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  • Sulfathiazole CAS 72-14-0 Benzenesulfonamide,4-amino-N-2-thiazolyl- CAS no 72-14-0 2-(p-Aminobenzenesulfonamido)thiazole

    Cas No: 72-14-0

  • USD $ 3.5-5.0 / Kiloliter

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72-14-0 Usage

Chemical Properties

white to cream powder

Originator

Tiazol,C. and C.

Definition

ChEBI: A 1,3-thiazole compound having a 4-aminobenzenesulfonamido group at the 2-position.

Manufacturing Process

116 parts 4-acetamidobenzolsufonyl chloride (prepared from acetanilide and chlorosulfonic acid) was mixed with 100 parts 2-aminothiasole in 1000 parts water by cooling and stirred for some hours. The bis-amide obtained was filtered off and re-crystallized from 50% ethanol to give bis-(pacetylaminobenzolsulfo)- 2-aminothiazol with MP: 129°C.10 parts above bis-amide was heated with 10% sodium hydroxide solution for 0.5 hour on water bath. On cooling and filtration the alkaline solution was acidified with glacial acetic acid. The amide obtained was cleared by recrystallized from water to give N1-2-thiazolylsulfanilamide; MP: 202°-203°C.

Brand name

Argazol;Bucosol;Chemiovis;Coryza;Crionil;Csp 500;Csp-250;Edifeno;Femakzem;Formotablin antidiarreico;Gyne-sulf;Gyn-sulf;Neosutrin;Polvos wilfe;Pomada wilfe;Prothiazol;Septex cream no. 2;Streptacillin;Sulfa-orzon;Sulfazol;Sulfhatose;Sulfintestin;Sulfopyrol;Sulfour;Sulfzol;Sulnac;Sulphatriad;Tampovagan pss;Thiadyl;Thiuramide;Tiadyl;Trimeto;Trisulpha;Trysul;Tylasul;Ufa 902-duo;Vetoprim mi;Wintrazol.

Therapeutic Function

Antibacterial

World Health Organization (WHO)

Sulfathiazole, a sulfonamide anti-infective agent, was introduced more than 25 years ago for the treatment of bacterial infections. The importance of sulfonamides has subsequently decreased as a result of increasing bacterial resistance and their replacement by antibiotics which are generally more active and less toxic. The sulfonamides are known to cause serious adverse effects such as renal toxicity, sometimes fatal exfoliative dermatitis and erythema multiforma and dangerous adverse reactions affecting blood formation such as agranulocytosis and haemolytic or aplastic anaemia. Although preparations remain available, use of the drug has been discontinued in many countries.

General Description

White crystalline powder. Is dimorphous: form I is consists of prismatic rods and form II of six-sided plates and prisms. Insoluble in water and soluble in dil aqueous acid and aqueous base.

Air & Water Reactions

May be sensitive to heat, air and light during long-term storage . Insoluble in water.

Reactivity Profile

Sulfathiazole is an amino acid.

Fire Hazard

Flash point data for Sulfathiazole are not available, but Sulfathiazole is probably combustible.

Pharmaceutical Applications

2-Sulfanilamidothiazole. A short-acting compound (half-life c. 4 h) with relatively high activity. Protein binding is c. 75%. Its use has declined because of a high incidence of side effects. It is one of the constituents of triple sulfonamide mixtures, of which local preparations are still available. Two compounds, phthalylsulfathiazole (sulfathalidine) and succinylsulfathiazole (sulfasuxidine) owe their activity to the slow liberation of sulfathiazole in the bowel. They are poorly soluble and very little is absorbed after oral administration. They were formerly used in the treatment of intestinal infections and in bowel preparation before surgery. They are available in multi-ingredient preparations in some countries.

Biochem/physiol Actions

Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.Mode of Action: Inhibits folic acid synthesis in prokaryotes.Anti-microbial Spectrum: Gram positive, Gram negative, ChlamydiaMode of Resistance: Alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

Safety Profile

Human poison by unspecified route. Experimental poison by intraperitoneal route, Moderately toxic by intravenous, subcutaneous, and parenteral routes. Mildly toxic by ingestion. Human systemic effects by unspecified route: conjunctiva irritation, tubule changes, and allergic skin dermatitis. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data, Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Check Digit Verification of cas no

The CAS Registry Mumber 72-14-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 2 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 72-14:
(4*7)+(3*2)+(2*1)+(1*4)=40
40 % 10 = 0
So 72-14-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12)

72-14-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (S0272)  Sulfathiazole  >98.0%(HPLC)(T)

  • 72-14-0

  • 25g

  • 175.00CNY

  • Detail
  • TCI America

  • (S0272)  Sulfathiazole  >98.0%(HPLC)(T)

  • 72-14-0

  • 100g

  • 490.00CNY

  • Detail
  • TCI America

  • (S0272)  Sulfathiazole  >98.0%(HPLC)(T)

  • 72-14-0

  • 500g

  • 1,390.00CNY

  • Detail
  • Alfa Aesar

  • (A10727)  Sulfathiazole, 99%   

  • 72-14-0

  • 100g

  • 448.0CNY

  • Detail
  • Alfa Aesar

  • (A10727)  Sulfathiazole, 99%   

  • 72-14-0

  • 500g

  • 1398.0CNY

  • Detail
  • Sigma-Aldrich

  • (S2158000)  Sulfathiazole  European Pharmacopoeia (EP) Reference Standard

  • 72-14-0

  • S2158000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (46902)  Sulfathiazole  VETRANAL, analytical standard

  • 72-14-0

  • 46902-250MG-R

  • 404.82CNY

  • Detail
  • Sigma-Aldrich

  • (S9876)  Sulfathiazole  analytical standard, ≥98.0%

  • 72-14-0

  • S9876-100G

  • 624.78CNY

  • Detail
  • Sigma-Aldrich

  • (S9876)  Sulfathiazole  analytical standard, ≥98.0%

  • 72-14-0

  • S9876-250G

  • 718.38CNY

  • Detail

72-14-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name sulfathiazole

1.2 Other means of identification

Product number -
Other names 2-Sulfanilamidothiazole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:72-14-0 SDS

72-14-0Synthetic route

N,N-bis(4-acetamidobenzenesulfonyl)-2-aminothiazole

N,N-bis(4-acetamidobenzenesulfonyl)-2-aminothiazole

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With water; sodium hydroxide at 75℃; for 0.75h; Reflux;75%
Multi-step reaction with 2 steps
1: ammonium hydroxide / water; acetone / 2.5 h / 65 °C
2: sodium hydroxide / water / 2 h / 65 °C
View Scheme
2-(p-Carbomethoxyaminobenzenesulfamido)thiazole
33119-99-2

2-(p-Carbomethoxyaminobenzenesulfamido)thiazole

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With calcium hydroxide In water for 2h; Heating;74.5%
2-bromo-1,3-thiazole
3034-53-5

2-bromo-1,3-thiazole

sulfanilamide
63-74-1

sulfanilamide

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With copper; potassium carbonate at 180 - 200℃;
2-thiazolylamine
96-50-4

2-thiazolylamine

4-chlorobenzenesulfonyl chloride
98-60-2

4-chlorobenzenesulfonyl chloride

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With pyridine Erhitzen des Reaktionsprodukts mit Kupferchlorid und konz. NH3 unter Druck auf 160-180grad;
With pyridine Erhitzen des Reaktionsprodukts mit Kupferchlorid und konz. NH3 unter Druck auf 160-180grad;
Nisulfazole
473-42-7

Nisulfazole

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With sodium hydroxide; iron(II) hydroxide
With hydrogenchloride; iron
With hydrogenchloride; tin
4'-(thiazol-2-ylsulfamoyl)acetanilide
127-76-4

4'-(thiazol-2-ylsulfamoyl)acetanilide

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With hydrogenchloride
With sodium hydroxide
With sodium hydroxide In water at 65℃; for 2h;
2-sulfanilylamino-thiazole-5-carboxylic acid
5664-51-7

2-sulfanilylamino-thiazole-5-carboxylic acid

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With nitrobenzene
With sodium hydroxide
at 180 - 190℃;
Erhitzen bis zur Schmelze;
4-acetylamino-N-[3-(4-acetylamino-benzenesulfonyl)-3H-thiazol-2-ylidene]-benzenesulfonamide
2183-24-6

4-acetylamino-N-[3-(4-acetylamino-benzenesulfonyl)-3H-thiazol-2-ylidene]-benzenesulfonamide

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With sodium hydroxide
With hydrogenchloride
With sodium hydroxide
2-thiazolylamine
96-50-4

2-thiazolylamine

4-aminobenzenesulfonyl chloride
24939-24-0

4-aminobenzenesulfonyl chloride

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With pyridine
4-phenylazo-benzenesulfonic acid thiazol-2-ylamide

4-phenylazo-benzenesulfonic acid thiazol-2-ylamide

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With sodium hydroxide; sodium dithionite
2-thiazolylamine
96-50-4

2-thiazolylamine

N-acetyl-sulfaniloyl chloride

N-acetyl-sulfaniloyl chloride

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
anschliessende Hydrolyse;
2-(4-chloro-benzenesulfonylamino)-thiazole-5-carboxylic acid ethyl ester
859486-36-5

2-(4-chloro-benzenesulfonylamino)-thiazole-5-carboxylic acid ethyl ester

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide
2: Erhitzen bis zur Schmelze
View Scheme
p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: aqueous NaOH
View Scheme
Multi-step reaction with 2 steps
1: ethyl acetate
2: aqueous HCl
View Scheme
Multi-step reaction with 2 steps
1: pyridine; aqueous acetone
2: aqueous HCl
View Scheme
Ni(H2NC6H4SO2NC3H2NS)2(ephedrine)2

Ni(H2NC6H4SO2NC3H2NS)2(ephedrine)2

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With mineral acid decompn. with strong mineral acid;
With mineral acid decompn. with strong mineral acid;
With mineral acid decompn. with strong mineral acid;
Ni(H2NC6H4SO2NC3H2NS)2(2-methylamino-1-phenyl-1-propanol)2

Ni(H2NC6H4SO2NC3H2NS)2(2-methylamino-1-phenyl-1-propanol)2

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With mineral acid decompn. with strong mineral acid;
With mineral acid decompn. with strong mineral acid;
With mineral acid decompn. with strong mineral acid;
Ni(H2NC6H4SO2NC3H2NS)2(pseudoephedrine)2

Ni(H2NC6H4SO2NC3H2NS)2(pseudoephedrine)2

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With mineral acid decompn. with strong mineral acid;
With mineral acid decompn. with strong mineral acid;
With mineral acid decompn. with strong mineral acid;
Ni(H2NC6H4SO2NC3H2NS)2(4-amino-morpholine)2

Ni(H2NC6H4SO2NC3H2NS)2(4-amino-morpholine)2

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
With mineral acid decompn. with strong mineral acid;
With mineral acid decompn. with strong mineral acid;
With mineral acid decompn. with strong mineral acid;
sulfanilic acid thiazol-2-ylamide; nickel (II)-salt

sulfanilic acid thiazol-2-ylamide; nickel (II)-salt

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HNO3 / not given
2: mineral acid
View Scheme
C23H32N6O7S2

C23H32N6O7S2

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2 h / 20 °C
2: acetonitrile; methanol; aq. phosphate buffer / 1 h / 37 °C / pH 7.4
View Scheme
C12H14N4O3S2*ClH

C12H14N4O3S2*ClH

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; N,N-dimethyl-formamide / acetonitrile / 24 h / 20 °C
2: 2 h / 20 °C
3: acetonitrile; methanol; aq. phosphate buffer / 1 h / 37 °C / pH 7.4
View Scheme
C17H22N4O5S2

C17H22N4O5S2

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methoxybenzene; hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
2: triethylamine; N,N-dimethyl-formamide / acetonitrile / 24 h / 20 °C
3: 2 h / 20 °C
4: acetonitrile; methanol; aq. phosphate buffer / 1 h / 37 °C / pH 7.4
View Scheme
C13H16N6O3S2*C2HF3O2

C13H16N6O3S2*C2HF3O2

A

Sulfathiazole
72-14-0

Sulfathiazole

B

C4H7N3O

C4H7N3O

Conditions
ConditionsYield
In methanol; aq. phosphate buffer; acetonitrile at 37℃; for 1h; pH=7.4;
2-thiazolylamine
96-50-4

2-thiazolylamine

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
Stage #1: 2-thiazolylamine; p-acetylaminobenzenesulfonyl chloride With pyridine In tetrahydrofuran at 20℃; for 6h;
Stage #2: With sodium hydroxide for 2h; Reflux;
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / acetonitrile / 12 h / 0 - 20 °C
2: hydrogen; palladium on activated charcoal / methanol / 24 h / 30 °C / 1551.49 Torr
View Scheme
Acetanilid
103-84-4

Acetanilid

Sulfathiazole
72-14-0

Sulfathiazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: chlorosulfonic acid / Heating
2: potassium carbonate / acetonitrile / Reflux
3: hydrogenchloride; water
View Scheme
C7H10N2O4
219774-63-7

C7H10N2O4

Sulfathiazole
72-14-0

Sulfathiazole

(E)-2-[(4-Amino-benzenesulfonyl)-thiazol-2-yl-amino]-3-(N'-methoxycarbonyl-hydrazino)-but-2-enoic acid methyl ester

(E)-2-[(4-Amino-benzenesulfonyl)-thiazol-2-yl-amino]-3-(N'-methoxycarbonyl-hydrazino)-but-2-enoic acid methyl ester

Conditions
ConditionsYield
With sodium methylate In tetrahydrofuran for 0.2h; Ambient temperature;97%
2-chloro-5-nitrobenzoylchloride
25784-91-2

2-chloro-5-nitrobenzoylchloride

Sulfathiazole
72-14-0

Sulfathiazole

N-[4-(Thiazol-2-yl)aminosulfonyl]phenyl-(2-chloro-5-nitrophenyl)carboxamide
312614-91-8

N-[4-(Thiazol-2-yl)aminosulfonyl]phenyl-(2-chloro-5-nitrophenyl)carboxamide

Conditions
ConditionsYield
With 2,4-dichlorophenoxyacetic acid dimethylamine97%
1-oxa-4-aza-spiro[4.4]nonane
176-29-4

1-oxa-4-aza-spiro[4.4]nonane

formaldehyd
50-00-0

formaldehyd

Sulfathiazole
72-14-0

Sulfathiazole

C17H22N4O3S2
1208127-46-1

C17H22N4O3S2

Conditions
ConditionsYield
In ethanol; water for 4h; Reflux;97%
4-(4-fluoro-benzoylamino)benzoyl chloride
735351-37-8

4-(4-fluoro-benzoylamino)benzoyl chloride

Sulfathiazole
72-14-0

Sulfathiazole

C23H17FN4O4S2
1369424-04-3

C23H17FN4O4S2

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 12h;96.6%
With triethylamine In tetrahydrofuran at 20℃;70%
C6H9N3O3
146000-76-2

C6H9N3O3

Sulfathiazole
72-14-0

Sulfathiazole

C15H18N6O5S2

C15H18N6O5S2

Conditions
ConditionsYield
With sodium methylate In tetrahydrofuran for 2h; Ambient temperature;96%
Sulfathiazole
72-14-0

Sulfathiazole

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

4-tetrazol-1-yl-N-thiazol-2-yl-benzenesulfonamide
313481-56-0

4-tetrazol-1-yl-N-thiazol-2-yl-benzenesulfonamide

Conditions
ConditionsYield
With sodium azide; acetic acid at 80 - 95℃;96%
formaldehyd
50-00-0

formaldehyd

Sulfathiazole
72-14-0

Sulfathiazole

1-Oxa-4-aza-spiro[4.6]undecane

1-Oxa-4-aza-spiro[4.6]undecane

C19H26N4O3S2
1208127-48-3

C19H26N4O3S2

Conditions
ConditionsYield
In ethanol; water for 4h; Reflux;96%
(R)-dihydro-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2(3H)-furanone
220352-11-4

(R)-dihydro-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2(3H)-furanone

Sulfathiazole
72-14-0

Sulfathiazole

(R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-(4-(N-thiazol-2-ylsulfamoyl)phenyl)butanamide
943654-01-1

(R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-(4-(N-thiazol-2-ylsulfamoyl)phenyl)butanamide

Conditions
ConditionsYield
Stage #1: Sulfathiazole With trimethylaluminum In dichloromethane at 0 - 20℃; for 0.833333h;
Stage #2: (R)-dihydro-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2(3H)-furanone In dichloromethane at 0 - 20℃; for 19.5h;
Stage #3: With hydrogenchloride In dichloromethane; water at 0℃; for 1.5h;
95%
Stage #1: Sulfathiazole With trimethylaluminum In dichloromethane at 0 - 20℃; for 0.833333h;
Stage #2: (R)-dihydro-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2(3H)-furanone In dichloromethane at 0 - 20℃; for 19.5h;
Stage #3: With hydrogenchloride In dichloromethane at 0℃; for 1.5h;
95%
2-imino-4,5,5-trimethyl-2,5-dihydrofuran-3-carboxamide
1108179-85-6

2-imino-4,5,5-trimethyl-2,5-dihydrofuran-3-carboxamide

Sulfathiazole
72-14-0

Sulfathiazole

4,5,5-trimethyl-2-(4-(N-thiazol-2-ylsulfamoyl)phenylimino)-2,5-dihydrofuran-3-carboxamide

4,5,5-trimethyl-2-(4-(N-thiazol-2-ylsulfamoyl)phenylimino)-2,5-dihydrofuran-3-carboxamide

Conditions
ConditionsYield
With acetic acid at 65 - 70℃;95%
Sulfathiazole
72-14-0

Sulfathiazole

2-cyano-N-(5-ethyl-[1,3,4]-thiadiazol-2-yl)acetamide
544431-10-9

2-cyano-N-(5-ethyl-[1,3,4]-thiadiazol-2-yl)acetamide

(E)-2-((5-ethyl-1,3,4-thiadiazol-2-yl)amino)-2-oxo-N-(4-(N-(thiazol-2-yl)sulfamoyl)phenyl)acetohydrazonoyl cyanide

(E)-2-((5-ethyl-1,3,4-thiadiazol-2-yl)amino)-2-oxo-N-(4-(N-(thiazol-2-yl)sulfamoyl)phenyl)acetohydrazonoyl cyanide

Conditions
ConditionsYield
Stage #1: Sulfathiazole With hydrogenchloride; sodium nitrite In water Cooling;
Stage #2: 2-cyano-N-(5-ethyl-[1,3,4]-thiadiazol-2-yl)acetamide With pyridine In water at 0 - 5℃;
95%
Sulfathiazole
72-14-0

Sulfathiazole

N-butyl-N-[2-(methacryloyloxy)ethyl]aniline
335672-84-9

N-butyl-N-[2-(methacryloyloxy)ethyl]aniline

trans-2-n-butyl-2-[4-({4-[(1,3-thiazol-2-ylamino)sulfonyl]phenyl}diazenyl)phenylamino]ethyl methacrylate
335672-99-6

trans-2-n-butyl-2-[4-({4-[(1,3-thiazol-2-ylamino)sulfonyl]phenyl}diazenyl)phenylamino]ethyl methacrylate

Conditions
ConditionsYield
Stage #1: Sulfathiazole With hydrogenchloride; acetic acid; sodium nitrite
Stage #2: N-butyl-N-[2-(methacryloyloxy)ethyl]aniline In hydrogenchloride; 2-methoxy-ethanol; acetic acid
93%
methyl 2-[4-(1H-indol-2-yl)phenoxy]acetate
1357149-34-8

methyl 2-[4-(1H-indol-2-yl)phenoxy]acetate

Sulfathiazole
72-14-0

Sulfathiazole

2-[4-(1H-indol-2-yl)phenoxy]-N-[4-(N-thiazol-2-ylsulfamoyl)phenyl]acetamide
1357149-23-5

2-[4-(1H-indol-2-yl)phenoxy]-N-[4-(N-thiazol-2-ylsulfamoyl)phenyl]acetamide

Conditions
ConditionsYield
With potassium carbonate In acetone for 10h;93%
Sulfathiazole
72-14-0

Sulfathiazole

O,O‐diethyl 2-iodoethoxymethylphosphonate

O,O‐diethyl 2-iodoethoxymethylphosphonate

diethyl (2-(4-(N-thiazol-2-ylsulfamoyl)phenylamino)ethoxy)methylphosphonate

diethyl (2-(4-(N-thiazol-2-ylsulfamoyl)phenylamino)ethoxy)methylphosphonate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 10 - 50℃; for 3h;93%
Sulfathiazole
72-14-0

Sulfathiazole

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

4-((2-chlorobenzylidene)amino)-N-(thiazol-2-yl)benzene sulfonamide

4-((2-chlorobenzylidene)amino)-N-(thiazol-2-yl)benzene sulfonamide

Conditions
ConditionsYield
With acetic acid In ethanol Reflux;92.42%
1-oxa-4-thiaspiro-<4,5>decan-2-one
1564-39-2

1-oxa-4-thiaspiro-<4,5>decan-2-one

Sulfathiazole
72-14-0

Sulfathiazole

4-(3-Oxo-1-thia-4-aza-spiro[4.5]dec-4-yl)-N-thiazol-2-yl-benzenesulfonamide

4-(3-Oxo-1-thia-4-aza-spiro[4.5]dec-4-yl)-N-thiazol-2-yl-benzenesulfonamide

Conditions
ConditionsYield
In pyridine for 2h; Heating;92%
Sulfathiazole
72-14-0

Sulfathiazole

5-chlorosalicyclaldehyde
635-93-8

5-chlorosalicyclaldehyde

4-((5-chloro-2-hydroxybenzylidene)amino)-N-(thiazol-2-yl)benzenesulfonamide
132649-33-3

4-((5-chloro-2-hydroxybenzylidene)amino)-N-(thiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
In ethanol for 3h; Reflux;92%
In ethanol at 100℃; Sealed tube;
phthalic anhydride
85-44-9

phthalic anhydride

Sulfathiazole
72-14-0

Sulfathiazole

4-(1,3-dioxoisoindolin-2-yl)-N-(2-thiazolyl)benzenesulfonamide
36340-59-7

4-(1,3-dioxoisoindolin-2-yl)-N-(2-thiazolyl)benzenesulfonamide

Conditions
ConditionsYield
With acetic acid at 120℃;92%
2-imino-3-carbamoyl-4-methyl-5,5-pentamethylene-2,5-dihydrofuran
1108179-88-9

2-imino-3-carbamoyl-4-methyl-5,5-pentamethylene-2,5-dihydrofuran

Sulfathiazole
72-14-0

Sulfathiazole

4-methyl-2-(4-(N-thiazol-2-ylsulfamoyl)phenylimino)-1-oxaspiro[4.5]dec-3-ene-3-carboxamide

4-methyl-2-(4-(N-thiazol-2-ylsulfamoyl)phenylimino)-1-oxaspiro[4.5]dec-3-ene-3-carboxamide

Conditions
ConditionsYield
With acetic acid at 65 - 70℃;92%
Sulfathiazole
72-14-0

Sulfathiazole

2,4-dihydroxy-5-(7-hydroxy-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-1-yl)benzaldehyde

2,4-dihydroxy-5-(7-hydroxy-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-1-yl)benzaldehyde

4-({2,4-dihydroxy-5-(7-hydroxy-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-1-yl)benzylidene}amino)-N-(thiazol-2-yl)benzenesulfonamide

4-({2,4-dihydroxy-5-(7-hydroxy-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-1-yl)benzylidene}amino)-N-(thiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
In ethanol for 2h; Heating;92%
Sulfathiazole
72-14-0

Sulfathiazole

1-cyanoacetyl-3,5-dimethylpyrazole
36140-83-7

1-cyanoacetyl-3,5-dimethylpyrazole

2-cyano-N-(4-(N-(thiazol-2 yl)sulfamoyl)phenyl)acetamide
33987-99-4

2-cyano-N-(4-(N-(thiazol-2 yl)sulfamoyl)phenyl)acetamide

Conditions
ConditionsYield
In benzene for 3h; Reflux;92%
2-chloro-6,7-dimethoxy-3H-quinazolin-4-one
27631-29-4

2-chloro-6,7-dimethoxy-3H-quinazolin-4-one

Sulfathiazole
72-14-0

Sulfathiazole

4-(2-chloro-6,7-dimethoxyquinazolin-4-ylamino)-N-(thiazol-2-yl)benzenesulfonamide monohydrochloride
1061768-00-0

4-(2-chloro-6,7-dimethoxyquinazolin-4-ylamino)-N-(thiazol-2-yl)benzenesulfonamide monohydrochloride

Conditions
ConditionsYield
In isopropyl alcohol for 2h; Heating;91%
In isopropyl alcohol for 24h; Reflux;72%
Sulfathiazole
72-14-0

Sulfathiazole

N-allyl isothiocyanate
57-06-7

N-allyl isothiocyanate

N-allyl-N'-(4-thiazol-2-ylsulfamoyl-phenyl)-thiourea
100796-66-5

N-allyl-N'-(4-thiazol-2-ylsulfamoyl-phenyl)-thiourea

Conditions
ConditionsYield
In ethanol Heating;91%
Sulfathiazole
72-14-0

Sulfathiazole

Stearoyl chloride
112-76-5

Stearoyl chloride

N-stearoyl-sulfanilic acid thiazol-2-ylamide
104158-71-6

N-stearoyl-sulfanilic acid thiazol-2-ylamide

Conditions
ConditionsYield
With pyridine for 48h; Ambient temperature;90%
Sulfathiazole
72-14-0

Sulfathiazole

malononitrile
109-77-3

malononitrile

N-(4-(N-(thiazol-2-yl)sulfamoyl)phenyl)carbonohydrazonoyl dicyanide
163803-58-5

N-(4-(N-(thiazol-2-yl)sulfamoyl)phenyl)carbonohydrazonoyl dicyanide

Conditions
ConditionsYield
Stage #1: Sulfathiazole With hydrogenchloride; sodium nitrite In water
Stage #2: malononitrile With sodium acetate In ethanol; water for 1h;
90%
Stage #1: Sulfathiazole With hydrogenchloride; sodium nitrite at 0 - 5℃;
Stage #2: malononitrile With sodium acetate In water for 0.5h; cooling;
Sulfathiazole
72-14-0

Sulfathiazole

silver nitrate

silver nitrate

Ag(1+)*C9H8N3O2S2(1-)={AgC9H8N3O2S2}
72774-33-5

Ag(1+)*C9H8N3O2S2(1-)={AgC9H8N3O2S2}

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 1h;90%
In water pH = 6.5 - 7.5;
BARBITURIC ACID
67-52-7

BARBITURIC ACID

Sulfathiazole
72-14-0

Sulfathiazole

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

N-(1,3-thiazol-2-yl)-4-{[(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino}benzenesulfonamide
338984-66-0

N-(1,3-thiazol-2-yl)-4-{[(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino}benzenesulfonamide

Conditions
ConditionsYield
In iso-butanol for 3h; Reflux;90%
4,6-dihydroxy-2-mercaptopyrimidine
504-17-6

4,6-dihydroxy-2-mercaptopyrimidine

Sulfathiazole
72-14-0

Sulfathiazole

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

4-{[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino}-N-(1,3-thiazol-2-yl)benzenesulfonamide
349566-54-7

4-{[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino}-N-(1,3-thiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
In iso-butanol for 3h; Reflux;90%

72-14-0Relevant articles and documents

USE OF LIME SLURRIES FOR SAPONIFYING CARBOMETHOXYSULFATHIAZOLE IN THE MANUFACTURE OF SULFATHIAZOLE

Kushkin, V. V.,Tupikina, V. G.

, p. 434 - 435 (1981)

-

-

Noll et al.

, p. 340 (1951)

-

Intensified Crystallization Processes for 1:1 Drug-Drug Cocrystals of Sulfathiazole-Theophylline, and Sulfathiazole-Sulfanilamide

Yeh, Kuan Lin,Lee, Tu

, p. 1339 - 1349 (2018/03/13)

The chemical synthesis and crystallization steps were integrated successfully for directly producing a 1:1 cocrystal of sulfathiazole-theophylline and a 1:1 cocrystal of sulfathiazole-sulfanilamide. The benefits of this process intensification were the reduction of number of steps, and the amount of energy consumption and solvent used. In addition, the overall cocrystal yields by Intensified Method I were much higher than the ones by the conventional method. Intensified Method I also gave high-purity cocrystals of ≥99%. Sulfathiazole not forming cocrystals with sulfanilamide by Intensified Method I was dissolved in the mother liquor by taking advantage of the pH-dependent solubility of sulfathiazole. Cocrystals of both sulfathiazole-theophylline and sulfathiazole-sulfanilamide systems remained stable under conditions of 40 °C and 75% relative humidity for a month.

Structure-based virtual screening and optimization of modulators targeting Hsp90-Cdc37 interaction

Wang, Lei,Li, Li,Zhou, Zi-Han,Jiang, Zheng-Yu,You, Qi-Dong,Xu, Xiao-Li

, p. 63 - 73 (2017/05/10)

Identification of novel Hsp90 inhibitors to disrupt Hsp90-Cdc37 protein-protein interaction (PPI) could be an alternative strategy to achieve Hsp90 inhibition. In this paper, a series of small molecules targeting Hsp90-Cdc37 complex are addressed and characterized. The molecules' key characters are determined by utilizing a structure-based virtual screening workflow, derivatives synthesis, and biological evaluation. Structural optimization and structure–activity relationship (SAR) analysis were then carried out on the virtual hit of VS-8 with potent activity, which resulted in the discovery of compound 10 as a more potent regulator of Hsp90-Cdc37 interaction with a promising inhibitory effect (IC50?=?27?μM), a moderate binding capacity (KD?=?40?μM) and a preferable antiproliferative activity against several cancer lines including MCF-7, SKBR3 and A549?cell lines (IC50?=?26?μM, 15?μM and 38?μM respectively). All the data suggest that compound 10 exhibits moderate inhibitory effect on Hsp90-Cdc37 and could be regard as a first evidence of a non-natural compound targeting Hsp90-Cdc37 PPI.

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