Araştırma Makalesi
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
Destekleyen Kurum
Bursa Uludag University Scientific Research Projects Unit
Proje Numarası
KUAP(F)-2015/22
Kaynakça
- 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.
- 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.
- 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.
- Larson A.R. (1988). Antioxidants of hiher Plants. Phytochemistry. 27, 969-978.
- 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.
- 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.
- Zheng W., Wang S.Y. (2001). Antioxidant activity and Phenolic Compounds in Selected herbs. Journal of Agricultural and Food Chemistry. 49, 5165-5170.
- Ulaş Y. (2019). Akıllı Malzemelerin Hazırlanmasında Kullanılacak Amin Türevi Monomerlerin Sentez ve Karakterizasyonu. Avrupa Bilim ve Teknolojisi Dergisi. 16, 242-246
- 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.
- Mandai H., Murota K., Suga S. (2012). Studies on the Petasis reaction of 2-pyridinecarbaldehyde Derivatives and Its Products. Heterocycles. 85, 1655-1669.
- Mandai H., Murota K., Sakai T. (2012). An improved protocol for Petasis reaction of 2-pyridinecarbaldehydes. Tetrahedron Letters. 51, 4779-4782.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- NCCLS, (1997). Performance standards for antimicrobial disk susceptibility test. Approved Standard, Wayne Pa, M2-A6.
- 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.
- Sharma O.P., Bhat T.K. (2009). DPPH antioxidant assay revisited. Food Chemistry. 113, 1202–1205.
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
Proje Numarası
KUAP(F)-2015/22
Kaynakça
- 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.
- 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.
- 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.
- Larson A.R. (1988). Antioxidants of hiher Plants. Phytochemistry. 27, 969-978.
- 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.
- 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.
- Zheng W., Wang S.Y. (2001). Antioxidant activity and Phenolic Compounds in Selected herbs. Journal of Agricultural and Food Chemistry. 49, 5165-5170.
- Ulaş Y. (2019). Akıllı Malzemelerin Hazırlanmasında Kullanılacak Amin Türevi Monomerlerin Sentez ve Karakterizasyonu. Avrupa Bilim ve Teknolojisi Dergisi. 16, 242-246
- 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.
- Mandai H., Murota K., Suga S. (2012). Studies on the Petasis reaction of 2-pyridinecarbaldehyde Derivatives and Its Products. Heterocycles. 85, 1655-1669.
- Mandai H., Murota K., Sakai T. (2012). An improved protocol for Petasis reaction of 2-pyridinecarbaldehydes. Tetrahedron Letters. 51, 4779-4782.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- NCCLS, (1997). Performance standards for antimicrobial disk susceptibility test. Approved Standard, Wayne Pa, M2-A6.
- 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.
- Sharma O.P., Bhat T.K. (2009). DPPH antioxidant assay revisited. Food Chemistry. 113, 1202–1205.
Toplam 22 adet kaynakça vardır.
Ayrıntılar
| Birincil Dil | İngilizce |
|---|---|
| Konular | Mühendislik |
| Bölüm | Makaleler |
| Yazarlar | |
| Proje Numarası | KUAP(F)-2015/22 |
| Yayımlanma Tarihi | 31 Ağustos 2019 |
| Yayımlandığı Sayı | Yıl 2019 Sayı: 16 |
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