Leniolisib
- Product Name
- Leniolisib
- CAS No.
- 1354690-24-6
- Chemical Name
- Leniolisib
- Synonyms
- CS-2818;CDZ 173;Leniolisib;leniolisib(CDZ 173);CDZ173;CDZ-173;CDZ 173;Rupatadine Impurity 2-d8;Leniolisib, 10 mM in DMSO;leniolisib (CDZ 173) ，S8752;inhibit,Inhibitor,Phosphoinositide 3-kinase,Leniolisib,PI3K,CDZ-173,CDZ 173;(S)-1-(3-((6-(6-Methoxy-5-(trifluoromethyl)pyridin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)pyrrolidin-1-yl)propan-1-one
- CBNumber
- CB03311734
- Molecular Formula
- C21H25F3N6O2
- Formula Weight
- 450.46
- MOL File
- 1354690-24-6.mol
Leniolisib Property
- storage temp.
- Store at -20°C
- solubility
- DMF:PBS (pH 7.2) (1:1):0.5(Max Conc. mg/mL);1.11(Max Conc. mM)
DMSO:71.67(Max Conc. mg/mL);159.09(Max Conc. mM)
Ethanol:16.5(Max Conc. mg/mL);36.63(Max Conc. mM) - form
- A crystalline solid
- color
- White to off-white
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.
N-Bromosuccinimide Price
- Product number
- 28078
- Product name
- Leniolisib
- Packaging
- 1mg
- Price
- $49
- Updated
- 2024/03/01
- Product number
- 28078
- Product name
- Leniolisib
- Packaging
- 25mg
- Price
- $770
- Updated
- 2024/03/01
- Product number
- 28078
- Product name
- Leniolisib
- Packaging
- 5mg
- Price
- $227
- Updated
- 2024/03/01
- Product number
- 28078
- Product name
- Leniolisib
- Packaging
- 10mg
- Price
- $403
- Updated
- 2024/03/01
- Product number
- CS-7524
- Product name
- Leniolisib
- Purity
- 99.25%
- Packaging
- 10mg
- Price
- $350
- Updated
- 2021/12/16
Leniolisib Chemical Properties,Usage,Production
Uses
Leniolisib (CDZ173) is a potent and selective PI3Kδ inhibitor. Leniolisib has the potential for immunodeficiency disorders treatment.
Biological Activity
Leniolisib (CDZ 173) is a potent and selective PI3Kδ inhibitor with IC50s of 0.244, 0.424, 2.23 and 0.011 μM for PI3Kα, PI3Kβ, PI3Kγ and PI3Kδ, respectively.
Synthesis
The synthesis of leniolisib starts with compound 1 as shown in Scheme 1 (Hoegenauer et al., 2016; Hoegenauer et al., 2017).
6-Benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (compound 1) is coupled with (S)-tert-butyl 3-aminopyrrolidine-1-carboxylate (compound 2) in the presence of triethylamine at 120 °C for 42 h to give compound 3 a 93% yield. The benzyl group is deprotected with 20% palladium hydroxide on carbon and ammonium formate in methanol at 65 °C for 2 h to give compound 4 a 66% yield. Compound 4 is coupled with 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine (compound 5) in the presence of sodium -tert-butoxide, tris(dibenzylideneacetone)dipalladium(0), 2-di-t-butylphosphino-2'-(N,N-dimethylamino)biphenyl in tert-butanol at 100 °C for 5 h to give compound 6 a 74% yield. Deprotection of the Boc group in DCM/TFA, followed by coupling with propionyl chloride in the presence of sodium bicarbonate in DCM at room temperature for 1 h gives the final compound 7 (leniolisib) a 76% yield.
in vivo
Oral leniolisib lead to a dose-dependent reduction in PI3K/AKT pathway activity and resolve the immune dysregulation with normalization of circulating transitional and na?ve B cells and reduction in PD-1+CD4+ and senescent CD57+CD8+ T cells. After 12 weeks of treatment, all patients show amelioration of lymphoproliferation with lymph node sizes and spleen volumes reduced by 39% (mean, range 26-57%) and 40% (mean, range: 13-65%), respectively[1].
target
| Target | Value |
| PI3Kδ (Cell-free assay) | 0.011 μM |
| PI3Kα (Cell-free assay) | 0.244 μM |
| 0.424 μM | |
| DNA-PK () | 0.88 μM |
| DNA-PK (Cell-free assay) | 0.88 μM |
IC 50
PI3Kδ: 11 nM (IC50); PI3Kα: 280 nM (IC50); PI3Kβ: 480 nM (IC50); PI3Kγ: 2.57 μM (IC50); DNA-PK: 880 nM (IC50)
References
[1] Rao V, et al. Effective 'Activated PI3Kd Syndrome' -targeted therapy with PI3Kd inhibitor leniolisib. The New England journal of medicine: NEJM. ISSN 0028-4793; 1533-4406 DOI:10.1182/blood-2017-08-801191
[2] Hoegenauer K, et al. Discovery of CDZ173 (Leniolisib), Representing a Structurally Novel Class of PI3K Delta-Selective Inhibitors. ACS Med Chem Lett. 2017 Aug 25;8(9):975-980. DOI:10.1021/acsmedchemlett.7b00293
Leniolisib Preparation Products And Raw materials
Raw materials
Preparation Products
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