In-vitro Antibacterial and Antifungal Screening of Newly Synthesized Trifluoromethylated N-Heterocyclic ketenimines and 1-aza butadiene Derivatives

Subject Areas : Journal of Chemical Health Risks

Rosa  Edris Ameri ¹ (Department of Chemistry, North Tehran Branch, Islamic Azad University, Iran)
Bita  Mohtat ² (Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran)
Eskandar  Alipour ³ (Department of Chemistry, North Tehran Branch, Islamic Azad University, Iran)
Nahid  Rahimifard ⁴ (Food and Drug Control Laboratories (FDCL), Ministry of health and medical Education (MOH), Sarv Saadat Laboratory,Tehran, Iran)
Behrooz  Mirza ⁵ (Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran)

Received: 2021-03-28 Accepted : 2021-06-07 Published : 2023-03-01

Keywords:

References:

1. Arvanitidou M., Katikaridou E., Douboyas J., Tsakris A., 2005. Prognostic factors for nosocomial bacteraemia outcome: a prospective study in a Greek teaching hospital. J Hosp Infect. 61(3), 219-24.

2. Uma maheswari Devi P., Srinivasa Reddy P., Usha Rani N.R., Reddanna P., 2000. Lipoxygenase metabolites of a-linolenic acid in the development of resistance in pigeonpea, Cajanus cajan (L.) Millsp., seedlings against Fusarium udum infection. European J Plant Path. 106(9), 857-865.

3. Colle J.G., Duguid J.P., Firaser A.G., Mannion B.P., 1989. Mackie & Mecartney Practical Medicinal Microbiology. 13th edn; Churchil: Edinburgh and London. 2, 553-558.

4. Lari A.R., Alaghehbandan R., Akhlaghi L., 2005. Burn wound infections and antimicrobial resistance in Tehran, Iran: an increasing problem. Ann. Burn. Fire Disasters. 18(2), 68-73.

5. Shahcheraghi F., Feizabadi M., Yamin V., Abiri R., Abedian Z., 2003. Serovar determination, drug resistance patterns and plasmid profiles of Pseudomonas aeruginosa isolated from burn patients at two hospitals of Tehran (IRAN). Burns, 29(6), 547-551.

6. Romão C.M.C.P.A., Faria Y.N.D., Pereira L.R., Asensi M.D., 2005. Susceptibility of clinical isolates of multiresistant Pseudomonas aeruginosa to a hospital disinfectant and molecular typing. Mem. Inst. Oswaldo Cruz. 100(5), 541-548.

7. Pereira M.D.F., Chevrot R., Rosenfeld E., Thiery V., Besson T., 2007. Synthesis, and evaluation of the antimicrobial activity of novel quinazolinones. J Enzyme Inhib Med Chem. 22(5), 577-583.

8. Tamaoki S., Yamauchi Y., Nakano Y., Sakano S., Asagarasu A., Sato M., 2007. Pharmacological properties of 3-amino-5, 6, 7, 8-tetrahydro-2-{4-[4-(quinolin-2-yl) piperazin-1-yl] butyl} quinazolin-4 (3H)-one (TZB-30878), a novel therapeutic agent for diarrhea-predominant irritable bowel syndrome (IBS) and its effects on an experimental IBS model. J Pharmacol Exp Ther. 322(3), 1315-1323.

9. Alafeefy A.M., Kadi A.A., Al-Deeb O.A., El-Tahir K.E., Al-jaber N.A., 2010. Synthesis, analgesic, and anti-inflammatory evaluation of some novel quinazoline derivatives. Eur J Med Chem. 45(11), 4947-4952.

10. Li Q., Mitscher L.A., Shen L.L., 2000. The 2‐pyridone antibacterial agents: bacterial topoisomerase inhibitors. Med Res Rev. 20(4), 231-93.

11. Cao Y., Zhang Y., Wu S., Yang Q., Sun X., Zhao J., Pei F., Guo Y., Tian C., Zhang Z., Wang H., Ma L., Liu J., Wang X., 2015. Synthesis and biological evaluation of pyridinone analogues as novel potent HIV-1 NNRTIs. Bioorg Med Chem. 23(1), 149-159.

12. Zhu S., Wang J., Chandrashekar G., Smith E., Liu X., Zhang Y. 2010. Synthesis and evaluation of 4-quinazolinone compounds as potential antimalarial agents. Eur J Med Chem. 25(9), 3864-3869.

13. Gülcan Ö., Erol D.D., Uzbay T., Aytemir M.D., 2001. Synthesis of 4(1H)-pyridinone derivatives and investigation of analgesic and antiinflammatory activities. Il Farmaco. 56(4), 251-256.

14. Cao S., Feng Y., Jiang Y., Liu S., Ding G., Li R., 2005. Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains. Bioorg Med Chem Lett. 15(7), 1915-1917.

15. Rahman M.U., Rathore A., Siddiqui A.A., Parveen G., Yar M.S., 2014. Synthesis and characterization of quinazoline derivatives: search for hybrid molecule as diuretic and antihypertensive agents. J Enzyme Inhib Med Chem. 29(5), 733-743.

16. El-Azab A.S., Abdel-Hamide S.G., Sayed-Ahmed M.M., Hassan G.S., El-Hadiyah T.M., Al-Shabanah O.A., Al-Deeb O.A. El-Subbagh H.I., 2013. Novel 4(3H)-quinazolinone analogs: synthesis and anticonvulsant activity. Med Chem Res. 22(6), 2815–2827.

17. Zhang J., Liu J., Ma Y., Ren D., Cheng P., Zhao J., Zhang F., Yao Y., 2016. One-pot synthesis and antifungal activity against plant pathogens of quinazolinone derivatives containing an amide moiety. Bioorg Med Chem Lett. 26 (9), 2273-2277.

18.Martin K., Szilvia B., Zsuzsa B., Jirina S. Jarmila V., 2017. Synthesis and biological evolution of hydrazones derived from 4-(trifluoromethyl)benzohydrazide. Bioorg Med Chem Lett. 27(23), 5185-5189.

19. Faria R.A., Nunes da Ponte M., Bogel-Łukasik E., 2015. Solubility studies on the system of trihexyl(tetradecyl)phosphonium bis[(trifluoromethyl)sulfonyl]amide) ionic liquid and pharmaceutical and bioactive compounds. Fluid Ph. Equilibria. 385(1), 1-9.

20. Luzina E.L., Popov A.V., 2014. Synthesis and anticancer activity evaluation of 3,4-mono- and bicyclosubstituted N-(het)aryl trifluoromethyl succinimides. J Fluor Chem. 168(12), 121-127.

21. Chernykh A.V., Feskov I.O., Chernykh A.V., Daniliuc C.G., Tolmachova N.A., Volochnyuk D.M., Radchenko D.S., 2016. Synthesis of fluorinated building blocks based on spiro[3.3]heptane scaffold. Tetrahedron. 72(7), 1036-1041.

22. Ameri R.E., Mohtat B., Alipour E., Mirza B., 2020. An isocyanide based three-component reaction under catalyst-free conditions for synthesis of new and stable trifluoromethylated ketenimines and 1-azabutadienes. Org Prep Proced Int. 52(1), 37-47.

23. Rahimifard N., Bagheri E., Asgarpanah G., Balajadeh B.K., Yazdi H.R., 2014. Antibacterial Activity of Total Extract, Petroleum Ether, Chloroform, Ethyl Acetate and Aqueous Fractions of Aerial Parts of Heliotropium bacciferum. J Med Plants. 13(52), 122-135.

24. Hakemi-Vala M., Mehrara M., Pourramezan M., Rahimifard N., 2017. Comparison the Antimicrobial Effects of the Flowering Aerial Parts of Glaucium vitellinum Boiss. and Buhse and Gaillonia aucheri Jaub. and Spach. Novelty in Biomedicine. 5(1), 24-29.

25. Rahimifard N., Naseri M.,2016. Bifidobacteria bifidum and Bifidobacteria infantis Effects on Salmonella enteritidis. J Pure Appl Microb. 10(3), 1885-1889.

26. Hafezian M., Asgarpanah J., Rahimifard N., 2016. Chemical Composition and Antimicrobial Activity of the Essential Oil from the Endemic Species Pycnocycla bashagardiana Mozaff. Lat Am J Pharm. 35(7), 1634-1639.

27. Rahimifard N., Moslemi L., Moghni M., Aghilee N., 2017. Antibacterial Effect of Dionysia revoluta Boiss.

Extracts on Acinetobacter bumannii Isolated from Wound of Burned Patients. Biosci Biotechnol Res Asia. 14(1), 219-224.

28. Brooks G., Carroll K.C., Butel J., Morse S., 2007. Medical Microbiology, 2rd ed., McGraw-Hill Medical: New York. pp. 258-273.