144564-95-4

Usage

Uses

Used in Pharmaceutical and Chemical Biology Research:
[N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid is utilized as a building block in the synthesis of nucleoside analogs, which are essential for the development of new pharmaceuticals and chemical biology research. The benzyloxy carbonyl group ensures the stability of the cytosine-1-yl group during the chemical synthesis process, allowing for selective deprotection when necessary to expose the reactive group for further reactions.
Used in Drug Discovery:
As a valuable chemical intermediate, [N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid contributes to the advancement of drug discovery by enabling the creation of novel nucleoside derivatives with potential therapeutic applications. [N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid's unique structure and protective group facilitate the development of new molecules with improved pharmacological properties and targeted effects on specific biological pathways.

Upstream product

• 212143-40-3 (N⁴-(benzyloxycarbonyl)cytosin-1-yl)acetic acid methyl ester 
• 149411-91-6 N-benzyloxycarbonyl cytosine 
• 501-53-1 benzyl chloroformate 
• 96-32-2 bromoacetic acid methyl ester 
• 55175-48-9 ethyl 2-(4-amino-2-oxopyrimidin-1(2H)-yl)acetate 
• 28230-32-2 3-hydroxy-3,4-dihydrobenzotriazine-4-one 
• 186046-91-3 methyl (cytosine-1-yl)acetate 

Downstream Products

• 149035-03-0 N⁴-(Z)-1-(carboxymethyl)cytosine pentafluorophenyl ester 
• 193621-93-1 [[2-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-((1S,2S)-2-tert-butoxycarbonylamino-cyclohexyl)-amino]-acetic acid ethyl ester 
• 189215-92-7 (2S,4R)-1-[2-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidine-2-carboxylic acid methyl ester 
• 345201-71-0 {(2-allyloxycarbonylamino-benzyl)-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid methyl ester 
• 399564-83-1 {(2-allyloxycarbonylamino-benzyl)-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid tert-butyl ester 
• 622367-01-5 (1-{[[1-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-3-methyl-butyl]-(3-methyl-butyl)-carbamoyl]-methyl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-carbamic acid benzyl ester 
• 625442-90-2 N-(2-pentacosa-10,12-diynoylaminoethyl)-N-(N⁴-(benzyloxycarbonyl)cytosin-1-ylacetyl)glycine methyl ester 
• 909866-96-2 {(3-benzyloxy-2-tert-butoxycarbonylamino-propyl)-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid ethyl ester 
• 868858-06-4 C₆₇H₇₄N₁₄O₁₄ 
• 886208-39-5 tert-butyl N^α-[[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl]-N^ε-(benzyloxycarbonyl)-L-lysinate 
• 937276-19-2 methyl N-[2-(N^α-benzyloxycarbonyl-N^β-tert-butoxycarbonyl-hydrazino)ethyl]-N-{[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl}glycinate 
• 937276-22-7 methyl N-[2-(N^β-benzyloxycarbonyl-N^α-tert-butoxycarbonylhydrazino)ethyl]-N-{[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl}glycinate 
• 915781-80-5 C₃₀H₃₄N₆O₁₀ 

Relevant academic research and scientific papers

Peptide Nucleic Acid with Double Face: Homothymine-Homocytosine Bimodal Cα-PNA (bm-Cα-PNA) Forms a Double Duplex of the bm-PNA2:DNA Triplex

Cα-bimodal peptide nucleic acids (bm-Cα-PNA) are PNAs with two faces and are designed homologues of PNAs in which each aminoethylglycine (aeg) repeating unit in the standard PNA backbone hosts a second nucleobase at Cα through a spacer chain with a triazole linker. Such bm-Cα-PNA with mixed sequences can form double duplexes by simultaneous binding to two complementary DNAs, one to the base sequence on t-amide side and the other to the bases on the Cα side chain. The synthesis of bm-Cα-PNA with homothymine (T7) on the t-amide face and homocytosine (C5) on the Cα side chain through the triazole linker was achieved by solid phase synthesis with the global click reaction. In the presence of complementary DNAs dA8 and dG6 at neutral pH, bm-Cα-PNA 1 forms a higher order pentameric double duplex of a triplex composed of two bm-Cα-PNA-C5:dG5 duplexes built on a core (bm-Cα-PNA-T7)2:dA8 triplex. Circular dichroism studies showed that assembly can be achieved by either triplex first and duplex later or vice versa. Isothermal titration calorimetry data indicated that the assembly is driven by favorable enthalpy. These results validate concurrent multiple complex formation by bimodal PNAs with additional nucleobases at Cα or Cγon the aeg-PNA backbone and open up ways to design programmed supramolecular assemblies.

Solution-phase parallel synthesis of acyclic nucleoside libraries of purine, pyrimidine, and triazole acetamides

Molecular diversity plays a pivotal role in modern drug discovery against phenotypic or enzyme-based targets using high throughput screening technology. Under the auspices of the Pilot Scale Library Program of the NIH Roadmap Initiative, we produced and report herein a diverse library of 181 purine, pyrimidine, and 1,2,4-triazole-N-acetamide analogues which were prepared in a parallel high throughput solution-phase reaction format. A set of assorted amines were reacted with several nucleic acid N-acetic acids utilizing HATU as the coupling reagent to produce diverse acyclic nucleoside N-acetamide analogues. These reactions were performed using 24 well reaction blocks and an automatic reagent-dispensing platform under inert atmosphere. The targeted compounds were purified on an automated purification system using solid sample loading prepacked cartridges and prepacked silica gel columns. All compounds were characterized by NMR and HRMS, and were analyzed for purity by HPLC before submission to the Molecular Libraries Small Molecule Repository (MLSMR) at NIH. Initial screening through the Molecular Libraries Probe Production Centers Network (MLPCN) program, indicates that several analogues showed diverse and interesting biological activities.

NEW SYNTHONS FOR THE SYNTHESIS OF CHIRAL PEPTIDE NUCLEIC ACIDS AND METHODS FOR PREPARING THE SAME

Novel l-acyl-3-amino-4-hydroxymethylpyiτolidine derivatives useful as PNA synthons optionally having protecting groups suitable of removal under mild conditions are disclosed having the formula (E) wherein: R1 is H or R-C(=O), wherein R is stra

Chiral peptide nucleic acid monomers (PNAM) with modified backbones

Convenient high yielding syntheses of optically pure PNAMs comprising l- or d-serine, l-lysine and l-arginine units linked to thymine or Cbz-cytosine are described. Simple workup and inexpensive reagents are employed and free amino acids are used as coupl

Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility

A novel class of compounds known as peptide nucleic acids, bind complementary DNA and RNA strands, and generally do so more strongly than the corresponding DNA or RNA strands while exhibiting increased sequence specificity and solubility. The peptide nucleic acids comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases, including 2,6-diaminopurine, attached to a polyamide backbone, and contain alkyl amine side chains.

Synthesis of PNA monomers and dimers by ugi four-component reaction

Peptide nucleic acids (PNA) have received great attention as tools in molecular biology and biotechnology, diagnostic agents, and potential antisense drugs. Many derivatives and analogues of PNA were designed and prepared to improve their physico-chemical

Cyclic PNA hexamer-based compound: Modelling, synthesis and inhibition of the HIV-1 RNA dimerization process

A cyclic molecule constituted by (i) a hexameric PNA moiety complementary to six among the nine residues of the dimerization initiation site loop of HIV-1 and (ii) a spacer tethering the N- to the C-extremities of the PNA, has been elaborated to inhibit the dimerization process of HIV-1 genome. This compound has been synthesized following a liquid-phase procedure (fully protected backbone approach). Preliminary agarose gel electrophoresis analyses have shown that the cyclic PNA conjugate is able to inhibit the HIV-1 dimerization.

Peptide nucleic acids having 2,6-diaminopurine nucleobases

A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than a corresponding DNA strand, and exhibit increased sequence specificity and binding affinity. The peptide nucleic acids of the invention comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone. Some PNAs of the invention also contain C1-C8alkylamine side chains.

Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility

A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than a corresponding DNA strand, and exhibit increased sequence specificity and solubility. The peptide nucleic acids comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone, and contain C1 -C8 alkylamine side chains. Methods of enhancing the solubility, binding affinity and sequence specificity of PNAs are provided.

Peptide nucleic acids having amino acid side chains

A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than the corresponding DNA or RNA strands, and exhibit increased sequence specificity and solubility. The peptide nucleic acids comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone, and contain alkylamine side chains.