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1477-24-3

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1477-24-3 Usage

General Description

5-Pyridin-4-yl-4H-[1,2,4]triazole-3-thiol is a chemical compound primarily known for its role in chemical research due to its specific molecular structure. 5-PYRIDIN-4-YL-4H-[1,2,4]TRIAZOLE-3-THIOL features a triazole ring, which is a five-membered aromatic ring with two nitrogen atoms, coupled with a pyridinyl functional group (a basic aromatic ring with one nitrogen atom) and a thiol group (an organosulfur compound that contains a carbon-bonded sulfhydryl). The compound's unique structural properties make it valuable for various applications in chemical and pharmaceutical research. However, details such as its physical and chemical properties, toxicity, and safety measures for handling and storage are not widely documented and depend largely on specifics of its synthesis and applications.

Check Digit Verification of cas no

The CAS Registry Mumber 1477-24-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,7 and 7 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1477-24:
(6*1)+(5*4)+(4*7)+(3*7)+(2*2)+(1*4)=83
83 % 10 = 3
So 1477-24-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H6N4S/c12-7-9-6(10-11-7)5-1-3-8-4-2-5/h1-4H,(H2,9,10,11,12)

1477-24-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1H-1,2,4-Triazole-3-thiol, 5-(4-pyridyl)-

1.2 Other means of identification

Product number -
Other names 5-(4-Pyridyl)-3-mercapto-1H-1,2,4-triazole

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:1477-24-3 SDS

1477-24-3Synthetic route

isoniazid
54-85-3

isoniazid

thiourea
17356-08-0

thiourea

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
Stage #1: isoniazid; thiourea at 170℃;
Stage #2: With sodium hydroxide
93.6%
N'-[1-Amino-1-pyridin-4-yl-meth-(Z)-ylidene]-hydrazinecarbodithioic acid methyl ester

N'-[1-Amino-1-pyridin-4-yl-meth-(Z)-ylidene]-hydrazinecarbodithioic acid methyl ester

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
With potassium hydroxide In methanol for 4h; Heating;85%
2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide
14397-24-1

2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
With sodium hydroxide at 150℃; for 0.05h; Microwave irradiation;76%
Stage #1: 2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide With sodium hydroxide for 3h; Reflux;
Stage #2: With acetic acid
C13H13N5S

C13H13N5S

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
In butan-1-ol for 6h; Heating;40%
tetralin
119-64-2

tetralin

2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide
14397-24-1

2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide
14397-24-1

2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide

ethanol
64-17-5

ethanol

sodium ethanolate
141-52-6

sodium ethanolate

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

isonicotinic acid hydrazide; thiocyanate

isonicotinic acid hydrazide; thiocyanate

A

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

B

2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide
14397-24-1

2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide

Conditions
ConditionsYield
at 140 - 150℃;
C14H15N5S

C14H15N5S

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
In butan-1-ol for 6h; Heating;
N-phenyl-4-pyridinecarbohydrazonamide

N-phenyl-4-pyridinecarbohydrazonamide

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / aq. HCl / 12 h
2: 40 percent / butan-1-ol / 6 h / Heating
View Scheme
C13H14N4

C13H14N4

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / aq. HCl / 12 h
2: butan-1-ol / 6 h / Heating
View Scheme
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2.5 h / 0 - 20 °C
2: tetrahydrofuran / 1.5 h / 0 - 20 °C
3: sodium hydroxide / 0.05 h / 150 °C / Microwave irradiation
View Scheme
4-(chlorocarbonyl)pyridine
14254-57-0

4-(chlorocarbonyl)pyridine

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 1.5 h / 0 - 20 °C
2: sodium hydroxide / 0.05 h / 150 °C / Microwave irradiation
View Scheme
isoniazid
54-85-3

isoniazid

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 10 h / Reflux
2: ammonium hydroxide / 10 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / 3 h / Reflux
2: sodium hydroxide / 3 h / Reflux
View Scheme
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrazine hydrate / ethanol / 5 h / Reflux
2: potassium hydroxide / ethanol / 10 h / Reflux
3: ammonium hydroxide / 10 h / Reflux
View Scheme
potassium 4-pyridinyldithiocarbazate
61019-32-7

potassium 4-pyridinyldithiocarbazate

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

Conditions
ConditionsYield
With ammonium hydroxide for 10h; Reflux;
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

ethyl 2-chloro-3-oxo-butyrate
609-15-4

ethyl 2-chloro-3-oxo-butyrate

ethyl 6-methyl-2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazole-5-carboxylate

ethyl 6-methyl-2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: 3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione; ethyl 2-chloro-3-oxo-butyrate In ethanol Reflux;
Stage #2: With sulfuric acid In ethanol Reflux;
89%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

3-chloropentane-2,4-dione
1694-29-7

3-chloropentane-2,4-dione

1-(6-methyl-(2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazol-5-yl))ethanone

1-(6-methyl-(2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazol-5-yl))ethanone

Conditions
ConditionsYield
Stage #1: 3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione; 3-chloropentane-2,4-dione In ethanol Reflux;
Stage #2: With sulfuric acid In ethanol Reflux;
78%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

[tris(triphenylphosphine) ruthenium(III) trichloride]
30050-39-6, 23311-38-8

[tris(triphenylphosphine) ruthenium(III) trichloride]

C7H5N4S(1-)*2Cl(1-)*Ru(3+)*2C18H15P

C7H5N4S(1-)*2Cl(1-)*Ru(3+)*2C18H15P

Conditions
ConditionsYield
In benzene Reflux;76%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

trichlorotris(triphenylarsine)ruthenium(III)
61769-11-7, 52620-83-4, 72747-39-8

trichlorotris(triphenylarsine)ruthenium(III)

C7H5N4S(1-)*2Cl(1-)*Ru(3+)*2C18H15As

C7H5N4S(1-)*2Cl(1-)*Ru(3+)*2C18H15As

Conditions
ConditionsYield
In benzene Reflux;76%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

[RuBr3(PPh3)3]
118519-70-3

[RuBr3(PPh3)3]

C7H5N4S(1-)*2Br(1-)*Ru(3+)*2C18H15P

C7H5N4S(1-)*2Br(1-)*Ru(3+)*2C18H15P

Conditions
ConditionsYield
In benzene Reflux;76%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

[tris(triphenylarsine) ruthenium(III) tribromide]
63632-06-4, 72747-40-1

[tris(triphenylarsine) ruthenium(III) tribromide]

C7H5N4S(1-)*2Br(1-)*Ru(3+)*2C18H15As

C7H5N4S(1-)*2Br(1-)*Ru(3+)*2C18H15As

Conditions
ConditionsYield
In benzene Reflux;76%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

ethyl (2-chloroaceto)acetate
638-07-3

ethyl (2-chloroaceto)acetate

ethyl 2-(2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazol-6-yl)acetate

ethyl 2-(2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazol-6-yl)acetate

Conditions
ConditionsYield
Stage #1: 3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione; ethyl (2-chloroaceto)acetate In ethanol Reflux;
Stage #2: With sulfuric acid In ethanol Reflux;
69%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

ethyl Bromopyruvate
70-23-5

ethyl Bromopyruvate

ethyl 2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazole-6-carboxylate

ethyl 2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazole-6-carboxylate

Conditions
ConditionsYield
Stage #1: 3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione; ethyl Bromopyruvate In ethanol Reflux;
Stage #2: With sulfuric acid In ethanol Reflux;
68%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

α-bromoacetophenone
70-11-1

α-bromoacetophenone

1-phenyl-2-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)ethanone

1-phenyl-2-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)ethanone

Conditions
ConditionsYield
With sodium acetate In methanol; N,N-dimethyl-formamide at 20℃; for 120h;67%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

α-bromoacetophenone
70-11-1

α-bromoacetophenone

6-phenyl-2(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazole

6-phenyl-2(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazole

Conditions
ConditionsYield
Stage #1: 3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione; α-bromoacetophenone In ethanol Reflux;
Stage #2: With sulfuric acid In ethanol Reflux;
67%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

ethyl 2-chloro-3-oxo-butyrate
609-15-4

ethyl 2-chloro-3-oxo-butyrate

ethyl 3-oxo-2-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)butanoate

ethyl 3-oxo-2-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)butanoate

Conditions
ConditionsYield
With sodium acetate In methanol; N,N-dimethyl-formamide at 20℃; for 168h;65%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

3-chloropentane-2,4-dione
1694-29-7

3-chloropentane-2,4-dione

3-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)pentane-2,4-dione

3-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)pentane-2,4-dione

Conditions
ConditionsYield
With sodium acetate In methanol; N,N-dimethyl-formamide at 20℃; for 168h;62%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

2-bromo-N-(2-(2-(4-ethylphenylamino)-2-oxoethylthio)benzo[d]thiazol-6-yl)acetamide

2-bromo-N-(2-(2-(4-ethylphenylamino)-2-oxoethylthio)benzo[d]thiazol-6-yl)acetamide

N-(4-ethylphenyl)-2-(6-(2-(5-(pyridin-4-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)benzo[d]thiazol-2-ylthio)acetamide

N-(4-ethylphenyl)-2-(6-(2-(5-(pyridin-4-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)benzo[d]thiazol-2-ylthio)acetamide

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 20℃; for 2h; regioselective reaction;61%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

chloroacetone
78-95-5

chloroacetone

1-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)propan-2-one

1-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)propan-2-one

Conditions
ConditionsYield
With sodium acetate In methanol; N,N-dimethyl-formamide at 20℃; for 168h;57%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

ethyl Bromopyruvate
70-23-5

ethyl Bromopyruvate

ethyl 2-oxo-3-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)propanoate

ethyl 2-oxo-3-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)propanoate

Conditions
ConditionsYield
With sodium acetate In methanol; N,N-dimethyl-formamide at 20℃; for 72h;57%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

chloroacetone
78-95-5

chloroacetone

6-methyl-2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazole

6-methyl-2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazole

Conditions
ConditionsYield
Stage #1: 3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione; chloroacetone In ethanol Reflux;
Stage #2: With sulfuric acid In ethanol Reflux;
56%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

1,3-Dichloroacetone
534-07-6

1,3-Dichloroacetone

6-chloromethyl-2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazole

6-chloromethyl-2-(pyridin-4-yl)thiazolo[3,2-b][1,2,4]triazole

Conditions
ConditionsYield
Stage #1: 3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione; 1,3-Dichloroacetone In ethanol Reflux;
Stage #2: With sulfuric acid In ethanol Reflux;
56%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

ethyl (2-chloroaceto)acetate
638-07-3

ethyl (2-chloroaceto)acetate

ethyl 3-oxo-4-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)butanoate

ethyl 3-oxo-4-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)butanoate

Conditions
ConditionsYield
With sodium acetate In methanol; N,N-dimethyl-formamide at 20℃; for 168h;54%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

1,3-Dichloroacetone
534-07-6

1,3-Dichloroacetone

1-chloro-3-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)propan-2-one

1-chloro-3-((3-(pyridin-4-yl)-1,2,4-triazol-5-yl)thio)propan-2-one

Conditions
ConditionsYield
With sodium acetate In methanol; N,N-dimethyl-formamide at 20℃; for 48h;50%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

2-Pyridin-4-yl-6,7-dihydro-5H-[1,2,4]triazolo[5,1-b][1,3]thiazin-6-ol
146198-13-2

2-Pyridin-4-yl-6,7-dihydro-5H-[1,2,4]triazolo[5,1-b][1,3]thiazin-6-ol

Conditions
ConditionsYield
With potassium hydroxide In methanol for 24h; Ambient temperature;31%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

epichlorohydrin
106-89-8

epichlorohydrin

2-Pyridin-4-yl-6,7-dihydro-5H-[1,2,4]triazolo[5,1-b][1,3]thiazin-6-ol
146198-13-2

2-Pyridin-4-yl-6,7-dihydro-5H-[1,2,4]triazolo[5,1-b][1,3]thiazin-6-ol

Conditions
ConditionsYield
With potassium hydroxide In methanol for 24h; Ambient temperature;31%
3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione
1477-24-3

3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

(2-chloroethyl)dimethylamine hydrochloride
4584-46-7

(2-chloroethyl)dimethylamine hydrochloride

N,N-dimethyl-2-<5'-(pyridin-4''-yl)-1',2',4'-triazol-3'-ylthio>ethylamine
88317-52-6

N,N-dimethyl-2-<5'-(pyridin-4''-yl)-1',2',4'-triazol-3'-ylthio>ethylamine

Conditions
ConditionsYield
With sodium methylate In ethanol for 4h; Heating;

1477-24-3Relevant articles and documents

Synthesis and Intramolecular Heterocyclization of Selected Isonicotinic Acid Thiocarbazides

Nurkenov,Karipova, G. Zh.,Seilkhanov,Satpaeva, Zh. B.,Fazylov,Nukhuly

, p. 1923 - 1926 (2019)

The reaction of isonicotinic acid hydrazide with ethyl-, allyl-, and cinnamoyl isothiocyanates has afforded the corresponding alkylthiosemicarbazides and the products of their intramolecular heterocyclization, 1,2,4-triazoles.

Reactivity of N1-dithioester substituted pyridinand pyrazincarboxamidrazones

Orlewska, Czeslawa,Pancechowska-Ksepko, Danuta,Foks, Henryk,Zwolska, Zofia,Augustynowicz-Kopec, Ewa

, p. 737 - 744 (2006)

The N1-dithioester substituted pyridin- and pyrazincarboxamidrazones underwent cyclocondensation to 5-methylsulfanyl-1,3,4- thiadiazole or 1,2,4-triazole derivatives, depending on the reaction conditions. With an excess of secondary amines, pyrazincarboxamidrazone dithioester gave 5-amino-1,3,4-thiadiazoles and with an ethanoloamine a 1,2,4-triazole derivative. Prepared compounds were evaluated as potential tuberculostatic agents, but the minimum inhibitory concentrations values indicated no significant activity. Copyright Taylor & Francis Group, LLC.

Structure-activity relationships of triazole-benzodioxine inhibitors of cathepsin X

Fonovi?, Ur?a Pe?ar,Gobec, Stanislav,Hrast, Martina,Knez, Damijan,Kos, Janko,Proj, Matic,Zidar, Nace

, (2020/03/24)

Cathepsin X is a cysteine carboxypeptidase that is involved in various physiological and pathological processes. In particular, highly elevated expression and activity of cathepsin X has been observed in cancers and neurodegenerative diseases. Previously, we identified compound Z9 (1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-((4-isopropyl-4H-1,2,4-triazol-3-yl)thio)ethan-1-one) as a potent and specific reversible cathepsin X inhibitor. Here, we have explored the effects of chemical variations to Z9 of either benzodioxine or triazol moieties, and the importance of the central ketomethylenethio linker. The ketomethylenethio linker was crucial for cathepsin X inhibition, whereas changes of the triazole heterocycle did not alter the inhibitory potencies to a greater extent. Replacement of benzodioxine moiety with substituted benzenes reduced cathepsin X inhibition. Overall, several synthesized compounds showed similar or improved inhibitory potencies against cathepsin X compared to Z9, with IC50 values of 7.1 μM–13.6 μM. Additionally, 25 inhibited prostate cancer cell migration by 21%, which is under the control of cathepsin X.

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