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

Description

N-(aminoiminomethyl)benzenesulphonamide, commonly known as sulam, is a sulfonamide antibiotic with potent antimicrobial properties. It functions by inhibiting the synthesis of folic acid, a crucial component for bacterial DNA and RNA production, thereby disrupting bacterial growth and reproduction. This mechanism of action makes sulam an effective agent against a broad spectrum of bacteria, offering a valuable therapeutic option for treating various infections.

Uses

Used in Pharmaceutical Industry:
Sulam is utilized as an antibiotic for the treatment of bacterial infections. Its broad-spectrum activity against a wide range of bacteria makes it a versatile choice for combating infections caused by both gram-positive and gram-negative organisms. The effectiveness of sulam in treating infections is attributed to its ability to interfere with the synthesis of folic acid, an essential nutrient for bacterial replication.
Used in Healthcare Settings:
In healthcare settings, sulam is employed as a therapeutic agent to clear bacterial infections under the guidance of healthcare professionals. Proper dosing and monitoring are crucial to ensure the safe and effective use of sulam, as well as to minimize the risk of potential side effects. Its role in treating infections contributes to the overall management of patients and the prevention of complications associated with bacterial diseases.

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

Downstream Products

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