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Pyridine, 2-bromo-5-(chloromethyl)(9CI) is an organic compound that belongs to the class of halopyridines, characterized by a pyridine ring substituted with a bromine atom at the 2nd position and a chloromethyl group at the 5th position. Pyridine, 2-bromo-5-(chloromethyl)(9CI) features a heterocyclic aromatic ring with nitrogen as the heteroatom, and its molecular structure is relatively complex. The physical properties of this compound, such as melting point, boiling point, and density, can vary depending on factors like purity.

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  • 168173-56-6 Structure
  • Basic information

    1. Product Name: Pyridine, 2-bromo-5-(chloromethyl)- (9CI)
    2. Synonyms: Pyridine, 2-bromo-5-(chloromethyl)- (9CI);2-BroMo-5-(chloroMethyl)pyridine
    3. CAS NO:168173-56-6
    4. Molecular Formula: C6H5BrClN
    5. Molecular Weight: 206.4676
    6. EINECS: N/A
    7. Product Categories: PYRIDINE
    8. Mol File: 168173-56-6.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 285ºC at 760 mmHg
    3. Flash Point: 126.2ºC
    4. Appearance: /
    5. Density: 1.631g/cm3
    6. Vapor Pressure: 0.00494mmHg at 25°C
    7. Refractive Index: 1.574
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    9. Solubility: N/A
    10. PKA: 0.02±0.10(Predicted)
    11. CAS DataBase Reference: Pyridine, 2-bromo-5-(chloromethyl)- (9CI)(CAS DataBase Reference)
    12. NIST Chemistry Reference: Pyridine, 2-bromo-5-(chloromethyl)- (9CI)(168173-56-6)
    13. EPA Substance Registry System: Pyridine, 2-bromo-5-(chloromethyl)- (9CI)(168173-56-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 168173-56-6(Hazardous Substances Data)

168173-56-6 Usage

Uses

Used in Chemical Research:
Pyridine, 2-bromo-5-(chloromethyl)(9CI) is used as a chemical intermediate for the synthesis of various complex organic molecules. Its unique structure allows for further functionalization and modification, making it a valuable compound in the field of chemical research.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, Pyridine, 2-bromo-5-(chloromethyl)(9CI) is used as a building block for the development of new drugs. Its chemical properties enable it to be incorporated into the structures of potential therapeutic agents, contributing to the discovery of novel medications with improved efficacy and safety profiles.

Check Digit Verification of cas no

The CAS Registry Mumber 168173-56-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,8,1,7 and 3 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 168173-56:
(8*1)+(7*6)+(6*8)+(5*1)+(4*7)+(3*3)+(2*5)+(1*6)=156
156 % 10 = 6
So 168173-56-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H5BrClN/c7-6-2-1-5(3-8)4-9-6/h1-2,4H,3H2

168173-56-6SDS

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 2-bromo-5-(chloromethyl)pyridine

1.2 Other means of identification

Product number -
Other names 2-bromo-5-chloromethyl pyridine

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:168173-56-6 SDS

168173-56-6Synthetic route

2-bromo-5-(hydroxymethyl)pyridine
122306-01-8

2-bromo-5-(hydroxymethyl)pyridine

2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

Conditions
ConditionsYield
Stage #1: 2-bromo-5-(hydroxymethyl)pyridine With thionyl chloride at -60℃; for 1h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
91%
With thionyl chloride In dichloromethane91%
With sodium hydroxide; thionyl chloride In water; toluene; acetonitrile
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
1.2: 0 - 20 °C
2.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 20 °C / Cooling with ice
View Scheme
6-bromonicotinaldehyde
149806-06-4

6-bromonicotinaldehyde

2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; ethanol / 20 °C / Inert atmosphere
2: thionyl chloride / 1 h / -60 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate
2: thionyl chloride
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 - 20 °C
2: thionyl chloride / dichloromethane / 2 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere
2: thionyl chloride / chloroform / 4 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol / 24 h / 20 °C / Inert atmosphere
2: thionyl chloride / dichloromethane
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

sodium cyanide
143-33-9

sodium cyanide

(6-bromopyridine-3-yl)acetonitrile
144873-99-4

(6-bromopyridine-3-yl)acetonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 48h;90%
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

C12H16F2N2O3

C12H16F2N2O3

3-(6-bromopyridin-3-ylmethyl)-4-(2,2-difluoroethylamino)-8-(methoxyimino)-1-oxaspiro[4.5]dec-3-en-2-one

3-(6-bromopyridin-3-ylmethyl)-4-(2,2-difluoroethylamino)-8-(methoxyimino)-1-oxaspiro[4.5]dec-3-en-2-one

Conditions
ConditionsYield
Stage #1: C12H16F2N2O3 With caesium carbonate In acetonitrile at 0 - 20℃; for 4h;
Stage #2: 2-bromo-5-pyridylmethyl chloride In acetonitrile for 12h; Reflux; regioselective reaction;
80%
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

4-(2,2-difluoroethylamino)-5,5-dimethylfuran-2(5H)-one

4-(2,2-difluoroethylamino)-5,5-dimethylfuran-2(5H)-one

3-(6-bromopyridin-3-ylmethyl)-4-(2,2-difluoroethylamino)-5,5-dimethylfuran-2(5H)-one

3-(6-bromopyridin-3-ylmethyl)-4-(2,2-difluoroethylamino)-5,5-dimethylfuran-2(5H)-one

Conditions
ConditionsYield
Stage #1: 4-(2,2-difluoroethylamino)-5,5-dimethylfuran-2(5H)-one With caesium carbonate In acetonitrile at 0 - 20℃; for 4h;
Stage #2: 2-bromo-5-pyridylmethyl chloride In acetonitrile for 12h; Reflux; regioselective reaction;
78%
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

C12H17F2NO3

C12H17F2NO3

3-(6-bromopyridin-3-ylmethyl)-4-(2,2-difluoroethylamino)-8-methoxy-1-oxaspiro[4.5]dec-3-en-2-one

3-(6-bromopyridin-3-ylmethyl)-4-(2,2-difluoroethylamino)-8-methoxy-1-oxaspiro[4.5]dec-3-en-2-one

Conditions
ConditionsYield
Stage #1: C12H17F2NO3 With caesium carbonate In acetonitrile at 0 - 20℃; for 4h;
Stage #2: 2-bromo-5-pyridylmethyl chloride In acetonitrile for 12h; Reflux; regioselective reaction;
74%
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

C11H15F2NO2

C11H15F2NO2

3-(6-bromopyridin-3-ylmethyl)-4-(2,2-difluoroethylamino)-1-oxaspiro[4.5]dec-3-en-2-one

3-(6-bromopyridin-3-ylmethyl)-4-(2,2-difluoroethylamino)-1-oxaspiro[4.5]dec-3-en-2-one

Conditions
ConditionsYield
Stage #1: C11H15F2NO2 With caesium carbonate In acetonitrile at 0 - 20℃; for 4h;
Stage #2: 2-bromo-5-pyridylmethyl chloride In acetonitrile for 12h; Reflux; regioselective reaction;
70%
N-methyl-4-hydroxypiperidine
106-52-5

N-methyl-4-hydroxypiperidine

2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

C12H17BrN2O

C12H17BrN2O

Conditions
ConditionsYield
Stage #1: N-methyl-4-hydroxypiperidine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;
Stage #2: 2-bromo-5-pyridylmethyl chloride In N,N-dimethyl-formamide at 0 - 20℃;
50%
4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

3-(6-bromo-3-pyridyl)methyl-2-imino-4-methyl-2,3-dihydrothiazole hydrochloride

3-(6-bromo-3-pyridyl)methyl-2-imino-4-methyl-2,3-dihydrothiazole hydrochloride

2-thiazolylamine
96-50-4

2-thiazolylamine

2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

3-(6-bromo-3-pyridyl)methyl-2-imino-2,3-dihydrothiazole hydrochloride

3-(6-bromo-3-pyridyl)methyl-2-imino-2,3-dihydrothiazole hydrochloride

2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

ammonium chloride

ammonium chloride

8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine
2244-59-9

8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine

10-[(2-bromo-5-pyridinyl)methyl]-8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine

10-[(2-bromo-5-pyridinyl)methyl]-8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane; ethyl acetate
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

C15H25BrFNO6P2
1365538-49-3

C15H25BrFNO6P2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium iodide / tetrahydrofuran
1.2: -78 - 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C
2.2: -78 - 20 °C
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

Tetraethyl methylenediphosphonate
1660-94-2

Tetraethyl methylenediphosphonate

C15H26BrNO6P2
1365538-50-6

C15H26BrNO6P2

Conditions
ConditionsYield
Stage #1: 2-bromo-5-pyridylmethyl chloride With sodium iodide In tetrahydrofuran
Stage #2: Tetraethyl methylenediphosphonate With n-butyllithium In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2,1-b][1,3,6]oxadiazocine hydrochloride

9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2,1-b][1,3,6]oxadiazocine hydrochloride

4-((6-bromopyridin-3-yl)methyl)-9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2,1-b][1,3,6]oxadiazocine
1437111-09-5

4-((6-bromopyridin-3-yl)methyl)-9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2,1-b][1,3,6]oxadiazocine

Conditions
ConditionsYield
Stage #1: 2-bromo-5-pyridylmethyl chloride With sodium iodide In acetone for 1h; Reflux;
Stage #2: 9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2,1-b][1,3,6]oxadiazocine hydrochloride With potassium carbonate In acetone
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

(S)-4-methyl-2-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-tetrazol-5-yl)methyl)pentanoic acid

(S)-4-methyl-2-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-tetrazol-5-yl)methyl)pentanoic acid

(S)-2-((S)-2-(6-bromopyridin-3-yl)-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-tetrazol-5-yl)ethyl)-4-methylpentanoic acid

(S)-2-((S)-2-(6-bromopyridin-3-yl)-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-tetrazol-5-yl)ethyl)-4-methylpentanoic acid

Conditions
ConditionsYield
Stage #1: (S)-4-methyl-2-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-tetrazol-5-yl)methyl)pentanoic acid With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 2-bromo-5-pyridylmethyl chloride In tetrahydrofuran at -78℃; for 5h;
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

(2S)-4-methyl-2-[(1S)-2-[6-(2-phenylpyrrolidin-1-yl)pyridin-3-yl]-1-(1H-tetrazol-5-yl)ethyl]pentanoic acid

(2S)-4-methyl-2-[(1S)-2-[6-(2-phenylpyrrolidin-1-yl)pyridin-3-yl]-1-(1H-tetrazol-5-yl)ethyl]pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: diisopropylamine; lithium diisopropyl amide; n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C
1.2: 5 h / -78 °C
2.1: caesium carbonate; bis(2-isobutyrylcyclohexanone) copper / N,N-dimethyl-formamide / 16 h / 100 °C / Glovebox
3.1: hydrogenchloride / water; ethanol / 16 h / 60 °C
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

(2S)-2-[(1S)-2-{6-[4-(2-aminoethyl)phenoxy]pyridin-3-yl}-1-(2H-tetrazol-5-yl)ethyl]-4-methylpentanoic acid

(2S)-2-[(1S)-2-{6-[4-(2-aminoethyl)phenoxy]pyridin-3-yl}-1-(2H-tetrazol-5-yl)ethyl]-4-methylpentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: diisopropylamine; lithium diisopropyl amide; n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C
1.2: 5 h / -78 °C
2.1: caesium carbonate; bis(2-isobutyrylcyclohexanone) copper / N,N-dimethyl-formamide / 20 h / 100 °C / Glovebox
3.1: trifluoroacetic acid / dichloromethane / 8 h / 25 °C
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

C30H44N6O3Si

C30H44N6O3Si

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: diisopropylamine; lithium diisopropyl amide; n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C
1.2: 5 h / -78 °C
2.1: caesium carbonate; bis(2-isobutyrylcyclohexanone) copper / N,N-dimethyl-formamide / 16 h / 100 °C / Glovebox
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

C28H42N6O4Si

C28H42N6O4Si

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: diisopropylamine; lithium diisopropyl amide; n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C
1.2: 5 h / -78 °C
2.1: caesium carbonate; bis(2-isobutyrylcyclohexanone) copper / N,N-dimethyl-formamide / 20 h / 100 °C / Glovebox
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

(E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline
853214-50-3

(E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4 h / Reflux
2: sodium hydride / tetrahydrofuran; mineral oil / 12 h
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

lithium (E)-5-[4-(dimethylamino)styryl]picolinate

lithium (E)-5-[4-(dimethylamino)styryl]picolinate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 4 h / Reflux
2.1: sodium hydride / tetrahydrofuran; mineral oil / 12 h
3.1: n-butyllithium / diethyl ether; hexane / 1.5 h / -40 °C
3.2: 0.75 h / -40 - 20 °C
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

(E)-5-[4-(dimethylamino)styryl]-N-[2-(2-hydroxybenzamido)ethyl]picolinamide

(E)-5-[4-(dimethylamino)styryl]-N-[2-(2-hydroxybenzamido)ethyl]picolinamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 4 h / Reflux
2.1: sodium hydride / tetrahydrofuran; mineral oil / 12 h
3.1: n-butyllithium / diethyl ether; hexane / 1.5 h / -40 °C
3.2: 0.75 h / -40 - 20 °C
4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 6 h / 0 - 40 °C
4.2: 12 h / 20 °C
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (6-bromo-3-pyridylmethyl)phosphonate
154321-18-3

diethyl (6-bromo-3-pyridylmethyl)phosphonate

Conditions
ConditionsYield
for 4h; Reflux;
for 4h; Reflux;
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

C15H18N4
1440677-15-5

C15H18N4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethyl phosphite; sodium hydride
2: hydrazine
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

C17H21N5S

C17H21N5S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethyl phosphite; sodium hydride
2: hydrazine
3: ethanol / 4 h / Reflux
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

C20H28N6S

C20H28N6S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethyl phosphite; sodium hydride
2: hydrazine
3: ethanol / 4 h / Reflux
View Scheme
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

(E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline
853214-50-3

(E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline

Conditions
ConditionsYield
With sodium hydride; triethyl phosphite Horner-Wadsworth-Emmons Olefination;
2-bromo-5-pyridylmethyl chloride
168173-56-6

2-bromo-5-pyridylmethyl chloride

5-((4-(dimethylamino)piperidin-1-yl)methyl)pyridin-2-amine

5-((4-(dimethylamino)piperidin-1-yl)methyl)pyridin-2-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / acetonitrile
2: ammonia; copper(I) oxide / methanol / 12 h / -78 - 70 °C / Sealed tube
View Scheme

168173-56-6Relevant articles and documents

CDK4/6 INHIBITORS AND USE THEREOF

-

, (2019/03/05)

The present disclosure relates to a compound of formula (I), or a pharmaceutically acceptable salt, a solvate, a stereoisomer, or tautomer thereof, a pharmaceutical composition comprising a compound of formula (A) or formula (B), and any subgenera thereof, and use of said compounds and compositions thereof, wherein R1, R2, R3a, R3b, R5, R6, X1, X2, Y and n are described herein.

A Copper Complex of a Thiosemicarbazone-Pyridylhydrazone Ligand Containing a Vinylpyridine Functional Group as a Potential Imaging Agent for Amyloid-β Plaques

McInnes, Lachlan E.,Noor, Asif,Roselt, Peter D.,McLean, Catriona A.,White, Jonathan M.,Donnelly, Paul S.

, p. 827 - 834 (2019/10/02)

Complexes containing positron-emitting radionuclides of copper have the potential to be of use for diagnostic imaging with positron emission tomography. Alzheimer's disease is characterised by the presence of amyloid-β plaques in the brain. A new thiosemicarbazone-pyridyl hydrazone tetradentate ligand with a pyridyl-4-vinylpyridine functional group was prepared with the aim of making a copper complex that binds to amyloid-β plaques to assist in the diagnosis of Alzheimer's disease. The ligand forms a charge neutral complex with copper(ii) that was characterised by X-ray crystallography and the electrochemical behaviour of the complex was investigated by cyclic voltammetry. The new ligand can be radiolabelled with positron-emitting copper-64 at room temperature in excellent radiochemical yields. The new complex interacts with synthetic amyloid-β fibrils and binds amyloid-β plaques present in post-mortem Alzheimer's disease brain tissue.

Rhenium and technetium complexes of thioamide derivatives of pyridylhydrazine that bind to amyloid-β plaques

Fletcher, Scott P.,Noor, Asif,Hickey, James L.,McLean, Catriona A.,White, Jonathan M.,Donnelly, Paul S.

, p. 1139 - 1151 (2018/07/13)

Abstract: Age-associated deposition of amyloid-β in cerebral blood vessels, a condition referred to as cerebral amyloid angiopathy, can contribute to stroke and dementia. This research aimed to design new radioactive technetium-99?m complexes that bind to amyloid-β plaques that have the potential to assist in diagnosis of cerebral amyloid angiopathy using single-photon-emitted computed tomography (SPECT) imaging. Six new pyridylthiosemicarbazide ligands containing either benzofuran or styrylpyridyl functional groups that are known to selectively bind to amyloid plaques were prepared. Non-radioactive isotopes of technetium are not available so rhenium was used as a surrogate for exploratory chemistry. The new ligands were used to prepare well-defined [Re-oxo]3+ complexes where two pyridylthiosemicarbazide ligands were coordinated to a single metal ion to give bivalent complexes with two amyloid-β targeting functional groups. The interaction of the [Re-oxo]3+ complexes with synthetic amyloid-β1-42 and with amyloid plaques in human brain tissue was investigated. Two ligands were selected to develop methods to prepare their [99mTc-oxo]3+ complexes at the tracer level. These technetium-99?m complexes are likely to be isostructural to their rhenium-oxo analogues.

Benzimidazole derivatives, preparation methods and uses theirof

-

, (2018/12/01)

The present invention relates to benzimidazole compounds useful in treating for protein kinase-associated disorders. There is also a need for compounds useful in the treatment or prevention of one or more symptoms of cancer, transplant rejections. Furthermore, there is a need for methods for modulating the activity of protein kinases, such as CDK4 and/or CDK6, using the compounds provided herein.

Synthesis of Oxorhenium(V) and Oxotechnetium(V) Complexes That Bind to Amyloid-β Plaques

Hayne, David J.,White, Jonathan M.,McLean, Catriona A.,Villemagne, Victor L.,Barnham, Kevin J.,Donnelly, Paul S.

, p. 7944 - 7953 (2016/08/24)

Alzheimer's disease is characterized by the presence of amyloid plaques in the brain. The primary constituents of the plaques are aggregated forms of the amyloid-β (Aβ) peptide. With the goal of preparing technetium-99m complexes that bind to Aβ plaques with the potential to be diagnostic imaging agents for Alzheimer's disease, new tetradentate ligands capable of forming neutral and lipophilic complexes with oxotechentium(V) and oxorhenium(V) were prepared. Nonradioactive isotopes of technetium are not available so rhenium was used as a surrogate for exploratory chemistry. Two planar tetradentate N3O ligands were prepared that form charge-neutral complexes with oxorhenium(v) as well as a ligand featuring a styrylpyridyl functional group designed to bind to Aβ plaques. All three ligands formed complexes with oxorhenium(V), and each complex was characterized by NMR spectroscopy, mass spectrometry, and X-ray crystallography. The oxorhenium(V) complex with a styrylpyridyl functional group binds to Aβ plaques present in post-mortem human brain tissue. The chemistry was extrapolated to technetium-99m at the tracer level for two of the ligands. The resulting oxotechnetium(V) complexes were sufficiently lipophilic and charge-neutral to suggest that they have the potential to cross the blood-brain barrier but exhibited modest stability with respect to exchange with histidine. The chemistry presented here identifies a strategy to integrate styrylpyridyl functional groups into tetradentate ligands capable of forming complexes with [M=O]3+ cores (M = Re or Tc).

Design and synthesis of active site inhibitors of the human farnesyl pyrophosphate synthase: Apoptosis and inhibition of ERK phosphorylation in multiple myeloma cells

Lin, Yih-Shyan,Park, Jaeok,De Schutter, Joris W.,Huang, Xian Fang,Berghuis, Albert M.,Sebag, Michael,Tsantrizos, Youla S.

, p. 3201 - 3215 (2012/05/20)

Human farnesyl pyrophosphate synthase (hFPPS) controls intracellular levels of FPP and post-translational prenylation of small GTPase proteins, which are essential for cell signaling and cell proliferation. Clinical investigations provide evidence that N-BP inhibitors of hFPPS are disease modifying agents that improve survival of multiple myeloma (MM) patients via mechanisms unrelated to their skeletal effects. A new series of N-BPs was designed that interact with a larger portion of the GPP subpocket, as compared to the current therapeutic drugs, and rigidify the 364KRRK367 tail of hFPPS in the closed conformation in the absence of IPP. An analogue of this series was used to demonstrate inhibition of the intended biological target, resulting in apoptosis and down-regulation of ERK phosphorylation in human MM cell lines.

BICYCLIC NITROIMIDAZOLES COVALENTLY LINKED TO SUBSTITUTED PHENYL OXAZOLIDINONES

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Page/Page column 41, (2009/10/22)

The current invention provides a series of bicyclic nitroimidazole- substituted phenyl oxazolidinones in which a bicyclic nitroimidazole pharmacophore is covalently bonded to a phenyl oxazolidinone, their pharmaceutical compositions, and the method of use of the compositions for prevention and treatment of bacterial infections. The bicyclic nitroimidazole-substituted phenyl oxazolidinones possess surprising antibacterial activity against wild- type and resistant strains of pathogens, and are therefore useful for the prevention, control and treatment of a number of human and veterinary bacterial infections caused by these pathogens, such as Mycobacterium tuberculosis.

4-(PYRIDIN-3-YL)-2-(PYRIDIN-2-YL)-1,2-DIHYDRO-3H-PYRAZOL-3-ONE DERIVATIVES AS SPECIFIC HIF-PROLYL-4-HYDROXYLASE INHIBITORS FOR TREATING CARDIOVASCULAR AND HAEMATOLOGICAL DISEASES

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Page/Page column 30, (2008/06/13)

The object of the invention is to provide new compounds which can be used for the treatment of diseases, in particular cardiovascular and haematological diseases. The present invention describes compounds which act as specific HIF-prolyl-4-hydroxylase inhibitors and which, because of this specific in vivo action mechanism, induce HIF target genes, such as erythropoietin, and the thus produced biological processes, such as erythropoiesis, after parenteral or oral administration. The present invention relates to compounds having the general formula (I), in which A stands for CH or N, R1 stands for a substituent selected from the group formed by (C1-C6)-alkyl, trifluoromethyl, halogen, cyano, nitro, hydroxy, (C1-C6)-alkoxy, amino, (C1-C6)-alkoxycarbonyl, hydroxycarbonyl and C(=O)-NH-R4; R2 stands for a substituent selected from the group formed by halogen, cyano, nitro, (C1-C6)-alkyl, trifluoromethyl, hydroxy, (C1-C6)-alkoxy, trifluoromethoxy, amino, hydroxycarbonyl and C(=O)-NH-R8; m equals 0, 1 or 2; n equals 0, 1, 2 or 3, it being possible for these meanings to be the same or different when R1 or R2 occurs multiple times; and R3 stands for hydrogen, (C1-C6)-alkyl or (C3-C7)-cycloalkyl. The invention also relates to the salts, solvates, and salt solvates of these compounds.

Aryl substituted dibenzoxazepine compounds, pharmaceutical compositions and methods of use

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, (2008/06/13)

The present invention provides substituted dibenzoxazepine compounds of Formula I: STR1 which are useful as analgesic agents for the treatment of pain, and for the treatment of prostaglandin E2 -mediated diseases, pharmaceutical compositions comprising a therapeutically-effective amount of a compound of Formula I in combination with a pharmaceutically-acceptable carrier, a method for eliminating or ameliorating pain in an animal, and a method for treating prostaglandin E2 -mediated diseases in an animal, comprising administering a therapeutically-effective amount of a compound of Formula I to the animal.

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