ChemicalBook > CAS DataBase List > 5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one

5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one

Product Name
5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one
CAS No.
877636-42-5
Chemical Name
5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one
Synonyms
ML221;CS-2842;ML 221;ML-221;ML221 >=98% (HPLC);ML221, 10 mM in DMSO;ML221; ML 221; ML-221;ML-221,inhibit,ML 221,Inhibitor,ML221;4-Oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate;5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one;4H-Pyran-4-one, 5-[(4-nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-
CBNumber
CB42750703
Molecular Formula
C17H11N3O6S
Formula Weight
385.35
MOL File
877636-42-5.mol
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5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one Property

Boiling point:
624.1±55.0 °C(Predicted)
Density 
1.54±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
solubility 
DMSO: soluble5mg/mL, clear (warmed)
pka
0.30±0.33(Predicted)
form 
powder
color 
white to beige
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0919
Product name
ML221
Purity
≥98% (HPLC)
Packaging
5mg
Price
$97.85
Updated
2025/07/31
Sigma-Aldrich
Product number
SML0919
Product name
ML221
Purity
≥98% (HPLC)
Packaging
25mg
Price
$406
Updated
2025/07/31
Cayman Chemical
Product number
27313
Product name
ML-221
Packaging
10mg
Price
$109
Updated
2024/03/01
Cayman Chemical
Product number
27313
Product name
ML-221
Packaging
50mg
Price
$475
Updated
2024/03/01
Cayman Chemical
Product number
27313
Product name
ML-221
Packaging
5mg
Price
$65
Updated
2024/03/01
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5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one Chemical Properties,Usage,Production

Description

ML-221 is an antagonist of the G protein-coupled receptor (GPCR) APJ (IC50 = 4.8 μM). It is selective for APJ over the angiotensin II type 1 (AT1) receptor (IC50 = >78 μM). ML-221 antagonizes apelin 13-induced activation of APJ in cAMP and β-arrestin recruitment assays (IC50s = 0.7 and 1.75 μM, respectively). It inhibits proliferation and angiogenesis in Mz-ChA-1 cholangiocarcinoma cells when used at concentrations ranging from 5 to 15 μM. In vivo, ML-221 (150 μg/kg) reduces tumor growth in a Mz-ChA-1 mouse xenograft model. Intrathecal injection of ML-221 (10 μg per animal) reduces mechanical allodynia and heat hyperalgesia induced by chronic constriction injury (CCI) of the sciatic nerve in rats. ML-221 also inhibits pathological angiogenesis and enhances normal vessel recovery in retinal ischemic regions in a mouse model of oxygen-induced retinopathy.

Uses

ML 221 is a functional antagonist of the apelin (APJ) receptor which is shown to treat or mediate the homeostasis of the cardiovascular system.

Definition

ChEBI: 4-nitrobenzoic acid [4-oxo-6-[(2-pyrimidinylthio)methyl]-3-pyranyl] ester is a nitrobenzoic acid.

Synthesis

941868-82-2

122-04-3

877636-42-5

5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (tricarboxylic acid) (0.55 g, 3.87 mmol) was used as starting material, which was dissolved in thionyl chloride (5 mL, 68.5 mmol), and stirred for 3 hours at room temperature. After completion of the reaction, the excess thionyl chloride was removed by distillation under reduced pressure to afford 2-(chloromethyl)-5-hydroxy-4H-pyran-4-one (0.61 g, 98% yield), the product was an off-white solid.1H NMR (500 MHz, DMSO-d6) δ: 8.13 (s, 1H), 6.57 (s, 1H), 4.66 (s, 2H). Step 2: Pyrimidine-2-thiol (161 mg, 1.433 mmol) was dissolved in 2 mL of methanol, sodium methanol solution (310 mg, 1.433 mmol) was added and stirred until completely dissolved. Acetonitrile (10 mL) and 2-(chloromethyl)-5-hydroxy-4H-pyran-4-one (230 mg, 1.433 mmol) were then added and stirred for 3 h at room temperature. The completion of the reaction was confirmed by LC/MS analysis. The solvent was removed under reduced pressure to afford the crude product 5-hydroxy-2-((pyrimidin-2-ylthio)methyl)-4H-pyran-4-one (406 mg, 96% yield) and an equimolar amount of NaCl, the product was a yellow solid, which could be used in the next reaction without further purification.1H NMR (500 MHz, CDCl3) δ: 8.52 (d, 2H, J=4.9 Hz) , 7.80 (s, 1H), 7.02 (t, 1H, J=4.8Hz), 6.63 (s, 1H), 4.23 (s, 2H). Step 3: 5-Hydroxy-2-((pyrimidin-2-ylthio)methyl)-4H-pyran-4-one (200 mg, 0.847 mmol), cesium carbonate (276 mg, 0.847 mmol), and 4-nitrobenzoyl chloride (220 mg, 1.185 mmol) were dissolved in acetonitrile (8 mL) and stirred overnight at room temperature. After the reaction was complete, the solvent was removed under reduced pressure to give a light yellow solid. The solid was partitioned with about 20 mL of 1:1 ethyl acetate and water. The target product, 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate, was insoluble in both phases and was collected by filtration. The solid was dried in vacuum to afford the target product (202 mg, 62% yield) as a brown solid.1H NMR (500 MHz, DMSO-d6) δ: 8.69 (d, 2H, J=4.8 Hz), 8.68 (s, 1H), 8.40 (d, 2H, J=8.8 Hz), 8.29 (d, 2H, J=8.8 Hz), 7.29 ( t, 1H, J=4.9Hz), 6.65 (s, 1H), 4.45 (s, 2H).13C NMR (125 MHz, DMSO-d6) δ: 171.2, 168.8, 165.9, 161.7, 158.1, 150.8, 149.9, 140.3, 133.0, 131.4, 124.2 118.0, 114.6, 31.2.

storage

Store at +4°C

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6656 - 6660,5
[2] Patent: US2014/5181, 2014, A1. Location in patent: Paragraph 0155

5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one Preparation Products And Raw materials

Raw materials

Preparation Products

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5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one Suppliers

China 69 India 1 United Kingdom 1 United States 11 USA 1 Global 83
Shanghai Lollane Biological Technology Co.,Ltd.
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021-52996696，15000506266 15000506266
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+86-21-52996696
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China
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EMMX Biotechnology LLC
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888-539-0666
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Shanghai EFE Biological Technology Co., Ltd.
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021-65675885 18964387627
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Shanghai YuanYe Biotechnology Co., Ltd.
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021-61312847; 18021002903
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Shanghai Chaolan Chemical Technology Center
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Shanghai SuperLan Chemcial Technique Centre
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010-50973130 18101056239
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Twochem Co.Ltd.
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021-58111628 15800915896
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sales@twochem.com
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Angel Pharmatech, Ltd.
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View Lastest Price from 5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one manufacturers

Career Henan Chemical Co
Product
5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one 877636-42-5
Price
US $9.80/KG
Min. Order
1g
Purity
≥99%
Supply Ability
100kg
Release date
2020-01-13

877636-42-5, 5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-oneRelated Search:

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  • 5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one
  • ML221
  • ML221; ML 221; ML-221
  • CS-2842
  • ML 221;ML-221
  • 4H-Pyran-4-one, 5-[(4-nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-
  • ML221 >=98% (HPLC)
  • 4-Oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate
  • ML-221,inhibit,ML 221,Inhibitor,ML221
  • ML221, 10 mM in DMSO
  • 877636-42-5
  • API