29569-30-0

Basic information

• Product Name: 5-carbamoylmethyluridine
• Synonyms: 5-carbamoylmethyluridine
• CAS NO: 29569-30-0
• Molecular Formula: C₁₁H₁₅N₃O₇
• Molecular Weight: 301.2527
• Mol File: 29569-30-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.653g/cm³
• Refractive Index: 1.639
• CAS DataBase Reference: 5-carbamoylmethyluridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-carbamoylmethyluridine(29569-30-0)
• EPA Substance Registry System: 5-carbamoylmethyluridine(29569-30-0)

Safety Data

• Hazardous Substances Data: 29569-30-0(Hazardous Substances Data)

Usage

Description

5-Carbamoylmethyluridine, also known as 5-Uridineacetamide, is a modified nucleoside belonging to the class of uridines. It is uridine in which the hydrogen at position 5 of the pyrimidine ring is substituted by a 2-amino-2-oxoethyl group. This modification makes it a putative cancer biomarker, indicating its potential role in cancer research and therapeutics.

Uses

Used in Cancer Research and Diagnosis:
5-Carbamoylmethyluridine is used as a biomarker for cancer, particularly due to its potential association with various types of cancer. Its presence in biological samples can help in the early detection, diagnosis, and monitoring of cancer progression.
Used in Pharmaceutical Development:
5-Carbamoylmethyluridine is used as a key component in the development of novel pharmaceuticals targeting cancer cells. Its unique structure allows for the design of drugs that can specifically interact with cancer-related biological pathways, potentially leading to more effective treatments with fewer side effects.
Used in Drug Delivery Systems:
Similar to gallotannin, 5-carbamoylmethyluridine can also be employed in the development of drug delivery systems. These systems can enhance the delivery, bioavailability, and therapeutic outcomes of drugs targeting cancer cells, by encapsulating 5-carbamoylmethyluridine or its derivatives within organic or metallic nanoparticles.

InChI:InChI=1/C11H15N3O7/c12-6(16)1-4-2-14(11(20)13-9(4)19)10-8(18)7(17)5(3-15)21-10/h2,5,7-8,10,15,17-18H,1,3H2,(H2,12,16)(H,13,19,20)/t5-,7-,8-,10-/m1/s1

Synthetic route

5-Hydroxy-uridin (957-77-7) + 2-(triphenylphosphoranylidene)acetamide (38821-11-3) → 5-(carbamoylmethyl)uridine (29569-30-0)

Conditions	Yield
In 1,4-dioxane Heating;	99%

2-thio-5-<(methylcarboxy)methyl>uridine (20299-15-4) → 5-(carbamoylmethyl)uridine (29569-30-0)

Conditions	Yield
With ammonium hydroxide In water at 25℃; for 18h; Substitution;	75%

5-<(methylcarboxy)methyl>uridine (29428-50-0) → 5-(carbamoylmethyl)uridine (29569-30-0)

Conditions	Yield
With ammonium hydroxide Ambient temperature;	61.6%
With ammonia In methanol for 48h;
With ammonia In methanol for 48h;
With ammonia In methanol at 20℃; for 48h;
With ammonium hydroxide In methanol at 20℃;

uridine (58-96-8) → 5-(carbamoylmethyl)uridine (29569-30-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: pyridine / 3 h / 60 °C 2: acetic anhydride; acetic acid; bromine / 0 - 20 °C 3: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 5: sodium methylate / methanol / 16 h / 50 °C 6: ammonia / methanol / 48 h View Scheme
Multi-step reaction with 6 steps 1: pyridine / 3 h / 60 °C 2: bromine; acetic anhydride; acetic acid / 0 - 20 °C / Sealed tube 3: triethylamine; dmap / dichloromethane / 0.5 h / 0 - 20 °C 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 5: sodium methylate; methanol / 16 h / 50 °C 6: ammonia / methanol / 48 h View Scheme
Multi-step reaction with 6 steps 1: pyridine / 3 h / 60 °C 2: bromine; acetic anhydride / acetic acid / 0 - 20 °C / Sealed tube 3: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 5: sodium methylate / methanol / 16 h / 50 °C 6: ammonia / methanol / 48 h / 20 °C View Scheme

Tri-O-acetyluridine (4105-38-8) → 5-(carbamoylmethyl)uridine (29569-30-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: acetic anhydride; acetic acid; bromine / 0 - 20 °C 2: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 4: sodium methylate / methanol / 16 h / 50 °C 5: ammonia / methanol / 48 h View Scheme
Multi-step reaction with 5 steps 1: bromine; acetic anhydride; acetic acid / 0 - 20 °C / Sealed tube 2: triethylamine; dmap / dichloromethane / 0.5 h / 0 - 20 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 4: sodium methylate; methanol / 16 h / 50 °C 5: ammonia / methanol / 48 h View Scheme
Multi-step reaction with 5 steps 1: bromine; acetic anhydride / acetic acid / 0 - 20 °C / Sealed tube 2: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 4: sodium methylate / methanol / 16 h / 50 °C 5: ammonia / methanol / 48 h / 20 °C View Scheme

5-bromo-2’,3’,5’-tri-O-acetyluridine (105659-31-2, 105659-32-3) → 5-(carbamoylmethyl)uridine (29569-30-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 3: sodium methylate / methanol / 16 h / 50 °C 4: ammonia / methanol / 48 h View Scheme
Multi-step reaction with 4 steps 1: triethylamine; dmap / dichloromethane / 0.5 h / 0 - 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 3: sodium methylate; methanol / 16 h / 50 °C 4: ammonia / methanol / 48 h View Scheme
Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 3: sodium methylate / methanol / 16 h / 50 °C 4: ammonia / methanol / 48 h / 20 °C View Scheme

5-bromo-N3-benzoyl-2’,3’,5’-tri-O-acetyluridine (1261157-39-4) → 5-(carbamoylmethyl)uridine (29569-30-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 2: sodium methylate / methanol / 16 h / 50 °C 3: ammonia / methanol / 48 h View Scheme
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 2: sodium methylate; methanol / 16 h / 50 °C 3: ammonia / methanol / 48 h View Scheme
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 2: sodium methylate / methanol / 16 h / 50 °C 3: ammonia / methanol / 48 h / 20 °C View Scheme

N3-benzoyl-2',3',5'-O-triacetoxyuridine-5-malonic acid dimethyl ester (1261157-40-7) → 5-(carbamoylmethyl)uridine (29569-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 16 h / 50 °C 2: ammonia / methanol / 48 h View Scheme
Multi-step reaction with 2 steps 1: sodium methylate; methanol / 16 h / 50 °C 2: ammonia / methanol / 48 h View Scheme
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 16 h / 50 °C 2: ammonia / methanol / 48 h / 20 °C View Scheme

triethylamine carbonate (15715-58-9) + 5-(carbamoylmethyl)uridine (29569-30-0) → 5-carbamoylmethyluridine-TP tetrakistriethylammonium salt

Conditions	Yield
Stage #1: 5-(carbamoylmethyl)uridine With trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 0℃; for 0.166667h; Stage #2: With trichlorophosphate for 2h; Inert atmosphere; Stage #3: triethylamine carbonate Further stages;	10.52%

triethylamine carbonate (15715-58-9) + 5-(carbamoylmethyl)uridine (29569-30-0) → 5-carbamoylmethyl-UTP tetrakis(triethylammonium) salt

Conditions	Yield
Stage #1: 5-(carbamoylmethyl)uridine With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 0℃; for 0.166667h; Stage #2: With trichlorophosphate for 2h; Inert atmosphere; Stage #3: triethylamine carbonate Further stages;	10.52%

5-(carbamoylmethyl)uridine (29569-30-0) → C11H14Cl2N3O8P

Conditions	Yield
Stage #1: 5-(carbamoylmethyl)uridine With trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 0℃; for 0.166667h; Stage #2: With trichlorophosphate for 2h; Inert atmosphere;

5-(carbamoylmethyl)uridine (29569-30-0) → C11H16N3O15P3

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 0.17 h / 0 °C 1.2: 2 h / Inert atmosphere 2.1: tributyl-amine; bis(tri-n-butylammonium) pyrophosphate / acetonitrile / 0.42 h View Scheme

5-(carbamoylmethyl)uridine (29569-30-0) → 5-carbamoylmethyl-UTP tetrakis(triethylammonium) salt

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 0.17 h / 0 °C 1.2: 2 h / Inert atmosphere 2.1: tributyl-amine; bis(tri-n-butylammonium) pyrophosphate / acetonitrile / 0.42 h 3.1: aq. buffer / 1 h / 20 °C View Scheme

Upstream product

• 1261157-40-7 N₃-benzoyl-2',3',5'-O-triacetoxyuridine-5-malonic acid dimethyl ester 
• 1261157-39-4 5-bromo-N3-benzoyl-2’,3’,5’-tri-O-acetyluridine 
• 105659-31-2 5-bromo-2’,3’,5’-tri-O-acetyluridine 
• 4105-38-8 Tri-O-acetyluridine 
• 58-96-8 uridine 
• 957-77-7 5-Hydroxy-uridin 
• 38821-11-3 2-(triphenylphosphoranylidene)acetamide 
• 20299-15-4 2-thio-5-<(methylcarboxy)methyl>uridine 
• 29428-50-0 5-<(methylcarboxy)methyl>uridine 

Relevant articles and documents

Isolation and characterization of 5-carbamoylmethyluridine and 5- carbamoylmethyl-2-thiouridine from human urine

Two new modified uracil nucleosides, 5-carbamoylmethyuridine (ncm5U, I) and 5-carbamoylmethyl-2-thiouridine (ncm5s2U, II) were isolated from a 24 hr collection of a normal human urine. The structures were assigned on the basis of UV, NMR and mass spectral data and confirmed by comparison of the spectral data and HPLC mobilities with those of authentic samples. On the basis of experimental data it appears possible that 5-carbamoylmethyl- 2-thio-uridine (ncm5s2U, II) may be a degradation product produced from a labile precursor by the chemical treatments during the isolation procedure. However, the other nucleoside (ncm5U,I) certainly appears to be of metabolic origin and was also found in the urines of one chronic myelogenous leukemia and one lung carcinoma patient.

ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.

MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides modified nucleosides, nucleotides, and nucleic acids, and methods of using them.