Yeni p-alkilaminofenol Bileşiklerinin Sentezi ve Antimikrobiyal ve Antioksidan Aktivitelerinin Araştırılması

Öz

Alkilaminofenoller antikanser aktivitelerine sahip iyi bilinen organik yapılardır. Bu çalışmada, yüksek verimlerle petasis reaksiyonuyla  bir seri (4,5,6)  alkilaminofenol bileşiği sentezlendi. Sentezlenen bileşikler 'H-NMR ve ¹³C-NMR ile karakterize edildi. Ardından,bu bileşiklerin antimikrobiyal ve antioksidan aktivitelerini incelendi. Elde edilen bileşikler, Gram pozitif ve Gram negatif bakterilere karşı test edildi. 4 nolu bileşiğin , 10 mg / mL konsantrasyonda antimikrobiyal aktivite gösterirken, 6 nolu bileşiğin, S. aureus'ta aktivite gösterdiği görüldü. Fenolik bileşikler proksimal ve antioksidan aktivitelerinden dolayı dikkat çekici yapılardır. Alkilaminofenoller fenolik yapıya sahip olduklarından antioksidan aktiviteleri de araştırılmıştır. Diyabete, kalp hastalığına ve kansere karşı yüksek antioksidan kapasiteye sahip ilaç aktif maddeleri;  ilk kez sentezlenmiştir.

Anahtar Kelimeler

• Alkilaminofenol

Synthesis of New p-Alkylaminophenol Compounds and Investigation of Their Antimicrobial and Antioxidant Activity

Öz

Alkylaminophenols are synthetic derivatives well known for their anticancer activity. In this work, we report the antimicrobial and antioxidant activity of such compounds. A series (4,5,6) of alkylaminophenol compounds were prepared with very high yields by Petasis reaction. Synthesized compounds were characterized by ¹H-NMR and ¹³C-NMR. The obtained compounds were tested against Gram-positive and Gram-negative bacteria. The compound 4 showed antimicrobial activity at a concentration of 10 mg/mL, while the 6 compound showed activity on S. aureus. Phenolic compounds have attracted attention due to their proximal and antioxidant activities. Since alkylaminophenols have phenolic structure, their antioxidant activity has been investigated. Thus, drug-active substances with high antioxidant capacity against diabetes, heart disease, and cancer were synthesized.

Anahtar Kelimeler

• Alkylaminophenol

Kaynakça

1. Neto I., Andrade J., Fernandes A.S., Reis C.P., Salunke J.K. et al.(2016). Multicomponent Petasis-borono Mannich Preparation of Alkylaminophenols and Antimicrobial Activity Studies. ChemMedChem. 11, 2015-2023.
2. Doan P., Karjalainen A., Chandraseelan J.G., Sandberg O., Yli-Harja O. et al.(2016). Synthesis and biological screening for cytotoxic activity of N-substituted indolines and morpholines. European Journal of Medicinal Chemistry. 120, 296-303. ‎
3. Doan P., Nguyen T., Yli-Harja O., Candeias N.R., Kandhavelu M. (2017). Effect of alkylaminophenols on growth inhibition and apoptosis of bone cancer cell. European Journal of Pharmaceutical Sciences. 7, 208-216.
4. Larson A.R. (1988). Antioxidants of hiher Plants. Phytochemistry. 27, 969-978.
5. Cotelle N., Bernier J.L., Catteau J.P., Wallet J.C., Gaydou E.M. (1996). Antioxidant properties of hydroxy-flavones. Free Radical Biology and Medicine. 20, 35-43.
6. Velioğlu Y.S., Mazza G., Gao L., Oomah B.D. (1998). Antioxidant Activity and Total Phenolics in Selected Fruits Vegetables and Grain Products. Journal of Agricultural and Food Chemistry. 10, 4113-4117.
7. Zheng W., Wang S.Y. (2001). Antioxidant activity and Phenolic Compounds in Selected herbs. Journal of Agricultural and Food Chemistry. 49, 5165-5170.
8. Ulaş Y. (2019). Akıllı Malzemelerin Hazırlanmasında Kullanılacak Amin Türevi Monomerlerin Sentez ve Karakterizasyonu. Avrupa Bilim ve Teknolojisi Dergisi. 16, 242-246

9. Petasis N.A., Akritopoulou I. (1993). The boronic acid mannich reaction: A new method for the synthesis of geometrically pure allylamines. Tetrahedron Letters. 34, 583-586.
10. Mandai H., Murota K., Suga S. (2012). Studies on the Petasis reaction of 2-pyridinecarbaldehyde Derivatives and Its Products. Heterocycles. 85, 1655-1669.
11. Mandai H., Murota K., Sakai T. (2012). An improved protocol for Petasis reaction of 2-pyridinecarbaldehydes. Tetrahedron Letters. 51, 4779-4782.
12. Candeias N.R., Veiros L.F., Afonso C.A.M., Gois P.M.P. (2009). Water: A Suitable Medium for the Petasis Borono-Mannich Reaction. European Journal of Organic Chemistry. 1859-1863.
13. Candeias N.R., Montalbano F., Cal P.M.S.D., Gois P.M.P. (2010). Boronic Acids and Esters in the Petasis-Borono Mannich Multicomponent Reaction. Chemical Review. 110, 6169-6193.
14. Rosholm T., Gois P.M.P., Franzen R., Candeias N.R. (2015). Glycerol as an Efficient Medium for the Petasis Borono-Mannich Reaction. ChemistryOpen. 4, 39-46.
15. Frauenlob R., Garcia C., Bradshaw G.A., Burke H.M., Bergin E.A (2012). Copper-Catalyzed Petasis Reaction for the Synthesis of Tertiary Amines and Amino Esters. Journal of Organic Chemistry. 77, 4445-4449.
16. Shi X., Hebrault D., Humora M., Kiesman W.F., Peng H. et al. (2012). Acceleration of Petasis Reactions of Salicylaldehyde Derivatives with Molecular Sieves. Journal of Organic Chemistry. 77, 1154-1160.
17. Reddy S.R.S., Reddy B.R.P., Reddy P.V.G. (2015). Chitosan: highly efficient, green, and reusable biopolymer catalyst for the synthesis of alkylaminophenols via Petasis borono-Mannich reaction. Tetrahedron Letters. 56, 4984-4989.
18. Ying L., Limin W., Yuanyuan Sui., Jianjun Y. (2010). Solvent-free Synthesis of Alkylaminophenols via Petasis-Boronic Mannich Reaction in One Pot without Catalysts. Chinese Journal of Chemistry. 28, 2039-2044.
19. Kaboudin B., Zangooei A., Kazemi F., Yokomatsu T. (2018). Catalyst-free Petasis-type reaction: Three-component decarboxylative coupling of boronic acids with proline and salicylaldehyde for the synthesis of alkylaminophenols. Tetrahedron Letters. 59, 1046-1049.
20. NCCLS, (1997). Performance standards for antimicrobial disk susceptibility test. Approved Standard, Wayne Pa, M2-A6.
21. Dimitrova D.Z, Nedialkov P., Kitanov G. (2010). Radical scavenging and antioxidant activities of methanolic extracts from Hypericum species growing in Bulgaria. Pharmacognosy Magazine. 6, 74-78.
22. Sharma O.P., Bhat T.K. (2009). DPPH antioxidant assay revisited. Food Chemistry. 113, 1202–1205.