55726-41-5

Usage

Classification

Synthetic acylated pyrimidine nucleoside analog.

Derivative

It is a derivative of cytarabine, a commonly used chemotherapy agent.

Potential applications

Antiviral and anticancer agent.

Anti-tumor activity

Promising anti-tumor activity in preclinical studies, particularly in breast and lung cancer models.

Antiviral activity

Demonstrated activity against a range of viruses, including herpes simplex virus and hepatitis B virus.

Research status

Ongoing research to explore its potential as a valuable addition to cancer and viral infection treatments.

InChI:InChI=1/C19H31N3O6/c1-2-3-4-5-6-7-8-9-15(24)20-14-10-11-22(19(27)21-14)18-17(26)16(25)13(12-23)28-18/h10-11,13,16-18,23,25-26H,2-9,12H2,1H3,(H,20,21,24,27)/t13-,16-,17+,18-/m1/s1

Upstream product

• 334-48-5 1-decanoic acid 
• 147-94-4 arabinosyl cytosine 

Relevant academic research and scientific papers

Preparation method for nano-assembly of novel cytarabine prodrug and application

The invention discloses a preparation method for a nano-assembly of a novel cytarabine prodrug and application. According to the invention, biocompatible decanoic acid is chosen as a hydrophobic material to be covalently bound with cytarabine, so that the novel cytarabine amphiphilic small-molecule prodrug, i.e., decanoate-cytarabine (DA-Ara), is synthesized, the prodrug can be self-assembled intonanorods in water by a nano-precipitation method, and when the nanorods are redispersed into water, a highly stable nanoscale oral medication preparation can be obtained. The result of an in-vitro cytotoxicity experiment indicates that the prodrug DA-Ara shows high sensitivity to human chronic cell leukemia cells K562, and can quickly take effect in inhibiting cells, the effect is persistent, andcytotoxicity is higher. The drug loading capacity of the oral preparation of the prodrug is high, the concentration of nano-suspension is high, the storage time is long, the stability is good, the oral preparation is easier to produce, store and transport, the safety is high, and a broad application prospect is provided for the oral medication method of cytarabine.

In-vitro transdermal penetration of cytarabine and its N4-alkylamide derivatives

Objectives: The aim of this study was to synthesise and determine the transdermal penetration of cytarabine alkylamide derivatives and assess the correlation of flux with physicochemical properties. Methods: The alkylamide derivatives of cytarabine were synthesised by acylation at the N4-amino group by the mixed anhydride method. The in-vitro permeation studies were performed using the Franz diffusion cell methodology. Furthermore, partition coefficients (n-octanol-water) and aqueous solubility of the N4-alkylamide derivatives of cytarabine were determined in order to obtain information about their lipophilicity and hydrophilicity. Key findings: The N4-alkylamides of cytarabine (acetyl, butanoyl, hexanoyl, octanoyl, and decanoyl derivatives) showed decreased hydrophilicity and increased lipophilicity. The log D values of the alkylamides were higher than that of the parent compound and increased linearly as the alkyl chain lengthened. N4-hexanoyl-4-amino-1-[(2R,3S,4R,5R)-3,4- dihydroxy-5-(hydroxymethyl)oxolan-2-yl] pyrimidin-2-one) showed the highest median steady-state flux (Jss) of 89.0 nmol/cm2 per h in the series, which shows a high statistical difference with the parent compound flux value (3.70 nmol/cm2 per h). Conclusions The prodrug approach appears to be a promising strategy for the enhancement of transdermal penetration of cytarabine.

N4 -acylarabinonucleosides

An N4 -acyl-1-β-D-arabinofuranosylcytosine having the following formula SPC1 Wherein R is an aliphatic acyl group having 3 to 35 carbon atoms. The compounds of this invention are useful as a cancer chemotherapeutic agent for controlling tumors, e.g., in mice, an insecticide, and a fungicidal surface active agent.