1H-Pyrazolo[3,4-b]pyrazine-3-carbonitrile, 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[3-[(3R)-1-(2-hydroxyethyl)-3-piperidinyl]-1-azetidinyl]-
![1H-Pyrazolo[3,4-b]pyrazine-3-carbonitrile, 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[3-[(3R)-1-(2-hydroxyethyl)-3-piperidinyl]-1-azetidinyl]- Structure](CAS/20210305/GIF/2174938-70-4.gif)
- CAS No.
- 2174938-70-4
- Chemical Name:
- 1H-Pyrazolo[3,4-b]pyrazine-3-carbonitrile, 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[3-[(3R)-1-(2-hydroxyethyl)-3-piperidinyl]-1-azetidinyl]-
- Synonyms
- CCR4-351;CCR4-IN-38;CCR4 antagonist 3;1H-Pyrazolo[3,4-b]pyrazine-3-carbonitrile, 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[3-[(3R)-1-(2-hydroxyethyl)-3-piperidinyl]-1-azetidinyl]-
- CBNumber:
- CB98997828
- Molecular Formula:
- C24H27Cl2N7O
- Molecular Weight:
- 500.42
- MDL Number:
- MOL File:
- 2174938-70-4.mol
1H-Pyrazolo[3,4-b]pyrazine-3-carbonitrile, 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[3-[(3R)-1-(2-hydroxyethyl)-3-piperidinyl]-1-azetidinyl]- Properties
| Boiling point | 696.6±55.0 °C(Predicted) |
|---|---|
| Density | 1.49±0.1 g/cm3(Predicted) |
| storage temp. | 4°C, away from moisture |
| solubility | DMSO : 190 mg/mL (379.68 mM; Need ultrasonic) |
| pka | 15.00±0.10(Predicted) |
| form | Solid |
| color | Light yellow to yellow |
1H-Pyrazolo[3,4-b]pyrazine-3-carbonitrile, 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[3-[(3R)-1-(2-hydroxyethyl)-3-piperidinyl]-1-azetidinyl]- Chemical Properties,Uses,Production
Biological Activity
CCR4 antagonist 3 is an orally active, potent and selective CCR4 antagonist. CCR4 antagonist 3, featuring a novel piperidinyl-azetidine motif, has IC50s of 22 nM and 50 nM in the calcium flux and CTX assay. CCR4 antagonist 3 has antitumor activity[1]. CCR4 antagonist 3 (compound 38) shows no activity in a CYP450 induction assay[1]. CCR4 antagonist 3 inhibits the migration of mouse iTreg cells with an IC50 of 39 nM, while the IC50 in human iTreg cells is 33 nM[1]. CCR4 antagonist 3 (compound 38; 50 mg/kg; PO; daily; for 40 days) significantly reduces the tumor growth[1]. CCR4 antagonist 3 (0.5 mg/kg; IV) has low clearance (CL=10.2 mL/min/kg), medium volume of distribution (Vss=5.2 L/kg), a T1/2 of 6.9 h, and good bioavailability (%F = 29) of oral dosing in mouse[1]. CCR4 antagonist 3 has low clearance (CL=7.3 mL/min/kg), a half-life of 12.7 hr, and is 44% bioavailable in dog. CCR4 antagonist 3 has low clearance (CL=3.7 mL/min/kg), a long terminal half-life (10.7 hr), and good bioavailability (%F = 41) in cynomolgus monkey[1].
References
[1]. Omar Robles, et al. Novel Piperidinyl-Azetidines as Potent and Selective CCR4 Antagonists Elicit Antitumor Response as Single Agent and in Combination with Checkpoint Inhibitors. J Med Chem. 2020 Jul 15.
1H-Pyrazolo[3,4-b]pyrazine-3-carbonitrile, 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[3-[(3R)-1-(2-hydroxyethyl)-3-piperidinyl]-1-azetidinyl]- Preparation Products And Raw materials
Raw materials
Preparation Products
1H-Pyrazolo[3,4-b]pyrazine-3-carbonitrile, 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[3-[(3R)-1-(2-hydroxyethyl)-3-piperidinyl]-1-azetidinyl]- Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Aladdin Scientific | +1-+1(833)-552-7181 | sales@aladdinsci.com | United States | 52927 | 58 |
| TargetMol Chemicals Inc. | 15002134094 | marketing@targetmol.cn | China | 19698 | 58 |
| Supplier | Advantage |
|---|---|
| Aladdin Scientific | 58 |
| TargetMol Chemicals Inc. | 58 |