24570-88-5

Basic information

• Product Name: 1-propyl-3-(p-tolylsulphonyl)urea
• Synonyms: 1-propyl-3-(p-tolylsulphonyl)urea;1-(p-Tolylsulfonyl)-3-propylurea;1-Tosyl-3-propylurea;4-Methyl-N-[(propylamino)carbonyl]benzenesulfonamide;N-(4-Methylphenylsulfonyl)-N'-propylurea;Einecs 246-322-7;1-propyl-3-(p-tolylsulfonyl)urea
• CAS NO: 24570-88-5
• Molecular Formula: C₁₁H₁₆N₂O₃S
• Molecular Weight: 256.32134
• EINECS: 246-322-7
• Mol File: 24570-88-5.mol

Chemical Properties

• Melting Point: 151-152 °C
• Appearance: /
• Density: 1.21g/cm³
• Refractive Index: 1.537
• PKA: 5.26±0.10(Predicted)
• CAS DataBase Reference: 1-propyl-3-(p-tolylsulphonyl)urea(CAS DataBase Reference)
• NIST Chemistry Reference: 1-propyl-3-(p-tolylsulphonyl)urea(24570-88-5)
• EPA Substance Registry System: 1-propyl-3-(p-tolylsulphonyl)urea(24570-88-5)

Safety Data

• Hazardous Substances Data: 24570-88-5(Hazardous Substances Data)

Usage

Mechanism of action

Inhibits thyroperoxidase PTU works by inhibiting the enzyme thyroperoxidase, which is necessary for the production of thyroid hormone, thus preventing excessive hormone production.

Form and administration

Tablet form, taken orally PTU is available as a medication in tablet form and is typically taken orally by patients.

Precautions

Use under doctor's guidance, potential side effects and interactions It is important to use PTU under the guidance of a doctor, as it can have serious side effects and interactions with other medications.

InChI:InChI=1/C11H16N2O3S/c1-3-8-12-11(14)13-17(15,16)10-6-4-9(2)5-7-10/h4-7H,3,8H2,1-2H3,(H2,12,13,14)

Upstream product

• 51506-31-1 N-(allylcarbamoyl)-4-methylbenzenesulfonamide 
• 110-78-1 Propyl isocyanate 
• 70-55-3 toluene-4-sulfonamide 
• 623-95-0 1,3-dipropylurea 
• 18522-92-4 sodium p-toluenesulfonamide 
• 14549-38-3 phenyl N-(n-propyl)carbamate 
• 107-10-8 propylamine 
• 917-61-3 sodium isocyanate 
• 98-59-9 p-toluenesulfonyl chloride 
• 91181-34-9 1-allyl-3-tosylthiourea 

Downstream Products

• 1888-33-1 N-acetyl-(4-methylbenzene)sulfonamide 

Relevant articles and documents

A facile synthesis of sulfonylureas: Via water assisted preparation of carbamates

A novel and simple approach to the synthesis of sulfonylureas has been reported. It involved the reaction of various amines with diphenyl carbonate to yield the corresponding carbamates, which subsequently reacted with different sulphonamides to produce different sulfonylureas in excellent yields. The first reaction of diphenyl carbonate with amines was carried out in aqueous:organic (H2O:THF, 90:10) medium at room temperature to produce carbamates that paved a straightforward route to sulfonylureas after reaction with sulfonamides. The above process avoided traditional multistep protocols and the use of hazardous, irritant, toxic and moisture sensitive reagents such as phosgene, isocyanates and/or chloroformates.

Design and development of sulfonylurea derivatives as zinc metalloenzyme modulators

Sulfonamide derivatives are an important class of zinc metalloenzyme inhibitors. While the sulfonylurea group is a bioisoster of sulfonamide, their effect on the modulation of metalloenzymes has never been studied. In the present work we synthesize and screen new sulfonylurea derivatives towards the zinc metalloenzymes, human Carbonic Anhydrase II (hCA II) and histone deacetylase 1 (HDAC 1). Specific sulfonylurea derivatives are found to inhibit hCA II with IC50 in the nano molar to micro molar range. Docking studies indicate the binding of the inhibitors to the mouth of the active site cavity thereby blocking access to the enzyme. Surprisingly sulfonylurea derivatives exhibit activation of HDAC 1 rather than inhibition. The activation of HDAC 1 is not uniform across the derivatives tested suggesting a specific mode that depends on structural features of the compounds. Extensive research has been performed on HDAC inhibitors due to their potential as anti-cancer agents, however relatively little has been reported in terms of HDAC activation. In this work, we present the distinctly divergent behavior of the same class of molecules namely sulfonylurea derivatives with respect to hCA II and HDAC 1 and attempt to provide an understanding of the same.

Mechanosynthesis of pharmaceutically relevant sulfonyl-(thio)ureas

We demonstrate the first application of mechanochemistry to conduct the synthesis of sulfonyl-(thio)ureas, including known anti-diabetic drugs tolbutamide, chlorpropamide and glibenclamide, in good to excellent isolated yields by either stoichiometric base-assisted or copper-catalysed coupling of sulfonamides and iso(thio)cyanates. the Partner Organisations 2014.

Lewis Acid Catalysed Preparation of some Carbamates and Sulphonylureas. Application to the Determination of Enantiomeric Purity of Chiral Alcohols

Lewis acids such as boron trifluoride-diethyl ether and aluminium chloride catalyze the reaction of alcohols and sulphonamides with isocyanates, affording carbamates and sulphonylureas, respectively, in acceptable yield.Applied to the formation of diastereoisomeric carbamates from chiral alcohols using Pirkle's reagents, , this technique provides a convenient method for determination of enantiomeric purity.