63-74-1

Basic information

• Product Name: Sulfanilamide
• Synonyms: p-amino-benzenesulfonamid;p-Aminobenzensulfonamide;p-Aminophenylsulfonamide;Prontalbin;Prontosil album;Prontosil i;Prontosil white;prontosilalbum
• CAS NO: 63-74-1
• Molecular Formula: C₆H₈N₂O₂S
• Molecular Weight: 172.2
• EINECS: 200-563-4
• Product Categories: SULFONAMIDE;Sulfonamides (Antibiotics for Research and Experimental Use);Antibiotics for Research and Experimental Use;Biochemistry;Amines;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Sulfur & Selenium Compounds;PRONTYLIN;Amines, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds;pharmaceutical
• Mol File: 63-74-1.mol
• Article Data: 63

Chemical Properties

• Melting Point: 164-166 °C(lit.)
• Boiling Point: 400.5 °C at 760 mmHg
• Flash Point: 196 °C
• Appearance: white to faintly beige/Liquid
• Density: 1.08
• Vapor Pressure: 0.00001 hPa (70 °C)
• Refractive Index: 1.6490 (estimate)
• Storage Temp.: 0-6°C
• Solubility: 5.37g/l
• PKA: pKa 10.65(H2O t = 25.0±0.5 I = 0.2) (Uncertain)
• Water Solubility: 7.5 g/L at 25 ºC
• Merck: 14,8925
• BRN: 511852
• CAS DataBase Reference: Sulfanilamide(CAS DataBase Reference)
• NIST Chemistry Reference: Sulfanilamide(63-74-1)
• EPA Substance Registry System: Sulfanilamide(63-74-1)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 24/25-36-22
• WGK Germany: 3
• RTECS: WO8400000
• F: 10
• TSCA: Yes
• HazardClass: 8
• Hazardous Substances Data: 63-74-1(Hazardous Substances Data)

Usage

Chemical Description

Sulfanilamide is then treated with isothiocyanates to produce 1-aroyl/alkanoyl-3-(4-aminosulfonyl phenyl)thioureas.

InChI:InChI=1/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)

Synthetic route

p-nitrobenzenesulfonamide (6325-93-5) → sulfanilamide (63-74-1)

Conditions	Yield
With hydrogen In methanol; ethyl acetate under 760.051 Torr; for 4h; Heating; Flow reactor; Green chemistry;	99%
With maghemite-palladium nanocomposite; hydrogen In ethanol; ethyl acetate at 30℃; for 0.0125h;	98%
With sodium tetrahydroborate In water at 20℃; for 0.5h; Green chemistry;	98%

4-azidobenzenesulfonamide (36326-86-0) → sulfanilamide (63-74-1)

Conditions	Yield
With D-glucose; potassium hydroxide In water at 85℃; for 0.0833333h; Green chemistry; chemoselective reaction;	99%

(p-aminobenzene)sulfonyl azide (14860-69-6) → sulfanilamide (63-74-1)

Conditions	Yield
With C24H21CuN3O3; sodium L-ascorbate In water; tert-butyl alcohol at 80℃; for 6h; Inert atmosphere;	98%
With C27H34ClN2ORu(1+)*Cl(1-); sodium formate In aq. phosphate buffer at 37℃; for 24h; pH=7.4;

chlorobenzene (108-90-7) → sulfanilamide (63-74-1)

Conditions	Yield
Stage #1: chlorobenzene With chlorosulfonic acid; ammonium chloride In 1,2-dichloro-ethane at 55℃; for 4h; Stage #2: With ammonia In water; 1,2-dichloro-ethane at 15 - 40℃; for 2h; Stage #3: With copper(l) iodide In water; 1,2-dichloro-ethane at 160℃; for 12h; Reagent/catalyst; Temperature;	97.5%

1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene (57-67-0) → bis(4-aminophenyl)disulfide (722-27-0) + sulfanilamide (63-74-1) + aniline (62-53-3) + 4-aminobenzene sulfonic acid (121-57-3)

Conditions	Yield
In methanol for 76h; Product distribution; Mechanism; Irradiation; λ=254 nm;	A n/a B 4.4% C 95.1% D 2.7%

tert-butyl (4-sulfamoylphenyl)carbamate (352542-64-4) → sulfanilamide (63-74-1)

Conditions	Yield
With H-β zeolite In dichloromethane for 10h; Heating;	91%

Acetanilid (103-84-4) → sulfanilamide (63-74-1)

Conditions	Yield
Stage #1: Acetanilid With chlorosulfonic acid; thionyl chloride; phosphorus pentoxide In tetrachloromethane at 60 - 90℃; Stage #2: With ammonia In tetrachloromethane at 50℃; for 3h;	86.98%
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / 55 h / 40 °C 1.2: 3 h / 65 °C 2.1: ammonium hydroxide / 1,2-dichloro-ethane / 2.5 h / 15 - 40 °C / Large scale 3.1: sodium hydroxide / 3 h / 90 °C / Large scale View Scheme

benzenesulfonamide (98-10-2) → sulfanilamide (63-74-1)

Conditions	Yield
With ammonia; dihydrogen peroxide In water; tert-butyl alcohol at 75℃; for 2h; Reagent/catalyst; Temperature; Molecular sieve;	82.3%

5-chloro-2,6-dimethyl-pyrimidin-4-ylamine (2858-20-0) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → N-[4-(dimethylamino-4-ylsulfonyl)phenyl]acetamide (54951-54-1) + sulfanilamide (63-74-1) + Sulfaclomid (4015-18-3) + C22H22ClN5O6S2 (84729-42-0) + 4-(4'-Acetylaminobenzensulfonyl)amino-5-chlor-2,6-dimethylpyrimidin (4049-04-1)

Conditions	Yield
With trimethylamine In dichloromethane at 33 - 40℃; for 10h; Mechanism; Product distribution; further amines;	A n/a B n/a C n/a D 70% E n/a

p-acetylaminobenzenesulfonamide (121-61-9) → sulfanilamide (63-74-1)

Conditions	Yield
With hydrogenchloride; water In ethanol for 1h; Reflux;	68%
With hydrogenchloride
With sodium hydroxide

4-acetamidobenzenesulfonyl azide (2158-14-7) → sulfanilamide (63-74-1)

Conditions	Yield
With hydrogenchloride In water at 5℃; for 0.583333h; Reflux;	60%

sulphapyridine (144-83-2) → 2-aminopyridine (504-29-0) + bis(4-aminophenyl)disulfide (722-27-0) + p-nitrobenzenesulfonamide (6325-93-5) + sulfanilamide (63-74-1) + aniline (62-53-3) + 4-aminobenzene sulfonic acid (121-57-3)

Conditions	Yield
In methanol for 48h; Product distribution; Mechanism; Irradiation; λ=254 nm;	A 15.6% B n/a C n/a D 6.1% E 29.1% F 20.1%

4-Chlorobenzenesulfonamide (98-64-6) → sulfanilamide (63-74-1)

Conditions	Yield
With ammonium hydroxide; copper; copper(II) sulfate at 150℃; under 44130.5 Torr;
With copper(I) oxide; ammonium hydroxide at 160℃;
With ammonium chloride; copper at 160℃;

N-formyl-sulfanilyl chloride (34894-11-6) → sulfanilamide (63-74-1)

Conditions	Yield
With ammonium hydroxide
Multi-step reaction with 2 steps 1: aqueous ammonia 2: aq. NaOH solution View Scheme

4,4'-(carbonylbis(azanediyl))dibenzenesulfonamide (1773-43-9) → sulfanilamide (63-74-1)

Conditions	Yield
With sulfuric acid at 150℃;
With sodium hydroxide at 100℃;

N-formyl-sulfanilic acid amide (829-72-1) → sulfanilamide (63-74-1)

Conditions	Yield
With water
With ammonium hydroxide
With sulfuric acid
With sodium hydroxide
Multi-step reaction with 2 steps 2: ethanolic NaOH-solution View Scheme

N-formyl-sulfanilic acid acetylamide (781-00-0) → sulfanilamide (63-74-1) + sulphaacetamide (144-80-9)

Conditions	Yield
With sodium hydroxide

4-amidobenzylsulfonamide (6306-24-7) → sulfanilamide (63-74-1)

Conditions	Yield
With alkaline aqueous sodium hypochlorite

(E)-4-(phenyldiazenyl)benzenesulfonamide (102840-86-8) → sulfanilamide (63-74-1)

Conditions	Yield
With hydrogenchloride; tin

(E)-4-(phenyldiazenyl)benzenesulfonamide (102840-86-8) → 4-(N'-phenyl-hydrazino)-benzenesulfonic acid amide (521972-91-8) + sulfanilamide (63-74-1)

Conditions	Yield
With sodium hydroxide; sodium dithionite

1-methyl-4-nitrosobenzene (623-11-0) + 1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene (57-67-0) → sulfanilamide (63-74-1)

hidrazobenzene-4,4'-disulfonamide (4392-55-6) → sulfanilamide (63-74-1) + C6H7N2O2S(1-)

Conditions	Yield
With Britton-Robinson buffer Rate constant; controlled potential electrolysis;

p-<(8-hydroxy-5-quinolyl)azo>benzenesulphonamide (16588-39-9) → 5-amino-8-hydroxyquinoline (13207-66-4) + sulfanilamide (63-74-1)

Conditions	Yield
In water; N,N-dimethyl-formamide for 1.5h; electrolysis at dropping mercury electrode;

4-(2,4-dihydroxy-phenylazo)-benzenesulfonic acid amide (140648-35-7) → 4-aminoresorcinol (13066-95-0) + sulfanilamide (63-74-1)

Conditions	Yield
In N,N-dimethyl-formamide Rate constant; Thermodynamic data; electrochemical reduction (HMDE electrode), various pHs (from 2.25 to 10.12);

4-(5-bromo-2-hydroxy-phenylazo)-benzenesulfonic acid amide (140648-38-0) → 2-amino-4-bromo-phenol (40925-68-6) + sulfanilamide (63-74-1)

Conditions	Yield
In N,N-dimethyl-formamide Rate constant; Thermodynamic data; electrochemical reduction (HMDE electrode), various pHs (from 3.22 to 10.00);

4-(5-Formyl-2-hydroxy-phenylazo)-benzenesulfonamide (140648-40-4) → sulfanilamide (63-74-1) + 3-amino-4-hydroxybenzaldehyde (163036-58-6)

Conditions	Yield
In N,N-dimethyl-formamide Rate constant; Thermodynamic data; electrochemical reduction (HMDE electrode), various pHs (from 3.10 to 10.34);

4-(2-Hydroxy-5-methoxy-phenylazo)-benzenesulfonamide (140648-36-8) → 2-amino-4-methoxyphenol (20734-76-3) + sulfanilamide (63-74-1)

Conditions	Yield
In N,N-dimethyl-formamide Rate constant; Thermodynamic data; electrochemical reduction (HMDE electrode), various pHs (from 2.03 to 10.00);

4-(4-Dimethylamino-2-hydroxy-phenylazo)-benzenesulfonamide (140648-37-9) → 2-amino-5-(dimethylamino)phenol (15103-39-6) + sulfanilamide (63-74-1)

Conditions	Yield
In N,N-dimethyl-formamide Rate constant; Thermodynamic data; electrochemical reduction (HMDE electrode), various pHs (from 2.03 to 10.00);

acetic anhydride (108-24-7) + sulfanilamide (63-74-1) → p-acetylaminobenzenesulfonamide (121-61-9)

Conditions	Yield
at 20℃; for 1h;	100%
In ethanol at 20 - 70℃; for 0.0166667h; other time tested;

sulfanilamide (63-74-1) → 4-azidobenzenesulfonamide (36326-86-0)

Conditions	Yield
With hydrogenchloride; sodium azide; sodium nitrite In water at 0 - 5℃; for 1h;	100%
With hydrogenchloride; sodium azide; sodium nitrite In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 25℃;	93%
Stage #1: sulfanilamide With hydrogenchloride; sodium nitrite In tetrahydrofuran; water; N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With sodium azide In tetrahydrofuran; water; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	90.6%

3-pyridinecarboxaldehyde (500-22-1) + sulfanilamide (63-74-1) → N4-(3-pyridylidene) sulfanilamide (74028-05-0)

Conditions	Yield
at 150 - 155℃; for 0.0833333h;	100%
In ethanol for 3h; Heating;

trifluoronitrosomethane (334-99-6) + sulfanilamide (63-74-1) → 4-(Trifluoromethyl-azo)-benzenesulfonamide

Conditions	Yield
In methanol at 20℃; for 24h;	100%

sulfanilamide (63-74-1) + trifluoroacetic anhydride (407-25-0) → 2,2,2-trifluoro-N-(4-sulfamoylphenyl)acetamide

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 0.5h;	100%
In 1,4-dioxane	100%
In 1,4-dioxane	97%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + sulfanilamide (63-74-1) → 4-Amino-N-dimethylaminomethylenebenzenesulfonamide

Conditions	Yield
In dichloromethane for 0.5h; Heating;	100%

methyl 2-chloroquinazoline-7-carboxylate (953039-79-7) + sulfanilamide (63-74-1) → methyl 2-(4-sulfamoyl-phenylamino)quinazoline-7-carboxylate

Conditions	Yield
In isopropyl alcohol at 90℃; for 2h;	100%

methyl 2-chloroquinazolin-6-carboxylate (1036755-96-0) + sulfanilamide (63-74-1) → Methyl 2-(4-sulfamoylphenylamino)quinazolin-6-carboxylate (1036743-15-3)

Conditions	Yield
at 90℃; for 2h;	100%

di-tert-butyl dicarbonate (24424-99-5) + sulfanilamide (63-74-1) → tert-butyl (4-sulfamoylphenyl)carbamate (352542-64-4)

Conditions	Yield
In 1,4-dioxane Reflux;	100%
With potassium hydroxide In tetrahydrofuran; water

4-nitrosobenzoic acid ethyl ester (7476-79-1) + sulfanilamide (63-74-1) → (E)-ethyl 4-((4-sulfamoylphenyl)diazenyl)benzoate

Conditions	Yield
With acetic acid In dichloromethane	100%

m-phenylenediamine (108-45-2) + sulfanilamide (63-74-1) → (E)-4-(2-(4-sulfonamido)diazenyl)benzene-1,3-diamine (103-12-8)

Conditions	Yield
Stage #1: sulfanilamide With hydrogenchloride; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: m-phenylenediamine With hydrogenchloride In water at 0℃; for 0.5h;	100%

3,6-dichlorpyridazine (141-30-0) + sulfanilamide (63-74-1) → sulfachloropyridazine sodium

Conditions	Yield
Stage #1: 3,6-dichlorpyridazine; sulfanilamide In dimethyl sulfoxide at 100℃; under 2250.23 Torr; for 10h; Stage #2: With sodium In water at 60℃; for 8h; Solvent; Reagent/catalyst;	99.5%

2,5-hexanedione (110-13-4) + sulfanilamide (63-74-1) → 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzenesulfonamide (26165-69-5)

Conditions	Yield
With iodine at 20℃; for 2h; Paal-Knorr Pyrrole Synthesis;	99%
With acetic acid at 120℃; for 3h;	86%
at 180℃; for 0.25h; Paal-Knorr pyrrole synthesis; Microwave irradiation;	75%
With ethanol; acetic acid

sulfanilamide (63-74-1) + phenylacetyl chloride (103-80-0) → N-[4-(aminosulfonyl)phenyl]-2-phenylacetamide

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 15h;	99%
With triethylamine In acetonitrile at 0 - 5℃;	35%
With pyridine

N,N'-bis(triethylgermyl)sulfanilamide + sulfanilamide (63-74-1) → N-triethylgermylsulfanilamide (566174-01-4)

Conditions	Yield
In chloroform-d1 org. compd. addn. to Ge-compd. soln. in NMR tube; complete conversion after 24 h at 20°C ((1)H-NMR monitoring);	99%

3-(triethoxypropyl) isocyanate (24801-88-5) + sulfanilamide (63-74-1) → C26H50N4O10SSi2 (1311165-68-0)

Conditions	Yield
In acetonitrile for 24h; Inert atmosphere; Reflux;	99%

benzaldehyde (100-52-7) + sulfanilamide (63-74-1) → benzylsulfamide (104-22-3)

Conditions	Yield
With (2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane; hydrogen In tetrahydrofuran at 100℃; under 15201 Torr; for 6h; Sealed tube; Molecular sieve; Autoclave; Green chemistry;	99%
With triethylsilane; palladium on carbon; TPGS-750-M In water at 45℃; for 12h;	78%
Multi-step reaction with 2 steps 1: chloroform; methanol / 18 h / Reflux 2: sodium tetrahydroborate / methanol / 4 h View Scheme
Multi-step reaction with 2 steps 1: formic acid / methanol / Reflux 2: sodium tetrahydroborate / methanol / 25 h / 0 - 25 °C View Scheme

sulfanilamide (63-74-1) + 2-chloro-4-(p-hydroxyphenyl)pyrimidine → 4-{[4-(4-hydroxyphenyl)pyrimidin-2-yl]amino}benzenesulfonamide (882875-01-6)

Conditions	Yield
With hydrogenchloride In ethanol at 160℃; for 2h; Microwave irradiation;	99%
With hydrogenchloride In ethanol Microwave irradiation;	99%

5-amino-4,6-dichloropyridimine (5413-85-4) + sulfanilamide (63-74-1) → 4-((5-amino-6-chloropyrimidin-4-yl)amino)benzenesulfonamide

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane; water Reflux;	99%

potassium thioacyanate (333-20-0) + sulfanilamide (63-74-1) + 3-chloropentane-2,4-dione (1694-29-7) → 5-Acetyl-4-methyl-2-<(p-sulphamylphenyl)amino>thiazole (88323-93-7)

Conditions	Yield
With silica sulfuric acid In neat (no solvent) at 20℃; for 0.416667h; Milling; Green chemistry;	99%

salicylaldehyde (90-02-8) + sulfanilamide (63-74-1) → 4-[(2-hydroxybenzylidene)amino]benzenesulfonamide (2067-06-3)

Conditions	Yield
In ethanol for 0.333333h; Reflux;	98.57%
In ethanol at 60℃; Microwave irradiation;	88%
With formic acid In methanol Reflux;	85%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + sulfanilamide (63-74-1) → 4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide (6949-34-4)

Conditions	Yield
In water for 3h; Reflux;	98%
In ethanol at 115℃; for 72h;	38.9%
With acetic acid; N,N-diethylaniline
In ethanol Reflux;

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + sulfanilamide (63-74-1) → 4-amino-N-[(dimethylamino)methylidene]benzenesulfonamide (6912-49-8)

Conditions	Yield
In neat (no solvent) at 20℃; under 760.051 Torr; for 0.25h; Green chemistry; chemoselective reaction;	98%

sulfanilamide (63-74-1) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(4-sulfamoylphenyl)acetamide (14949-01-0)

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 0℃;	98%
With potassium carbonate In acetone at 0 - 20℃;	95%
In acetone at 20 - 95℃; for 1h;	89%

sulfanilamide (63-74-1) + triphenylphosphine (603-35-0) → N-<(p-aminophenyl)sulfonyl>triphenylphospha-λ5-azene (95978-84-0)

Conditions	Yield
With diethylazodicarboxylate In tetrahydrofuran at 0 - 25℃; for 12h;	98%
With diethylazodicarboxylate In tetrahydrofuran at 0℃;	79%

sulfanilamide (63-74-1) + 3,4-diethoxy-3-cyclobuten-1,2-dione (5231-87-8) → 4-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-benzenesulfonamide

Conditions	Yield
In ethanol Substitution; Heating;	98%

tetrachlorophthalic anhydride (117-08-8) + sulfanilamide (63-74-1) → 4-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)benzenesulfonamide (88062-88-8)

Conditions	Yield
With acetic acid at 130℃; for 2h;	98%
With acetic acid for 24h; Reflux;

sulfanilamide (63-74-1) + 4-(bromoacetyl)toluene (619-41-0) → 4-((2-oxo-2-(p-tolyl)ethyl)amino)benzenesulfonamide (1595285-57-6)

Conditions	Yield
In methanol for 4h; Reflux;	98%

Upstream product

• 98-64-6 4-Chlorobenzenesulfonamide 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 34894-11-6 N-formyl-sulfanilyl chloride 
• 1773-43-9 4,4'-(carbonylbis(azanediyl))dibenzenesulfonamide 
• 829-72-1 N-formyl-sulfanilic acid amide 
• 781-00-0 N-formyl-sulfanilic acid acetylamide 
• 6306-24-7 4-amidobenzylsulfonamide 
• 102840-86-8 (E)-4-(phenyldiazenyl)benzenesulfonamide 
• 121-61-9 p-acetylaminobenzenesulfonamide 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 57-67-0 1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene 
• 2858-20-0 5-chloro-2,6-dimethyl-pyrimidin-4-ylamine 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 144-83-2 sulphapyridine 

Downstream Products

• 105540-83-8 N-[2-bromo-3ξ-(5-nitro-[2]thienyl)-allylidene]-sulfanilic acid amide 
• 102440-73-3 N-[2-bromo-3ξ-(5-nitro-[2]thienyl)-allylidene]-sulfanilic acid acetylamide 
• 110152-64-2 N-(pyridine-2-thiocarbonyl)-sulfanilic acid-(pyridine-2-thiocarbonylamide) 
• 72-14-0 Sulfathiazole 
• 103646-59-9 N⁴-(2-pyrolylidene) sulfanilamide 
• 50571-16-9 N⁴-(2-furfurylidene) sulfanilamide 
• 72751-82-7 4-(2-formyl-pyrrol-1-yl)-benzenesulfonic acid amide 
• 144-83-2 sulphapyridine 
• 599-81-5 4-amino-N-pyridin-3-yl-benzenesulfonamide 
• 1886-79-9 N-(4-sulfamoyl-phenyl)-malamic acid 
• 116-44-9 sulfapyrazine 
• 68-35-9 sulfadiazine 
• 74028-18-5 N-indol-3-ylmethyl-sulfanilic acid amide 
• 5470-06-4 N,N-succinyl-sulfanilic acid amide 

Relevant articles and documents

Electrochemical Behavior of Azobenzene-4,4'-disulfonamide at Pyrolitic Graphite Electrode

The electrochemical reduction of azobenzene-4,4'-disulfonamide (1), an oxidation product of sulfanilamide, has been studied at Pyrolytic graphite electrode, over a wide pH range of 3.0 to 10.6 in the Britton Robinson buffers, by electrochemical and spectroscopic techniques.Under cyclic voltammetric conditions the 2e-, 2H+ reduction of this compound was found to give hydrazobenzene-4,4'-disulfonamide which has been characterised using IR, mp, mass and NMR spectra.Under controlled potential electrolysis, the presence of two electron withdrawing -SO2NH2 groups was found to cause the slow disproportionation -3 s-1> of the hydrazo compound and sulfanilamide has been found as the major product of reduction.A plausible mechanism for the ECE reduction of 1 is suggested.

Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture

The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The molecular recognition preferences of the protease favor basic, positively charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-molecular inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC50 0.24 μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclinical development.

Hydroboration reduction reaction of aromatic nitro compounds without transition metal catalysis

The invention relates to a hydroboration reduction reaction of aromatic nitro compounds without transition metal catalysis. According to the method, triethyl boron and potassium tert-butoxide are used as catalysts for the first time, and an aromatic nitro compound and pinacol borane which is low in price and easy to obtain can be conveniently catalyzed to be subjected to a hydroboration reduction reaction under mild conditions to prepare aromatic amine products. Compared with a traditional method, the method generally has the advantages that the catalyst is cheap and easy to obtain, operation is convenient, and reaction is safe. The selective hydroboration reduction reaction of the non-transition metal reagent catalyzed aromatic nitro compound and pinacol borane is realized for the first time, and a practical new reaction strategy is provided for laboratory preparation or industrial production of aromatic amine products.