2079-89-2

Usage

Uses

Used in Pharmaceutical and Biomedical Research:
3-Aminopropionitrile fumarate is used as a lysyl oxidase (LOX) inhibitor for various applications in pharmaceutical and biomedical research. It is utilized to inhibit collagen cross-linking during microtissue formation and culture, which is essential for studying the role of LOX in tissue development and remodeling.
Used in Cellular and Molecular Biology:
In the field of cellular and molecular biology, 3-aminopropionitrile fumarate is used in transwell migration and invasion assays. It helps researchers investigate the role of LOX in cell migration and invasion processes, which are crucial for understanding the mechanisms of cancer metastasis and other cellular processes.
Used in Enzyme Activity Assays:
3-Aminopropionitrile fumarate is also used in lysyl oxidase (LOX) activity assays. These assays are vital for studying the enzymatic activity of LOX and its regulation, which can provide insights into the development of potential therapeutic agents targeting LOX.
Used in Organoid Culture Studies:
In organoid culture studies, 3-aminopropionitrile fumarate is used to investigate the requirement of LOX activity for inducing hypoxia-inducible factor (HIF)2A-dependent stiffness in mouse organoids. This application helps researchers understand the role of LOX in tissue stiffness and its implications in various diseases, including cancer and fibrosis.

Biochem/physiol Actions

3-Aminopropionitrile (β-Aminopropionitrile (BAPN)) functions as an irreversible inhibitor of lysyl oxidase (LOX), an enzyme involved in collagen cross-linking.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. An experimental teratogen. When heated to decomposition it emits toxic fumes of NO, and CN-. See also NITRILES.

InChI:InChI=1/C4H4O4.2C3H6N2/c5-3(6)1-2-4(7)8;2*4-2-1-3-5/h1-2H,(H,5,6)(H,7,8);2*1-2,4H2/b2-1-;;

Synthetic route

di-tert-butyl dicarbonate (24424-99-5) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-<(tert-butoxycarbonyl)amino>propionitrile (53588-95-7)

Conditions	Yield
With triethylamine In dichloromethane for 12h; Heating;	96%
With sodium hydroxide In diethyl ether; water for 12h;	91%

β-aminopropionitrile monofumarate salt (2079-89-2) + benzyl chloroformate (501-53-1) → 3-<<(benzyloxy)carbonyl>amino>propionitrile (18877-96-8)

Conditions	Yield
With sodium hydroxide for 0.5h; Ambient temperature;	82%
With sodium hydroxide In diethyl ether; water for 4h;	35.0 g
With sodium hydroxide In diethyl ether; water for 2h; pH=10;

β-aminopropionitrile monofumarate salt (2079-89-2) + p-toluenesulfonyl chloride (98-59-9) → N-(β-cyanoethyl)-p-toluenesulfonamide (2619-22-9)

Conditions	Yield
With sodium hydroxide In water; ethyl acetate pH=10;	78%

1-(4-fluorophenyl)-5-methyl-1,4-hexanedione (104568-68-5) + β-aminopropionitrile monofumarate salt (2079-89-2) → 2-<2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrol-1-yl>-1-cyanoethane (104568-69-6)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;	73%

1-(4-methoxyphenyl)pentane-1,4-dione (2108-54-5) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(4-Methoxy-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile (123184-27-0)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(p-chlorophenyl)-1,4-pentanedione (53842-12-9) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(4-Chloro-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile (123184-28-1)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-cyclohexyl-1,4-pentanedione (61771-79-7) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Cyclohexyl-5-methyl-pyrrol-1-yl)-propionitrile (123184-34-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-norborn-5-en-2-yl-pentane-1,4-dione (70353-45-6) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Bicyclo[2.2.1]hept-5-en-2-yl-5-methyl-pyrrol-1-yl)-propionitrile (123184-35-0)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-([1,1'-biphenyl]-4-yl)pentane-1,4-dione (63472-37-7) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Biphenyl-4-yl-5-methyl-pyrrol-1-yl)-propionitrile (123184-26-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

3,8-Diethyl-decane-4,7-dione (123184-08-7) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2,5-Bis-(1-ethyl-propyl)-pyrrol-1-yl]-propionitrile (123184-50-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(4-fluoro-phenyl)-pentane-1,4-dione (123183-95-9) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(4-Fluoro-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile (123184-24-7)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-[2-(methoxy)phenyl]-pentane-1,4-dione (104562-48-3) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2-Methoxy-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile (123184-31-6)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(naphthalen-2-yl)pentane-1,4-dione (123183-98-2) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Methyl-5-naphthalen-2-yl-pyrrol-1-yl)-propionitrile (123184-32-7)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(naphthalen-1-yl)pentane-1,4-dione (123263-79-6) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Methyl-5-naphthalen-1-yl-pyrrol-1-yl)-propionitrile (123184-33-8)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(3-Methoxy-phenyl)-pentane-1,4-dione (123183-97-1) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(3-Methoxy-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile (123184-30-5)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-Cyclopropyl-4-(4-fluoro-phenyl)-butane-1,4-dione (123184-04-3) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-Cyclopropyl-5-(4-fluoro-phenyl)-pyrrol-1-yl]-propionitrile (123184-39-4)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2-Fluoro-phenyl)-5-methyl-hexane-1,4-dione (123184-10-1) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2-Fluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (123184-42-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2-Chloro-phenyl)-5-methyl-hexane-1,4-dione + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2-Chloro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (123184-48-5)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-Bicyclo[2.2.2]oct-5-en-2-yl-pentane-1,4-dione (123183-99-3) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Bicyclo[2.2.2]oct-5-en-2-yl-5-methyl-pyrrol-1-yl)-propionitrile (123184-36-1)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(3-Fluoro-phenyl)-5-methyl-hexane-1,4-dione (123184-09-8) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(3-Fluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (125333-93-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2-Methoxy-phenyl)-5-methyl-hexane-1,4-dione (123184-12-3) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-Isopropyl-5-(2-methoxy-phenyl)-pyrrol-1-yl]-propionitrile (123184-44-1)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

5-Ethyl-1-(4-fluoro-phenyl)-heptane-1,4-dione (123184-03-2) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(1-Ethyl-propyl)-5-(4-fluoro-phenyl)-pyrrol-1-yl]-propionitrile (123184-38-3)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2,5-Dimethyl-phenyl)-5-methyl-hexane-1,4-dione + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2,5-Dimethyl-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (123184-46-3)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2,4-Difluoro-phenyl)-5-methyl-hexane-1,4-dione (123184-11-2) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2,4-Difluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (123184-43-0)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-Cyclobutyl-4-(4-fluoro-phenyl)-butane-1,4-dione (123184-05-4) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-Cyclobutyl-5-(4-fluoro-phenyl)-pyrrol-1-yl]-propionitrile (123184-40-7)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1,1-Diphenyl-hexane-2,5-dione (123184-00-9) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Benzhydryl-5-methyl-pyrrol-1-yl)-propionitrile (123184-37-2)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

5,5,5-Trifluoro-1-(4-fluoro-phenyl)-pentane-1,4-dione (123184-07-6) + β-aminopropionitrile monofumarate salt (2079-89-2) → 2-(4-fluorophenyl)-5-trifluoromethyl-1H-pyrrole-1-propanenitrile (104568-91-4)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-[3-(trifluoromethyl)phenyl]pentane-1,4-dione (123183-96-0) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-Methyl-5-(3-trifluoromethyl-phenyl)-pyrrol-1-yl]-propionitrile (123184-29-2)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-Cyclohexyl-4-(4-fluoro-phenyl)-butane-1,4-dione (123184-06-5) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-Cyclohexyl-5-(4-fluoro-phenyl)-pyrrol-1-yl]-propionitrile (123184-41-8)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2-Isopropoxy-phenyl)-5-methyl-hexane-1,4-dione + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2-Isopropoxy-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (123184-47-4)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

Downstream Products

• 53588-95-7 3-<(tert-butoxycarbonyl)amino>propionitrile 
• 123184-28-1 3-[2-(4-Chloro-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile 
• 123184-34-9 3-(2-Cyclohexyl-5-methyl-pyrrol-1-yl)-propionitrile 
• 123184-26-9 3-(2-Biphenyl-4-yl-5-methyl-pyrrol-1-yl)-propionitrile 
• 123184-24-7 3-[2-(4-Fluoro-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile 
• 123184-31-6 3-[2-(2-Methoxy-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile 
• 104568-69-6 2-<2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrol-1-yl>-1-cyanoethane 
• 123184-42-9 3-[2-(2-Fluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile 
• 123184-48-5 3-[2-(2-Chloro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile 
• 125333-93-9 3-[2-(3-Fluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile 
• 123184-44-1 3-[2-Isopropyl-5-(2-methoxy-phenyl)-pyrrol-1-yl]-propionitrile 
• 123184-46-3 3-[2-(2,5-Dimethyl-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile 
• 123184-43-0 3-[2-(2,4-Difluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile 
• 123184-40-7 3-[2-Cyclobutyl-5-(4-fluoro-phenyl)-pyrrol-1-yl]-propionitrile