Antimicrobial Investigation and Synthesis of Novel 1H-Pyrazole-4- (5H)-yl Diazene Derivatives

Öz

In this study, firstly, ethyl 1-(4-bromophenyl)-2-(1,3,5-triphenyl-1H-pyrazol-4-(5H)-ylidene)

hydrazine (1), which has starting material, was synthesized. A series of new 1H-pyrazol-4-yl diazene (2a-h)

derivatives were synthesized from reaction the obtained starting material and various hydrazines. The synthesized

compounds were confirmed by spectral methods such as elemental analysis, IR and NMR. Antibacterial activity of

the compounds were investigated by disc diffusion method against to Gram (+) and Gram (-) bacteria. Gentamicin

and Cefotaxime antibiotics were used as the control group. None of the doses showed any antibacterial activity

compared to the control.

Anahtar Kelimeler

• Antimicrobial,control group,hydrazine,hydrazono,pyrazole

Yeni 1H-Pirazol-4-(5H)-il Diazen Türevlerinin Sentezi ve Antimikrobiyal Aktivitelerinin İncelenmesi

Öz

Bu çalışmada, ilk olarak başlangıç maddesi olan etil 1-(4-bromofenil)-2-(1,3,5-trifenil-1H-pirazol-4-(5H)-

ilden)hidrazinin (1) sentezi gerçekleştirildi. Elde edilen başlangıç maddesi çeşitli hidrazinlerle etkileştirilerek

bir seri yeni 1H-pirazol-4-il diazen (2a-h) türevleri sentezlendi. Sentezlenen bileşikler elementel analiz, IR ve

NMR gibi spektral yöntemlerle karakterize edildi. Sentezlenen bileşiklerin antibakteriyel aktiviteleri Gram (+)

ve Gram (-) bakteriler üzerinde disk difüzyon yöntemi kullanılarak araştırıldı. Kontrol grubu olarak Gentamisin,

Cefotaxime antibiyotikleri kullanılırken sentezlenen bileşiklerin kontrol grubu ile karşılaştırıldığında herhangi bir

dozun antibakteriyel aktivite göstermediği gözlendi.

Anahtar Kelimeler

• Antimikrobiyal,hidrazin,hidrazon,kontrol grup,pirazol

Kaynakça

1. Adam NM, Wilson SP, Duvert P, 2012. The development of penflufen as a seed treatment for potatoes in northern Europe. In The Dundee Conference. Crop Protection in Northern Britain, 28-29 February 2012, Cambridge.
2. Bustos C, Alvarez-Thon L, Cárcamo JG, Garland MT, Sánchez C, 2011. 2-[2-(4-Bromophenyl)hydrazinylidene]-1,3-diphenylpropane-1,3-dione, Acta Crystallographica E 67: 1426-1431.
3. Cetin A, Gündüz B, Menges N, Bildirici I, 2017. Unsymmetrical pyrazole-based new semiconductor oligomer: synthesis and optical properties, Polymer Bulletin 74: 2593-2604.
4. Çetin A, 2016. Synthesis of pyrazoles via electrophilic cyclization of alkynes containing thiophene, Letters in Organic Chemistry 13: 310-315.
5. Çetin A, Bildirici İ, 2016. A study on synthesis and antimicrobial activity of 4-acyl-pyrazoles, Journal of Saudi Chemical Society
6. Dohare P, Ansari KR, Quraishi MA, Obot IB, 2017. Pyranpyrazole derivatives as novel corrosion inhibitors for mild steel useful for industrial pickling process: Experimental and Quantum Chemical study, Journal of Industrial and Engineering Chemistry 52: 197-210.
7. Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A, 2011. From 2000 to Mid-2010: a fruitful decade for the synthesis of pyrazoles, Chemical Reviews 111: 6984-7034.
8. Gondek E, 2013. Photovoltaic solar cells based on pyrazole derivative, Materials Letter 112: 94-99.

9. Hainzl D, Casida JE, 1996. Fipronil insecticide: novel photochemical desulfinylation with retention of neurotoxicity, Proceedings of the National Academy of Sciences 93: 12764-12767.
10. Hamama WS, El‐Gohary HG, Soliman M, Zoorob HHA, 2012. Versatile synthesis, pm3‐semiempirical, antibacterial and antitumor evaluation of some bioactive pyrazoles, Journal Heterocyclic Chemistry 49: 543-554.
11. Heller ST, Natarajan SR. 2006. 1,3-Diketones from acid chlorides and ketones: a rapid and general one-pot synthesis of pyrazoles, Organic Letters 8: 2675-2678.
12. Isloor AM, Vijesh AM, Shetty P, Sundershan S, Fun HK, 2013. New pyrazole derivatives containing 1, 2, 4-triazoles and benzoxazoles as potent antimicrobial and analgesic agents, European Journal Medicinal Chemistry 62: 410-415.
13. Joule JA, Mills K, 2012. Heterocyclic chemistry at a glance. Third Edition, London, UK. 230 p.
14. Kaushik D, Kumar R, Khan SA, Chawla G, 2012. Pharmacological screening for anti-inflammatory, analgesic activity of pyrazolyl derivatives along with molecular docking studies. Med Chem Res 21: 3646-3655.
15. Küçükgüzel ŞG, Şenkardeş S, 2015. Recent advances in bioactive pyrazoles. Euro J Med Chem 97: 786-815.
16. Radi S, Salhi S, Radi A, 2010. Synthesis and preliminary biological activity of some new pyrazole derivatives as acyclonucleoside analogues. Lett Drug Des Discov 7: 27-30.
17. Sanger DJ, Morel E, Perrault G, 1996. Comparison of the pharmacological profiles of the hypnotic drugs, zaleplon and zolpidem. Euro J Pharma 313: 35-42.
18. Shaw AT, Kim DW, Nakagawa K, Seto T, Crinó L, Ahn MJ, Wu Y L, 2013. Crizotinib versus chemotherapy in advanced ALK-positive lung cancer, New England Journal of Medicine, 368: 2385-2394.
19. Stakhira P, Cherpak V, Khomyak S, Volynyuk D, Hotra Z, Voznyak L, Oliynyk O, 2011. Properties of 2, 6-di-tert-butyl-4-(2, 5-diphenyl-3, 4-dihydro-2H-pyrazol-3-yl)-phenol as hole-transport material for life extension of organic light emitting diodes. Opt Mater 33: 1727-173.
20. Varghese B, Al-Busafi SN, Suliman FO, Al-Kindy SM, 2017. Unveiling a versatile heterocycle: pyrazoline-a review, RSC Advances, 7: 46999-47016.
21. Villafañe F, Gómez-Iglesias P, Guyon F, Khatyr A, Ulrich G, Knorr M, Martín-Alvarez JM, 2015. Luminescent rhenium (I) tricarbonyl complexes with pyrazolylamidino ligands: photophysical, electrochemical, and computational studies. Dalton Transactions 44: 17516-17528.
22. Walsh JK, Fry J, Erwin CW, Scharf M, Roth T, Vogel GW, 1998. Efficacy and tolerability of 14-day administration of zaleplon 5mg and 10mg for the treatment of primary insomnia, Clinical Drug Investigation 16: 347-354.
23. Zaidan MR, Noor Rain A, Badrul AR, Adlin A, Norazah A, Zakiah I. 2005. In vitro screening of five local medicinal plants for antibacterial activity using disc diffusion method. Trop Biomed 22: 165-170.
24. Zolfigol MA, Ayazi-Nasrabadi R, Baghery S, Khakyzadeh V, Azizian S, 2016. Applications of a novel nano magnetic catalyst in the synthesis of 1, 8-dioxo-octahydroxanthene and dihydropyrano [2, 3-c] pyrazole derivatives, Journal of Molecular Catalysis A: Chemical 418: 54-67.