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144-82-1

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144-82-1 Usage

Chemical Description

Sulfamethizole is a sulfonamide antibiotic used to treat bacterial infections.

Description

Sulfamethizole is a broad spectrum sulfonamide antibiotic (MIC90s = 1.25-5,000 μg/ml against clinical isolates of E. coli and K. pneumoniae). It inhibits dihydropteroate synthase, an enzyme involved in folate biosynthesis. Formulations containing sulfamethizole have previously been used to treat urinary tract infections.

Originator

Thiosulfil,Ayerst,US,1953

Uses

Different sources of media describe the Uses of 144-82-1 differently. You can refer to the following data:
1. This drug has antibacterial activity with respect to streptococci, pneumococci, staphylococci, meningococci, gonococci, colon bacillus, pathogenic dysentery, and others. It is not very toxic. It is generally used for acute, uncomplicated infections of the urinary tract that are caused by sensitive organisms. Because it is removed quickly from the organism by the kidneys, the level of drug in the plasma remains low, and therefore it is not used for treating infections that are localized in the urinary tract. Sulfisoxazole is the more preferred drug. Synonyms of this drug are urosol, rufol, thiosulfil, and others.
2. Sulfonamide antibacterial.
3. Sulfamethizole is a sulfonamide based antibiotic that exhibit bactericidal activities towards gram-negative bacteria. Sulfamehizole was shown to be effective in treating gram-negative Bacillus AmpC en zyme in elderly patients with lower respiratory tract infection and as well as against microbs responsible for tuberculosis.

Definition

ChEBI: A sulfonamide consisting of a 1,3,4-thiadiazole nucleus with a methyl substituent at C-5 and a 4-aminobenzenesulfonamido group at C-2.

Manufacturing Process

To 10 grams acetaldehyde-thiosemicarbazone in 80 grams pyridine gradually 20 grams p-acetaminobenzolsulfonyl chloride is added. The reaction mixture is heated about 1 hour on a water bath and is then charged in 1 liter water, to which some acetic acid is added. The bottom sediment is sucked off and washed with water, after which it is crystallized by alcohol. 20 grams of the condensation product thus obtained is cleared in 100 cc water at about 30°C, after which 45 grams calcium ferricyanide dissolved in about 100 cc water is added. The reaction mixture is made slightly alkaline and held at a temperature of about 80°C for 2 to 3 hours. It is important that the reaction mixture during the whole period of 2 to 3 hours is steadily held alkaline.After the said 2 to 3 hours the liquid is cooled and the bottom sediment, which has a greenish color, is filtered off. The liquid sucked off eventually is treated with active carbon, filtered and made slightly acid by means of acetic acid, at which 2-amino-benzolsulfonamido-5-methyl-1,3,4-thiodiazol (melting point 204° to 206°C) is precipitated.

Brand name

Thiosulfil (Wyeth);3p methazol;Amer-azo;Azocline;Azotrex;Dorsec;Lucatyl;Methisul;Micturol ampicilina seda;Nicene;Orozl;Procijec;Proklar-m;Rp 2145;S-methizole;Spasmo-harnosal;Starisil;Suladyne;Sulfa gram;Thiosulfil a;Tiosulfan;Uratrac;Urolex;Uroluxcosil;Uro-nebactin;Uropeutic;Urotrex.

Therapeutic Function

Antibacterial

World Health Organization (WHO)

Sulfamethizole, a sulfonamide anti-infective agent, was introduced in 1953 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. However sulfamethizole, which is rapidly eliminated, retains a place in the treatment of urinary infections in some countries whereas in others its use has been discontinued.

General Description

Different sources of media describe the General Description of 144-82-1 differently. You can refer to the following data:
1. Sulfamethizole’splasma half-life is 2.5 hours. This compound is a white crystallinepowder soluble 1:2,000 in water.
2. White powder.

Air & Water Reactions

Insoluble in water.

Fire Hazard

Flammability data is lacking for SULFAMETHIZOLE. SULFAMETHIZOLE is probably non-flammable.

Pharmaceutical Applications

2-Sulfanilamido-5-methyl-1,3,4-thiodiazole. A short-acting sulfonamide (plasma half-life 2.5 h). Protein binding is c. 85%. About 60% is excreted in the urine within 5 h. It was formerly widely used in the treatment of urinary tract infection.

Synthesis

Sulfamethizole, N1-(5-methyl-1,3,4-thiadiazole-2-yl)sulfanilamide (33.1.15), is synthesized in two ways. According to the first, 5-amino-2-methyl-1,3,4- thiadiazole is reacted with 4-nitrobenzenesulfonyl chloride to make a nitro derivative (33.1.14), which is then reduced using iron filings in acetic acid to give the desired sulfamethizole.The second method of making sulfamethizole consists of reacting 4-acetylaminobenzene sulfonyl chloride with thiosemicarbazone of acetaldehyde, and subsequent oxidative cyclization of the product (33.1.16) to the substituted 1,3,4-thiadiazole in the presence of potassium ferricyanide in base, along with the simultaneous removal of the protective acetyl group.

Check Digit Verification of cas no

The CAS Registry Mumber 144-82-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 4 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 144-82:
(5*1)+(4*4)+(3*4)+(2*8)+(1*2)=51
51 % 10 = 1
So 144-82-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)

144-82-1 Well-known Company Product Price

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

  • (S0360)  Sulfamethizole  >98.0%(HPLC)(T)

  • 144-82-1

  • 25g

  • 900.00CNY

  • Detail
  • Sigma-Aldrich

  • (S2050000)  Sulfamethizole  European Pharmacopoeia (EP) Reference Standard

  • 144-82-1

  • S2050000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (S5632)  Sulfamethizole  analytical standard, ≥99% (HPLC)

  • 144-82-1

  • S5632-10G

  • 506.61CNY

  • Detail
  • Sigma-Aldrich

  • (S5632)  Sulfamethizole  analytical standard, ≥99% (HPLC)

  • 144-82-1

  • S5632-25G

  • 975.78CNY

  • Detail
  • Sigma-Aldrich

  • (46842)  Sulfamethizole  VETRANAL, analytical standard

  • 144-82-1

  • 46842-250MG-R

  • 404.82CNY

  • Detail

144-82-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name sulfamethizole

1.2 Other means of identification

Product number -
Other names SulfaMethizole

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:144-82-1 SDS

144-82-1Synthetic route

N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-nitrobenzenesulfonamide
349621-24-5

N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-nitrobenzenesulfonamide

sulfamethizole
144-82-1

sulfamethizole

Conditions
ConditionsYield
With hydrogenchloride; iron In ethanol; water for 3h; Reflux;100%
N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide
39719-87-4

N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide

sulfamethizole
144-82-1

sulfamethizole

Conditions
ConditionsYield
Stage #1: N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide With hydrogenchloride In water for 0.5h; Reflux;
Stage #2: With sodium carbonate In water
72%
Stage #1: N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide With hydrogenchloride In water for 0.5h; Reflux;
Stage #2: With sodium carbonate In water
72%
With hydrogenchloride
With sodium hydroxide
5-methyl-1,3,4-thiadiazol-2-amine
108-33-8

5-methyl-1,3,4-thiadiazol-2-amine

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

sulfamethizole
144-82-1

sulfamethizole

Conditions
ConditionsYield
anschliessend Erwaermen mit Eisen in wss.-aethanol. HCl;
5-methyl-1,3,4-thiadiazol-2-amine
108-33-8

5-methyl-1,3,4-thiadiazol-2-amine

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

sulfamethizole
144-82-1

sulfamethizole

Conditions
ConditionsYield
With pyridine anschliessend Erwaermen mit wss. NaOH;
With hydrogenchloride
acetaldehyde thiosemicarbazone
2302-95-6

acetaldehyde thiosemicarbazone

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

sulfamethizole
144-82-1

sulfamethizole

Conditions
ConditionsYield
With pyridine anschliessend Erwaermen mit Ca32 in wss.-alkal. Loesung;
acetyl chloride
75-36-5

acetyl chloride

1-acetyl-4--thiosemicarbazide

1-acetyl-4--thiosemicarbazide

sulfamethizole
144-82-1

sulfamethizole

Conditions
ConditionsYield
anschliessend Hydrolysieren mit Mineralsaeure;
p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

sulfamethizole
144-82-1

sulfamethizole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: aqueous HCl
View Scheme
Multi-step reaction with 2 steps
1: pyridine / 1 h / 95 °C
2: hydrogenchloride / water / 0.5 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: pyridine / 0 - 95 °C
2: hydrogenchloride / water / 0.5 h / Reflux
View Scheme
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

sulfamethizole
144-82-1

sulfamethizole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane; pyridine / 2 h / 20 °C
2: hydrogenchloride / iron / ethanol; water / 3 h / Reflux
View Scheme
sulfamethizole
144-82-1

sulfamethizole

2,3-isopropylidene-glyceraldehyde
15186-48-8

2,3-isopropylidene-glyceraldehyde

4-({[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylene}amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

4-({[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylene}amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dimethyl sulfoxide; toluene Condensation;100%
sulfamethizole
144-82-1

sulfamethizole

methyl 3-formyl-5-iodobenzoate

methyl 3-formyl-5-iodobenzoate

methyl 3-iodo-5-((4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenylamino)-methyl)benzoate

methyl 3-iodo-5-((4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenylamino)-methyl)benzoate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;99%
2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

sulfamethizole
144-82-1

sulfamethizole

4-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide
1204290-30-1

4-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
In ethanol at 115℃; for 72h;98%
tetrafluoroboric acid

tetrafluoroboric acid

sulfamethizole
144-82-1

sulfamethizole

sodium nitrite
7632-00-0

sodium nitrite

C9H8N5O2S2(1+)*BF4(1-)

C9H8N5O2S2(1+)*BF4(1-)

Conditions
ConditionsYield
In water at 0℃; for 0.75h; Inert atmosphere;96%
sulfamethizole
144-82-1

sulfamethizole

n-decanoyl chloride
112-13-0

n-decanoyl chloride

N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)decanamide
1191951-65-1

N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)decanamide

Conditions
ConditionsYield
With pyridine at 95℃; for 1h;95%
With pyridine at 0 - 95℃;95%
5-bromo-3-methoxysalicylaldehyde
5034-74-2

5-bromo-3-methoxysalicylaldehyde

sulfamethizole
144-82-1

sulfamethizole

(E)-4-((5-bromo-2-hydroxy-3-methoxy benzylidene)amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

(E)-4-((5-bromo-2-hydroxy-3-methoxy benzylidene)amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 78℃; for 6h;92%
sulfamethizole
144-82-1

sulfamethizole

Methacryloyl chloride
920-46-7

Methacryloyl chloride

methacryloyl sulfamethizole

methacryloyl sulfamethizole

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 20℃; for 1.5h; Cooling with ice;91%
5-bromosalicyclic acid
89-55-4

5-bromosalicyclic acid

sulfamethizole
144-82-1

sulfamethizole

(E)-4-((5-bromo-2-hydroxybenzylidene)amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

(E)-4-((5-bromo-2-hydroxybenzylidene)amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 78℃; for 6h;90%
1,8-Naphthalic anhydride
81-84-5

1,8-Naphthalic anhydride

sulfamethizole
144-82-1

sulfamethizole

4-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

4-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With triethylamine In ethanol at 80℃; for 10h;85%
4-chlorobenzoquinazoline
33987-02-9

4-chlorobenzoquinazoline

sulfamethizole
144-82-1

sulfamethizole

4-(benzo[g]quinazolin-4-ylamino)-N-(5-methyl-1,3,4-thiadiazol-2yl)benzenesulfonamide

4-(benzo[g]quinazolin-4-ylamino)-N-(5-methyl-1,3,4-thiadiazol-2yl)benzenesulfonamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 24h; Reflux;82%
2-chloro-6-methylnicotinonitrile
28900-10-9

2-chloro-6-methylnicotinonitrile

sulfamethizole
144-82-1

sulfamethizole

4-(3-cyano-6-methylpyridin-2-ylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

4-(3-cyano-6-methylpyridin-2-ylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 18h; Reflux;82%
2-chloromethyl-1H-benzimidazole
4857-04-9

2-chloromethyl-1H-benzimidazole

sulfamethizole
144-82-1

sulfamethizole

4-[(1H-Benzoimidazol-2-ylmethyl)-amino]-N-(5-methyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide
107090-15-3

4-[(1H-Benzoimidazol-2-ylmethyl)-amino]-N-(5-methyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide

Conditions
ConditionsYield
In methanol for 4h; Heating;81%
ethanol
64-17-5

ethanol

sulfamethizole
144-82-1

sulfamethizole

3-Formylchromone
17422-74-1

3-Formylchromone

4-{[(2-ethoxy-4-oxo-2H-chromen-3(4H)ylidene)methyl]amino}-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide
1449215-86-4

4-{[(2-ethoxy-4-oxo-2H-chromen-3(4H)ylidene)methyl]amino}-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid Heating;81%
sulfamethizole
144-82-1

sulfamethizole

2-hydroxynaphthalene-1-carbaldehyde
708-06-5

2-hydroxynaphthalene-1-carbaldehyde

4-{(E)-[(2-hydroxynaphthalen-1-yl)methylidene]amino}-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

4-{(E)-[(2-hydroxynaphthalen-1-yl)methylidene]amino}-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 6h; Reflux;81%
sulfamethizole
144-82-1

sulfamethizole

2-Chloromethyl-4(7)-nitro-benzimidazole
99876-68-3

2-Chloromethyl-4(7)-nitro-benzimidazole

N-(5-Methyl-[1,3,4]thiadiazol-2-yl)-4-[(4-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide
107090-22-2

N-(5-Methyl-[1,3,4]thiadiazol-2-yl)-4-[(4-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide

Conditions
ConditionsYield
In methanol for 4h; Heating;80%
sulfamethizole
144-82-1

sulfamethizole

methyl 3-formyl-5-(6-methoxypyridin-3-yl)benzoate

methyl 3-formyl-5-(6-methoxypyridin-3-yl)benzoate

methyl 3-(6-methoxypyridin-3-yl)-5-((4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenylamino)methyl)benzoate

methyl 3-(6-methoxypyridin-3-yl)-5-((4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenylamino)methyl)benzoate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;80%
4-chloro-2-phenylquinazoline
6484-25-9

4-chloro-2-phenylquinazoline

sulfamethizole
144-82-1

sulfamethizole

N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-(2-phenylquinazolin-4-ylamino)benzenesulfonamide

N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-(2-phenylquinazolin-4-ylamino)benzenesulfonamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 22h; Reflux;80%
sulfamethizole
144-82-1

sulfamethizole

(E)-3-(N,N-dimethylamino)-1-(3,4-dimethoxyphenyl)-2-propen-1-one
127172-22-9

(E)-3-(N,N-dimethylamino)-1-(3,4-dimethoxyphenyl)-2-propen-1-one

Z-4-(3-(3,4-dimethoxyphenyl)-3-oxoprop-1-enylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Z-4-(3-(3,4-dimethoxyphenyl)-3-oxoprop-1-enylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With acetic acid In ethanol for 22h; Reflux;80%
sulfamethizole
144-82-1

sulfamethizole

N-allyl isothiocyanate
57-06-7

N-allyl isothiocyanate

C13H15N5O2S3

C13H15N5O2S3

Conditions
ConditionsYield
In butan-1-ol Heating;79%
sulfamethizole
144-82-1

sulfamethizole

methyl iodide
74-88-4

methyl iodide

(Z)-N-(3,5-dimethyl-1,3,4-thiadiazol-2(3H)-ylidene)-4-(dimethylamino)benzenesulfonamide

(Z)-N-(3,5-dimethyl-1,3,4-thiadiazol-2(3H)-ylidene)-4-(dimethylamino)benzenesulfonamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 24h;79%
formaldehyd
50-00-0

formaldehyd

sulfamethizole
144-82-1

sulfamethizole

N-(4-carbamoylphenyl)nicotinamide
418790-13-3

N-(4-carbamoylphenyl)nicotinamide

N-[4-({[4-(5-methyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenylamino]-methyl}-carbamoyl)-phenyl]-nicotinamide

N-[4-({[4-(5-methyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenylamino]-methyl}-carbamoyl)-phenyl]-nicotinamide

Conditions
ConditionsYield
Stage #1: formaldehyd; N-(4-carbamoyl-phenyl)-nicotinamide With hydrogenchloride In methanol at 0℃; for 0.5h; pH=3.5;
Stage #2: sulfamethizole Heating;
78%
sulfamethizole
144-82-1

sulfamethizole

((E)-3-(3-(dimethylamino)acryloyl))-2H-chromen-2-one
371756-61-5

((E)-3-(3-(dimethylamino)acryloyl))-2H-chromen-2-one

(Z)-N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-(3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-enylamino)benzenesulfonamide

(Z)-N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-(3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-enylamino)benzenesulfonamide

Conditions
ConditionsYield
In ethanol for 21h; Reflux;77%
sulfamethizole
144-82-1

sulfamethizole

(Z)-3-(dimethylamino)-1-(10H-phenothiazin-2-yl)prop-2-en-1-one

(Z)-3-(dimethylamino)-1-(10H-phenothiazin-2-yl)prop-2-en-1-one

(Z)-N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-(3-oxo-3-(10H-phenothiazine-2yl)prop-1-enylamino)benzenesulfonamide

(Z)-N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-(3-oxo-3-(10H-phenothiazine-2yl)prop-1-enylamino)benzenesulfonamide

Conditions
ConditionsYield
In ethanol for 18h; Reflux;77%
sulfamethizole
144-82-1

sulfamethizole

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-chloro-N-[4-(5-methyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-acetamide
24694-13-1

2-chloro-N-[4-(5-methyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-acetamide

Conditions
ConditionsYield
With triethylamine In acetone at 20℃; Cooling with ice;76%
2-(chloromethyl)-5-nitro-1H-benzo[d]imidazole
14625-39-9

2-(chloromethyl)-5-nitro-1H-benzo[d]imidazole

sulfamethizole
144-82-1

sulfamethizole

N-(5-Methyl-[1,3,4]thiadiazol-2-yl)-4-[(5-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide
107090-30-2

N-(5-Methyl-[1,3,4]thiadiazol-2-yl)-4-[(5-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide

Conditions
ConditionsYield
In methanol for 4h; Heating;73%
sulfamethizole
144-82-1

sulfamethizole

4-propyl-phenyl isothiocyanate
718604-99-0

4-propyl-phenyl isothiocyanate

N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-{[(4-propylphenyl)carbamothioyl]amino}benzenesulfonamide

N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-{[(4-propylphenyl)carbamothioyl]amino}benzenesulfonamide

Conditions
ConditionsYield
In acetone at 20 - 80℃; for 6.5h;70%
sulfamethizole
144-82-1

sulfamethizole

acetic anhydride
108-24-7

acetic anhydride

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

4-(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

4-(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
Stage #1: acetic anhydride; 5-Bromo-2-aminobenzoic acid for 4h; Reflux;
Stage #2: sulfamethizole With acetic acid for 4h; Reflux;
70%
sulfamethizole
144-82-1

sulfamethizole

acetic anhydride
108-24-7

acetic anhydride

5-chloroanthranilic acid
635-21-2

5-chloroanthranilic acid

4-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

4-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions
ConditionsYield
Stage #1: acetic anhydride; 5-chloroanthranilic acid for 4h; Reflux;
Stage #2: sulfamethizole With acetic acid for 4h; Reflux;
69%

144-82-1Related news

Solubility and Preferential Solvation of Sulfanilamide, SULFAMETHIZOLE (cas 144-82-1) and Sulfapyridine in Methanol + Water Mixtures at 298.15 K09/28/2019

The equilibrium solubilities of sulfanilamide, sulfamethizole and sulfapyridine in methanol + water mixtures at 298.15 K were determined and the preferential solvation parameters were derived from their thermodynamic solution properties by means of the inverse Kirkwood–Buff integrals. In all ca...detailed

144-82-1Relevant articles and documents

MODULATORS OF IMMUNOINHIBITORY RECEPTOR PD-1, AND METHODS OF USE THEREOF

-

Page/Page column 52, (2011/07/30)

Disclosed are an assay to identify modulators of the PD-1 :PD-L pathway and PD-1 :PD-L pathway modulators, e.g., compounds and pharmaceutical compositions thereof. Methods for treating diseases influenced by modulation of the PD-1 :PD-L pathway such as, for example, autoimmune diseases, inflammatory disorders, allergies, transplant rejection, cancer, immune deficiency, and other immune system-related disorders, are also disclosed.

SMALL MOLECULE INHIBITORS OF THE PLECKSTRIN HOMOLOGY DOMAIN AND METHODS FOR USING SAME

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, (2009/12/02)

Pleckstrin homology domain binding compounds, pharmaceutical compositions including such compounds, and methods for their use are described herein.

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