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14949-00-9

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14949-00-9 Usage

Chemical Properties

White Solid

Uses

Acetazolamide intermediate.

Safety Profile

An experimental teratogen. Whenheated to decomposition it emits very toxic fumes ofNOx, Na2O, and SOx.

Check Digit Verification of cas no

The CAS Registry Mumber 14949-00-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,9,4 and 9 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 14949-00:
(7*1)+(6*4)+(5*9)+(4*4)+(3*9)+(2*0)+(1*0)=119
119 % 10 = 9
So 14949-00-9 is a valid CAS Registry Number.
InChI:InChI=1/C2H4N4O2S2/c3-1-5-6-2(9-1)10(4,7)8/h(H2,3,5)(H2,4,7,8)

14949-00-9 Well-known Company Product Price

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  • USP

  • (1005048)  Acetazolamide Related Compound D  United States Pharmacopeia (USP) Reference Standard

  • 14949-00-9

  • 1005048-25MG

  • 14,500.98CNY

  • Detail

14949-00-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Amino-1,3,4-thiadiazole-2-sulfonamide

1.2 Other means of identification

Product number -
Other names 5-AMINO-1,3,4-THIADIAZOLE-2-SULFONAMIDE

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:14949-00-9 SDS

14949-00-9Synthetic route

acetazolamide
59-66-5

acetazolamide

5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 4h; Reflux;100%
With hydrogenchloride In methanol; water for 18h; Reflux;98%
With hydrogenchloride; water In methanol for 18h; Reflux;98%
acetazolamide
59-66-5

acetazolamide

A

5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With water at 25℃; Thermodynamic data; effect of pH (1.68 - 8.17), two buffer species (phosphate and citrate), ionic strength and temperature on stability of title compound; Ea;
5-amino-2-sulfamoyl-1,3,4-thiadiazole monohydrochloride
120208-98-2

5-amino-2-sulfamoyl-1,3,4-thiadiazole monohydrochloride

5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In water pH=7;
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

4-(dimethylamino)chalcone
22965-98-6, 72758-79-3, 1030-27-9

4-(dimethylamino)chalcone

5-[(E)-3-(4-Dimethylamino-phenyl)-1-phenyl-prop-2-en-(Z)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

5-[(E)-3-(4-Dimethylamino-phenyl)-1-phenyl-prop-2-en-(Z)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

Conditions
ConditionsYield
In ethanol for 8h; Heating;97%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

(E)-4-(3,4,5-trimethoxyphenyl)but-3-en-2-one
19039-94-2

(E)-4-(3,4,5-trimethoxyphenyl)but-3-en-2-one

5-[(E)-1-Methyl-3-(3,4,5-trimethoxy-phenyl)-prop-2-en-(E)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

5-[(E)-1-Methyl-3-(3,4,5-trimethoxy-phenyl)-prop-2-en-(E)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

Conditions
ConditionsYield
In ethanol for 8h; Heating;97%
succinic acid anhydride
108-30-5

succinic acid anhydride

5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

4-oxo-4-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino)butanoic acid
78851-85-1

4-oxo-4-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino)butanoic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 12h;96%
In acetonitrile Reflux;85.5%
In N,N-dimethyl-formamide at 50℃;33%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

2,4,6-tri(trideuteromethyl)pyrylium perchlorate

2,4,6-tri(trideuteromethyl)pyrylium perchlorate

2,4,6-(trimethyl-d9)-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

2,4,6-(trimethyl-d9)-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

Conditions
ConditionsYield
In dichloromethane Ambient temperature;92%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

(E)-1-(4-methoxyphenyl)-3-(4-nitrophenyl)-2-propen-1-one
6552-67-6, 30925-59-8, 77636-36-3

(E)-1-(4-methoxyphenyl)-3-(4-nitrophenyl)-2-propen-1-one

5-[(E)-1-(4-Methoxy-phenyl)-3-(4-nitro-phenyl)-prop-2-en-(Z)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

5-[(E)-1-(4-Methoxy-phenyl)-3-(4-nitro-phenyl)-prop-2-en-(Z)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

Conditions
ConditionsYield
In ethanol for 8h; Heating;92%
potassium cyanate
590-28-3

potassium cyanate

5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

5-ureido-1,3,4-thiadiazole-2-sulfonamide
109907-71-3

5-ureido-1,3,4-thiadiazole-2-sulfonamide

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 50℃;90%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

methyl isocyanate
624-83-9

methyl isocyanate

5-(N'-methylureido)-1,3,4-thiadiazole-2-sulfonamide
32873-77-1

5-(N'-methylureido)-1,3,4-thiadiazole-2-sulfonamide

Conditions
ConditionsYield
In ethyl acetate for 1h; Heating;90%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

(2E)-1-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
105686-91-7

(2E)-1-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one

5-[(E)-1-(4-Methoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-prop-2-en-(Z)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

5-[(E)-1-(4-Methoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-prop-2-en-(Z)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

Conditions
ConditionsYield
In ethanol for 8h; Heating;90%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

quinoline-8-sulfonyl chloride
18704-37-5

quinoline-8-sulfonyl chloride

quinoline-8-sulfonic acid (5-sulfamoyl-[1,3,4]thiadiazol-2-yl)-amide

quinoline-8-sulfonic acid (5-sulfamoyl-[1,3,4]thiadiazol-2-yl)-amide

Conditions
ConditionsYield
With triethylamine In acetonitrile at 4℃; Alkylation;90%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

Deoxycholic acid
83-44-3

Deoxycholic acid

5-(3α,12α-dihydroxy-5-β-cholan-24-amido)-1,3,4-thiazole-2-sulfonamide

5-(3α,12α-dihydroxy-5-β-cholan-24-amido)-1,3,4-thiazole-2-sulfonamide

Conditions
ConditionsYield
Stage #1: Deoxycholic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at 20℃; for 24h;
Stage #2: 5-amino-1, 3, 4-thiadiazole-2-sulfonamide In tetrahydrofuran for 48h; Heating;
90%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

2,4,6-triphenylpyrilium perchlorate
1484-88-4

2,4,6-triphenylpyrilium perchlorate

2,4,6-triphenyl-4-methyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

2,4,6-triphenyl-4-methyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

Conditions
ConditionsYield
In dichloromethane Ambient temperature;89%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

2,4-Dimethyl-6-o-tolyl-pyranylium; perchlorate

2,4-Dimethyl-6-o-tolyl-pyranylium; perchlorate

2-(2-methylphenyl)-4,6-dimethyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

2-(2-methylphenyl)-4,6-dimethyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

Conditions
ConditionsYield
In dichloromethane Ambient temperature;89%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

1,3,4-Trimethyl-5,6,7,8-tetrahydro-isochromenylium; perchlorate

1,3,4-Trimethyl-5,6,7,8-tetrahydro-isochromenylium; perchlorate

5,6,7,8-tetrahydro-1,3,4-trimethyl-2-N-(2-sulfonamido-1,3,4-thiadiazol-5-yl)isoquinolinium perchlorate

5,6,7,8-tetrahydro-1,3,4-trimethyl-2-N-(2-sulfonamido-1,3,4-thiadiazol-5-yl)isoquinolinium perchlorate

Conditions
ConditionsYield
In dichloromethane Ambient temperature;89%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

dehydrocholic acid
81-23-2

dehydrocholic acid

5-(3,7,12-trioxo-5-β-cholan-24-amido)-1,3,4-thiadiazole-2-sulfonamide

5-(3,7,12-trioxo-5-β-cholan-24-amido)-1,3,4-thiadiazole-2-sulfonamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;89%
With thionyl chloride In tetrahydrofuran for 12h;82%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

(E)-1-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one
1037642-78-6

(E)-1-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one

5-[(E)-1-(4-Amino-phenyl)-3-(3,4,5-trimethoxy-phenyl)-prop-2-en-(Z)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

5-[(E)-1-(4-Amino-phenyl)-3-(3,4,5-trimethoxy-phenyl)-prop-2-en-(Z)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

Conditions
ConditionsYield
In ethanol for 8h; Heating;87%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

cholic acid
81-25-4

cholic acid

5-(3α,7α,12α-trihydroxy-5-β-cholan-24-amido)-1,3,4-thiazole-2-sulfonamide

5-(3α,7α,12α-trihydroxy-5-β-cholan-24-amido)-1,3,4-thiazole-2-sulfonamide

Conditions
ConditionsYield
Stage #1: cholic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at 20℃; for 24h;
Stage #2: 5-amino-1, 3, 4-thiadiazole-2-sulfonamide In tetrahydrofuran for 48h; Heating;
87%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

(2E)-1-(4-methoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one
396725-25-0

(2E)-1-(4-methoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one

5-[(E)-1-(4-Methoxy-phenyl)-3-(3-nitro-phenyl)-prop-2-en-(Z)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

5-[(E)-1-(4-Methoxy-phenyl)-3-(3-nitro-phenyl)-prop-2-en-(Z)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

Conditions
ConditionsYield
In ethanol for 8h; Heating;86%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

1-adamantylacetyl chloride
19835-38-2

1-adamantylacetyl chloride

5-(1-Adamantylacetamido)-1,3,4-thiadiazole-2-sulfonamide

5-(1-Adamantylacetamido)-1,3,4-thiadiazole-2-sulfonamide

Conditions
ConditionsYield
With water In acetonitrile Acylation;86%
With triethylamine In acetonitrile at 0 - 20℃;
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

propionic acid anhydride
123-62-6

propionic acid anhydride

N-(2-sulfamoyl-1,3,4-thiadiazol-5-yl)propionamide
98-75-9

N-(2-sulfamoyl-1,3,4-thiadiazol-5-yl)propionamide

Conditions
ConditionsYield
In acetonitrile at 0℃; Reflux;85.2%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

2,3,4,6-Tetramethyl-pyrylium-perchlorat

2,3,4,6-Tetramethyl-pyrylium-perchlorat

2,3,4,6-tetramethyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

2,3,4,6-tetramethyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

Conditions
ConditionsYield
In methanol Heating;85%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

2,6-Bis(2-methylphenyl)-4-methyl-pyrylium perchlorate

2,6-Bis(2-methylphenyl)-4-methyl-pyrylium perchlorate

2,6-bis(2-methylphenyl)-4-methyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

2,6-bis(2-methylphenyl)-4-methyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

Conditions
ConditionsYield
In methanol for 3h; Heating;85%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

Lithocholic acid
434-13-9

Lithocholic acid

5-(3α-hydroxy-5-β-cholan-24-amido)-1,3,4-thiazole-2-sulfonamide

5-(3α-hydroxy-5-β-cholan-24-amido)-1,3,4-thiazole-2-sulfonamide

Conditions
ConditionsYield
Stage #1: Lithocholic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at 20℃; for 24h;
Stage #2: 5-amino-1, 3, 4-thiadiazole-2-sulfonamide In tetrahydrofuran for 48h; Heating;
85%
2-bromo-N-(3'-fluorophenyl)acetamide
73392-04-8

2-bromo-N-(3'-fluorophenyl)acetamide

5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

A

5-N-(2-[N-{3-fluorophenyl}acetamido])-5-amino-1,3,4-thiadiazole-2-sulfonamide

5-N-(2-[N-{3-fluorophenyl}acetamido])-5-amino-1,3,4-thiadiazole-2-sulfonamide

B

5-N,N-bis(2-[N-{3-fluorophenyl}acetamido])-5-amino-1,3,4-thiadiazole-2-sulfonamide

5-N,N-bis(2-[N-{3-fluorophenyl}acetamido])-5-amino-1,3,4-thiadiazole-2-sulfonamide

Conditions
ConditionsYield
Stage #1: 5-amino-1, 3, 4-thiadiazole-2-sulfonamide With potassium carbonate In N,N-dimethyl-formamide at -20℃; for 0.0833333h;
Stage #2: 2-bromo-N-(3'-fluorophenyl)acetamide In N,N-dimethyl-formamide
A 85%
B 66%
Stage #1: 5-amino-1, 3, 4-thiadiazole-2-sulfonamide With potassium carbonate In N,N-dimethyl-formamide
Stage #2: 2-bromo-N-(3'-fluorophenyl)acetamide In N,N-dimethyl-formamide at -20℃;
A 23%
B 66%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

2,4,6-trimethyl-3-phenylpyrylium perchlorate

2,4,6-trimethyl-3-phenylpyrylium perchlorate

2,4,6-triamethyl-3-phenyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

2,4,6-triamethyl-3-phenyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

Conditions
ConditionsYield
In methanol Heating;84%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

2-(2-Chloro-phenyl)-4,6-dimethyl-pyranylium; perchlorate

2-(2-Chloro-phenyl)-4,6-dimethyl-pyranylium; perchlorate

2-(2-chorophenyl)-4,6-dimethyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

2-(2-chorophenyl)-4,6-dimethyl-1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorate

Conditions
ConditionsYield
In methanol for 3h; Heating;84%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

4-(4-N,N-dimethylaminophenyl)-3-buten-2-one
30625-58-2

4-(4-N,N-dimethylaminophenyl)-3-buten-2-one

5-[(E)-3-(4-Dimethylamino-phenyl)-1-methyl-prop-2-en-(E)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

5-[(E)-3-(4-Dimethylamino-phenyl)-1-methyl-prop-2-en-(E)-ylideneamino]-[1,3,4]thiadiazole-2-sulfonic acid amide

Conditions
ConditionsYield
In ethanol for 8h; Heating;84%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

3,4,5-Trimethoxybenzoyl chloride
4521-61-3

3,4,5-Trimethoxybenzoyl chloride

5-(3,4,5-Trimethoxybenzamido)-1,3,4-thiadiazole-2-sulfonamide

5-(3,4,5-Trimethoxybenzamido)-1,3,4-thiadiazole-2-sulfonamide

Conditions
ConditionsYield
With water In acetonitrile Acylation;84%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

8-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)octanoic acid
126631-93-4

8-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)octanoic acid

(9H-fluoren-9-yl)methyl (8-oxo-8-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino)octyl)carbamate

(9H-fluoren-9-yl)methyl (8-oxo-8-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino)octyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;84%
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

5-(Adamantyl-1-carboxamido)-1,3,4-thiadiazole-2-sulfonamide

5-(Adamantyl-1-carboxamido)-1,3,4-thiadiazole-2-sulfonamide

Conditions
ConditionsYield
With triethylamine In acetonitrile at 4℃; for 5h;83%
With water In acetonitrile Acylation;82%
With pyridine In acetonitrile at 0 - 20℃;75.2%
With triethylamine In acetonitrile at 0 - 20℃;

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Iikuni, Shimpei,Kitano, Anna,Watanabe, Hiroyuki,Shimizu, Yoichi,Ono, Masahiro

, (2020)

Carbonic anhydrase-IX (CA-IX) is an attractive target for detecting tumors associated with a poor prognosis. We previously reported a [99mTc]hydroxamamide complex based on ureidosulfonamide as a CA-IX ligand ([99mTc]URB2A), which showed a favorable affinity for CA-IX high-expressing cells in vitro and tumors in vivo; however, radioactivity retention in the blood pool suggested a high background signal on imaging. To improve the pharmacokinetics of [99mTc]URB2A, in this study, we designed and synthesized [99mTc]ISB2 based on imidazothiadiazole sulfonamide, which exhibited greater CA-IX affinity and faster clearance from the blood pool than ureidosulfonamide in studies using corresponding 111In-labeled compounds, and evaluated its utility for CA-IX imaging. In an in vitro cell binding assay, [99mTc]ISB2 markedly bound to CA-IX high-expressing (HT-29) cells; moreover, its binding was greater than that of [99mTc]URB2A. In an in vivo biodistribution assay, [99mTc]ISB2 showed faster clearance from the blood pool than [99mTc]URB2A; however, lower HT-29 tumor accumulation was observed. Further structural modification of [99mTc]ISB2 to improve its stability may lead to the development of a useful [99mTc]hydroxamamide complex for CA-IX imaging.

Carbonic anhydrase inhibitors. V: Pyrylium salts in the synthesis of isozyme-specific inhibitors

Supuran,Manole,Dinculescu,Schiketanz,Gheorghiu,Puscas,Balaban

, p. 716 - 719 (1992)

Syntheses and physicochemical properties of 2,4,6-tri-,2,3,4,6-tetra-, or 2,3,4,5,6-pentasubstituted 1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorates are presented. The new compounds, putative inhibitors of membrane-bound carbonic anhydrase, were tested for inhibitory action on the bovine red cell enzyme.

Improved molecular recognition of Carbonic Anhydrase IX by polypeptide conjugation to acetazolamide

Yang, Jie,Koruza, Katarina,Fisher, Zo?,Knecht, Wolfgang,Baltzer, Lars

, p. 5838 - 5848 (2017)

The small molecule inhibitor acetazolamide (AZM) was conjugated to a set of designed polypeptides and the resulting conjugates were evaluated for their affinity to Human Carbonic Anhydrase II (HCA II) using surface plasmon resonance. The dissociation constant of the AZM-HCA II complex was 38 nM and that of the AZM conjugated polypeptide (4-C10L17-AZM) to HCA II was found to be 4 nM, an affinity enhancement of a factor of 10 due to polypeptide conjugation. For Human Carbonic Anhydrase IX (HCA IX) the dissociation constant of AZM was 3 nM, whereas that of the 4-C10L17-AZM conjugate was 90 pM, a 33-fold affinity enhancement. This dramatic affinity increase due to polypeptide conjugation was achieved for a small molecule ligand with an already high affinity to the target protein. This supports the concept that enhancements due to polypeptide conjugation are not limited to small molecule ligands that bind proteins in the mM to μM range but may be used also for nM ligands to provide recognition elements with dissociation constants in the pM range. Evaluations of two HCA IX constructs that do not carry the proteoglycan (PG) domain did not show significant affinity differences between AZM and the polypeptide conjugate, providing evidence that the improved binding of 4-C10L17-AZM to HCA IX emanated from interactions between the polypeptide segment and the PG domain found only in one carbonic anhydrase, HCA IX.

Preformulation studies of acetazolamide: effect of pH, two buffer species, ionic strength, and temperature on its stability.

Parasrampuria,Gupta

, p. 855 - 857 (1989)

Using an HPLC method, the effect of pH, two buffer species (phosphate and citrate), ionic strength, and temperature on the stability of acetozolamide has been studied. The optimum pH of stability appears to be 4. The buffers and ionic strength did not affect the decomposition constant. There was a direct relationship between the activation energies and pH values, with an energy of activation (Ea) value of 16.61 kcal/mol at pH 4. The un-ionized acetazolamide is subject to specific acid-base catalysis. The KH and KOH values have been estimated to be 0.23 and 1.56 d-1, respectively. These preformulation studies can be used to develop a stable oral liquid dosage form of acetazolamide.

Salts of 5-amino-2-sulfonamide-1,3,4-thiadiazole, a structural and analog of acetazolamide, show interesting carbonic anhydrase inhibitory properties, diuretic, and anticonvulsant action

Diaz, Jorge R. A.,Camí, Gerardo Enrique,Liu-González, Malva,Vega, Daniel R.,Vullo, Daniela,Juárez, Américo,Pedregosa, José C.,Supuran, Claudiu T.

, p. 1102 - 1110 (2016)

Three salts of 5-amino-2-sulfonamide-1,3,4-thiadiazole (Hats) were prepared and characterized by physico-chemical methods. The p-toluensulfonate, the methylsulfonate, and the chlorhydrate monohydrate salts of Hats were evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors (CAIs) and as anticonvulsants and diuretics, since many CAIs are clinically used as pharmacological agents. The three Hats salts exhibited diuretic and anticonvulsant activities with little neurotoxicity. The human (h) isoforms hCA I, II, IV, VII, IX, and XII were inhibited in their micromolar range by these salts, whereas pathogenic beta and gamma CAs showed similar, weak inhibitory profiles.

A red-shifted photochromic sulfonylurea for the remote control of pancreatic beta cell function

Broichhagen,Frank,Johnston,Mitchell,?mid,Marchetti,Bugliani,Rutter,Trauner,Hodson

, p. 6018 - 6021 (2015)

Azobenzene photoresponsive elements can be installed on sulfonylureas, yielding optical control over pancreatic beta cell function and insulin release. An obstacle to such photopharmacological approaches remains the use of ultraviolet-blue illumination. Herein, we synthesize and test a novel yellow light-activated sulfonylurea based on a heterocyclic azobenzene bearing a push-pull system.

Infrared and raman spectra of 5-amino-1,3,4-thiadiazole-2-sulfonamide (Hats). Experimental data and quantum chemistry calculations

Camí,Chufán,Pedregosa,Varetti

, p. 119 - 127 (2001)

The infrared and Raman spectra in the range 4000-50 cm-@ were obtained for 5-amino-1,3,4-thiadiazole-2-sulfonamide. The molecular geometry was optimized by means of the DFT methods of quantum chemistry (B3LYP/6-31G**), resulting in a structure which agrees quite well with that obtained by X-ray diffraction. The wavenumbers corresponding to the normal modes of vibration were calculated using the same approximation and the associated force field converted to a set of local symmetry coordinates, with subsequent calculation of the potential energy distribution. An assignment of the observed bands is proposed on the basis of such calculations and the comparison with related molecules.

Synthesis and properties of two new membrane-impermeant high-molecular-weight carbonic anhydrase inhibitors

Conroy, Curtis W.,Wynns, George C.,Maren, Thomas H.

, p. 262 - 272 (1996)

The synthesis and inhibitory properties and stability of two nontoxic high-molecular-weight carbonic anhydrase inhibitors (F 3500 and POBUMS) are reported. F 3500 was prepared by the covalent linkage of aminobenzolamide, a potent carbonic anhydrase (CA) inhibitor, to polyoxyethylene bisacetic acid (MW 3350). Linkage of the same inhibitor to polybutadiene maleic acid copolymer (MW 20,000) gave POBUMS. They contained on a mole percentage basis 0.11-0.28% unreacted aminobenzolamide as contaminant. F 3500 and POBUMS were approximately equipotent as carbonic anhydrase inhibitors on a weight basis with K(i) at 37°C for CA II and CA IV of approximately 0.5 and 10 μg/ml, respectively. They showed a maximum release of 28% aminobenzolamide when heated at 70°C for 3 days at pH 10.5 and were completely stable toward enzymatic hydrolysis (protease and peptidase at 25°C). They were not membrane permeable as judged by their inability to bind to intracellular CA II in intact red cells, nor were they actively uptaken in rat kidney slices. Rats injected with F 3500 (200 mg/kg) showed no toxicity and excreted 93% of the polymer unchanged in the urine in 3 h. The two polymers should prove useful for in vivo and in vitro studies of selective CA IV inhibition in membranes.

Synthesis, molecular docking analysis and biological evaluations of saccharide-modified thiadiazole sulfonamide derivatives

Zhang, Zuo-Peng,Zhong, Ye,Han, Zhen-Bin,Zhou, Lin,Su, Hua-Sheng,Wang, Jian,Liu, Yang,Cheng, Mao-Sheng

, (2021/05/26)

A series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent enzyme inhibitory activity. The impacts of some compounds on the viability of HT-29, MDA-MB-231, and MG-63 human cancer cell lines were examined under both normoxic and hypoxic conditions, and they showed certain inhibitory effects on cell viability. Moreover, it was found that the series of compounds had the ability to raise the pH of the tumor cell microenvironment. All the results proved that saccharide-modified thiadiazole sulfonamides have important research prospects for the development of CA IX inhibitors.

RADIOACTIVE IMIDAZOTHIADIAZOLE DERIVATIVE COMPOUND

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Paragraph 0085-0087; 0112; 0113, (2021/10/22)

The present invention provides a radiolabeled compound represented by the following formula (1), which is a radioactive imidazothiadiazole derivative compound having an affinity for CA-IX, or a salt thereof. wherein n is an integer of 1 to 4, and L represents a radionuclide or a mono- to tetravalent group containing a radionuclide.

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