2038-03-1

Basic information

• Product Name: 4-(2-Aminoethyl)morpholine
• Synonyms: LABOTEST-BB LT02100621;4-(2-AMINOETHYL)MORPHOLINE;4-MORPHOLINEETHANAMINE;2-MORPHOLINOETHYLAMINE;2-MORPHOLIN-4-YL-ETHYLAMINE;2-(4-MORPHOLINO)ETHYLAMINE;4-Morpholineethaneamine;2-(4-MORPHOLINO)ETHYLAMINE 97%
• CAS NO: 2038-03-1
• Molecular Formula: C₆H₁₄N₂O
• Molecular Weight: 130.19
• EINECS: 218-011-6
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Morpholines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Morpholines/Thiomorpholines
• Mol File: 2038-03-1.mol
• Article Data: 38

Chemical Properties

• Melting Point: 24 °C
• Boiling Point: 205 °C(lit.)
• Flash Point: 347 °F
• Appearance: Clear colorless to pale yellow/Liquid After Melting
• Density: 0.992 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.289mmHg at 25°C
• Refractive Index: n20/D 1.476(lit.)
• Storage Temp.: Room temperature.
• PKA: pK1: 4.06(+2);pK2: 9.15(+1) (25°C)
• Water Solubility: soluble
• Sensitive: Air Sensitive
• BRN: 104378
• CAS DataBase Reference: 4-(2-Aminoethyl)morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-Aminoethyl)morpholine(2038-03-1)
• EPA Substance Registry System: 4-(2-Aminoethyl)morpholine(2038-03-1)

Safety Data

• Hazard Codes: C,T
• Statements: 22-34-43-24-40-23/24/25
• Safety Statements: 26-36/37/39-45-22
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 2
• RTECS: QD7350000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2038-03-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to pale yellow liq. after melting

Uses

Different sources of media describe the Uses of 2038-03-1 differently. You can refer to the following data:
1. 4-(2-Aminoethyl)morpholine is used as a ligand and reacts with nickel(II) nitrite to form trans-bis[4-(2-aminoethyl)morpholine]dinitronickel(II).
2. 4-(2-Aminoethyl)morpholine is widely used in biomedical applications as this moiety serves as an important lysosome-targeting group. Some of its applications include:Synthesis of the lysosome-targetable fluorescent probe for hydrogen sulfide imaging in living cells.Synthesis of 1,8-naphthalimide conjugated Troger′s bases as deoxyribonucleic acid (DNA) targeting fluorescent probe.Synthesis of intramolecular charge transfer-photoinduced electron transfer-fluorescence resonance energy transfer (ICT-PET-FRET) fluorescent probe for monitoring pH changes in living cells.It is also used as a precursor to synthesize a variety of antimicrobial agents.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 34, p. 1805, 1991 DOI: 10.1021/jm00110a008

InChI:InChI=1/C6H14N2O/c7-1-2-8-3-5-9-6-4-8/h1-7H2/p+2

Synthetic route

2-(2-morpholin-4-ylethyl)-1H-isoindole-1,3(2H)-dione (6820-90-2) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With hydrazine hydrate In ethanol for 24h; Reflux;	95%
With hydrazine hydrate In ethanol at 20℃; Reflux;	95%
With hydrogenchloride
With hydrazine hydrate In ethanol Reflux;
With hydrazine hydrate In ethanol for 18h; Reflux;

ethylenediamine (107-15-3) + 3-oxa-1,5-dichloropentane (111-44-4) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With sodium carbonate In acetonitrile for 24h; Heating;	95%

4-(2-benzyloxycarbonylaminoethyl)-N-morpholine → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20 - 25℃; for 5h; Large scale;	91.3%

3-(morpholin-4-yl)propionic acid hydrazide (59737-33-6) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With trifluoroacetic acid; sodium nitrite In water at 0 - 80℃; Curtius rearrangement;	87%

4-(2-azido-ethyl)-morpholine (660395-39-1) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 30℃; for 18h; Inert atmosphere;	77%

4-morpholinoacetonitrile (5807-02-3) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3.33333h;	72%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h; Reflux;	72%
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reflux;	72%
With ethanol; sodium; toluene
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h; Reflux;

ethyleneimine (151-56-4) + morpholine (110-91-8) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With ethanol; sulfuric acid
With ethanol; sulfuric acid

morpholine (110-91-8) + chloroethylamine (689-98-5) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

N-(2-chlorethyl)morpholine (3240-94-6) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With ammonium hydroxide
Multi-step reaction with 2 steps 1: toluene 2: aqueous HCl View Scheme

4-morpholinoacetonitrile (5807-02-3) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + bis(2-morpholinylethyl)amine (200623-49-0)

Conditions	Yield
With methanol; nickel at 50℃; under 88260.9 Torr; Hydrogenation;
With ammonia; nickel Hydrogenation;
With ammonia; cobalt at 90℃; under 180 Torr; Hydrogenation;

ethylenediamine (107-15-3) + 3-oxa-1,5-dichloropentane (111-44-4) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 1,2-dimorpholylethane (1723-94-0) + bis-[2-(2-amino-ethylamino)-ethyl]-ether (80042-24-6)

3-oxa-1,5-dichloropentane (111-44-4) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 1,2-dimorpholylethane (1723-94-0)

Conditions	Yield
With ethylenediamine
With ethylenediamine

morpholine (110-91-8) + 2-chloroethanamine hydrochloride (870-24-6) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With sodium hydroxide 1) H2O; Yield given. Multistep reaction;

morpholinoethyl amide (5625-98-9) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether Ambient temperature;	24.05 g

(2-Morpholin-4-yl-ethylamino)-diphenyl-methanol (80500-16-9) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + benzophenone (119-61-9)

Conditions	Yield
With water In acetonitrile at 30℃; Rate constant;

ethylenediamine (107-15-3) + 3-oxa-1,5-dichloropentane (111-44-4) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 4,4'-ethanediyl-di-morpholine

6-chloro-5-ethylamino-3-methoxy-pyrazine-2-carboxylic acid 2-morpholin-4-yl-ethylamide (57796-58-4) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 6-chloro-5-ethylamino-3-methoxy-pyrazine-2-carboxylic acid (57796-33-5)

morpholine (110-91-8) + ethanolamine (141-43-5) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With HZSM-5 In water at 300℃; Temperature;

4-(2-chloroethyl)morpholine hydrochride (3647-69-6) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide / acetonitrile; water / 80 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 30 °C / Inert atmosphere View Scheme

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + acetoacetic acid methyl ester (105-45-3) → methyl 3-<(2'-morpholinoethyl)amino>but-2-enoate

Conditions	Yield
In methanol at 25℃; for 10h;	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + para-chlorobenzoic acid (74-11-3) → moclobemide (71320-77-9)

Conditions	Yield
With tetramethylorthosilicate In toluene at 110℃; for 1h; Inert atmosphere;	100%
With zirconocene dichloride In toluene at 110℃; for 24h; Inert atmosphere; sealed tube;	86%
With [((CH3)5Cp)2Zr(H2O)2OSO2C8F17]+[OSO2C8F17]-*THF In tetrahydrofuran at 100℃; for 12h; Catalytic behavior; Reagent/catalyst; Temperature;	85%

3-nitroindeno[1,2-c]isochromene-5,11-dione (884902-28-7) + 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) → 5,6-dihydro-6-(2-morpholinyl-1-ethyl)-3-nitro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline

Conditions	Yield
In chloroform at 20℃; for 16h;	100%
In chloroform at 20℃; for 16h;	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + di-tert-butyl dicarbonate (24424-99-5) → (2-morpholin-4-yl-ethyl)-carbamic acid tert-butyl ester

Conditions	Yield
With indium(III) bromide at 30 - 35℃; for 0.0833333h;	100%
With perchloric acid at 30 - 35℃; for 0.0833333h;	100%
In water at 20℃;	94%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 4-phenyl-1-butylamine (13214-66-9) + 3-bromomethylbenzoic acid (6515-58-8) → C32H39N3O4

Conditions	Yield
Multistep reaction.;	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + C17H15FO5 + formaldehyd (50-00-0) → 4-[5-(4-fluorobenzyl)furan-2-carbonyl]-3-hydroxy-1-(2-morpholine-4-ylethyl)-1,5-dihydropyrrol-2-one

Conditions	Yield
In 1,4-dioxane	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + pyridine-4-carbaldehyde (872-85-5) → pyridine-4-carboxaldehyde-[2-(4-morpholinyl)ethyl]imine (165806-88-2)

Conditions	Yield
With magnesium sulfate	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) → pyridine-4-carboxaldehyde-[2-(4-morpholinyl)ethyl]imine (165806-88-2)

Conditions	Yield
	100%
	100%
	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + trifluoromethanesulfonic acid 2-nitronaphthalen-1-yl ester (253270-06-3) → (2-morpholin-4-yl-ethyl)-(2-nitro-naphthalen-1-yl)-amine (934976-13-3)

Conditions	Yield
In acetonitrile at 150℃; for 0.0833333h; microwave irradiation;	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + N-(2-iodopyrimidin-5-yl)-2-methyl-5-nitrobenzamide → 2-methyl-N-(2-(2-morpholinoethylamino)pyrimidin-5-yl)-5-nitrobenzamide (925896-88-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In Isopropyl acetate at 70℃; for 4h;	100%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 70℃; for 4h;

3-butoxy-4-(hydroxy-methyl-amino)-cyclobut-3-ene-1,2-dione (871917-43-0) + 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) → 3-(hydroxy-methyl-amino)-4-(2-morpholin-4-yl-ethylamino)-cyclobut-3-ene-1,2-dione (1078060-52-2)

Conditions	Yield
In methanol at 20℃; for 5h; Combinatorial reaction / High throughput screening (HTS);	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 4-(5-methyl-2-phenyl-1H-indole-7-yl)amino-cyclohexane-1-carboxylic acid (1120333-44-9) → 4-(5-methyl-2-phenyl-1H-indol-7-ylamino)-cyclohexanecarboxylic acid (2-morpholin-4-yl-ethyl)-amide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 8h;	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + methyl 3-(chlorosulfonyl)-4-methoxybenzoate (192323-12-9) → methyl 4-methoxy-3-(N-(2-morpholinoethyl)sulfamoyl)benzoate (1610860-95-1)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 3-bromo-5-chlorosalicylaldehyde (19652-32-5) → 2-bromo-4-chloro-6-[(2-morpholin-4-ylethylimino)methyl]phenol (1118461-58-7)

Conditions	Yield
In methanol for 1h; Reflux;	100%
In ethanol at 20℃; for 0.5h;

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + Isopropenyl acetate (108-22-5) → N-(2-morpholinoethyl)acetamide (101724-54-3)

Conditions	Yield
In neat (no solvent) at 20℃; for 0.666667h; Green chemistry;	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + vinyl benzoate (769-78-8) → N-(2-morpholinoethyl)benzamide (4476-13-5)

Conditions	Yield
In neat (no solvent) at 20℃; for 0.666667h; Green chemistry;	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 1,4-benzenediacetyl dichloride (21062-19-1) → N,N’-bis(2-(morpholin-4-yl)ethyl)-1,4-di(aminocarbonylmethyl)benzene

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + ethyl 5-((2S,4aR,6R,7R,8R,8aR)-8-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-7-hydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-1,3,4-oxadiazole-2-carboxylate → 5-((2S,4aR,6R,7R,8R,8aR)-8-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-7-hydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-N-(2-morpholinoethyl)-1,3,4-oxadiazole-2-carboxamide

Conditions	Yield
In tetrahydrofuran at 20℃; for 16.5h;	100%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 3-Chloro-6-(4-chloro-phenyl)-4-phenyl-pyridazine (116776-62-6) → [6-(4-Chloro-phenyl)-4-phenyl-pyridazin-3-yl]-(2-morpholin-4-yl-ethyl)-amine

Conditions	Yield
for 6h; Heating;	99%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + N-Methylisatoic anhydride (10328-92-4) → 2-Methylamino-N-(2-morpholin-4-yl-ethyl)-benzamide (185409-41-0)

Conditions	Yield
With isatoic anhydride resin In dichloromethane Ambient temperature; 1.) 14 h; 2.) 90 min;	99%
In 1,4-dioxane at 60℃; for 3h;	76.9%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 4-fluoro-3-nitrobenzoyl chloride (400-94-2) → 4-fluoro-N-(2-morpholin-4-yl-ethyl)-3-nitro-benzamide

Conditions	Yield
With triethylamine In dichloromethane at 23℃; for 1h;	99%
In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	88%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 3-chloro-6-isopropyl-1,2,4-benzotriazine 1-oxide (763132-25-8) → 6-isopropyl-N-[3-(4-morpholinyl)ethyl]-1,2,4-benzotriazin-3-amine 1-oxide

Conditions	Yield
In 1,2-dimethoxyethane for 8h; Heating;	99%
In methanol; 1,2-dimethoxyethane	99%
In 1,2-dimethoxyethane for 2h; Heating / reflux;	99%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 5-bromo-2-toluenesulfonyl chloride (139937-37-4) → 4-bromo-2-methyl-N-(2-morpholin-4-yl-ethyl)benzene sulfonamide (869663-64-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 40℃; for 18h;	99%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + Methyl 4-chlorobenzoate (1126-46-1) → moclobemide (71320-77-9)

Conditions	Yield
With sodium t-butanolate In neat (no solvent) at 20℃; for 1h; Inert atmosphere; Schlenk technique; Green chemistry;	99%
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 23℃; for 15h; Inert atmosphere; chemoselective reaction;	90%
With zirconium(IV) oxide In diethylene glycol dimethyl ether at 160℃; under 3750.38 Torr; Flow reactor; Green chemistry;	80%
In diethyl ether
With family VIII carboxylesterase EstCE1 In dimethyl sulfoxide at 25℃; for 42h; Enzymatic reaction;

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + tert-butyl acetoacetate (1694-31-1) → (Z)-tert-butyl 3-(2-morpholinoethylamino)but-2-enoate (1240195-04-3)

Conditions	Yield
With silica gel at 20℃; for 18h;	99%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 1-(4-fluorobenzyl)-5-(methoxycarbonyl)-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid (932396-34-4) → methyl 1-(4-fluorobenzyl)-3-((2-(morpholin-4-yl)ethyl)carbamoyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (1261531-19-4)

Conditions	Yield
Stage #1: 1-(4-fluorobenzyl)-5-(methoxycarbonyl)-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 4-(2-AMINOETHYL)MORPHOLINE In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	99%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + ethyl 1-(2-bromoethyl)-3-phenyl-1H-pyrazole-5-carboxylate (1101861-35-1) → 5-(2-morpholinoethyl)-2-phenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one (1310071-08-9)

Conditions	Yield
With potassium iodide for 0.0166667h; Microwave irradiation;	99%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + ethyl 1-(2-bromoethyl)-3-(4-chlorophenyl)-1H-pyrazole-5-carboxylate (1101861-37-3) → 2-(4-chlorophenyl)-5-(2-morpholinoethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one (1310071-12-5)

Conditions	Yield
With potassium iodide for 0.0166667h; Microwave irradiation;	99%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 2-acetylpyridine (1122-62-9) → (2-morpholin-4-ylethyl)-(1-pyridin-2-ylethylidene)amine (1310040-01-7)

Conditions	Yield
In methanol for 0.5h; Reflux;	99%
In ethanol for 2h; Reflux;	61.5%
In methanol

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 1-Chloro-4-iodobenzene (637-87-6) + carbon monoxide (201230-82-2) → moclobemide (71320-77-9)

Conditions	Yield
With triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 80℃; for 18h; Glovebox; Sealed tube; Inert atmosphere;	99%
With 1,4-diaza-bicyclo[2.2.2]octane; 9-{[5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenyl-λ4-phosphanyl}-O-methanesulfonyl-8-methyl-8λ4-aza-9-palladatricyclo[8.4.0.02,7]tetradeca-1(14),2,4,6,10,12-hexaene-9,9-bis(ylium)-10-uid-9-olate In tetrahydrofuran at 80℃; for 16h; Sealed tube;	98%
With potassium carbonate In toluene at 120℃; under 1034.32 Torr; for 24h;	94%

Upstream product

• 3240-94-6 N-(2-chlorethyl)morpholine 
• 151-56-4 ethyleneimine 
• 110-91-8 morpholine 
• 660395-39-1 4-(2-azido-ethyl)-morpholine 
• 3647-69-6 4-(2-chloroethyl)morpholine hydrochride 
• 141-43-5 ethanolamine 
• 59737-33-6 3-(morpholin-4-yl)propionic acid hydrazide 
• 57796-58-4 6-chloro-5-ethylamino-3-methoxy-pyrazine-2-carboxylic acid 2-morpholin-4-yl-ethylamide 
• 107-15-3 ethylenediamine 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 80500-16-9 (2-Morpholin-4-yl-ethylamino)-diphenyl-methanol 
• 5625-98-9 morpholinoethyl amide 
• 870-24-6 2-chloroethanamine hydrochloride 
• 6820-90-2 2-(2-morpholin-4-ylethyl)-1H-isoindole-1,3(2H)-dione 

Downstream Products

• 106018-39-7 4-hydroxy-N-(2-morpholinoethyl)benzamide 
• 116210-90-3 cyclohexyl-phenyl-acetic acid-(2-morpholino-ethylamide) 
• 859813-77-7 (4-methyl-6-nitro-[2]quinolyl)-(2-morpholino-ethyl)-amine 
• 4476-13-5 N-[2-(4-morpholinyl)ethyl]benzamide 
• 3948-64-9 N-(2-morpholinoethyl)-4-nitrobenzamide 
• 102552-78-3 2-benzyl-benzoic acid-(2-morpholino-ethylamide) 
• 17050-06-5 2-(2-morpholino-ethylamino)-5,5-diphenyl-1,5-dihydro-imidazol-4-one 
• 101939-61-1 N-(2-morpholino-ethyl)-4-sulfanilyl-aniline 
• 14299-33-3 4-propoxy-benzoic acid-(2-morpholino-ethylamide) 
• 101438-49-7 2-phenyl-butyric acid-(2-morpholino-ethylamide) 
• 93143-42-1 3,4,5-trimethoxy-N-(2-morpholin-4-yl-ethyl)-benzamide 
• 17785-41-0 benzylidene-(2-morpholin-4-yl-ethyl)-amine 

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The invention concerns a compound according to formula (I), wherein 3 n 11, wherein R comprises or consists of a heterocycle comprising one tertiary amino group providing the binding of R to the rest of the molecule and at least three carbon atoms, wherein all carbon atoms of the heterocycle are unsubstituted or wherein R is a fused bicyclic compound comprising the heterocycle and one further cyclic compound.

New pyrido[3,4-g]quinazoline derivatives as CLK1 and DYRK1A inhibitors: synthesis, biological evaluation and binding mode analysis

Cdc2-like kinase 1 (CLK1) and dual specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) are involved in the regulation of alternative pre-mRNA splicing. Dysregulation of this process has been linked to cancer progression and neurodegenerative diseases, making CLK1 and DYRK1A important therapeutic targets. Here we describe the synthesis of new pyrido[3,4-g]quinazoline derivatives and the evaluation of the inhibitory potencies of these compounds toward CDK5, CK1, GSK3, CLK1 and DYRK1A. Introduction of aminoalkylamino groups at the 2-position resulted in several compounds with low nanomolar affinity and selective inhibition of CLK1 and/or DYRK1A. Their evaluation on several immortalized or cancerous cell lines showed varying degree of cell viability reduction. Co-crystal structures of CLK1 with two of the most potent compounds revealed two alternative binding modes of the pyrido[3,4-g]quinazoline scaffold that can be exploited for future inhibitor design.