Merck SIP Agonist

Base Information

• Chemical Name: Merck SIP Agonist
• CAS No.: 635701-59-6
• Molecular Formula: C23H25N3O3
• Molecular Weight: 391.469
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70439828
• Wikidata: Q27076476
• Pharos Ligand ID: NPULWKPCUSAN
• ChEMBL ID: CHEMBL194419
• Mol file: 635701-59-6.mol

Synonyms:Merck SIP Agonist;635701-59-6;CAY10734;1-(4-(5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid;1,2,4-oxadiazole_based compound 26;CHEMBL194419;1-[[4-[5-[4-(2-methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic Acid;3-Azetidinecarboxylic acid, 1-[[4-[5-[4-(2-methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]-;compound 26 [PMID: 16190743];1-[4-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]benzyl]azetidine-3-carboxylic acid;1-[[4-[5-[4-(2-methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3-azetidinecarboxylic acid;3-Azetidinecarboxylic acid,1-[[4-[5-[4-(2-methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]-;1-(4-(5-(4-(2-Methylpropyl)phenyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid;1-[(4-{5-[4-(2-methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl}phenyl)methyl]azetidine-3-carboxylic acid;3-azetidinecarboxylic acid,1-((4-(5-(4-(2-methylpropyl)phenyl)-1,2,4-oxadiazol-3-yl)phenyl)methyl)-;D04LOE;GTPL2929;SCHEMBL5383882;BDBM22209;DTXSID70439828;SHQNRSGKLNMHOS-UHFFFAOYSA-N;BCP21841;AKOS022179846;1,2,4-oxadiazole based compound, 26;CS-0004247;J-504119;Q27076476;1-[[4-[5-[4-(2-methylpropyl)phenyl]-1,2,4-oxadiazol-3-ly]phenyl]methyl]-3-Azetidinecarboxylic acid

Chemical Property of Merck SIP Agonist

Chemical Property:

• Boiling Point: 565.9±60.0 °C(Predicted)
• PKA: 2.66±0.20(Predicted)
• PSA: 79.46000
• Density: 1.228±0.06 g/cm3(Predicted)
• LogP: 4.05640
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 391.18959167
• Heavy Atom Count: 29
• Complexity: 536

Purity/Quality:

98.5% ^*data from raw suppliers

CAY10734 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1=CC=C(C=C1)C2=NC(=NO2)C3=CC=C(C=C3)CN4CC(C4)C(=O)O
• Description: CAY10734 is an agonist of sphingosine-1-phosphate receptor 1 (S1P1; IC50 = 0.6 nM). It selectively binds S1P1 over S1P2, S1P3, and S1P4 receptors (IC50s = >10,000, 12,000, and 70 nM, respectively) but does also bind S1P5 receptors (IC50 = 1 nM) in radioligand binding assays. CAY10734 reduces the number of peripheral blood lymphocytes in mice, rats, and dogs, with the maximal response achieved when administered at doses of 10, 0.5, and 0.5 mg/kg, respectively. It increases graft survival in a rat skin allograft model when administered at a dose of 5 mg/kg per day in combination with cyclosporin A (CsA; ).

Technology Process of Merck SIP Agonist

There total 6 articles about Merck SIP Agonist which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde (635701-88-1) + 3-azetidinecarboxylic acid (36476-78-5) → 1-{4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzyl}-3-azetidine carboxylic acid (635701-59-6)

Guidance literature:

4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde; 3-azetidinecarboxylic acid; With acetic acid; In tetrahydrofuran; methanol; at 20 ℃; for 2h;

With sodium cyanoborohydride; In tetrahydrofuran; methanol; at 20 ℃; for 16h;

Reference yield:

4-Cyanobenzyl alcohol (874-89-5) → 1-{4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzyl}-3-azetidine carboxylic acid (635701-59-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / hydroxyamine hydrochloride; sodium bicarbonate / methanol / 5 h / Heating

2.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 0.5 h / 20 °C

2.2: 16.5 g / dimethylformamide / 2 h / 140 °C

3.1: 11.9 g / oxalyl chloride; DMSO; N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / -78 - 20 °C

4.1: AcOH / methanol / 0.33 h / 20 °C

4.2: 74 percent / sodium cyanoborohydride / methanol / 1 h

With oxalyl dichloride; hydroxylamine hydrochloride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0503244

Reference yield:

4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzyl alcohol (635702-24-8) → 1-{4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzyl}-3-azetidine carboxylic acid (635701-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 11.9 g / oxalyl chloride; DMSO; N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / -78 - 20 °C

2.1: AcOH / methanol / 0.33 h / 20 °C

2.2: 74 percent / sodium cyanoborohydride / methanol / 1 h

With oxalyl dichloride; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1021/jm0503244

upstream raw materials:

4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde

3-azetidinecarboxylic acid

(E)-N′-hydroxy-4-(hydroxymethyl)benzimidamide

4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzyl alcohol

Refernces

• 1、 Li, Zhen,Chen, Weirong,Hale, Jeffrey J.,Lynch, Christopher L.,Mills, Sander G.,Hajdu, Richard,Keohane, Carol Ann,Rosenbach, Mark J.,Milligan, James A.,Shei, Gan-Ju,Chrebet, Gary,Parent, Stephen A.,Bergstrom, James,Card, Deborah,Forrest, Michael,Quackenbush, Elizabeth J.,Wickham, L. Alexandra,Vargas, Hugo,Evans, Rose M.,Rosen, Hugh,Mandala, Suzanne. "Discovery of potent 3,5-diphenyl-1,2,4-oxadiazole sphingosine-1-phosphate-1 (S1P1) receptor agonists with exceptional selectivity against S1P2 and S1P3". . p. 6169 - 6173. Retrieved 2007/10/03.
• 2、 -. "1-((5-ARYL-1,2,4-OXADIAZOL-3-YL)BENZYL)AZETIDINE-3-CARBOXYLATES AND 1-((5-ARYL-1,2,4-OXADIAZOL-3-YL)BENZYL)PYRROLIDINE-3-CARBOXYLATES AS EDG RECEPTOR AGONISTS". Page 50. . Retrieved 2010/02/06.