73742-45-7

Basic information

• Product Name: 2,4(1H,3H)-Pyrimidinedione,5-chloro-6-(chloromethyl)-(9CI)
• Synonyms: 5-Chloro-6-(chloromethyl) pyrimidin-;5-chloro-6-(chloromethyl)-1H-pyrimidine-2,4-dione;2,4(1H,3H)-Pyrimidinedione,5-chloro-6-(chloromethyl)-(9CI);2,4(1H,3H)-PyriMidinedione, 5-chloro-6-(chloroMethyl)-;5-chloro-6-(chloromethyl)-2,4(1H,3H)-Pyrimidinedione;Tipiracil Intermediates
• CAS NO: 73742-45-7
• Molecular Formula: C₅H₄Cl₂N₂O₂
• Molecular Weight: 195.005
• EINECS: 1592732-453-0
• Product Categories: HALOMETYL
• Mol File: 73742-45-7.mol
• Article Data: 24

Chemical Properties

• Melting Point: 270-275 °C (decomp)
• Appearance: /
• Density: 1.63g/cm³
• Refractive Index: 1.583
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 5.73±0.10(Predicted)
• CAS DataBase Reference: 2,4(1H,3H)-Pyrimidinedione,5-chloro-6-(chloromethyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Pyrimidinedione,5-chloro-6-(chloromethyl)-(9CI)(73742-45-7)
• EPA Substance Registry System: 2,4(1H,3H)-Pyrimidinedione,5-chloro-6-(chloromethyl)-(9CI)(73742-45-7)

Safety Data

• Hazardous Substances Data: 73742-45-7(Hazardous Substances Data)

Usage

General Description

2,4(1H,3H)-Pyrimidinedione,5-chloro-6-(chloromethyl)-(9CI) is a chemical compound that belongs to the class of pyrimidinedione derivatives. It is also known as Chloromethyl 5-chloro-6-oxo-1,6-dihydropyrimidine-2-carboxylate. 2,4(1H,3H)-Pyrimidinedione,5-chloro-6-(chloromethyl)-(9CI) has potential therapeutic applications, particularly in the field of medicinal chemistry. It may have biological activities and could be used in the synthesis of novel drug molecules with potential pharmacological properties. It is important for researchers to study and understand its chemical structure, properties, and potential uses in drug development and other scientific applications.

InChI:InChI=1/C5H4Cl2N2O2/c6-1-2-3(7)4(10)9-5(11)8-2/h1H2,(H2,8,9,10,11)

Upstream product

• 50610-49-6 5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil 
• 7647-01-0 hydrogenchloride 
• 65-86-1 orotic acid 
• 88-00-6 ethyl 2,4-dichloro-3-oxobutanoate 
• 57-13-6 urea 
• 6153-44-2 methyl orotate 
• 91447-90-4 methyl 5-chloro-2,6-dioxo-3H-pyrimidine-4-carboxylate 
• 22126-44-9 6-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione 
• 36327-91-0 orotoaldehyde 
• 626-48-2 6-Methyluracil 
• 18592-13-7 6-chloromethyluracil 

Downstream Products

• 183204-74-2 Tipiracil 
• 16018-87-4 5-chloro-6-methyluracil 

Relevant articles and documents

Design of Novel Inhibitors of Human Thymidine Phosphorylase: Synthesis, Enzyme Inhibition, in Vitro Toxicity, and Impact on Human Glioblastoma Cancer

Overexpressed human thymidine phosphorylase (hTP) has been associated with cancer aggressiveness and poor prognosis by triggering proangiogenic and antiapoptotic signaling. Designed as transition-state analogues by mimicking the oxacarbenium ion, novel pyrimidine-2,4-diones were synthesized and evaluated as inhibitors of hTP activity. The most potent compound (8g) inhibited hTP in the submicromolar range with a noncompetitive inhibition mode with both thymidine and inorganic phosphate substrates. Furthermore, compound 8g was devoid of apparent toxicity to a panel of mammalian cells, showed no genotoxicity signals, and had low probability of drug-drug interactions and moderate in vitro metabolic rates. Finally, treatment with 8g (50 mg/(kg day)) for 2 weeks (5 days/week) significantly reduced tumor growth using an in vivo glioblastoma model. To the best of our knowledge, this active compound is the most potent in vitro hTP inhibitor with a kinetic profile that cannot be reversed by the accumulation of any enzyme substrates.

Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 1: Discovery of novel orally active inhibitors of human thymidine phosphorylase

A series of novel 6-methylene-bridged uracil derivatives have been prepared as inhibitors of human thymidine phosphorylase (TP). To enhance the in vivo antitumor activity of fluorinated pyrimidine 2′-deoxyribonucleosides such as 2′-deoxy-5-(trifluoromethyl)uridine (F3dThd), a potent TP inhibitor preventing their degradation to an inactive compound, has become a target of medicinal chemistry. We present here the synthesis and evaluation of novel human TP inhibitors. Introduction of an N-substituted aminomethyl side chain at the 6-position of 5-chlorouracil has improved water solubility and enhanced inhibitory activity compared with the known TP inhibitor, 6-amino-5-chlorouracil. Compound 42 was reasonably well absorbed in mice after oral administration. When combined with F3dThd, compound 42 exerted its TP inhibitory potency by increasing the maximum plasma concentrations of the former as evidenced in experiments with monkeys. Positive changes in pharmacokinetic profile were accompanied by the enhanced in vivo antitumor activity of this combination when compared to F3dThd alone, in mice bearing human tumor xenografts. Both biochemical and pharmacological effects appeared to fit the concept as anticipated.

SOLID STATE FORMS OF 5-CHLORO-6-[(2-IMINOPYRROLIDIN-1-YL)METHYL]PYRIMIDINE-2,4-(1H,3H)-DIONE HYDROCHLORIDE AND THEIR PROCESSES FOR THE PREPARATION THEREOF

The present invention relates to solid state forms of 5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4-(1H,3H)-dione hydrochloride compound of formula-1a and their processes for the preparation thereof and an improved process for the preparation of 5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4-(1H,3H)-dione hydrochloride. The present inventors also provides an amorphous polymorph of the combination drug consisting of 2'-deoxy-5-(trifluoromethyl) uridine and 5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4-(1H,3H)-dione monohydrochloride and its process for the preparation.

PROCESS FOR THE PREPARATION OF TIPIRACIL HYDROCHLORIDE

The present invention relates to a process for preparation of tipiracil of formula (I) or salt thereof.