GPR39-C3

Base Information

• Chemical Name: GPR39-C3
• CAS No.: 1621175-65-2
• Molecular Formula: C₁₈H₁₉ClN₆O₂S
• Molecular Weight: 418.907
• Mol file: 1621175-65-2.mol

Synonyms:

Chemical Property of GPR39-C3

Chemical Property:

• Boiling Point: 662.1±65.0 °C(Predicted)
• PKA: 7.43±0.10(Predicted)
• Density: 1.462±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

TC-G 1008 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: GPR39-C3 is a potent agonist of the orphan G protein-coupled receptor GPR39 with EC50 values of 0.8 and 0.4 nM for cAMP production in HEK293 cells expressing human and rat receptors, respectively. It is selective for GPR39 over a panel of kinases (IC50s = >10 μM), ghrelin and neurotensin-1 receptors (IC50s = >30 μM), and a variety of enzymes, transporters, or G protein-coupled receptors. GPR39-C3 increases secretion of glucagon-like peptide 1 (GLP-1; ) in STC-1 mouse enteroendocrine cells (EC50 = 0.06 μM) and is protective against cytokine-induced cell death in INS-1E rat insulinoma cells (EC50 = 0.02 μM). In vivo, GPR39-C3 (30 mg/kg) increases the amount of active GLP-1 in sera by 6-fold in glucose-challenged mice when administered concurrently with a dipeptidyl peptidase 4 (DPP-4) inhibitor.
• Uses: TC-G 1008 is the first potent, selective, and orally bioavailable GPR39 agonist.

Technology Process of GPR39-C3

There total 6 articles about GPR39-C3 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: 87.0%

N-(3-chloro-4-(((2-chloro-6-(pyridin-2-yl)pyrimidin-4-yl)amino)methyl)phenyl)methanesulfonamide + methylamine (74-89-5) → N-[3-chloro-4-[[[2-(methylamino)-6-(2-pyridinyl)-4-pyrimidinyl]amino]methyl]phenyl]methanesulfonamide (1621175-65-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethanol; at 130 ℃; for 0.5h; Microwave irradiation; Sealed tube;

DOI:10.1021/ml500240d

Reference yield:

N-(4-(aminomethyl)-3-chlorophenyl)methanesulfonamide (882424-28-4) + C10H9ClN4 → N-[3-chloro-4-[[[2-(methylamino)-6-(2-pyridinyl)-4-pyrimidinyl]amino]methyl]phenyl]methanesulfonamide (1621175-65-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 160 - 180 ℃; Microwave irradiation; Sealed tube;

DOI:10.1021/ml500240d

Reference yield:

4-amino-2-chlorobenzonitrile (20925-27-3) → N-[3-chloro-4-[[[2-(methylamino)-6-(2-pyridinyl)-4-pyrimidinyl]amino]methyl]phenyl]methanesulfonamide (1621175-65-2)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 0 - 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 °C / Reflux

3: N-ethyl-N,N-diisopropylamine / acetonitrile / 160 - 180 °C / Microwave irradiation; Sealed tube

With pyridine; lithium aluminium tetrahydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ml500240d

upstream raw materials:

N-(4-(aminomethyl)-3-chlorophenyl)methanesulfonamide

4-amino-2-chlorobenzonitrile

N-(3-chloro-4-cyanophenyl)methanesulfonamide

methylamine