ARQ 092
- Product Name
- ARQ 092
- CAS No.
- 1313883-00-9
- Chemical Name
- ARQ 092
- Synonyms
- MK-7075);ARQ092 HCl;Miransertib HCl;ARQ092 Hydrochloride;Miransertib HCl (ARQ 092);Miransertib (ARQ 092) HCl;Miransertib hydrochloride;Miransertib (ARQ 092) HCl ，S8339;3-(3-(4-(1-Aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine hydrochloride
- CBNumber
- CB83373055
- Molecular Formula
- C27H25ClN6
- Formula Weight
- 468.99
- MOL File
- 1313883-00-9.mol
ARQ 092 Property
- storage temp.
- Store at -20°C
- solubility
- DMSO: 75 mg/mL (159.92 mM);Ethanol: 4 mg/mL (8.53 mM)
- form
- Solid
- color
- Light yellow to brown
- Water Solubility
- Water: Insoluble
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
- A803512
- Product name
- ARQ092
- Purity
- 98+%
- Packaging
- 1mg
- Price
- $39
- Updated
- 2021/12/16
- Product number
- A803512
- Product name
- ARQ092
- Purity
- 98+%
- Packaging
- 5mg
- Price
- $77
- Updated
- 2021/12/16
- Product number
- A803512
- Product name
- ARQ092
- Purity
- 98+%
- Packaging
- 10mg
- Price
- $131
- Updated
- 2021/12/16
- Product number
- A803512
- Product name
- ARQ092
- Purity
- 98+%
- Packaging
- 25mg
- Price
- $208
- Updated
- 2021/12/16
- Product number
- A803512
- Product name
- ARQ092
- Purity
- 98+%
- Packaging
- 50mg
- Price
- $270
- Updated
- 2021/12/16
ARQ 092 Chemical Properties,Usage,Production
Uses
Miransertib hydrochloride (ARQ-092 hydrochloride) is a potent, orally active, selective and allosteric Akt inhibitor with IC50s of 2.7 nM, 14 nM and 8.1 nM for Akt1, Akt2, Akt3, respectively. Miransertib hydrochloride is also a potent the AKT1-E17K mutant protein inhibitor and has the potential for PI3K/AKT-driven tumors and Proteus syndrome research[1]. Miransertib hydrochloride is effective against Leishmania[2].
Synthesis
1313881-69-4
1313883-00-9
Step 4: Tert-butyl (1 -(4-(2-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamate (4.1 g) was dissolved in dichloromethane (100 mL), and a dioxane solution (20 mL) of 4.0 M HCl was slowly added. The reaction mixture was stirred at room temperature for 2.5 hours. After completion of the reaction, ether (50 mL) was added to the suspension and the solid was collected by filtration to afford 3-(3-(4-(1-aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine hydrochloride (4.032 g, white solid). The product was characterized by 1H NMR (DMSO-d6, 400 MHz) and LCMS: 1H NMR δ 8.94 (s, 3H), 8.47 (bs, 1H), 8.38 (d, J = 8.8 Hz, 1H), 8.19-8.15 (m, 1H), 8.10-8.03 (m, 3H), 7.93-7.88 (m, 1H), 7.76 (d, J = 8.4 Hz, 1H), 7.69 (d, J = 8.4 Hz, 2H), 7.52-7.40 (m, 3H), 6.92 (t, J = 7.6 Hz, 1H), 2.70-2.57 (m, 4H), 2.29-2.20 (m, 1H), 1.90-1.80 (m, 1H); LCMS: m/z 433 [M + H]+. Calculated elemental analysis (C29H27ON7-3.06HCl-0.01C4H8O2-0.03C4H10O): C 59.61, H 5.28, N 15.36; measured values: C 59.62, H 5.05, N 15.36.
in vivo
Miransertib (ARQ-092; Compound 21a) shows good absolute oral bioavailability in rats (5 mg/kg) and monkeys (10 mg/kg) with F values of 62% and 49%, respectively. The half-life is longer in rats compared to monkeys with t1/2 values of 17 h in rats versus 7 h in monkeys. The Cmax is 198 ng/mL and 258 ng/mL and the AUCinf was 5496 h?ng/mL and 2960 h?ng/mL in rats and monkeys, respectively[1].
Miransertib (ARQ-092; Compound 21a) inhibits tumor growth in a human xenograft mouse model of endometrial adenocarcinoma[1].
IC 50
Akt1: 2.7 nM (IC50); Leishmania; Akt3: 8.1 nM (IC50); Akt2: 174 nM (IC50); Akt1 E17K mutant
References
[1] Lapierre JM, et al. Discovery of 3-(3-(4-(1-Aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine (ARQ 092): An Orally Bioavailable, Selective, and Potent Allosteric AKT Inhibitor. J Med Chem. 2016 Jul 14;59(13):6455-69. DOI:10.1021/acs.jmedchem.6b00619
[2] Devki Nandan, et al. Miransertib (ARQ 092), an orally-available, selective Akt inhibitor is effective against Leishmania. PLoS One. 2018 Nov 6;13(11):e0206920. DOI:10.1371/journal.pone.0206920
ARQ 092 Preparation Products And Raw materials
Raw materials
Preparation Products
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