Synthesis of Acyl Derivatives of Prolyl-leucinamides
Synthetic routes to prolyl-leucinamide, N -benzyl(prolyl)leucinamide, and N -(prolyl-leucyl)morpholine were proposed. Treatment of these compounds with benzoyl chloride or acetyl chloride in the presence of triethylamine afforded the corresponding ( N -acylprolyl)leucinamides. Acyl derivatives of N...
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| Published in: | Russian journal of organic chemistry Vol. 56; no. 1; pp. 82 - 89 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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Pleiades Publishing
2020
Springer Nature B.V |
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| Abstract | Synthetic routes to prolyl-leucinamide,
N
-benzyl(prolyl)leucinamide, and
N
-(prolyl-leucyl)morpholine were proposed. Treatment of these compounds with benzoyl chloride or acetyl chloride in the presence of triethylamine afforded the corresponding (
N
-acylprolyl)leucinamides. Acyl derivatives of
N
-benzyl(prolyl)-leucinamide, and
N
-(prolyl-leucyl)morpholine were also synthesized by condensation of (
N
-benzoylprolyl)-leucine or (
N
-acetylprolyl)leucine with benzylamine or morpholine in the presence of
N, N
′-dicyclohexyl-carbodiimide. |
|---|---|
| AbstractList | Synthetic routes to prolyl-leucinamide,
N
-benzyl(prolyl)leucinamide, and
N
-(prolyl-leucyl)morpholine were proposed. Treatment of these compounds with benzoyl chloride or acetyl chloride in the presence of triethylamine afforded the corresponding (
N
-acylprolyl)leucinamides. Acyl derivatives of
N
-benzyl(prolyl)-leucinamide, and
N
-(prolyl-leucyl)morpholine were also synthesized by condensation of (
N
-benzoylprolyl)-leucine or (
N
-acetylprolyl)leucine with benzylamine or morpholine in the presence of
N, N
′-dicyclohexyl-carbodiimide. Synthetic routes to prolyl-leucinamide, N-benzyl(prolyl)leucinamide, and N-(prolyl-leucyl)morpholine were proposed. Treatment of these compounds with benzoyl chloride or acetyl chloride in the presence of triethylamine afforded the corresponding (N-acylprolyl)leucinamides. Acyl derivatives of N-benzyl(prolyl)-leucinamide, and N-(prolyl-leucyl)morpholine were also synthesized by condensation of (N-benzoylprolyl)-leucine or (N-acetylprolyl)leucine with benzylamine or morpholine in the presence of N, N′-dicyclohexyl-carbodiimide. |
| Author | Haidukevich, V. A. Knizhnikov, V. A. Kievitskaya, D. V. Popova, L. A. |
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| Cites_doi | 10.1016/j.peptides.2018.08.011 10.1128/IAI.02878-14 10.1021/cr200398y 10.15227/orgsyn.053.0025 10.2174/092986712801323243 10.1016/j.peptides.2007.10.006 10.3390/molecules13051111 |
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| Keywords | tert-butyloxycarbonylprolyl-leucine methyl ester acyl derivatives of prolyl-leucinamide morpholine prolyl-leucinamide benzylamine |
| Language | English |
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| References | de CarvalhoMPAbrahamWRCurr. Med. Chem.20121935641:CAS:528:DC%2BC38XhtF2itbrK10.2174/092986712801323243 Gordashnikova, E.I., Gaidukevich, V.A., Popova, L.A., and Knizhnikov, V.A., Vestsi Nats. Akad. Navuk Belarusi, Ser. Khim. Navuk, 2016, no. 2, p. 50. SalagaMBiniendaADraczkowskiPKossonPKordekRJozwiakKFichnaJPeptides2018108341:CAS:528:DC%2BC1cXhs1GqtL7O10.1016/j.peptides.2018.08.011 BorthwickADChem. Rev.201211236411:CAS:528:DC%2BC38XmvV2ns78%3D10.1021/cr200398y Yushkin, D.V., Bartashevich, V.A., Zubreichuk, Z.P., Murashova, M.Yu., Popova, L.A., and Knizhnikov, V.A., Vestsi Nats. Akad. Navuk Belarusi, Ser. Khim. Navuk, 2014, no. 4, p. 56. RagnarssonUKarlssonSMSandbergBELarssonL-EOrg. Synth.197353251:CAS:528:DyaE2cXkslyhsrY%3D10.15227/orgsyn.053.0025 LiJAShaYMolecules20081311111:CAS:528:DC%2BD1cXmvVSlsrY%3D10.3390/molecules13051111 PanWKastinAJPeptides20072824111:CAS:528:DC%2BD2sXhtlCqsrnJ10.1016/j.peptides.2007.10.006 KimKKimNJKimSYKimIHKimKSLeeGRInfect. Immun.201583115010.1128/IAI.02878-14 W Pan (2516_CR5) 2007; 28 2516_CR7 K Kim (2516_CR1) 2015; 83 M Salaga (2516_CR2) 2018; 108 2516_CR6 MP de Carvalho (2516_CR4) 2012; 19 JA Li (2516_CR8) 2008; 13 AD Borthwick (2516_CR3) 2012; 112 U Ragnarsson (2516_CR9) 1973; 53 |
| References_xml | – volume: 108 start-page: 34 year: 2018 ident: 2516_CR2 publication-title: Peptides doi: 10.1016/j.peptides.2018.08.011 contributor: fullname: M Salaga – volume: 83 start-page: 1150 year: 2015 ident: 2516_CR1 publication-title: Infect. Immun. doi: 10.1128/IAI.02878-14 contributor: fullname: K Kim – volume: 112 start-page: 3641 year: 2012 ident: 2516_CR3 publication-title: Chem. Rev. doi: 10.1021/cr200398y contributor: fullname: AD Borthwick – ident: 2516_CR7 – volume: 53 start-page: 25 year: 1973 ident: 2516_CR9 publication-title: Org. Synth. doi: 10.15227/orgsyn.053.0025 contributor: fullname: U Ragnarsson – volume: 19 start-page: 3564 year: 2012 ident: 2516_CR4 publication-title: Curr. Med. Chem. doi: 10.2174/092986712801323243 contributor: fullname: MP de Carvalho – ident: 2516_CR6 – volume: 28 start-page: 2411 year: 2007 ident: 2516_CR5 publication-title: Peptides doi: 10.1016/j.peptides.2007.10.006 contributor: fullname: W Pan – volume: 13 start-page: 1111 year: 2008 ident: 2516_CR8 publication-title: Molecules doi: 10.3390/molecules13051111 contributor: fullname: JA Li |
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| Snippet | Synthetic routes to prolyl-leucinamide,
N
-benzyl(prolyl)leucinamide, and
N
-(prolyl-leucyl)morpholine were proposed. Treatment of these compounds with benzoyl... Synthetic routes to prolyl-leucinamide, N-benzyl(prolyl)leucinamide, and N-(prolyl-leucyl)morpholine were proposed. Treatment of these compounds with benzoyl... |
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| StartPage | 82 |
| SubjectTerms | Acetyl chloride Chemistry Chemistry and Materials Science Derivatives Leucine Morpholine Organic Chemistry Triethylamine |
| Title | Synthesis of Acyl Derivatives of Prolyl-leucinamides |
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