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5005-36-7

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5005-36-7 Usage

Chemical Properties

Off-White Crystalline Solid

Uses

Different sources of media describe the Uses of 5005-36-7 differently. You can refer to the following data:
1. The major metabolite of Antigastrin, a-Phenyl-a-(2-pyridyl)thioacetamide (SC 15396) and other thioamides
2. The major metabolite of Antigastrin, α-Phenyl-α-(2-pyridyl)thioacetamide (SC 15396) and other thioamides.

Check Digit Verification of cas no

The CAS Registry Mumber 5005-36-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,0,0 and 5 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 5005-36:
(6*5)+(5*0)+(4*0)+(3*5)+(2*3)+(1*6)=57
57 % 10 = 7
So 5005-36-7 is a valid CAS Registry Number.
InChI:InChI=1/C13H10N2/c14-10-12(11-6-2-1-3-7-11)13-8-4-5-9-15-13/h1-9,12H

5005-36-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Phenyl-2-(pyridin-2-yl)acetonitrile

1.2 Other means of identification

Product number -
Other names α-Phenyl-α-(2-pyridyl)acetonitrile

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:5005-36-7 SDS

5005-36-7Synthetic route

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

bromobenzene
108-86-1

bromobenzene

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With potassium tert-butylate; palladium diacetate; nixantphos In 1,4-dioxane at 60℃; for 10h; Inert atmosphere; Sealed tube;97%
2-chloropyridine
109-09-1

2-chloropyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With sodium amide In toluene at 0 - 30℃; for 17h;90%
With sodium amide In toluene at 20℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere;84.2%
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 110℃; for 0.0166667h; microwave irradiation;68%
2-chloropyridine
109-09-1

2-chloropyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

sodium amide

sodium amide

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
In ethyl acetate; toluene90%
In ethyl acetate; toluene90%
In ethyl acetate; toluene90%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 110℃; for 0.0166667h; microwave irradiation;73%
With potassium hydroxide In dimethyl sulfoxide at 50℃; for 14h;60.4%
With potassium tert-butylate; Aliquat 336 at 85℃; for 1h;52%
2-iodopyridine
5029-67-4

2-iodopyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 110℃; for 0.0166667h; microwave irradiation;68%
2-fluoropyridine
372-48-5

2-fluoropyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 110℃; for 0.0166667h; microwave irradiation;67%
2-methoxypyridine
1628-89-3

2-methoxypyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran Product distribution; Heating; var. methoxy-N-heteroaromatics;39%
With sodium hydride 1.) THF, reflux, 30 min, 2.) reflux; Yield given. Multistep reaction;
2,6-Dibromopyridine
626-05-1

2,6-Dibromopyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

A

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

B

2-bromo-6-(α-cyanobenzyl)pyridine
84960-28-1

2-bromo-6-(α-cyanobenzyl)pyridine

C

2,6-bis(α-cyanobenzyl)pyridine
112170-37-3

2,6-bis(α-cyanobenzyl)pyridine

Conditions
ConditionsYield
With potassium amide In ammonia for 0.25h; Irradiation;A n/a
B 34%
C 36%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With ammonia; potassium; ferric nitrate 1.) 30 min, 2.) ether, irradiated 1.5h; Yield given. Multistep reaction. Yields of byproduct given;
With ammonia; potassium; ferric nitrate 1.) 30 min, 2.)ether, irradiating 1.5h; Yield given. Multistep reaction. Yields of byproduct given;
2-(1-Cyano-2-dimethylammonio-1-phenylethyl)-1-dimethylaminomethylpyridinium-dichlorid

2-(1-Cyano-2-dimethylammonio-1-phenylethyl)-1-dimethylaminomethylpyridinium-dichlorid

A

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

B

N,N-dimethyl(methylene)ammonium chloride
30354-18-8

N,N-dimethyl(methylene)ammonium chloride

C

3-Dimethylamino-2-phenyl-2-pyridin-2-yl-propionitrile; hydrochloride

3-Dimethylamino-2-phenyl-2-pyridin-2-yl-propionitrile; hydrochloride

D

2-(Cyano-phenyl-methyl)-1-dimethylaminomethyl-pyridinium; chloride

2-(Cyano-phenyl-methyl)-1-dimethylaminomethyl-pyridinium; chloride

Conditions
ConditionsYield
Product distribution;
2-chloropyridine
109-09-1

2-chloropyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With sodium amide In toluene at 20℃;A 32.5 %Chromat.
B 60.4 %Chromat.
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-phenyl-2-(pyridin-2-yl)acetamide
7251-52-7, 171927-46-1

2-phenyl-2-(pyridin-2-yl)acetamide

Conditions
ConditionsYield
Stage #1: phenyl-pyridin-2-yl-acetonitrile With sulfuric acid at 10 - 20℃; for 16h;
Stage #2: With sodium hydroxide In water at 10 - 30℃; pH=12;
100%
Stage #1: phenyl-pyridin-2-yl-acetonitrile With sulfuric acid at 10 - 20℃; for 12h;
Stage #2: With water; sodium hydroxide at 10℃; pH=12;
95.8%
With sulfuric acid
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In toluene for 3h;99%
With oxygen; potassium carbonate In water; dimethyl sulfoxide Ambient temperature;48%
With oxygen; sodium hydride 1.) THF, 5 min; Yield given. Multistep reaction;
N-(bromomethyl)phtalimide
5332-26-3

N-(bromomethyl)phtalimide

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-propionitrile
122376-77-6

3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-propionitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide 1.) r.t., 1 h, 2.) 80 deg C, 1 h;81%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-(3-bromopropyl)isoindole-1,3-dione
5460-29-7

2-(3-bromopropyl)isoindole-1,3-dione

5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-pentanenitrile
122376-90-3

5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-pentanenitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide 1.) r.t., 1 h, 2.) 140 deg C, 5 h;77%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

methyl iodide
74-88-4

methyl iodide

2-methyl-2-phenyl-2-(pyridin-2-yl)acetonitrile
139764-31-1

2-methyl-2-phenyl-2-(pyridin-2-yl)acetonitrile

Conditions
ConditionsYield
Stage #1: phenyl-pyridin-2-yl-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: methyl iodide In tetrahydrofuran at -78 - 25℃;
76%
With sodium amide; toluene
With 1,4-dioxane; sodium amide
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-chloro-2-phenyl-2-(pyridine-2-yl)acetonitrile
1228894-25-4

2-chloro-2-phenyl-2-(pyridine-2-yl)acetonitrile

Conditions
ConditionsYield
Stage #1: phenyl-pyridin-2-yl-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h;
Stage #2: With 2-chloro-2-fluoro-2-phenylacetonitrile In tetrahydrofuran at -78℃; for 0.0833333h;
76%
1-(Diethylaminocarbonyl)aziridine
21392-71-2

1-(Diethylaminocarbonyl)aziridine

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

4-(3,3-Diethylureido)-2-phenyl-2-(2-pyridyl)butyronitril
94559-23-6

4-(3,3-Diethylureido)-2-phenyl-2-(2-pyridyl)butyronitril

Conditions
ConditionsYield
With sodium hydride In tert-butyl alcohol for 96h; Ambient temperature;74%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

3-methylethynyl methyl carbonate
95314-72-0

3-methylethynyl methyl carbonate

C17H14N2

C17H14N2

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2-(dicyclohexylphosphino)-2'-methylbiphenyl In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;74%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

ethyl bromoacetate
105-36-2

ethyl bromoacetate

ethyl 3-cyano-3-phenyl-3-(2-pyridyl)propionate

ethyl 3-cyano-3-phenyl-3-(2-pyridyl)propionate

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 20℃;71%
With sodium amide; toluene
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

α-phenyl-2-pyridineacetamide

α-phenyl-2-pyridineacetamide

Conditions
ConditionsYield
With sulfuric acid at 95℃; for 2h;70%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-fluoro-2-phenyl-2-(pyridin-2-yl)acetonitrile

2-fluoro-2-phenyl-2-(pyridin-2-yl)acetonitrile

Conditions
ConditionsYield
Stage #1: phenyl-pyridin-2-yl-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: With N-fluorobis(benzenesulfon)imide In tetrahydrofuran at -78 - 25℃;
70%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

N-(diphenylcarbamoyl)-aziridine
52204-95-2

N-(diphenylcarbamoyl)-aziridine

4-(3,3-Diphenylureido)-2-phenyl-2-(2-pyridyl)butyronitril
94559-38-3

4-(3,3-Diphenylureido)-2-phenyl-2-(2-pyridyl)butyronitril

Conditions
ConditionsYield
With sodium hydride In tert-butyl alcohol for 24h; Ambient temperature;68%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-butyronitrile
122376-78-7

4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-butyronitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide 1.) r.t., 1 h, 2.) 140 deg C, 5 h;67%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

cis-1-(3-chloropropyl)-2,6-dimethylpiperidine monohydrochloride
63645-17-0

cis-1-(3-chloropropyl)-2,6-dimethylpiperidine monohydrochloride

α-<3-(2,6-dimethyl-1-piperidinyl)propyl>-α-phenyl-2-pyridineacetonitrile
130275-51-3

α-<3-(2,6-dimethyl-1-piperidinyl)propyl>-α-phenyl-2-pyridineacetonitrile

Conditions
ConditionsYield
With potassium hydroxide In butanone for 24h; Heating;67%
methanol
67-56-1

methanol

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

(RS)-phenyl-pyridin-2-yl-acetic acid methyl ester
26483-64-7

(RS)-phenyl-pyridin-2-yl-acetic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride; water at 4 - 20℃;62%
Stage #1: methanol; phenyl-pyridin-2-yl-acetonitrile With hydrogenchloride at 0℃; for 0.333333h;
Stage #2: at 23℃; for 18h;
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-phenyl-2-(pyridin-2-yl)ethan-1-amine
95898-97-8

2-phenyl-2-(pyridin-2-yl)ethan-1-amine

Conditions
ConditionsYield
With sodium tetrahydroborate; iodine In tetrahydrofuran for 3h; Reduction; Heating;60%
With ammonium hydroxide; hydrogen In water at 50℃;49%
Multi-step reaction with 2 steps
1: 81 percent / 1.) NaH / dimethylformamide / 1.) r.t., 1 h, 2.) 80 deg C, 1 h
2: 75percent H2SO4 / 150 °C
View Scheme
Stage #1: phenyl-pyridin-2-yl-acetonitrile With sodium tetrahydroborate; iodine In tetrahydrofuran Reflux;
Stage #2: With potassium hydroxide In methanol at 20℃;
N-benzoylaziridine
7646-66-4

N-benzoylaziridine

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

4-(Benzoylamino)-2-phenyl-2-(2-pyridyl)butyronitril
94559-36-1

4-(Benzoylamino)-2-phenyl-2-(2-pyridyl)butyronitril

Conditions
ConditionsYield
With sodium hydride In tert-butyl alcohol for 24h; Ambient temperature;51%
N-ethoxycarbonylaziridine
671-51-2

N-ethoxycarbonylaziridine

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-<(Ethoxycarbonyl)imino>-3-phenyl-3-(2-pyridyl)pyrrolidin
94559-47-4

2-<(Ethoxycarbonyl)imino>-3-phenyl-3-(2-pyridyl)pyrrolidin

Conditions
ConditionsYield
With Biphenyl natrium In tetrahydrofuran for 4h; Heating;37%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide
342403-52-5

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide

C

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile
147092-44-2

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile

Conditions
ConditionsYield
With potassium hydroxide; 1-chloro-3-hydroxypropane at 50℃; for 24h;A 28%
B 32%
C 7%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

1-chloro-3-hydroxypropane
627-30-5

1-chloro-3-hydroxypropane

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide
342403-52-5

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide

C

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile
147092-44-2

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile

Conditions
ConditionsYield
With potassium hydroxide; dimethyl sulfoxide at 50℃; for 24h;A 28%
B 32%
C 7%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide
342403-52-5

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide

C

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile
147092-44-2

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile

Conditions
ConditionsYield
With potassium hydroxide; dimethyl sulfoxide; 1-chloro-3-hydroxypropane at 50℃; for 24h;A 28%
B 32%
C 7%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

3-methylethynyl methyl carbonate
95314-72-0

3-methylethynyl methyl carbonate

C17H14N2

C17H14N2

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;23%

5005-36-7Relevant articles and documents

Synthesis of novel pyrido[1,2-c]pyrimidine derivatives with 6-fluoro-3-(4-piperidynyl)-1,2-benzisoxazole moiety as potential ssri and 5-ht1a receptor ligands

Król, Marek,?lifirski, Grzegorz,Kleps, Jerzy,Ulenberg, Szymon,Belka, Mariusz,Baczek, Tomasz,Siwek, Agata,Stachowicz, Katarzyna,Szewczyk, Bernadeta,Nowak, Gabriel,Duszyńska, Beata,Herold, Franciszek

, p. 1 - 21 (2021/03/01)

Two series of novel 4-aryl-2H-pyrido[1,2-c]pyrimidine (6a–i) and 4-aryl-5,6,7,8-tetrahydropyrido[1,2-c]pyrimidine (7a–i) derivatives were synthesized. The chemical structures of the new compounds were confirmed by1H and13C NMR spectroscopy and ESI-HRMS spectrome-try. The affinities of all compounds for the 5-HT1A receptor and serotonin transporter protein (SERT) were determined by in vitro radioligand binding assays. The test compounds demonstrated very high binding affinities for the 5-HT1A receptor of all derivatives in the series (6a–i and 7a–i) and generally low binding affinities for the SERT protein, with the exception of compounds 6a and 7g. Extended affinity tests for the receptors D2, 5-HT2A, 5-HT6 and 5-HT7 were conducted with regard to selected compounds (6a, 7g, 6d and 7i). All four compounds demonstrated very high affinities for the D2 and 5-HT2A receptors. Compounds 6a and 7g also had high affinities for 5-HT7, while 6d and 7i held moderate affinities for this receptor. Compounds 6a and 7g were also tested in vivo to identify their functional activity profiles with regard to the 5-HT1A receptor, with 6a demonstrating the activity profile of a presynaptic agonist. Metabolic stability tests were also conducted for 6a and 6d.

Structure-activity relationship and cardiac safety of 2-aryl-2-(pyridin-2-yl)acetamides as a new class of broad-spectrum anticonvulsants derived from Disopyramide

?tengl, Milan,Chodkowski, Andrzej,Dawidowski, Maciej,El Harchi, Aziza,Hancox, Jules C.,Jarkovska, Dagmar,Konopelski, Piotr,Król, Marek,Mistrova, Eliska,Podsadni, Piotr,Popowicz, Grzegorz M.,Sviglerova, Jitka,Szuberski, Piotr,Szulczyk, Bart?omiej,Tur?o, Jadwiga,Ufnal, Marcin,Wróbel, Martyna Zofia,Zhang, Yihong

, (2020/03/17)

A series of 2-aryl-2-(pyridin-2-yl)acetamides were synthesized and screened for their anticonvulsant activity in animal models of epilepsy. The compounds were broadly active in the ‘classical’ maximal electroshock seizure (MES) and subcutaneous Metrazol (scMET) tests as well as in the 6 Hz and kindling models of pharmacoresistant seizures. Furthermore, the compounds showed good therapeutic indices between anticonvulsant activity and motor impairment. Structure-activity relationship (SAR) trends clearly showed the highest activity resides in unsubstituted phenyl derivatives or compounds having ortho- and meta- substituents on the phenyl ring. The 2-aryl-2-(pyridin-2-yl)acetamides were derived by redesign of the cardiotoxic sodium channel blocker Disopyramide (DISO). Our results show that the compounds preserve the capability of the parent compound to inhibit voltage gated sodium currents in patch-clamp experiments; however, in contrast to DISO, a representative compound from the series 1 displays high levels of cardiac safety in a panel of in vitro and in vivo experiments.

Synthesis of new 5,6,7,8-tetrahydropyrido[1,2-c]pyrimidine derivatives with rigidized tryptamine moiety as potential SSRI and 5-HT1A receptor ligands

?lifirski, Grzegorz,Król, Marek,Kleps, Jerzy,Podsadni, Piotr,Belka, Mariusz,B?czek, Tomasz,Siwek, Agata,Stachowicz, Katarzyna,Szewczyk, Bernadeta,Nowak, Gabriel,Bojarski, Andrzej,Kozio?, Anna E.,Tur?o, Jadwiga,Herold, Franciszek

, p. 383 - 397 (2019/07/19)

Extended studies in the 4-aryl-pyrido[1,2-c]pyrimidine group resulted in 27 new compounds (10.1-10.27), 5,6,7,8-tetrahydropyrido[1,2-c]pyrimidine derivatives. In vitro tests (RBA) were carried out for 10.1-10.27 compounds in order to determine their affinity to 5-HT1A receptor and SERT protein. 10.1-10.3, 10.6, 10.7, 10.16 and 10.27 compounds had high binding ability to both molecular targets (5-HT1A Ki = 8–87 nM; SERT Ki = 8–52 nM). For these compounds (10.1-10.3, 10.6, 10.7, 10.16, 10.27) further in vitro, in vivo and metabolic stability tests were performed. In vitro studies in the extended receptor profile (D2, 5-HT2A, 5-HT6 and 5-HT7) showed their selectivity towards 5-HT1A receptor and SERT protein. In vivo tests revealed that compounds 10.7 and 10.16 had the properties of presynaptic antagonists of the 5-HT1A receptor. The redesign of the 2H-pyrido[1,2-c]pyrimidine residue present in the terminal part towards 5,6,7,8-tetrahydropyrido[1,2-c]pyrimidine resulted in the improved metabolic stability and enhanced affinity to both molecular targets (5-HT1A-R and SERT) compared to the precursors.

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