Öz
Bu çalışmada, sübstitüe fenetilaminlerden (8-12) karbonildiimidazol (CDI) ile ılıman şartlarda simetrik ve asimetrik bazı üre türevleri (13-22) sentezlenmiştir. Bunun için öncelikle sübstitüe fenetilaminler karbonildiimidazol ile su içerisinde reaksiyona sokulmuş ve imidazolid ara ürününün oluşmasından sonra ikinci bir sübstitüe fenetilamin (8-12) verilerek hedef ürünler (13-22) % 43 - % 66 arasında verimlerle sentezlenmiştir. Bunun için öncelikle sübstitüe fenetilaminler karbonildiimidazol ile su içerisinde reaksiyona sokulmuş ve imidazolid ara ürününün oluşmasından sonra ikinci bir sübstitüe fenetilamin (8-12) verilerek hedef ürünler (13-22) % 43 - % 66 arasında verimlerle sentezlenmiştir.
Anahtar Kelimeler
Simetrik üre asimetrik üre sübstitüe fenetilamin karbonildiimidazol
Destekleyen Kurum
Erzurum Teknik Üniversitesi
Proje Numarası
2019/15
Teşekkür
Bu çalışma, Erzurum Teknik Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi tarafından “2019/15” kodlu proje ile desteklenmiştir.
Kaynakça
- Boonlarppradab C, Suriyachadkun C, Supothina S, Laksanacharoen P, 2016. Amethysione and amethysamide, new metabolites from Streptosporangium amethystogenes BCC 27081. The Journal of Antibiotics, 69: 459-463.
- Byrne B, Rotchild R, 1999. 1H NMR studies of drugs with achiral and chiral lanthanide shift reagents: applications to the anticonvulsant pheneturide. Chirality, 11 (7): 529-535.
- Cannon JG, 1985. Dopamine agonists: structure-activity relationships. Progress in Drug Research, 29: 303-414.
- Chaturvedi D, 2011. Recent Developments on the Carbamation of Amines. Current Organic Chemistry, 15 (10): 1593-1624.
- Choi SS, Cha BY, Kagami I, Lee YS, Sasaki H, Suenaga K, Teruya T, Yonezawa T, Nagai K, Woo JT, 2011. N,N՜-diphenethylurea isolated from Okinawan ascidian Didemnum molle enhances adipocyte differentiation in 3T3-L1 cells. The Journal of Antibiotics, 64: 277-280.
- Diaz DJ, Darko AK, White LM, 2007. Transition Metal‐Catalyzed Oxidative Carbonylation of Amines to Ureas. European Journal of Organic Chemistry, 2007 (27): 4453-4465.
- Hanson GR, Venturelli PJ, Fleckenstein AE, 2005. Drugs and society. Jones and Bartlett Publishers, 9. Baskı, S. 588, Ontario-CANADA.
- Klegeris A, Korkina LG, Greenfield SA, 1995. Autoxidation of dopamine: a comparison of luminescent and spectrophotometric detection in basic solutions. Free Radical Biology & Medicine, 18: 215-222.
- Madhava G, Subbaiah KV, Sreenivasulu R, and Naga Raju C, 2012. Synthesis of novel urea and thiourea derivatives of diphenylphosphoramidate and their antimicrobial activity. Der Pharmacia Lettre, 4 (4): 1194-1201.
- Manickam M, Jalani HB, Pillaiyar T, Boggu PR, Sharma N, Venkateswararao E, Li YJ, Jeon ES, Son MJ, Woo SH, Jung SH, 2018. Design and synthesis of sulfonamidophenylethylureas as novel cardiac myosin activator. European Journal of Medicinal Chemistry, 143: 1869-1887.
- McMorris TC, Chimmani R, Alisala K, Staake MD, Banda G, Kelner MJ, 2010. Structure-activity studies of urea, carbamate, and sulfonamide derivatives of acylfulvene. Journal of Medicinal Chemistry, 53 (3): 1109-1116.
- Padiya KJ, Gavade S, Kardile B, Tiwari M, Bajare S, Mane M, Gaware V, Varghese S, Harel D, and Kurhade S, 2012. Unprecedented “In Water” Imidazole Carbonylation: Paradigm Shift for Preparation of Urea and Carbamate. Organic Letters, 14 (11): 2814–2817.
- Pochampally J, Valeru A, Macha R, Kishorekumar A, Tigulla P, Gandu B, Gangagnirao A, 2014. Design, Efficient new synthesis, evaluation of antimicrobial activity and molecular modelling studies of novel aryl substituted urea derivatives. Der Pharma Chemica, 6 (2): 269-282.
- Sellami M, Chaari A, Aissa I, Bouaziz M, Gargouri Y, 2013. Newly synthesized dopamine ester derivatives and assessment of their antioxidant, antimicrobial and hemolytic activities. Process Biochemistry, 48: 1481-1487.
- Tundo P, Selva M, 2002. The Chemistry of Dimethyl Carbonate. Accounts of Chemical Research, 35 (9): 706-716.
Öz
In this study, some symmetrical and non-symmetrical urea derivatives (13-22) have been synthesized from substituted phenethylamines (8-12) with carbonyldiimidazole (CDI) under mild conditions. For this purpose, substituted phenethylamines were reacted with carbonyldiimidazole in water, and after the formation of the imidazolide intermediate, the corresponding products (13-22) have been synthesized in yields between 43% - 66% by giving a second substituted phenethylamine (8-12). For this purpose, substituted phenethylamines were reacted with carbonyldiimidazole in water, and after the formation of the imidazolide intermediate, the corresponding products (13-22) have been synthesized in yields between 43% - 66% by giving a second substituted phenethylamine (8-12).
Anahtar Kelimeler
Symmetrical urea non-symmetrical urea substituted phenethylamine carbonyldiimidazole
Proje Numarası
2019/15
Kaynakça
- Boonlarppradab C, Suriyachadkun C, Supothina S, Laksanacharoen P, 2016. Amethysione and amethysamide, new metabolites from Streptosporangium amethystogenes BCC 27081. The Journal of Antibiotics, 69: 459-463.
- Byrne B, Rotchild R, 1999. 1H NMR studies of drugs with achiral and chiral lanthanide shift reagents: applications to the anticonvulsant pheneturide. Chirality, 11 (7): 529-535.
- Cannon JG, 1985. Dopamine agonists: structure-activity relationships. Progress in Drug Research, 29: 303-414.
- Chaturvedi D, 2011. Recent Developments on the Carbamation of Amines. Current Organic Chemistry, 15 (10): 1593-1624.
- Choi SS, Cha BY, Kagami I, Lee YS, Sasaki H, Suenaga K, Teruya T, Yonezawa T, Nagai K, Woo JT, 2011. N,N՜-diphenethylurea isolated from Okinawan ascidian Didemnum molle enhances adipocyte differentiation in 3T3-L1 cells. The Journal of Antibiotics, 64: 277-280.
- Diaz DJ, Darko AK, White LM, 2007. Transition Metal‐Catalyzed Oxidative Carbonylation of Amines to Ureas. European Journal of Organic Chemistry, 2007 (27): 4453-4465.
- Hanson GR, Venturelli PJ, Fleckenstein AE, 2005. Drugs and society. Jones and Bartlett Publishers, 9. Baskı, S. 588, Ontario-CANADA.
- Klegeris A, Korkina LG, Greenfield SA, 1995. Autoxidation of dopamine: a comparison of luminescent and spectrophotometric detection in basic solutions. Free Radical Biology & Medicine, 18: 215-222.
- Madhava G, Subbaiah KV, Sreenivasulu R, and Naga Raju C, 2012. Synthesis of novel urea and thiourea derivatives of diphenylphosphoramidate and their antimicrobial activity. Der Pharmacia Lettre, 4 (4): 1194-1201.
- Manickam M, Jalani HB, Pillaiyar T, Boggu PR, Sharma N, Venkateswararao E, Li YJ, Jeon ES, Son MJ, Woo SH, Jung SH, 2018. Design and synthesis of sulfonamidophenylethylureas as novel cardiac myosin activator. European Journal of Medicinal Chemistry, 143: 1869-1887.
- McMorris TC, Chimmani R, Alisala K, Staake MD, Banda G, Kelner MJ, 2010. Structure-activity studies of urea, carbamate, and sulfonamide derivatives of acylfulvene. Journal of Medicinal Chemistry, 53 (3): 1109-1116.
- Padiya KJ, Gavade S, Kardile B, Tiwari M, Bajare S, Mane M, Gaware V, Varghese S, Harel D, and Kurhade S, 2012. Unprecedented “In Water” Imidazole Carbonylation: Paradigm Shift for Preparation of Urea and Carbamate. Organic Letters, 14 (11): 2814–2817.
- Pochampally J, Valeru A, Macha R, Kishorekumar A, Tigulla P, Gandu B, Gangagnirao A, 2014. Design, Efficient new synthesis, evaluation of antimicrobial activity and molecular modelling studies of novel aryl substituted urea derivatives. Der Pharma Chemica, 6 (2): 269-282.
- Sellami M, Chaari A, Aissa I, Bouaziz M, Gargouri Y, 2013. Newly synthesized dopamine ester derivatives and assessment of their antioxidant, antimicrobial and hemolytic activities. Process Biochemistry, 48: 1481-1487.
- Tundo P, Selva M, 2002. The Chemistry of Dimethyl Carbonate. Accounts of Chemical Research, 35 (9): 706-716.
Ayrıntılar
| Birincil Dil | Türkçe |
|---|---|
| Konular | Kimya Mühendisliği |
| Bölüm | Kimya / Chemistry |
| Yazarlar | |
| Proje Numarası | 2019/15 |
| Yayımlanma Tarihi | 1 Eylül 2020 |
| Gönderilme Tarihi | 7 Şubat 2020 |
| Kabul Tarihi | 5 Mayıs 2020 |
| Yayımlandığı Sayı | Yıl 2020 Cilt: 10 Sayı: 3 |