Bazı Yeni Pirazollerin Sentezlenmesi

Öz

Bu makalede; ilk olarak, başlangıç materyali olan 2- 2- 4-bromofenil hidrazin -1- 2- hidroksifenil -3-fenilpropan-1,3-dion 1 sentezlendi. Sonra, başlangıç materyali ve çeşitli hidrazinlerin reaksiyonu vasıtasıyla yeni substitue pirazol türevleri 2a-e elde edildi. Yeni sentezlenen bileşiklerin yapıları spektroskopik yöntemler tarafından belirlendi

Anahtar Kelimeler

• Heterosiklik bileşikler,Hidrazin,1,3-diketon,Pirazolin

Synthesis of some new pyrazoles

Öz

In this paper; Firstly, 2- 2- 4-bromophenyl hydrazino -1- 2- hydroxyphenyl -3-phenylpropane-1,3-dione 1 , which is starting material, was synthesized. Then, the new substituted pyrazoles derivatives 2a-e were obtained via the reaction starting material and various hydrazines. The structures of new synthesized compounds were determined by spectroscopic methods.

Anahtar Kelimeler

• heterocyclic compound,hydrazine,1,3-diketone,pyrazoline

Kaynakça

1. Bailey, DM., Hansen, PE., Hlavac, AG., Baizman, ER., Pearl, J., DeFelice, AF., Feigenson, ME. 1985. 3, 4-Diphenyl-1Hpyrazole-1-propanamine antidepressants. J Med. Chem., 28: 256-260.
2. Bekhit, AA., Abdel-Aziem, T. 2004. Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents. Bioorg. Med. Chem., 12: 1935-1945.
3. Bondock, S., Fadaly, W., Metwally, MA. 2010. Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Euro. J. Med. Chem., 45: 3692-3701.
4. Cetin, A. 2016. Synthesis of Pyrazoles via Electrophilic Cyclization of Alkynes Containing Thiophene. Lett. Org. Chem., 13: 310-315.
5. Çetin, A., Bildirici, İ. 2016. A study on synthesis and antimicrobial activity of 4-acyl-pyrazoles. J.Saud. Chem. Soc,.
6. Du, S., Tian, Z., Yang, D., Li, X., Li, H., Jia, C., Qin, Z. 2015. Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1Hpyrazole-4-carboxylic Acid Amides. Molecules, 20: 8395-8408.
7. Fustero, S., Román, R., Sanz-Cervera, J. F., Simón-Fuentes, A., Cunat, A. C., Villanova, S., Murguia, M. 2008. Improved regioselectivity in pyrazole formation through the use of fluorinated alcohols as solvents: synthesis and biological activity of fluorinated tebufenpyrad analogs. J. Org. Chem., 73: 3523-3529.
8. Hainzl, D., Casida, JE. 1996. Fipronil insecticide: novel photochemical desulfinylation with retention of neurotoxicity. Proc Natl Acad Sci., 93: 12764-12767.

9. Heller, S. T., Natarajan, SR. 2006. 1, 3-Diketones from acid chlorides and ketones: A rapid and general one-pot synthesis of pyrazoles. Org. Let., 8: 2675-2678.
10. Hernández-Vázquez, E., Salgado-Barrera, S., RamírezEspinosa, JJ., Estrada-Soto, S., Hernández-Luis, F. 2016. Synthesis and molecular docking of N′-arylidene-5- (4-chlorophenyl)-1-(3, 4-dichlorophenyl)-4-methyl-1Hpyrazole-3-carbohydrazides as novel hypoglycemic and antioxidant dual agents. Bioorg. Med. Chem., 24: 2298-2306.
11. Lan, R., Liu, Q., Fan, P., Lin, S., Fernando, SR., McCallion, D., Makriyannis, A. 1999. Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. J. Med. Chem., 42: 769-776.
12. McCann, ME., Donald, R., Zhang, D., Brideau, C., Black, WC., Hanson, PD., Hickey, GJ. 2004. In vitro effects and in vivo efficacy of a novel cyclooxygenase-2 inhibitor in dogs with experimentally induced synovitis. Am. J Vet. Res., 65: 503-512.
13. Penning, TD., Talley, JJ., Bertenshaw, SR., Carter, JS., Collins, PW., Docter, S., Rogers, RS. 1997. Synthesis and biological evaluation of the 1, 5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1 H-pyrazol-1-yl] benzenesulfonamide (SC-58635, celecoxib). J. Med. Chem., 40: 1347-1365.
14. Terrett, NK., Bell, AS., Brown, D., Ellis, P. 1996. Sildenafil (Viagra TM), a potent and selective inhibitor of type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction. Bioorg. Med. Chem., 6: 1819-1824.
15. Toure, BB., Hall, DG. 2009. Natural product synthesis using multicomponent reaction strategies. Chem. Rev., 109: 4439- 4486.