202391-71-7

Usage

Uses

Used in Biochemical Research:
5-(3-Aminopropyl)-1H-imidazol-2-amine is used as a ligand for metal ion binding, facilitating the study of metal ion interactions and their roles in biological systems.
Used in Pharmaceutical Development:
5-(3-Aminopropyl)-1H-imidazol-2-amine serves as a precursor in the synthesis of pharmaceutical drugs, contributing to the development of new therapeutic agents.
Used in the Study of Biological Processes:
5-(3-Aminopropyl)-1H-imidazol-2-amine is utilized in the investigation of various biological processes, potentially aiding in the understanding of molecular mechanisms and pathways.
Used in Organic Synthesis:
As a versatile chemical intermediate, 5-(3-Aminopropyl)-1H-imidazol-2-amine is used in the synthesis of a range of organic molecules, expanding its applications across different chemical and industrial fields.

InChI:InChI=1/C6H12N4/c7-3-1-2-5-4-9-6(8)10-5/h4H,1-3,7H2,(H3,8,9,10)

Upstream product

• 80822-61-3 [3-(2-Amino-1H-imidazol-4-yl)-propyl]-urea; hydrochloride 
• 420-04-2 CYANAMID 
• 81084-75-5 ornithine methyl ester 
• 1069-31-4 DL-ornithine hydrochloride 
• 84772-29-2 ornithine ethyl ester dihydrochloride 
• 80822-62-4 4-(3-aminopropyl)-1H-imidazol-2-ylamine dihydrochloride 
• 6384-10-7 (S)-ornithine methyl ester 

Downstream Products

• 1565631-37-9 tert-butyl (1'S,4R)-(1'-(2-amino-1,4,5,6,7,8-hexahydroimidazo[4,5-c]azepin-4-yl)-2'-phenylethyl)carbamate 
• 1565631-56-2 C₂₀H₂₉N₅O₂ 
• 1565631-47-1 benzyl (1'S,4R)-(1'-(2-amino-1,4,5,6,7,8-hexahydroimidazo[4,5-c]azepin-4-yl)ethyl)carbamate 
• 1565631-64-2 benzyl (1'S,4S)-(1'-(2-amino-1,4,5,6,7,8-hexahydroimidazo[4,5-c]azepin-4-yl)ethyl)carbamate 
• 34649-22-4 oroidin 

Relevant academic research and scientific papers

Clathrodin, hymenidin and oroidin, and their synthetic analogues as inhibitors of the voltage-gated potassium channels

We have prepared three alkaloids from the Agelas sponges, clathrodin, hymenidin and oroidin, and a series of their synthetic analogues, and evaluated their inhibitory effect against six isoforms of the Kv1 subfamily of voltage-gated potassium channels, Kv1.1-Kv1.6, expressed in Chinese Hamster ovary (CHO) cells using automated patch clamp electrophysiology assay. The most potent inhibitor was the (E)-N-(3-(2-amino-1H-imidazol-4-yl)allyl)-4,5-dichloro-1H-pyrrole-2-carboxamide (6g) with IC50 values between 1.4 and 6.1 μM against Kv1.3, Kv1.4, Kv1.5 and Kv1.6 channels. All compounds tested displayed selectivity against Kv1.1 and Kv1.2 channels. For confirmation of their activity and selectivity, compounds were additionally evaluated in the second independent system against Kv1.1-Kv1.6 and Kv10.1 channels expressed in Xenopus laevis oocytes under voltage clamp conditions where IC50 values against Kv1.3-Kv1.6 channels for the most active analogues (e.g. 6g) were lower than 1 μM. Because of the observed low sub-micromolar IC50 values and fairly low molecular weights, the prepared compounds represent good starting points for further optimisation towards more potent and selective voltage-gated potassium channel inhibitors.

Second generation 2-aminoimidazole based advanced glycation end product inhibitors and breakers

The formation of advanced glycation end-products (AGE) as a result of the action of reducing sugars on host macromolecules plays a role in increased morbidity of diabetic patients. There are currently no clinically available therapeutics for the preventio

Diastereoselective pictet-spengler reactions of a tethered 2-aminoimidazole

The diastereoselective Pictet-Spengler reaction of aminopropyl-2- aminoimidazole with enantiopure aldehydes has been investigated. With amino acid-derived aldehydes, anti stereochemistry is favoured, with a diastereoselectivity up to 92% achievable. The absolute stereochemistry of the products was determined through synthesis of a rigid derivative and from NMR data in combination with molecular modelling. The diastereoselectivity was shown to be dependent on the steric bulk of the amino acid side chain and independent of the nitrogen protecting group. Lewis acids catalysed the reaction but did not affect the diastereoselectivity.

A convenient strategy for synthesizing the Agelas alkaloids clathrodin, oroidin, and hymenidin and their (un)saturated linker analogs

A convenient strategy for the scalable synthesis of the 2-aminoimidazole alkaloids, clathrodin, oroidin, and hymenidin derived from marine Agelas species and their analogs possessing a saturated or unsaturated linker moiety is described. The key intermediates, 4-(3-aminopropyl)-1H-imidazol-2-amine and (E)-4-(3-aminoprop-1-en-1-yl)-1H-imidazol-2-amine were obtained through two different synthetic pathways starting from l-ornithine and benzyl 1,2-dihydropyridine-1-carboxylate respectively, using (i) an innovative combination of Weinreb amide strategy with di-Boc protection, and (ii) a modified pyridine-1(2H)-carboxylate based strategy. Convenient access to these 2-aminoimidazole amines is crucial for the synthesis of libraries of clathrodin, oroidin, and hymenidin analogs.