Synthesis and Reactions of New Chiral Linear Carboxamides with an Incorporated Peptide Linkage Using Nalidixic Acid and Amino Acids as Starting Materials
-
Nagy M. Khalifa
4b
A series of chiral linear carboxamide derivatives (2- 15) with an incorporated peptide linkage have been prepared via the coupling of 1-ethyl-1,4-dihydro-7-methyl-4-oxo-quinoline-3-carboxylic acid (nalidixic acid, 1) with appropriate amino acid methyl esters. Coupling of 1 with amino acid methyl esters gave the corresponding peptide methyl esters 2, which were hydrolyzed with methanolic sodium hydroxide to the corresponding acids 3. Hydrazinolysis of esters 2with hydrazine hydrate afforded the corresponding acid hydrazide derivatives 4. The latter compounds were coupled with appropriate aldehydes or acetophenone derivatives to afford the corresponding Schiff base derivatives 5 and 6, respectively. The hydrazide derivative was reacted with phenyl isothiocyanate or carbonyl derivatives to give the corresponding thiosemicarbazide 7 and compounds 8- 10, respectively. Also, 4b was treated with acid monoanhydrides to give the corresponding imide derivatives 11- 13. Finally, 4b was reacted with tetracarboxylic acid dianhydride derivatives to afford the corresponding diimido carboxamide derivatives 14 and 15
Graphical Abstract
Synthesis and Reactions of New Chiral Linear Carboxamides with an Incorporated Peptide Linkage Using Nalidixic Acid and Amino Acids as Starting Materials
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
Artikel in diesem Heft
- Structural Diversity of Hydrogen-Bonded Networks of [Co(NH3)6]3+ Complex Cations and Acetylenedicarboxylic Acid Anions
- Different Structural Models of YB2C2 and GdB2C2 on the Basis of Single-Crystal X-Ray Data
- An Alternative Crystal Structure of Yb26B12O57 – X-Ray Structure Determination on Flux-synthesized Single Crystals
- Assembly of Zn(II) Coordination Polymers Based on Tetrachloroterephthalate and Dipyridyl-type Ligands
- The Silicides YT2Si2 (T =Co, Ni, Cu, Ru, Rh, Pd): A Systematic Study by 89Y Solid-state NMR Spectroscopy
- Mechanothermal Synthesis of SrSnO3
- A Dimeric Copper(II) Complex of Oxalate and Oxamide Dioxime Ligands: Synthesis, Crystal Structure, Thermal Stability, and Magnetic Properties
- Dicationic Methyl Complexes of the Rare-Earth Elements
- Orthoamide und Iminiumsalze, LXXXIII [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: Triformamid (Triformylamin) / Orthoamides and Iminium Salts LXXXIII [1]. The Synthesis of Strong Formylating Reagents on Large Preparative Scale: Triformamide (Triformylamine)
- Synthesis and Reactions of New Chiral Linear Carboxamides with an Incorporated Peptide Linkage Using Nalidixic Acid and Amino Acids as Starting Materials
- Sesquiterpenoids and Diterpenes from Chamaecyparis obtusa var. breviramea f. crippsii
- The New Ternary Silicide ErCo3Si2
- Crystal Structure and NMR Study of Tetrakis(acetonitrile)silver(I) Fluorosulfonate [Ag(CH3CN)4]+[SO3F]–
- Convenient Synthesis and Molecular Structure of PPN[RhCl2(CO)2] (PPN+ = Bis(triphenylphosphane)iminium)
Artikel in diesem Heft
- Structural Diversity of Hydrogen-Bonded Networks of [Co(NH3)6]3+ Complex Cations and Acetylenedicarboxylic Acid Anions
- Different Structural Models of YB2C2 and GdB2C2 on the Basis of Single-Crystal X-Ray Data
- An Alternative Crystal Structure of Yb26B12O57 – X-Ray Structure Determination on Flux-synthesized Single Crystals
- Assembly of Zn(II) Coordination Polymers Based on Tetrachloroterephthalate and Dipyridyl-type Ligands
- The Silicides YT2Si2 (T =Co, Ni, Cu, Ru, Rh, Pd): A Systematic Study by 89Y Solid-state NMR Spectroscopy
- Mechanothermal Synthesis of SrSnO3
- A Dimeric Copper(II) Complex of Oxalate and Oxamide Dioxime Ligands: Synthesis, Crystal Structure, Thermal Stability, and Magnetic Properties
- Dicationic Methyl Complexes of the Rare-Earth Elements
- Orthoamide und Iminiumsalze, LXXXIII [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: Triformamid (Triformylamin) / Orthoamides and Iminium Salts LXXXIII [1]. The Synthesis of Strong Formylating Reagents on Large Preparative Scale: Triformamide (Triformylamine)
- Synthesis and Reactions of New Chiral Linear Carboxamides with an Incorporated Peptide Linkage Using Nalidixic Acid and Amino Acids as Starting Materials
- Sesquiterpenoids and Diterpenes from Chamaecyparis obtusa var. breviramea f. crippsii
- The New Ternary Silicide ErCo3Si2
- Crystal Structure and NMR Study of Tetrakis(acetonitrile)silver(I) Fluorosulfonate [Ag(CH3CN)4]+[SO3F]–
- Convenient Synthesis and Molecular Structure of PPN[RhCl2(CO)2] (PPN+ = Bis(triphenylphosphane)iminium)
