55726-44-8

Basic information

• Product Name: 1-β-D-Arabinofuranosyl-4-stearoylaminopyrimidin-2(1H)-one
• Synonyms: 1-β-D-Arabinofuranosyl-4-octadecanoylamino-1,2-dihydropyrimidin-2-one;1-β-D-Arabinofuranosyl-4-stearoylaminopyrimidin-2(1H)-one
• CAS NO: 55726-44-8
• Molecular Formula: C27H47N3O6
• Molecular Weight: 509.683
• Mol File: 55726-44-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.2g/cm³
• Refractive Index: 1.564
• CAS DataBase Reference: 1-β-D-Arabinofuranosyl-4-stearoylaminopyrimidin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-β-D-Arabinofuranosyl-4-stearoylaminopyrimidin-2(1H)-one(55726-44-8)
• EPA Substance Registry System: 1-β-D-Arabinofuranosyl-4-stearoylaminopyrimidin-2(1H)-one(55726-44-8)

Safety Data

• Hazardous Substances Data: 55726-44-8(Hazardous Substances Data)

Usage

Type

Synthetic nucleoside analog

Explanation

S-110 is a man-made compound that resembles natural nucleosides.

Explanation

S-110 is derived from cytarabine, a nucleoside used in the treatment of leukemia and lymphoma.
3. Anti-cancer activity

Explanation

S-110 has demonstrated the ability to inhibit cancer cell growth and induce apoptosis (programmed cell death).
4. Enhanced antitumor activity compared to cytarabine

Explanation

S-110 shows improved effectiveness in fighting cancer compared to its predecessor, cytarabine.
5. Overcoming resistance to cytarabine

Explanation

S-110 can effectively target cancer cells that have developed resistance to cytarabine-based treatments.

Explanation

S-110 works by blocking the replication of cancer cells and triggering their death through apoptosis.
7. Potential treatment for various types of cancer

Explanation

S-110 is being researched as a possible treatment option for a range of cancer types.
8. Promise as a novel and effective therapeutic agent

Explanation

S-110 shows potential as a new and powerful cancer treatment option.

Basis

Modified form of cytarabine

Mechanism of action

Inhibition of cancer cell replication and induction of apoptosis

InChI:InChI=1/C27H47N3O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(32)28-22-18-19-30(27(35)29-22)26-25(34)24(33)21(20-31)36-26/h18-19,21,24-26,31,33-34H,2-17,20H2,1H3,(H,28,29,32,35)/t21-,24-,25+,26-/m1/s1

Upstream product

• 638-08-4 stearic anhydride 
• 147-94-4 arabinosyl cytosine 

Relevant articles and documents

Lipophilic 5'-(Alkyl phosphate) Esters of 1-β-D-Arabinofuranosylcytosine and Its N4-Acyl and 2,2'-Anhydro-3'-O-acyl Derivatives as Potential Prodrugs

Lipophilic 5'-(alkyl phosphate) esters of 1-β-D-arabinofuranosylcytosine (ara-C) and several N4-acyl and 3'-O-acyl-2,2'-anhydro derivatives of ara-C were synthesized as potential prodrugs of ara-C 5'-monophosphate (ara-CMP).Alkylphosphorylation of ara-C, N4-palmitoyl-ara-C, and N4-stearoyl-ara-C was achieved in a single continuous operation by allowing the nucleoside to react with POCl3 in trimethyl or triethyl phosphate and adding the appropriate anhydrous alcohol directly to the intermediate phosphorodichloridate without isolation.Similar reaction of cytidine yielded cytidine 5'-(alkyl phosphate) esters, which on treatment with myristoyl or palmitoyl chloride in the presence of boron trifluoride gave 3'-O-acyl-2,2'-anhydro-ara-C 5'-(alkyl phosphate) esters.Ara-C 5'-(n-butyl phosphate) (1b), N4-palmitoyl-ara-C 5'-(n-butyl phosphate) (1h), and 2,2'-anhydro-3'-O-palmitoyl-ara-C 5'-(n-butyl phosphate) (2h) were tested against L1210/ara-C leukemia in mice in the hope that this kinase-deficient tumor would respond to treatment with these "prephosphorylated" derivatives, but no activity was observed.Of the simple 5'-(alkyl phosphate) esters tested in culture against L1210 leukemic cells, only ara-C 5'-(glyceryl phosphate) (1g) showed toxicity comparable to ara-CMP (ID50 = 0.35 and 0.65 μM, respectively), suggesting that β-hydroxyalkyl phosphate esters may be worthwhile to examine further as prodrugs of ara-CMP.