AdipoRon

Base Information

• Chemical Name: AdipoRon
• CAS No.: 924416-43-3
• Molecular Formula: C27H28N2O3
• Molecular Weight: 428.531
• European Community (EC) Number: 809-728-0
• UNII: ND7UVH6GKJ
• ChEMBL ID: CHEMBL3393145
• Nikkaji Number: J3.236.573F
• Wikipedia: AdipoRon
• Mol file: 924416-43-3.mol

Synonyms:AdipoRon

Chemical Property of AdipoRon

Chemical Property:

• Boiling Point: 645.3±55.0 °C(Predicted)
• PKA: 13.92±0.20(Predicted)
• PSA: 58.64000
• Density: 1.21±0.1 g/cm3(Predicted)
• LogP: 4.40600
• Storage Temp.: room temp
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 428.20999276
• Heavy Atom Count: 32
• Complexity: 582

Purity/Quality:

98%,99%, ^*data from raw suppliers

AdipoRon ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC1NC(=O)COC2=CC=C(C=C2)C(=O)C3=CC=CC=C3)CC4=CC=CC=C4
• Description: Adiponectin expressed by adipocytes exerts antidiabetic effects by binding to adiponectin receptor (AdipoR)1, which activates AMPK pathways, and AdipoR2, which activates PPARα pathways. AdipoRon is an orally active small molecule AdipoR agonist that binds AdipoR1 and AdipoR2 with KD values of 1.8 and 3.1 μM, respectively. At 50 mg/kg, it acts similarly to adiponectin, activating AMPK and PPARα pathways and reducing insulin resistance and glucose intolerance in wild type mice fed a high-fat diet and in genetically obese db/db mice.
• Uses: AdipoRon is an AdipoR agonist and activates AMPK and PPAR-α pathways in the muscle and liver. AdipoRon ameliorated diabetes of genetically obese rodent model db/db mice, and prolonged the shortened lifespan of db/db mice on a high-fat diet. AdipoRon is a promising therapeutic approach for the treatment of obesity-related diseases such as type 2 diabetes.

Technology Process of AdipoRon

There total 3 articles about AdipoRon 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: 49.0%

4-amino-1-benzylpiperidine (50541-93-0) + 2-(4-benzoylphenoxy)-acetic acid (6322-83-4) → 2-(4-benzoylphenoxy)-N-[1-(phenylmethyl)-4-piperidinyl]-acetamide (924416-43-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;

DOI:10.1002/jms.3545

Reference yield:

4-Hydroxybenzophenone (1137-42-4) → 2-(4-benzoylphenoxy)-N-[1-(phenylmethyl)-4-piperidinyl]-acetamide (924416-43-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium methylate / methanol

2: sodium hydroxide; water / methanol

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine

With water; sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In methanol;

DOI:10.1002/jms.3545

Reference yield:

methyl 2-(4-benzoylphenoxy)acetate (57682-09-4) → 2-(4-benzoylphenoxy)-N-[1-(phenylmethyl)-4-piperidinyl]-acetamide (924416-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; water / methanol

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine

With water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In methanol;

DOI:10.1002/jms.3545

upstream raw materials:

4-amino-1-benzylpiperidine

2-(4-benzoylphenoxy)-acetic acid

4-Hydroxybenzophenone

methyl 2-(4-benzoylphenoxy)acetate

Refernces

• 1、 Dib, Josef,Schl?rer, Nils,Sch?nzer, Wilhelm,Thevis, Mario. "Studies on the collision-induced dissociation of adipoR agonists after electrospray ionization and their implementation in sports drug testing". . p. 407 - 417. Retrieved 2015/03/30.