

Kai, L.; Ming-Liang, L.; Lian-Shun, F.; Lan-Ying, S.; Ye-Xin, S.;

Zeng-Quan, W. Eur. J. Med. Chem.2012, 47, 619-625.

Park, I.K.;Lee, S.G.; Shin, S.C.;Park, J.D.; Ahin, Y.J. J.

Agric.Food. Chem. 2002, 50, 1866-1870.

Perumal, R.V.; Adiraj, M.A.; Shanmugagpandiyan, P. Indian

Drugs 2001,381, 156-159.

Hagenbach, R.E.; Gysin, H. Experentia 1952,8, 184-188.

Ilenna, B.; Dobre, V.; Nicluescu-duvaz, I. J. Prakt. Chem.1985,

, 667-674

Ramalingan,C.; Balasubramanian Kabilan, S.; Vasudevan, M.

Med. Chem. Res. 2003, 12, 41-55.

Schneller, S. Adv. Heterocycl. Chem.1975, 18, 59-97.

Brown, M.J.; Carter, P.S.; Fenwick, A.E.; Fosberry, A.P.;

Hamprecht, D.W.; Hibbs, M.J.; Jarvest, R.L,; Mensah, L.;

Milner,P.H.; O’Hanlon, P.J.; Pope, A.J.; Richardson Casy, A.;

Coates,J.; Rostron,C. J.Pharm. Pharmaco.1976, 28, 106-110

Quaglia, W.; Pigini, M.; Piergentili, A.; Giannella, M.; Gentili,

F.; Marucci, G.; Carrieri, A.; Carotti, A.; Poggesi, E.; Leonardi,

A.; Melchiorre, C. J. Med. Chem.2002, 45, 1633–1643

Van Vliet, L.A.; Rodenhuis, N.; Dijkstra, D.; Wikström, H.;

Pugsley, T.A.; Serpa, K.A.; Meltzer, L.T.; Heffner, T.G.; Wise,

L.D.; Lajiness, M.E.; Huff, R.M.; Svensson, K.; Sundell, S.;

Lundmark, M.J. Med. Chem.2000, 43, 2871–2882.

Rogier, J. D.J.; Carter, J.S.; Talley, J.J. Patent CA

A1 2001

Yang, Y.C.; Lee, S.G.; Lee, H.K.; Kim, M.K.; Lee, S.H.; Lee,

H.S. J. Agric. Food.Chem.2002, 50, 3765–37

Sun, R.; Li, Y.; Lv, M.; Xiong, L.;Wang, Q. Bioorg. Med.

Chem. Lett.2010, 20,4693-4699.

Talontsi, F.M.; Matasyoh, J.C.; Ngoumfo, R.M.; Chepkorir, R.

Pest Biochem. Physiol. 2011, 99, 82-85.

Wing, K.D.Science 1988, 241, 467-469

Baliah, V.;Noller, C.R. J. Am. Chem. Soc.1948, 70, 3853-3858

Manilal, A.; Sujith, S.; Kiran, G.S.; Selvin, J.; Shakir, C.;

Gandhimathi, R. J. Mar. Sci.Technol. 2009, 17, 67-73.

Sampath, N.; Ponnuswamy, M.N.; Nethaji, M. Cryst. Res.

Technol. 2006, 41, 192-197.

Bauer, A.W.; Kirby, W.M.;Sherris, J.C.;Turck, M.Am. J. Clin.

Pathol. 1966, 39, 493-496.

Petersdorf, R.G.;Sherris, J.C. Am. J. Med. 1965, 39, 766-779.

Collins, A.H.; Gillespie, S.H., in:Microbiological Methods

(second ed.), Butterworth, London, Medical Microbiology-

IllustratedButterworth-Heinemann, London, 1994, 234-237.

Varma, R.S. Antifungal agents:past, present, and

futureprospects, National Academy of Chemistry and Biology,

Lucknow, India. 1998.

Published

2019-04-23

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