Synthesis and Reactions of New Chiral Linear Dipeptide Candidates Using Nalidixic Acid as Starting Material
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Nagy M. Khalifa
A series of dipeptide heterocyclic derivatives 4-15 were synthesized using methyl 2-{[(1-ethyl- 7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridin-3-yl)carbonyl]amino}-3-ethylbutanoate (3) as starting material. Treatment of 3 with L-phenylalanine methyl ester hydrochloride afforded the corresponding dipeptide methyl ester derivative 4, which was treated with hydrazine hydrate to afford the dipeptide acid hydrazide 5. Compound 5 was coupled with aldehyde and acetophenone derivatives to afford the corresponding Schiff bases 6a-f. The hydrazide derivative 5 was reacted with ethyl acetoacetate or acetone to give compounds 7 and 8, respectively. Reaction of 5 with carbon disulfide at different conditions afforded compounds 9 and 10, which were treated with hydrazine hydrate to give the 1-amino-2-dipeptido-1,3,4-triazole derivative 11. In addition, 5 was reacted with phenyl isothiocyanate to give the thiosemicarbazide derivative 12, which was cyclized with sodium hydroxide to the dipeptido 1-phenyl-1,3,4-triazole derivative 13. Finally, treatment of 13 with methyl iodide afforded the S-methyl derivative 14, which was reacted with hydrazine hydrate to give the hydrazine derivative 15.
Graphical Abstract
Synthesis and Reactions of New Chiral Linear Dipeptide Candidates Using Nalidixic Acid as Starting Material
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Articles in the same Issue
- Synthesis and Crystal Structure of a “High-temperature” Phase of Li[H2NC(O)NH], the Missing Alkali-Metal Ureate
- Strukturen von polaren Magnesiumorganylen: Synthese und Struktur von Basen-Addukten des Bis(pentamethylcyclopentadienyl)magnesiums
- The Mixed-valent Mercury(I/II) Compounds Hg3(HAsO4)2 and Hg6As2O10
- New Intermetallic Zinc Compounds with Ordering Variants of the KHg2 and LT-SrZn5 Type
- Effects of Metal Ions and N-Donor Ligands with Different Coordination Characters on the Construction of d10 Metal-organic Complexes with Selective Photocatalytic Activities
- Synthesis and Characterization of Novel Re(BIAN)(CO)3Cl Derivatives Including the First Example of a Water-soluble Tricarbonyl Rhenium(I) Complex with Bis(imino)acenaphthene Ligands
- Hydrothermal Synthesis and Crystal Structure of a One-dimensional Cobalt (II) Coordination Polymer with Two Organic Ligands
- Vinylsilylferrocenes and Ethynyl(vinyl)silylferrocenes. Synthesis, Multinuclear Magnetic Resonance Study and DFT Calculations
- One-pot Multi-component Synthesis of Mono- and Bis-indolylimidazole Derivatives Using Zn2+@KSF and Their Antibacterial Activity
- Catalyst-free, Solvent-promoted and Scalable Multicomponent Synthesis of 3-Aminoalkylated Indoles via a Mannich-type Reaction
- Synthesis and Reactions of New Chiral Linear Dipeptide Candidates Using Nalidixic Acid as Starting Material
- Synthesis and Characterization of Ammonium Acesulfamate
- Two Rare Hydroazulene-type Sesquiterpenes from the Roots of Aristolochia yunnanensis
- Spiroalkaloids and Coumarins from the Stem Bark of Pauridiantha callicarpoides
