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  • 2380-63-4 Structure
  • Basic information

    1. Product Name: 4-Aminopyrazolo[3,4-d]pyrimidine
    2. Synonyms: TIMTEC-BB SBB004205;1H-PYRAZOLO[3,4-D]PYRIMIDIN-4-YLAMINE;1H-PYRAZOLO[3,4-D]PYRIMIDIN-4-AMINE;4-AMINOPYRAZOLO[3,4-D]PYRIMIDINE;4-AMINO-1H-PYRAZOLO[3,4-D]PYRIMIDINE;ADENINE ANTIMETABOLITE;1H-Pyrazolo[3,4-d]pyrimidine, 4-amino-;4 APP
    3. CAS NO:2380-63-4
    4. Molecular Formula: C5H5N5
    5. Molecular Weight: 135.13
    6. EINECS: 219-174-6
    7. Product Categories: PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines;Heterocyclic Compounds;Heterocycles;Heterocycle-Pyrimidine series
    8. Mol File: 2380-63-4.mol
    9. Article Data: 42
  • Chemical Properties

    1. Melting Point: >325 °C(lit.)
    2. Boiling Point: 238.81°C (rough estimate)
    3. Flash Point: 244.382 °C
    4. Appearance: Light tan solid
    5. Density: 1.3795 (rough estimate)
    6. Vapor Pressure: 0.00118mmHg at 25°C
    7. Refractive Index: 1.7000 (estimate)
    8. Storage Temp.: -20°C Freezer
    9. Solubility: N/A
    10. PKA: 12.12±0.20(Predicted)
    11. Water Solubility: Insoluble in water.
    12. BRN: 5824
    13. CAS DataBase Reference: 4-Aminopyrazolo[3,4-d]pyrimidine(CAS DataBase Reference)
    14. NIST Chemistry Reference: 4-Aminopyrazolo[3,4-d]pyrimidine(2380-63-4)
    15. EPA Substance Registry System: 4-Aminopyrazolo[3,4-d]pyrimidine(2380-63-4)
  • Safety Data

    1. Hazard Codes: T
    2. Statements: 25-36/37/38-23/24/25
    3. Safety Statements: 26-36/37/39-45-22-36
    4. RIDADR: UN 2811 6.1/PG 3
    5. WGK Germany: 3
    6. RTECS: UR0717000
    7. TSCA: Yes
    8. HazardClass: 6.1
    9. PackingGroup: III
    10. Hazardous Substances Data: 2380-63-4(Hazardous Substances Data)

2380-63-4 Usage

Description

4-Aminopyrazolo[3,4-d]pyrimidine is an organic compound characterized by its light tan solid appearance. It is a heterocyclic compound with a unique chemical structure that features a pyrazolo[3,4-d]pyrimidine ring system and an amino group attached to the 4th position. 4-Aminopyrazolo[3,4-d]pyrimidine has been found to possess significant biological activities, making it a potential candidate for various pharmaceutical and chemical applications.

Uses

Used in Pharmaceutical Industry:
4-Aminopyrazolo[3,4-d]pyrimidine is used as a therapeutic agent for the treatment of hypercholesterolemia in rats. It has been shown to decrease serum cholesterol markedly, which can be beneficial in managing and reducing the risk of cardiovascular diseases associated with high cholesterol levels.
Used in Chemical Research:
As a heterocyclic compound with a unique structure, 4-Aminopyrazolo[3,4-d]pyrimidine can be used as a building block or intermediate in the synthesis of more complex molecules for various applications in the chemical industry. Its reactivity and functional groups can be exploited to create novel compounds with specific properties and potential uses.
Used in Drug Design and Development:
The biological activity of 4-Aminopyrazolo[3,4-d]pyrimidine makes it a promising candidate for drug design and development. Researchers can use this compound as a starting point to develop new drugs targeting various diseases and conditions, particularly those related to cholesterol metabolism and cardiovascular health.

Check Digit Verification of cas no

The CAS Registry Mumber 2380-63-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,8 and 0 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2380-63:
(6*2)+(5*3)+(4*8)+(3*0)+(2*6)+(1*3)=74
74 % 10 = 4
So 2380-63-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H5N5/c6-4-3-1-9-10-5(3)8-2-7-4/h1-2H,(H3,6,7,8,9,10)

2380-63-4 Well-known Company Product Price

  • Brand
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  • TCI America

  • (A1041)  4-Aminopyrazolo[3,4-d]pyrimidine  >97.0%(HPLC)(T)

  • 2380-63-4

  • 100mg

  • 260.00CNY

  • Detail
  • TCI America

  • (A1041)  4-Aminopyrazolo[3,4-d]pyrimidine  >97.0%(HPLC)(T)

  • 2380-63-4

  • 1g

  • 790.00CNY

  • Detail
  • TCI America

  • (A1041)  4-Aminopyrazolo[3,4-d]pyrimidine  >97.0%(HPLC)(T)

  • 2380-63-4

  • 5g

  • 1,990.00CNY

  • Detail
  • Alfa Aesar

  • (L03519)  4-Amino-1H-pyrazolo[3,4-d]pyrimidine, 98%   

  • 2380-63-4

  • 250mg

  • 271.0CNY

  • Detail
  • Alfa Aesar

  • (L03519)  4-Amino-1H-pyrazolo[3,4-d]pyrimidine, 98%   

  • 2380-63-4

  • 1g

  • 698.0CNY

  • Detail
  • Alfa Aesar

  • (L03519)  4-Amino-1H-pyrazolo[3,4-d]pyrimidine, 98%   

  • 2380-63-4

  • 5g

  • 3226.0CNY

  • Detail
  • Aldrich

  • (A77806)  4-Aminopyrazolo[3,4-d]pyrimidine  98%

  • 2380-63-4

  • A77806-250MG

  • 216.45CNY

  • Detail
  • Aldrich

  • (A77806)  4-Aminopyrazolo[3,4-d]pyrimidine  98%

  • 2380-63-4

  • A77806-1G

  • 579.15CNY

  • Detail
  • Aldrich

  • (A77806)  4-Aminopyrazolo[3,4-d]pyrimidine  98%

  • 2380-63-4

  • A77806-5G

  • 2,366.91CNY

  • Detail

2380-63-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Aminopyrazolo[3,4-d]pyrimidine

1.2 Other means of identification

Product number -
Other names 1H-Pyrazolo[3,4-d]pyrimidin-4-amine

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:2380-63-4 SDS

2380-63-4Synthetic route

3-Amino-4-cyanopyrazole
16617-46-2

3-Amino-4-cyanopyrazole

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
at 180℃;100%
at 170℃; for 5h; Inert atmosphere;94%
for 1h; Reflux;93%
3-amino-4-cyano-2H-pyrazole
16617-46-2

3-amino-4-cyano-2H-pyrazole

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
at 180℃; Inert atmosphere;95%
at 180℃; for 2h; Microwave irradiation;93%
at 180℃; for 2h; Microwave irradiation;93%
3-Amino-4-cyanopyrazole
16617-46-2

3-Amino-4-cyanopyrazole

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
In formamide87%
3-Amino-4-cyanopyrazole
16617-46-2

3-Amino-4-cyanopyrazole

A

lH-pyrazolo[3,4-d]pyrimidin-4-ylamine

lH-pyrazolo[3,4-d]pyrimidin-4-ylamine

B

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
In formamideA n/a
B 87%
formamidine acetic acid
3473-63-0

formamidine acetic acid

3-amino-4-cyano-2H-pyrazole
16617-46-2

3-amino-4-cyano-2H-pyrazole

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
at 120℃; for 45h; Temperature; Concentration; Inert atmosphere;84.1%
In ethanol for 5h; Reflux;75%
N1,N1-dimethyl-N2-[4-cyanopyrazol-5-yl]formamidine
78972-81-3

N1,N1-dimethyl-N2-[4-cyanopyrazol-5-yl]formamidine

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
With ammonium hydroxide for 5h; Heating;80%
4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

3-bromo-4-aminopyrazolo<3,4-d>pyrimidine
83255-86-1

3-bromo-4-aminopyrazolo<3,4-d>pyrimidine

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 60℃; for 3h;100%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 80℃; for 5h;92%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 60℃;91%
4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine
151266-23-8

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
With N-iodo-succinimide In N,N-dimethyl-formamide at 80℃;100%
With N-iodo-succinimide In N,N-dimethyl-formamide at 80℃; for 5h;98%
With N-iodo-succinimide In N,N-dimethyl-formamide for 12h;97%
4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Hexafluoroacetone
684-16-2

Hexafluoroacetone

2,2,4,4-tetrakis(trifluoromethyl)-2,8-dihydro<1,3,5>oxadiazino<3,4-c>pyrazolopyrimidine
125509-32-2

2,2,4,4-tetrakis(trifluoromethyl)-2,8-dihydro<1,3,5>oxadiazino<3,4-c>pyrazolopyrimidine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 24h;95%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

C15H21N5O4

C15H21N5O4

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 20℃; Inert atmosphere;90%
[(3aR,4S,6R, 6aR)-2,2-dimethyl-6-vinyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl] trifluoromethanesulfonate
1373333-65-3

[(3aR,4S,6R, 6aR)-2,2-dimethyl-6-vinyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl] trifluoromethanesulfonate

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

1-((3aS,4R,6R,6aR)-2,2-dimethyl-6-vinyltetrahydro-3aHcyclopenta[d][1,3]dioxol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

1-((3aS,4R,6R,6aR)-2,2-dimethyl-6-vinyltetrahydro-3aHcyclopenta[d][1,3]dioxol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
Stage #1: 4-Aminopyrazolo<3,4-d>pyrimidin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Mitsunobu Displacement;
Stage #2: [(3aR,4S,6R, 6aR)-2,2-dimethyl-6-vinyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl] trifluoromethanesulfonate In dichloromethane; N,N-dimethyl-formamide; mineral oil at 20℃; for 16h; Mitsunobu Displacement;
88%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine
151266-23-8

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 12h;86%
In N,N-dimethyl-formamide at 80℃; Concentration; Solvent;
4-phenoxyiodobenzene
2974-94-9

4-phenoxyiodobenzene

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;82%
Cyclopentyl bromide
137-43-9

Cyclopentyl bromide

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine
21254-14-8

1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 110℃;80%
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
6974-32-9

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

(2R,3R,4R,5R)-2-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate
854020-39-6

(2R,3R,4R,5R)-2-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In nitromethane for 2h; Heating;79%
With boron trifluoride diethyl etherate In nitromethane for 1.5h; Reflux;59%
With boron trifluoride diethyl etherate In nitromethane Reflux;42%
C16H18F4O5S

C16H18F4O5S

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

1-((3aS,4R,6S,6aR)-6-(4-fluorobenzyl)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

1-((3aS,4R,6S,6aR)-6-(4-fluorobenzyl)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
Stage #1: 4-Aminopyrazolo<3,4-d>pyrimidin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h;
Stage #2: C16H18F4O5S In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h;
78%
2'-Deoxyguanosine
961-07-9

2'-Deoxyguanosine

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine
17318-21-7

4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
With purine nucleoside phosphorylase at 50℃; pH=7; aq. phosphate buffer; Enzymatic reaction;77%
copper (II) carbonate hydroxide

copper (II) carbonate hydroxide

(carboxymethyl(4-methylbenzyl)amino)acetic acid
166826-77-3

(carboxymethyl(4-methylbenzyl)amino)acetic acid

water
7732-18-5

water

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

[Cu2(N-(p-methylbenzyl)iminodiacetate)2(μ2-N1,N8-4-aminopyrazolo[3,4-d]pyrimidine)(water)2]*4water

[Cu2(N-(p-methylbenzyl)iminodiacetate)2(μ2-N1,N8-4-aminopyrazolo[3,4-d]pyrimidine)(water)2]*4water

Conditions
ConditionsYield
Stage #1: copper (II) carbonate hydroxide; (carboxymethyl(4-methylbenzyl)amino)acetic acid In water at 50℃;
Stage #2: water; 4-Aminopyrazolo<3,4-d>pyrimidin In isopropyl alcohol for 1h;
75%
1-(tert-Butoxycarbonyl)-3-(methanesulfonyloxy)piperidine
129888-60-4

1-(tert-Butoxycarbonyl)-3-(methanesulfonyloxy)piperidine

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

tert-butyl 3-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate
1374250-98-2

tert-butyl 3-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃;72%
Stage #1: 4-Aminopyrazolo<3,4-d>pyrimidin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h;
Stage #2: 1-(tert-Butoxycarbonyl)-3-(methanesulfonyloxy)piperidine In N,N-dimethyl-formamide; mineral oil at 100℃; for 16h;
50%
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

9-(2'-hydroxyethyl)adenine
100524-24-1

9-(2'-hydroxyethyl)adenine

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide for 2h; Heating;71%
copper (II) carbonate hydroxide

copper (II) carbonate hydroxide

water
7732-18-5

water

(carboxymethyl(4-fluorobenzyl)amino)acetic acid
1813-23-6

(carboxymethyl(4-fluorobenzyl)amino)acetic acid

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

[Cu4(N-(p-fluorobenzyl)iminodiacetate)4(μ2-N8,N9-4-aminopyrazolo[3,4-d]pyrimidine)2(water)]*water

[Cu4(N-(p-fluorobenzyl)iminodiacetate)4(μ2-N8,N9-4-aminopyrazolo[3,4-d]pyrimidine)2(water)]*water

Conditions
ConditionsYield
Stage #1: copper (II) carbonate hydroxide; (carboxymethyl(4-fluorobenzyl)amino)acetic acid In water at 50℃;
Stage #2: water; 4-Aminopyrazolo<3,4-d>pyrimidin In isopropyl alcohol for 1h;
65%
1-azido-2,3-epoxypropane
80044-09-3

1-azido-2,3-epoxypropane

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

1-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-3-azido-propan-2-ol

1-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-3-azido-propan-2-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;64%
4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

phenylboronic acid
98-80-6

phenylboronic acid

N-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
99973-41-8

N-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper diacetate; caesium carbonate In N,N-dimethyl-formamide at 60℃; for 12h; Chan-Lam Coupling;62%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

formaldehyd
50-00-0

formaldehyd

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

1-(N-methylpiperazinomethyl)-4-(N-methylpiperazinomethylamino)pyrazolo<3,4-d>pyrimidine
83255-90-7

1-(N-methylpiperazinomethyl)-4-(N-methylpiperazinomethylamino)pyrazolo<3,4-d>pyrimidine

Conditions
ConditionsYield
In water60%
2'-deoxyuridine
951-78-0

2'-deoxyuridine

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine
17318-21-7

4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
With purine nucleoside phosphorylase In dimethyl sulfoxide at 50℃; for 72h; pH=7; aq. phosphate buffer; Enzymatic reaction;60%
at 37℃; for 16h; alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli, ammonium acetate buffer pH 5.7;
4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

benzyl alcohol
100-51-6

benzyl alcohol

N-benzyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
58360-86-4

N-benzyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With samarium diiodide; potassium tert-butylate In tetrahydrofuran; toluene at 140℃; for 1.5h; Microwave irradiation; Inert atmosphere;59%

2380-63-4Downstream Products

2380-63-4Relevant articles and documents

Discovery of novel selective Janus kinase 2 (JAK2) inhibitors bearing a 1H-pyrazolo[3,4-d]pyrimidin-4-amino scaffold

Yin, Yuan,Chen, Cheng-Juan,Yu, Ru-Nan,Shu, Lei,Zhang, Tian-Tai,Zhang, Da-Yong

, p. 1562 - 1576 (2019/03/06)

Janus kinases (JAKs) regulate various cancers and immune responses and are targets for the treatment of cancers and immune diseases. A new series of 1H-pyrazolo[3,4-d]pyrimidin-4-amino derivatives were synthesized and optimized by introducing a functional 3,5-disubstituted-1H-pyrazole moiety into the C-3 moiety of pyrazole template, and then were biologically evaluated as potent Janus kinase 2 (JAK2) inhibitors. Among these molecules, inhibitors 11f, 11g, 11h and 11k displayed strong activity and selectivity against the JAK2 kinase, with IC50 values of 7.2 nM, 6.5 nM, 8.0 nM and 9.7 nM, respectively. In particular, the cellular inhibitory assay and western blot analysis further support the JAK2 selectivity of compound 11g also in cells. Furthermore, compound 11g also exhibited potent inhibitory activity in lymphocytes proliferation assay and delayed hypersensitivity assay. Taken together, the novel JAK2 selective inhibitors discovered in this study may be potential lead compounds for new drug discovery via further development of more potent and selective JAK2 inhibitors.

Structure-based design and synthesis of 1H-pyrazolo[3,4-d]pyrimidin-4-amino derivatives as Janus kinase 3 inhibitors

Yin, Yuan,Chen, Cheng-Juan,Yu, Ru-Nan,Wang, Zhi-Jian,Zhang, Tian-Tai,Zhang, Da-Yong

, p. 4774 - 4786 (2018/08/24)

Janus kinases (JAKs) regulate various inflammatory and immune responses and are targets for the treatment of inflammatory and immune diseases. Here we report the discovery and optimization of 1H-pyrazolo[3,4-d]pyrimidin-4-amino as covalent JAK3 inhibitors that exploit a unique cysteine (Cys909) residue in JAK3. Our optimization study gave compound 12a, which exhibited potent JAK3 inhibitory activity (IC50 of 6.2 nM) as well as excellent JAK kinase selectivity (>60-fold). In cellular assay, 12a exhibited potent immunomodulating effect on IL-2-stimulated T cell proliferation (IC50 of 9.4 μM). Further, compound 12a showed efficacy in delayed hypersensitivity assay. The data supports the further investigation of these compounds as novel JAKs inhibitors.

CYCLIC DI-NUCLEOTIDE COMPOUNDS AND METHODS OF USE

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Paragraph 0250, (2017/10/11)

Disclosed are cyclic-di-nucleotide cGAMP analogs, methods of synthesizing the compounds, pharmaceutical compositions comprising the compounds thereof, and use of compounds and compositions in medical therapy.

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