40546-33-6

Basic information

• Product Name: 3-(1H-IMIDAZOL-4-YL)-PROPYLAMINE
• Synonyms: 3-(1H-IMIDAZOL-4-YL)-PROPYLAMINE;1H-imidazole-4-propylamine;imidazolyl-4-propylamine;1H-Imidazole-4-(1-propanamine);1H-Imidazole-4-propan-1-amine;4-(3-Aminopropyl)-1H-imidazole;VUF-8326;3-(1H-iMidazol-4-yl)propan-1-aMine
• CAS NO: 40546-33-6
• Molecular Formula: C₆H₁₁N₃
• Molecular Weight: 125.17164
• EINECS: 254-968-6
• Mol File: 40546-33-6.mol

Chemical Properties

• Boiling Point: 333.2°C at 760 mmHg
• Flash Point: 181.8°C
• Appearance: /
• Density: 1.098g/cm³
• Vapor Pressure: 0.000138mmHg at 25°C
• Refractive Index: 1.553
• PKA: 14?+-.0.10(Predicted)
• CAS DataBase Reference: 3-(1H-IMIDAZOL-4-YL)-PROPYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1H-IMIDAZOL-4-YL)-PROPYLAMINE(40546-33-6)
• EPA Substance Registry System: 3-(1H-IMIDAZOL-4-YL)-PROPYLAMINE(40546-33-6)

Safety Data

• Hazardous Substances Data: 40546-33-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H11N3/c7-3-1-2-6-4-8-5-9-6/h4-5H,1-3,7H2,(H,8,9)

Upstream product

• 3465-72-3 urocanic Acid 
• 53958-94-4 3-(1H-imidazol-4-yl)propionic acid methyl ester hydrochloride 
• 138408-28-3 3-(1H-Imidazol-4-yl)propanamid Hydrochlorid 
• 54260-89-8 trans-4-imidazoleacrylic acid methyl ester hydrochloride 
• 84461-00-7 1-diazo-5-phthalimido-2-pentanone 
• 41306-64-3 2-(5-bromo-4-oxo-pentyl)-isoindole-1,3-dione 
• 3197-25-9 2-(4-oxopentyl)isoindole-1,3-dione 
• 5891-21-4 5-chloro-2-pentanone 
• 33550-98-0 N-[3-(1⁽³⁾H-imidazol-4-yl)-propyl]-phthalimide 
• 33550-96-8 3-(1H-Imidazol-4-yl)propannitril 
• 565446-44-8 3-(1-Trityl-1H-imidazol-4-yl)-propionitrile 
• 154312-79-5 1-trityl-4-(2-cyanoethyl)imidazole 
• 41306-67-6 [3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)-propyl]-guanidine; hydrochloride 

Downstream Products

• 106467-07-6 N-Benzoyl-N'-{2-[2-(4-chloro-benzyl)-5-methyl-1H-imidazol-4-ylmethylsulfanyl]-ethyl}-N''-[3-(1H-imidazol-4-yl)-propyl]-guanidine 
• 106467-13-4 N-Benzoyl-N'-[3-(1H-imidazol-4-yl)-propyl]-N''-{3-[2-(tetrahydro-pyrimidin-2-ylideneamino)-thiazol-4-yl]-propyl}-guanidine 
• 112758-44-8 N-Benzoyl-N'-[3-(1H-imidazol-4-yl)-propyl]-N''-[2-(2-pyridin-2-yl-1H-imidazol-4-ylmethylsulfanyl)-ethyl]-guanidine 
• 106467-09-8 N-Benzoyl-N'-[2-(2-dimethylaminomethyl-thiazol-4-ylmethylsulfanyl)-ethyl]-N''-[3-(1H-imidazol-4-yl)-propyl]-guanidine 
• 106467-05-4 N-Benzoyl-N'-[3-(1H-imidazol-4-yl)-propyl]-N''-[2-(1-methyl-1H-imidazol-2-ylmethylsulfanyl)-ethyl]-guanidine 
• 106467-08-7 N-Benzoyl-N'-[2-(2-dimethylaminomethyl-5-methyl-1H-imidazol-4-ylmethylsulfanyl)-ethyl]-N''-[3-(1H-imidazol-4-yl)-propyl]-guanidine 
• 106669-02-7 N-Benzoyl-N'-(2-benzylsulfanyl-1-methyl-ethyl)-N''-[3-(1H-imidazol-4-yl)-propyl]-guanidine 
• 106668-55-7 N-Benzoyl-N'-[3-(1H-imidazol-4-yl)-propyl]-N''-[2-(naphthalen-1-ylmethylsulfanyl)-ethyl]-guanidine 
• 106686-42-4 N-Benzoyl-N'-[3-(1H-imidazol-4-yl)-propyl]-N''-[2-(5-methylsulfanyl-1H-imidazol-4-ylmethylsulfanyl)-ethyl]-guanidine 
• 106668-54-6 N-Benzoyl-N'-(2-benzylsulfanyl-ethyl)-N''-[3-(1H-imidazol-4-yl)-propyl]-guanidine 
• 126856-40-4 6-[4-[4-[3-(1H-Imidazol-4-yl)propylamino-carbonyl]piperazin-1-yl]-3-nitro-phenyl]-4,5-dihydro-5-methyl-3(2H)pyridazinone 

Relevant articles and documents

New Histamine-Related Five-Membered N-Heterocycle Derivatives as Carbonic Anhydrase I Activators

A series of histamine (HST)-related compounds were synthesized and tested for their activating properties on five physiologically relevant human Carbonic Anhydrase (hCA) isoforms (I, II, Va, VII and XIII). The imidazole ring of HST was replaced with different 5-membered heterocycles and the length of the aliphatic chain was varied. For the most interesting compounds some modifications on the terminal amino group were also performed. The most sensitive isoform to activation was hCA I (KA values in the low micromolar range), but surprisingly none of the new compounds displayed activity on hCA II. Some derivatives (1, 3a and 22) displayed an interesting selectivity for activating hCA I over hCA II, Va, VII and XIII.

Synthesis and structure-activity relationships of cyanoguanidine-type and structurally related histamine H4 receptor agonists

Recently, we identified high-affinity human histamine H3 (hH3R) and H4 receptor (hH4R) ligands among a series of NG-acylated imidazolylpropylguanidines, which were originally designed as histamine H2 receptor (H2R) agonists. Aiming at selectivity for hH4R, the acylguanidine group was replaced with related moieties. Within a series of cyanoguanidines, 2-cyano-1-[4-(1H-imidazol-4-yl)butyl]-3-[(2-phenylthio)ethyl]guanidine (UR-PI376, 67) was identified as the most potent hH4R agonist (pEC50=7.47, α=0.93) showing negligible hH1R and hH2R activities and significant selectivity over the hH3R (pKB=6.00, α=-0.28), as determined in steady-state GTPase assays using membrane preparations of hHxR-expressing Sf9 cells. In contrast to previously described selective H4R agonists, this compound and other 3-substituted derivatives are devoid of agonistic activity at the other HR subtypes. Modeling of the binding mode of 67 suggests that the cyanoguanidine moiety forms chargeassisted hydrogen bonds not only with the conserved Asp-94 but also with the hH4R-specific Arg-341 residue. 2-Carbamoyl-1-[2-(1H-imidazol-4-yl)ethyl]-3-(3-phenylpropyl)guanidine (UR-PI97, 88) was unexpectedly identified as a highly potent and selective hH3R inverse agonist (pKB=8.42, >300-fold selectivity over the other HR subtypes). 2009 American Chemical Society.

Synthesis of (Z)- and (E)-3-(1H-imidazol-4-yl)-2-propenamine and some 3-(1H-imidazol-4-yl)propanamines

3-(1H-Imidazol-4-yl)propanamine (6, homohistamine), an essential intermediate for the synthesis of potent impromidine-type histamine H2 receptor agonists, is efficiently prepared from trans-urocanic acid (1) by reduction of the methyl ester 2 and conversion to the saturated amide 4.Dehydration with thionyl chloride yields the nitrile 5 which is subsequently reduced to 6.Side-chain methylated 3-(1H-imidazol-4-yl)propanamines 12 are available from 1H-imidazole-4-carbaldehyde (7) and 1-(1H-imidazol-4-yl)ethanone (8), respectively, via unsaturated nitriles 10 and stepwise reduction.Cyclization of the appropiate 4-bromo-5-oxohexanenitriles 14α with formamidine in liquid ammonia and reduction of the obtained nitriles 15 furnishes ring-methylated amines 16. (E)-3-(1H-Imidazol-4-yl)-2-propenamine is obtained in six steps from the trans-ester 2 while (Z)-23 is accessible by treating 7 with triphenyl(2-phthalimidoethyl)phosphonium bromide (17) and final deprotection.These primary amines are valuable intermediates for the synthesis of impromidine analogues. Key Words: Homohistamine / Imidazole derivatives / 2-Propenamine derivatives / Impromidine

Synthesis and histamine H2-receptor activity of heterocyclic impromidine analogues.

Analogues of the H2-agonist impromidine with unsubstituted or substituted aromatic or non-aromatic heterocycles instead of the 5-methylimidazole group were prepared via the benzoylguanidine method and tested for H2-agonistic and H1-antagonistic activity in the guinea-pig isolated right atrium and ileum, respectively. Compounds with unsubstituted 2- or 3-pyridyl, 2-pyrazinyl, or 5-pyrimidyl thioether portion proved to be about equipotent in the atrium (about 2-4x histamine). Highest potency was found in the 5-chloro-3-pyridylthioethylguanidine 8h, that is about 20 times more potent as an H2-agonist than histamine, corresponding to about 8 times the activity of the unsubstituted parent compound 8g. It is demonstrated by the piperidinyl- and morpholinylalkyl guanidines 8m-o that an aromatic ring is not required in the affinity-conferring moiety of H2-agonists (8n: 1.3x histamine). Replacement of the (5-methylimidazol-4-yl)methylthio group in the H2-antagonist cimetidine by halogenated pyridyl, pyrazinyl and pyrimidinyl thioethers resulted in compounds inactive as H2-antagonists, giving further evidence for differences in the structural requirements of the affinity-conferring portions of H2-agonists and antagonists and their mode of interaction with the receptor protein.

An Alternative Synthesis of Homohistamine and Structurally Related (Imidazole-4-yl)alkylamines

Bromination of N-(4-oxopentyl)phthalimide (3) leads to isomeric bromoketones 2a and 2e, which undergo cyclisation with formamidine in liquid ammonia to yield homohistamine (1a) and 5-methylhistamine (1e).Similarly racemic α-methyl- (1b) and 2-methylhomohistamine (1c) are synthesized.The resolution of 1b is achieved using (+)- and (-)-di-O-(4-toluoyl)tartaric acid. 1 are intermediates in the synthesis of impromidine like, H2-histaminergic compounds. - Key words: Bromination of Methylketones, Halomethylketones, Histamine H2-Agonists, Homohistamine, Chiral Aminoalkylimidazoles

CERTAIN THIAZOLES AND OXAZOLES

The compounds are N,N'-substituted thioureas, ureas and guanidines which are H-2 histamine receptor inhibitors. Two compounds of this invention are N,N'-bis 2-((4-methyl-5-imidazolyl)methylthio) ethyl!thiourea and N,N'-bis 2-((4-methyl-5-imidazolyl)methylthio)ethyl!-N"-cyanoguanidine. "

PHARMACEUTICAL COMPOSITIONS AND METHOD OF INHIBITING H-1 AND H-2 HISTAMINE RECEPTORS

Pharmaceutical compositions and methods of inhibiting H-1 and H-2 histamine receptors by administering an antihistamine and an H-2 histamine receptor inhibitor. Exemplary of the antihistamine in the compositions and methods of this invention is mepyramine and exemplary of the H-2 histamine receptor inhibitor is N-methyl-N'-4-(5)-imidazolyl) butyl!thiourea.

PHARMACEUTICAL COMPOSITIONS AND METHODS OF INHIBITING H-1 AND H-2 HISTAMINE RECEPTORS

Pharmaceutical compositions and methods of inhibiting H-1 and H-2 histamine receptors by administering an antihistamine and an H-2 histamine receptor inhibitor. Exemplary of the antihistamine in the compositions and methods of this invention is mepyramine and exemplary of the H-2 histamine receptor inhibitor is N-cyano-N'-methyl-N"-2-((4-methyl-5-imidazolyl)-methylthio)ethyl!guanidine. "

PHARMACEUTICAL COMPOSITIONS AND METHODS OF INHIBITING HISTAMINE ACTIVITY WITH CARBOXAMIDINE COMPOUNDS

Pharmaceutical compositions and methods of inhibiting histamine activity with N-heterocyclic-alkylcarboxamidines.