N-[[[3-[(Benzoyl)amino]phenyl]amino](thioxo)methyl]-3,4,5-trimethoxybenzamide

Base Information

• Chemical Name: N-[[[3-[(Benzoyl)amino]phenyl]amino](thioxo)methyl]-3,4,5-trimethoxybenzamide
• CAS No.: 330829-30-6
• Molecular Formula: C24H23N3O5S
• Molecular Weight: 465.52
• European Community (EC) Number: 694-371-1
• DSSTox Substance ID: DTXSID90980483
• Wikidata: Q82966439
• ChEMBL ID: CHEMBL2031084
• Mol file: 330829-30-6.mol

Synonyms:MRT 10;330829-30-6;MRT-10;N-[[[3-[(Benzoyl)amino]phenyl]amino](thioxo)methyl]-3,4,5-trimethoxybenzamide;N-[(3-Benzamidophenyl)carbamothioyl]-3,4,5-trimethoxybenzamide;CHEMBL2031084;6384-24-3;N-((3-Benzamidophenyl)carbamothioyl)-3,4,5-trimethoxybenzamide;Oprea1_307096;SCHEMBL12129860;DTXSID90980483;n-(3-benzamidophenylcarbamothioyl)-3,4,5-trimethoxybenzamide;EX-A7242;BDBM50383034;STK099293;AKOS000619111;NCGC00386664-02;MRT-10, >=98% (HPLC);MS-28575;HY-108507;CS-0029030;E98716;AG-690/15430158;J-019016;N-[[[3-Benzoylamino)phenyl]amino]thioxomethyl]-3,4,5-trimethoxybenzamide;N-[3-({[(3,4,5-trimethoxybenzoyl)amino]carbothioyl}amino)phenyl]benzamide;3,4,5-trimethoxy-N-({3-[(phenylcarbonyl)amino]phenyl}carbamothioyl)benzamide;N-{[(3-{[Hydroxy(phenyl)methylidene]amino}phenyl)imino](sulfanyl)methyl}-3,4,5-trimethoxybenzene-1-carboximidic acid

Chemical Property of N-[[[3-[(Benzoyl)amino]phenyl]amino](thioxo)methyl]-3,4,5-trimethoxybenzamide

Chemical Property:

• PSA: 144.03000
• LogP: 5.27080
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥15mg/mL
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 465.13584202
• Heavy Atom Count: 33
• Complexity: 659

Purity/Quality:

≥98% ^*data from raw suppliers

MRT 10 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,N
• Statements: 41-50
• Safety Statements: 26-39-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C(=O)NC(=S)NC2=CC=CC(=C2)NC(=O)C3=CC=CC=C3
• Description: MRT10 is an antagonist of the Smoothened (Smo) receptor with an IC50 value of 0.64 μM in a luciferase reporter assay. It also inhibits bodipy-cyclopamine binding to the murine Smo receptor (IC50 = 0.5 μM) when expressed in HEK293 cells.
• Uses: MRT 10, is a novel, high-affinity antagonist smoothened (Smo) receptor antagonist. It displaces labeled cyclopamine from Smo with an IC50 of 500 nM, and inhibits shh-induced Gli-reporter activity in Shh-light2 cells (IC50 = 0.64 μM).

Technology Process of N-[[[3-[(Benzoyl)amino]phenyl]amino](thioxo)methyl]-3,4,5-trimethoxybenzamide

There total 6 articles about N-[[[3-[(Benzoyl)amino]phenyl]amino](thioxo)methyl]-3,4,5-trimethoxybenzamide 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:

N-(3-nitrophenyl)benzamide (4771-08-8) → MRT-10 (330829-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; ammonium formate / isopropyl alcohol / Inert atmosphere; Microwave irradiation

2: acetone / 1 h / Inert atmosphere; Reflux

With palladium 10% on activated carbon; ammonium formate; In isopropyl alcohol; acetone;

DOI:10.1021/jm2013369

Reference yield:

Eudesmic acid (118-41-2) → MRT-10 (330829-30-6)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl dichloride

2: acetone / 0.33 h / Inert atmosphere; Reflux

3: acetone / 1 h / Inert atmosphere; Reflux

With oxalyl dichloride; In acetone;

DOI:10.1021/jm2013369

Reference yield:

3,4,5-Trimethoxybenzoyl chloride (4521-61-3) → MRT-10 (330829-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1: acetone / 0.33 h / Inert atmosphere; Reflux

2: acetone / 1 h / Inert atmosphere; Reflux

In acetone;

DOI:10.1021/jm2013369

upstream raw materials:

ammonium thiocyanate

3,4,5-Trimethoxybenzoyl chloride

N-Benzoyl-m-phenylendiamin

N-(3-nitrophenyl)benzamide

Downstream raw materials:

MRT-14

N-(N-(3-benzamidophenyl)carbamimidoyl)-3,4,5-trimethoxybenzamide

Refernces

• 1、 Solinas, Antonio,Faure, Hélène,Roudaut, Hermine,Traiffort, Elisabeth,Schoenfelder, Angèle,Mann, André,Manetti, Fabrizio,Taddei, Maurizio,Ruat, Martial. "Acylthiourea, acylurea, and acylguanidine derivatives with potent Hedgehog inhibiting activity". . p. 1559 - 1571. Retrieved 2012/04/17.