4392-37-4

Basic information

• Product Name: N-(aminoiminomethyl)benzenesulphonamide
• Synonyms: N-(aminoiminomethyl)benzenesulphonamide;N-Amidinobenzenesulfonamide;Einecs 224-512-0;2-phenylsulfonylguanidine;N-(Diamino-methylene)benzenesulfonamide;BENZENESULFONAMIDE, N-(AMINOIMINOMETHYL)-
• CAS NO: 4392-37-4
• Molecular Formula: C₇H₉N₃O₂S
• Molecular Weight: 199.23026
• EINECS: 224-512-0
• Mol File: 4392-37-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 412°Cat760mmHg
• Flash Point: 203°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 5.36E-07mmHg at 25°C
• CAS DataBase Reference: N-(aminoiminomethyl)benzenesulphonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(aminoiminomethyl)benzenesulphonamide(4392-37-4)
• EPA Substance Registry System: N-(aminoiminomethyl)benzenesulphonamide(4392-37-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 4392-37-4(Hazardous Substances Data)

Usage

General Description

N-(aminoiminomethyl)benzenesulphonamide, also known as sulam, is a chemical compound that belongs to the class of sulfonamide antibiotics. It is used to treat various bacterial infections by inhibiting the growth and reproduction of bacteria. Sulam works by interfering with the synthesis of folic acid, which is essential for the production of DNA and RNA in bacteria. This disruption leads to the death of the bacteria, ultimately clearing the infection. Sulam has been found to be effective against a wide range of bacteria, making it a valuable tool in the treatment of various infections. However, it is important to use this compound under the direction of a healthcare professional to ensure proper dosing and monitoring for potential side effects.

InChI:InChI=1/C7H9N3O2S/c8-7(9)10-13(11,12)6-4-2-1-3-5-6/h1-5H,(H4,8,9,10)/p+1

Upstream product

• 131543-46-9 Glyoxal 
• 50-01-1 guanidine hydrochloride 
• 79109-63-0 N-benzenesulfonyl-N'-cyano-guanidine 
• 537698-16-1 N¹-benzoyl-N³-phenylsulfonylguanidine 
• 593-85-1 diguanidine carbonate 
• 98-09-9 benzenesulfonyl chloride 
• 88609-02-3 4-azidobenzenesulphonylguanidine 
• 7647-01-0 hydrogenchloride 
• 57-67-0 1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene 
• 98-10-2 benzenesulfonamide 
• 113-00-8 guanidine nitrate 
• 13068-20-7 N-bis-(methylsulfanylmethylene)benzenesulfonamide 

Downstream Products

• 537698-16-1 N¹-benzoyl-N³-phenylsulfonylguanidine 
• 13068-57-0 N-(1H-benzoimidazol-2-yl)-benzenesulfonamide 
• 57053-64-2 N-benzenesulfonylcarbamimidoyl-thioacetamide 
• 58287-43-7 N-(5-methyl-[1,2,4]thiadiazol-3-yl)-benzenesulfonamide 
• 857488-74-5 N-benzenesulfonyl-N'-(4-nitro-benzoyl)-guanidine 

Relevant articles and documents

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Structure-based drug designing, scoring, and synthesis of some substituted sulphonylureas/guanidine-based derivatives as hypoglycemic agents

Objective: The present work deals with the designing, scoring, synthesis and, characterization of 1-(4-(2-(4-Substitutedphenylamino)-2-oxoethyl)phenylsulfonyl)-3-(4-substitutedbenzoyl)urea (5A-5B),1-(4-(2-(4-substitutedphenylamino)-2-oxoethyl)phenylsulfonyl)-3-(4-substituted-benzoyl)guanidine(5C-5E) and, 1-(4-Substitutedbenzoyl)-3-(4-(2-oxo-2-(piperazin-1-yl)ethyl)phenylsulfonyl)urea (5F-5H) based derivatives as hypoglycemic agents. Methods: Docking calculations were performed to predict the binding affinity between the AKR1C1 complexes and sulphonylureas compounds using the Glide docking program. Docking studies on LigPrep treated ligands were carried out to predict the binding pocket of protein 4YVP using the docking program. The QikProp program was used to predict the ADME/T properties of the analogues. All these newly synthesized compounds were screened for their in vivo hypoglycemic activity by most relevant animal models like alloxan-induced diabetic rats by measuring blood plasma concentration compared with reference drug glibenclamide. Results: Novel compounds 1-(4-(2-(4-Substitutedphenylamino)-2-oxoethyl)phenylsulfonyl)-3-(4-substitutedbenzoyl)urea (5A-5B), 1-(4-(2-(4-substitutedphenylamino)-2-oxoethyl)phenylsulfonyl)-3-(4-substitutedbenzoyl) guanidine (5C-5E), and 1-(4-Substitutedbenzoyl)-3-(4-(2-oxo-2-(piperazin-1-yl)ethyl)phenylsulfonyl)urea (5F-5H) were synthesised and characterized using spectral and analytical data. The results of molecular docking and in vivo hypoglycemic activity, all compounds have shown considerable activity with respect to glibenclimide, but compounds 5D (52.49±7.73) and 5E(48.18±4.22)are equipotent with respect to activity as compared to standard glibenclamide(55.97±3.19). Conclusion: Compounds 5D and 5E have exhibited good hypoglycemic activity,hence both the derivatives will consider as a lead molecule and further some modification in their structures to get a more potent anti-diabetic agent.

Ring-expansion of Azidobenzenesulphonamides and Azidobenzamides

4-Azidobenzenesulphonamides and 2- and 4-azidobenzamides undergo phototransformation to 2-alkoxy-3H-azepines in alcohols but the yields are low.Ring-expansion of 4-azidobenzenesulphonamide and 4-azidobenzenesulphonylguanidine in aqueous tetrahydrofuran to 3H-azepin-2(1H)-ones proceeds via a singlet nitrene pathway; thermolysis of 4-azidobenzenesulphonamide in aqueous dioxane gave only the triplet-derived product, sulphanilamide.Efficient de-azidation of 4-azidobenzesulphonamides and 4-azidobenzamides can be accomplished by heating the azides at 105 deg C in hydrazine hy drate.The crystallographic analysis of 5-sulphamoyl-3H-azepin-2(1H)-one shows the molecule to be non-planar with the azepine ring puckered in a boat form.The lactam configuration is confirmed with the carbonyl group having a bond length of 1.231 Angstroem.