(3aR,6aR)-N-(4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-yl)-1-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxamide
- Product Name
- (3aR,6aR)-N-(4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-yl)-1-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxamide
- CAS No.
- 1353644-70-8
- Chemical Name
- (3aR,6aR)-N-(4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-yl)-1-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxamide
- Synonyms
- HMPL309;HMPL 309;HMPL-309;EOS-61583;Theliatinib;Theliatinib (HMPL-309);ThTheliatinib (HMPL-309);HMPL-309;HMPL 309;HMPL309;Theliatinib, 10 mM in DMSO;(3aR,6aR)-N-(4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-yl)-1-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxamide
- CBNumber
- CB23142246
- Molecular Formula
- C25H26N6O2
- Formula Weight
- 442.51
- MOL File
- 1353644-70-8.mol
(3aR,6aR)-N-(4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-yl)-1-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxamide Property
- Boiling point:
- 675.6±55.0 °C(Predicted)
- Density
- 1.35±0.1 g/cm3(Predicted)
- storage temp.
- Store at -20°C
- solubility
- DMSO: 5 mg/mL (11.30 mM)
- pka
- 13.59±0.20(Predicted)
- form
- Solid
- color
- White to off-white
- InChIKey
- FSXCKIBROURMFT-VGSWGCGISA-N
- SMILES
- N1(C)CC[C@]2([H])CN(C(NC3C(OC)=CC4C(C=3)=C(NC3=CC=CC(C#C)=C3)N=CN=4)=O)C[C@]12[H]
N-Bromosuccinimide Price
- Product number
- CS-0027986
- Product name
- Theliatinib
- Purity
- 99.88%
- Packaging
- 5mg
- Price
- $240
- Updated
- 2021/12/16
- Product number
- CS-0027986
- Product name
- Theliatinib
- Purity
- 99.88%
- Packaging
- 10mg
- Price
- $390
- Updated
- 2021/12/16
- Product number
- CS-0027986
- Product name
- Theliatinib
- Purity
- 99.88%
- Packaging
- 25mg
- Price
- $780
- Updated
- 2021/12/16
- Product number
- CS-0027986
- Product name
- Theliatinib
- Purity
- 99.88%
- Packaging
- 50mg
- Price
- $1300
- Updated
- 2021/12/16
- Product number
- CS-0027986
- Product name
- Theliatinib
- Purity
- 99.88%
- Packaging
- 100mg
- Price
- $2200
- Updated
- 2021/12/16
(3aR,6aR)-N-(4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-yl)-1-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxamide Chemical Properties,Usage,Production
Uses
Theliatinib (Xiliertinib) is a potent, ATP-competitive, orally active and highly selective EGFR inhibitor with a Ki of 0.05 nM and an IC50 of 3 nM. Theliatinib has an IC50 of 22 nM for EGFR T790M/L858R mutant. Theliatinib shows >50-fold selectivity for EGFR than other kinases[1]. Theliatinib is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Biological Activity
Theliatinib (HMPL-309) is a potent EGFR inhibitor with a Ki value of 0.05 nM for EGFR and IC50 values of 3 nM and 22 nM for EGFR and EGFR T790M/L858R mutant, respectively. It is more than 50-fold selective for EGFR over 72 other kinases.
in vitro
Compared with erlotinib or gefitnib, theliatinib has stronger binding affinity to wild-type EGFR and is more difficult to be replaced by ATP, which makes theliatinib have better target binding effect, and the EGFR-activated tumors have stronger antitumor activity.
in vivo
Theliatinib has concentration-dependent antitumor activity in a series of patient-derived esophageal cancer xenograft models. But aberrant activation or genetic mutation of other targets such as PI3K and FGFR attenuates the antitumor activity of EGFR inhibitors, especially theliatinib.
target
| Target | Value |
| WT EGFR (Cell-free assay) | < td style="border-bottom: 1px dotted #ccc;padding: 5px;"> 3 nM|
| EGFR T790M/L858R (Cell-free assay) | 22 nM |
IC 50
EGFR: 3 nM (IC50); EGFR: 0.05 nM (Ki); EGFR (L858R/T790M): 22 nM (IC50)
References
[1] Ren Y, et al. Anti-tumor efficacy of theliatinib in esophageal cancer patient-derived xenografts models with epidermal growth factor receptor (EGFR) overexpression and gene amplification. Oncotarget. 2017 Apr 19;8(31):50832-50844. DOI:10.18632/oncotarget.17243
(3aR,6aR)-N-(4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-yl)-1-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxamide Preparation Products And Raw materials
Raw materials
Preparation Products
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