| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
Purity: ≥98%
BMS-986169 is a novel and potent negative allosteric modulator of GluN2B which is a N-methyl-d-aspartate receptor subtype. BMS-986169 has potential to be used in major depressive disorder. BMS-986169 exhibited high binding affinity for the GluN2B allosteric site (Ki = 4.0 nM) and selective inhibition of GluN2B receptor function (IC50 = 24 nM) in cells. BMS-986169 has demonstrated an acceptable safety and toxicology profile and was selected as a preclinical candidate for further evaluation in major depressive disorder.
| ln Vitro |
The chemical syntheses of BMS-986169 and its corresponding prodrug BMS-986163
Suzuki coupling of the commercial boronate ester 14 with 4-benzyloxybromobenzene, followed by hydroboration/oxidation of the resulting product 15 provided the racemic trans-hydroxypiperidine (±)-16. The first eluting enantiomer (S,S)-16, obtained from preparative chiral supercritical fluid chromatography (SFC), was fully deprotected to afford the phenolic piperidine (S,S)-17. The bromopyrrolidinone (±)-21, obtained in two steps from benzylamine 18, was coupled with (S,S)-17 to provide hydroxypiperidine 22 as a mixture of diastereomers. Retentive deoxyfluorination of 22 and separation of the lactam diastereomers provided compound 23 and BMS-986169. The relative and absolute stereochemistry of BMS-986169 was unambiguously established through single crystal X-ray diffraction using anomalous scattering refinement.27 Preparation of the prodrug BMS-986163 was accomplished through reaction with phosphorus oxychloride and hydrolytic workup. |
|---|---|
| References |
| Molecular Formula |
C23H27FN2O2
|
|---|---|
| Molecular Weight |
382.471089601517
|
| Exact Mass |
382.205
|
| CAS # |
1801151-08-5
|
| Related CAS # |
1801151-09-6 ;1801151-08-5;
|
| PubChem CID |
91820646
|
| Appearance |
Typically exists as solid at room temperature
|
| LogP |
3.8
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
28
|
| Complexity |
529
|
| Defined Atom Stereocenter Count |
3
|
| SMILES |
F[C@@H]1CN(CC[C@H]1C1C=CC(=CC=1)O)[C@H]1C(N(CC2C=CC(C)=CC=2)CC1)=O
|
| InChi Key |
UNVYDSCXINFREZ-BHDDXSALSA-N
|
| InChi Code |
InChI=1S/C23H27FN2O2/c1-16-2-4-17(5-3-16)14-26-13-11-22(23(26)28)25-12-10-20(21(24)15-25)18-6-8-19(27)9-7-18/h2-9,20-22,27H,10-15H2,1H3/t20-,21+,22+/m0/s1
|
| Chemical Name |
(R)-3-((3S,4S)-3-fluoro-4-(4-hydroxyphenyl)piperidin-1-yl)-1-(4-methylbenzyl)pyrrolidin-2-one
|
| Synonyms |
BMS-986169; BMS 986169; BMS986169
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6146 mL | 13.0729 mL | 26.1458 mL | |
| 5 mM | 0.5229 mL | 2.6146 mL | 5.2292 mL | |
| 10 mM | 0.2615 mL | 1.3073 mL | 2.6146 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
 ACS Med Chem Lett.2018 Apr 13;9(5):472-477. |
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