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741709-63-7

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741709-63-7 Usage

Uses

Different sources of media describe the Uses of 741709-63-7 differently. You can refer to the following data:
1. suzuki reaction
2. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs. It is used in suzuki reactions.

Check Digit Verification of cas no

The CAS Registry Mumber 741709-63-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 7,4,1,7,0 and 9 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 741709-63:
(8*7)+(7*4)+(6*1)+(5*7)+(4*0)+(3*9)+(2*6)+(1*3)=167
167 % 10 = 7
So 741709-63-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H15BN2O2/c1-11(2)12(3,4)17-13(16-11)9-5-6-10(7-14)15-8-9/h5-6,8H,1-4H3

741709-63-7 Well-known Company Product Price

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  • TCI America

  • (C3126)  2-Cyano-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine  >98.0%(T)

  • 741709-63-7

  • 200mg

  • 430.00CNY

  • Detail
  • TCI America

  • (C3126)  2-Cyano-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine  >98.0%(T)

  • 741709-63-7

  • 1g

  • 1,490.00CNY

  • Detail
  • Alfa Aesar

  • (H54689)  2-Cyanopyridine-5-boronic acid pinacol ester, 96%   

  • 741709-63-7

  • 250mg

  • 1852.0CNY

  • Detail
  • Alfa Aesar

  • (H54689)  2-Cyanopyridine-5-boronic acid pinacol ester, 96%   

  • 741709-63-7

  • 1g

  • 5557.0CNY

  • Detail

741709-63-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Cyanopyridine-5-Boronic Acid Pinacol Ester

1.2 Other means of identification

Product number -
Other names 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile

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:741709-63-7 SDS

741709-63-7Synthetic route

2-Cyano-5-bromopyridine
97483-77-7

2-Cyano-5-bromopyridine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

Conditions
ConditionsYield
With potassium acetate; palladium dichloride In dichloromethane; dimethyl sulfoxide at 90℃; for 6h;85%
With triisopropylsilanethiol; N,N,N',N'-tetramethylguanidine In acetonitrile at 30℃; for 2h; Reagent/catalyst; Irradiation; Inert atmosphere; Sealed tube;68%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 25h;64%
5-bromo-pyridine-2-carbaldehyde
31181-90-5

5-bromo-pyridine-2-carbaldehyde

2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / I2; aq. NH3 / tetrahydrofuran / 4 h / 20 °C
2: 64 percent / PdCl2(dppf); KOAc / dimethylsulfoxide / 25 h / 80 °C
View Scheme
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

C-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-methylamine
880495-82-9

C-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-methylamine

Conditions
ConditionsYield
With hydrogen; acetic acid; palladium on activated charcoal at 20℃; for 16h;100%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

tert-butyl [(1S)-1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]carbamate

tert-butyl [(1S)-1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]carbamate

tert-butyl {(1S)-1-[5-chloro-3-(6-cyanopyridin-3-yl)-2-methoxy-4-methylphenyl]ethyl}carbamate

tert-butyl {(1S)-1-[5-chloro-3-(6-cyanopyridin-3-yl)-2-methoxy-4-methylphenyl]ethyl}carbamate

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In acetonitrile at 95℃; for 2h; Inert atmosphere;91%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

tert-butyl (((3S,3aS)-7-bromo-1-oxo-3,3a-dihydro-1H,9H-benzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

tert-butyl (((3S,3aS)-7-bromo-1-oxo-3,3a-dihydro-1H,9H-benzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

tert-butyl (((3S,3aS)-7-(6-cyanopyridin-3-yl)-1-oxo-3,3a-dihydro-1H,9H-benzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

tert-butyl (((3S,3aS)-7-(6-cyanopyridin-3-yl)-1-oxo-3,3a-dihydro-1H,9H-benzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; dimethyl sulfoxide at 100℃; for 5h; Inert atmosphere;89%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

tert-butyl 4-((5-bromo-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate
954123-89-8

tert-butyl 4-((5-bromo-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

tert-butyl 4-((5-(6-cyanopyridin-3-yl)-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate
954123-95-6

tert-butyl 4-((5-(6-cyanopyridin-3-yl)-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

Conditions
ConditionsYield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 120℃; for 1h; Sealed tube; Microwave irradiation;88%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

tert-butyl (((3S,3aS)-7-bromo-6-fluoro-1-oxo-3,3a-dihydro-1H,9hbenzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

tert-butyl (((3S,3aS)-7-bromo-6-fluoro-1-oxo-3,3a-dihydro-1H,9hbenzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

tert-butyl (((3S,3aS)-7-(6-cyanopyridin-3-yl)-6-fluoro-1-oxo-3,3a-dihydro-1H,9H-benzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

tert-butyl (((3S,3aS)-7-(6-cyanopyridin-3-yl)-6-fluoro-1-oxo-3,3a-dihydro-1H,9H-benzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; dimethyl sulfoxide at 100℃; for 5h; Inert atmosphere;88%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

5-Bromo-2-chloropyrimidine
32779-36-5

5-Bromo-2-chloropyrimidine

2,5-bis-(2'-cyanopyridin-5'-yl)-pyrimidine
951657-94-6

2,5-bis-(2'-cyanopyridin-5'-yl)-pyrimidine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; water; toluene at 80℃; Suzuki coupling; Inert atmosphere;78%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

7-tert-butoxycarbonyl-2-exo-(2′-amino-3′-bromo-5′-pyridinyl)-7-azabicyclo[2.2.1]heptane

7-tert-butoxycarbonyl-2-exo-(2′-amino-3′-bromo-5′-pyridinyl)-7-azabicyclo[2.2.1]heptane

7-tert-butoxycarbonyl-2-exo-[2'-amino-3'-(6-cyanopyridin-3-yl)-5'-pyridinyl]-7-azabicyclo[2.2.1]heptane

7-tert-butoxycarbonyl-2-exo-[2'-amino-3'-(6-cyanopyridin-3-yl)-5'-pyridinyl]-7-azabicyclo[2.2.1]heptane

Conditions
ConditionsYield
With sodium carbonate; tris-(o-tolyl)phosphine; palladium diacetate In 1,2-dimethoxyethane; water at 80℃; for 5h; Suzuki coupling;74%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

6-bromomethyl-4-(3-chloro-phenyl)-5-fluoro-benzothiazole
1155287-84-5

6-bromomethyl-4-(3-chloro-phenyl)-5-fluoro-benzothiazole

5-[4-(3-chloro-phenyl)-5-fluoro-benzothiazol-6-ylmethyl]-pyridine-2-carbonitrile
1155286-87-5

5-[4-(3-chloro-phenyl)-5-fluoro-benzothiazol-6-ylmethyl]-pyridine-2-carbonitrile

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; for 1.25h;73%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

(6S)-6-[(4-iodobenzyl)oxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol
281225-12-5

(6S)-6-[(4-iodobenzyl)oxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol

5-[4-({[(6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl]oxy}methyl)phenyl]-2-pyridinecarbonitrile
1257425-59-4

5-[4-({[(6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl]oxy}methyl)phenyl]-2-pyridinecarbonitrile

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In ethanol; water; toluene for 0.666667h; Suzuki coupling; Inert atmosphere; Reflux;73%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

5-(2-formylphenyl)pyridine-2-carbonitrile
1033804-84-0

5-(2-formylphenyl)pyridine-2-carbonitrile

Conditions
ConditionsYield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 100℃; for 0.166667h; Microwave irradiation;72%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 100℃; for 0.166667h; Microwave irradiation; Sealed tube;72%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

1-(5-bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea
1160789-92-3

1-(5-bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea

1-(5-(6-cyanopyridin-3-yl)-6-fluorobenzo[d]thiazol-2-yl)-3-ethylurea
1160790-79-3

1-(5-(6-cyanopyridin-3-yl)-6-fluorobenzo[d]thiazol-2-yl)-3-ethylurea

Conditions
ConditionsYield
Stage #1: 2-cyanopyridine-5-boronic acid pinacol ester; 1-(5-bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea With potassium phosphate In water; N,N-dimethyl-formamide for 0.25h;
Stage #2: bis-triphenylphosphine-palladium(II) chloride In water; N,N-dimethyl-formamide at 100℃; for 2.25h;
71%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanol
1382996-38-4

1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanol

5-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]pyridine-2-carbonitrile
1426699-27-5

5-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]pyridine-2-carbonitrile

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In water; acetonitrile at 95℃; for 2h; Inert atmosphere;70%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In water; acetonitrile at 95℃; for 2h; Inert atmosphere;70%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

6-bromo-8-methylimidazo[1,2-a]pyridine
217435-65-9

6-bromo-8-methylimidazo[1,2-a]pyridine

5-(8-methylimidazo[1,2-a]pyridin-6-yl)picolinonitrile
1611001-20-7

5-(8-methylimidazo[1,2-a]pyridin-6-yl)picolinonitrile

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;68.5%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

C18H17BrF2N4O
1214908-78-7

C18H17BrF2N4O

C24H20F2N6O
1214909-17-7

C24H20F2N6O

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 150℃; for 0.5h; Inert atmosphere; microwave oven;68%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

6-bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridine
1417334-55-4

6-bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridine

5-(8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl)picolinonitrile
1611002-02-8

5-(8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl)picolinonitrile

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;67.8%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

N-{[(3S,3aS)-7-bromo-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

N-{[(3S,3aS)-7-bromo-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

N-(((3S,3aS)-7-(6-cyanopyridin-3-yl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)acetamide
1341208-63-6

N-(((3S,3aS)-7-(6-cyanopyridin-3-yl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)acetamide

Conditions
ConditionsYield
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 2h; Suzuki coupling;65%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

C28H50IN5O4Si2
930595-71-4

C28H50IN5O4Si2

C34H53N7O4Si2
930596-22-8

C34H53N7O4Si2

Conditions
ConditionsYield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,2-dimethoxyethane; water for 3h; Heating / reflux;63%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

5-(3,4-dimethoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl trifluoromethanesulfonate

5-(3,4-dimethoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl trifluoromethanesulfonate

5-((3,4-dimethoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl)picolinonitrile

5-((3,4-dimethoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl)picolinonitrile

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium acetate; palladium diacetate In ethanol; toluene at 80℃; for 48h; Inert atmosphere;63%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

(2R, 3R)-3-(3-bromo-6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazin-5(4H)-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
1575607-48-5

(2R, 3R)-3-(3-bromo-6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazin-5(4H)-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

(2R,3R)-3-(3-(2-cyano-pyridin-5-yl)-6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazin-5(4H)-yl)-2-(2,4-difluoro-phenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
1575607-70-3

(2R,3R)-3-(3-(2-cyano-pyridin-5-yl)-6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazin-5(4H)-yl)-2-(2,4-difluoro-phenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 80℃; for 12h;61.6%
2-cyanopyridine-5-boronic acid pinacol ester
741709-63-7

2-cyanopyridine-5-boronic acid pinacol ester

2-bromo-5-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-5,6-dihydro-4H-thieno[3,2-c]pyrrol-4-one

2-bromo-5-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-5,6-dihydro-4H-thieno[3,2-c]pyrrol-4-one

5-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-2-(2-cyanopyridin-5-yl)-5,6-dihydro-4H-thieno[3,2-c]pyrrol-4-one

5-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-2-(2-cyanopyridin-5-yl)-5,6-dihydro-4H-thieno[3,2-c]pyrrol-4-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 80℃; for 10h; Suzuki Coupling; Inert atmosphere;61.6%

741709-63-7Relevant articles and documents

Polysulfide Anions as Visible Light Photoredox Catalysts for Aryl Cross-Couplings

Li, Haoyu,Tang, Xinxin,Pang, Jia Hao,Wu, Xiangyang,Yeow, Edwin K. L.,Wu, Jie,Chiba, Shunsuke

supporting information, p. 481 - 487 (2021/01/13)

Polysulfide anions are endowed with unique redox properties, attracting considerable attentions for their applications in alkali metals-sulfur batteries. However, the employment of these anionic species in redox catalysis for small molecule synthesis remains underdeveloped due to their moderate-poor electrochemical potential in the ground state, whereas some of them are characterized by photoabsorptions in visible spectral regions. Herein, we disclose the use of polysulfide anions as visible light photoredox catalysts for aryl cross-coupling reactions. The reaction design enables single-electron reduction of aryl halides upon the photoexcitation of tetrasulfide dianions (S42-). The resulting aryl radicals are engaged in (hetero)biaryl cross-coupling, borylation, and hydrogenation in a redox catalytic regime involving S4?-/S42- and S3?-/S32- redox couples.

ALKYNE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS

-

Page/Page column 76; 77; 86; 87; 98; 99, (2016/05/02)

Provided are compounds of formula (Ia) and pharmaceutically acceptable salts thereof, wherein A, B, R 1, R 2, m and n are as defined herein, which are active as inhibitors of S-Nitrosoglutathione reductase (GSNOR). These compounds prevent, inhibit, or suppress the action of GSNOR and are therefore useful in the treatment of GSNOR mediated diseases, disorders, syndromes or conditions such as, e.g., pulmonary hypertension, acute respiratory distress syndrome (ARDS), asthma, bronchospasm, cough, pneumonia, pulmonary fibrosis, interstitial lung diseases, cystic fibrosis and chronic obstructive pulmonary disease (COPD).

Synthesis and antiprotozoal activity of dicationic m-terphenyl and 1,3-dipyridylbenzene derivatives

Patrick, Donald A.,Ismail, Mohamed A.,Arafa, Reem K.,Wenzler, Tanja,Zhu, Xiaohua,Pandharkar, Trupti,Jones, Susan Kilgore,Werbovetz, Karl A.,Brun, Reto,Boykin, David W.,Tidwell, Richard R.

, p. 5473 - 5494 (2013/07/26)

4,4″-Diamidino-m-terphenyl (1) and 36 analogues were prepared and assayed in vitro against Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Plasmodium falciparum, and Leishmania amazonensis. Twenty-three compounds were highly active against T. b. rhodesiense or P. falciparum. Most noteworthy were amidines 1, 10, and 11 with IC50 of 4 nM against T. b. rhodesiense, and dimethyltetrahydropyrimidinyl analogues 4 and 9 with IC50 values of ≤ 3 nM against P. falciparum. Bis-pyridylimidamide derivative 31 was 25 times more potent than benznidazole against T. cruzi and slightly more potent than amphotericin B against L. amazonensis. Terphenyldiamidine 1 and dipyridylbenzene analogues 23 and 25 each cured 4/4 mice infected with T. b. rhodesiense STIB900 with four daily 5 mg/kg intraperitoneal doses, as well as with single doses of ≤10 mg/kg. Derivatives 5 and 28 (prodrugs of 1 and 25) each cured 3/4 mice with four daily 25 mg/kg oral doses.

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