N4-Acetylsulfaphenazole

Base Information

• Chemical Name: N4-Acetylsulfaphenazole
• CAS No.: 855-91-4
• Molecular Formula: C17H16 N4 O3 S
• Molecular Weight: 356.405
• DSSTox Substance ID: DTXSID60234703
• Nikkaji Number: J38.347C
• Wikidata: Q83116525
• ChEMBL ID: CHEMBL4761172
• Mol file: 855-91-4.mol

Synonyms:N(4)-acetylsulfaphenzazole;N4-acetylsulfaphenazole

Chemical Property of N4-Acetylsulfaphenazole

Chemical Property:

• PSA: 104.96000
• Density: 1.35g/cm³
• LogP: 4.43480
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 356.09431156
• Heavy Atom Count: 25
• Complexity: 549

Purity/Quality:

N4-Acetylsulfaphenazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=CC=C(C=C1)S(=O)(=O)NC2=CC=NN2C3=CC=CC=C3
• Uses: N4-Acetylsulfaphenazole is an intermediate in the synthesis of Sulfaphenazole (S689020), an inhibitor for mammalian CYP2C9, an enzyme of the cytochrome P450 family allowing for pharmacological application.

Technology Process of N4-Acetylsulfaphenazole

There total 4 articles about N4-Acetylsulfaphenazole 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: 60.0%

1-phenylpyrazol-5-amine (826-85-7) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → N4-Acetylsulfaphenazole (855-91-4)

Guidance literature:

In pyridine; at 95 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.bmcl.2021.127924

Reference yield:

ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate (16078-71-0) → N4-Acetylsulfaphenazole (855-91-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous H₂SO₄

With sulfuric acid;

Reference yield:

3-(N'-phenyl-hydrazino)-propionitrile (26955-79-3) → N4-Acetylsulfaphenazole (855-91-4)

Guidance literature:

Multi-step reaction with 2 steps

1: bei aufeinanderfolgender Umsetzung mit Fe₂(SO₄)3 in wss.H₂SO₄ und mit wss.NaOH

upstream raw materials:

1-phenylpyrazol-5-amine

p-acetylaminobenzenesulfonyl chloride

ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate

3-(N'-phenyl-hydrazino)-propionitrile

Downstream raw materials:

sulfaphenazole

Refernces

• 1、 Chen, Hui,Wang, Bin,Li, Peng,Yan, Hong,Li, Gang,Huang, Haihong,Lu, Yu. "The optimization and characterization of functionalized sulfonamides derived from sulfaphenazole against Mycobacterium tuberculosis with reduced CYP 2C9 inhibition". supporting information. . Retrieved 2021/03/26.