54260-89-8

Usage

InChI:InChI=1/C7H8N2O2.ClH/c1-11-7(10)3-2-6-4-8-5-9-6;/h2-5H,1H3,(H,8,9);1H/b3-2+;

Upstream product

• 67-56-1 methanol 
• 3465-72-3 urocanic Acid 
• 3465-72-3 (E)-3-(1H-imidazol-4-yl)propenoic acid 

Downstream Products

• 195053-89-5 4-(3-aminopropyl)-1-(triphenylmethyl)-imidazole 
• 195053-88-4 2-[3-(1-trityl-1H-imidazol-4-yl)propyl]isoindoline-1,3-dione 
• 152030-49-4 3-(1-trityl-1H-imidazol-4-yl)propan-1-ol 
• 112547-04-3 (E)-N-[3-(1-Triphenylmethyl-1H-imidazol-4-yl)allyl]phthalimid 
• 132553-79-8 3-(1-trityl-1H-imidazol-4-yl)prop-2-enamine 
• 138408-38-5 (E)-3-(1-Triphenylmethyl-1H-imidazol-4-yl)allylchlorid Hydrochlorid 
• 138408-37-4 1-(triphenylmethyl)-4-(3-hydroxyprop-1-enyl)imidazole 
• 40546-33-6 3-[imidazol-4⁽⁵⁾-yl]propylamine 

Relevant academic research and scientific papers

3,4,5-TRISUBSTITUTED-1,2,4-TRIAZOLES AND 3,4,5-TRISUBSTITUTED-3-THIO-1,2,4-TRIAZOLES AND USES THEREOF

The present disclosure describes novel compounds that are somatostatin receptor type 4 agonists.

Synthesis of 7-15N-oroidin and evaluation of utility for biosynthetic studies of pyrrole-imidazole alkaloids by microscale 1H-15N HSQC and FTMS

Numerous marine-derived pyrrole-imidazole alkaloids (PIAs), ostensibly derived from the simple precursor oroidin, 1a, have been reported and have garnered intense synthetic interest due to their complex structures and in some cases biological activity; however very little is known regarding their biosynthesis. We describe a concise synthesis of 7-15N-oroidin (Id) from urocanic acid and a direct method for measurement, of 15N incorporation by pulse labeling and analysis by 1D 1H-15N HSQC NMR and FTMS. Using a mock pulse labeling experiment, we estimate the limit of detection (LOD) for incorporation of newly biosynthesized PIA by 1D 1H-15N HSQC to be 0.96 μg equivalent of 15N-oroidin (2.4 nmole) in a background of 1500 μg of unlabeled oroidin. (about 1 part per 1600). 7-15N-Oroidin will find utility in biosynthetic feeding experiments with live sponges to provide direct information to clarify the pathways leading to more complex pyrrole-imidazole alkaloids.

New high affinity H3 receptor agonists without a basic side chain

In this study, we replaced the basic amine function of the known histamine H3 receptor agonists imbutamine or immepip with non-basic alcohol or hydrocarbon moieties. All compounds in this study show a moderate to high affinity for the cloned human H3 receptor and, unexpectedly, almost all of them act as potent agonists. Moreover, in the alcohol series, we consistently observed an increased selectivity for the human H3 receptor over the human H4 receptor, but none of the compounds in this series possess increased affinity and functional activity compared to their alkylamine congeners. In this new series of compounds VUF5657, 5-(1H-imidazol-4-yl)-pentan-1-ol, is the most potent histamine H3 receptor agonist (pKi = 8.0 and pEC50 = 8.1) with a 320-fold selectivity at the human H3 receptor over the human H 4 receptor.

Ring-substituted imidazoles as a new class of anti-tuberculosis agents

We describe in vitro anti-Mycobacterium tuberculosis activities of ring-substituted-1H-imidazole-4-carboxylic acid derivatives (1-6), and 3-(2-alkyl-1H-imidazol-4-yl)-propionic acid derivatives (7-13) against drug-sensitive and drug-resistant M. tuberculosis H37Rv strains. The most effective analogues, 2f (R=R1=c-C5H9), and 2h (R=R1=c-C6H11) have produced >90% inhibition at a concentration of 6.25 μg/ml in the drug-sensitive screen. Upon further evaluation against drug-resistant strains, both analogues 2f and 2h produced an MIC value of 25.0 μg/ml. The observation of significant anti-tuberculosis activity in some of these analogues describes the discovery of novel ring-substituted-1H-imidazole-4-carboxylic acid ethyl esters as a new class of anti-tuberculosis agents.

Inhibitors of prenyl-protein transferase

The present invention is directed to macrocyclic compounds which inhibit prenyl-protein transferase (FTase) and the prenylation of the oncogene protein Ras. The invention is further directed to chemothera-peutic compositions containing the compounds of this invention and methods for inhibiting prenyl-protein transferase and the prenylation of the oncogene protein Ras.

PYRAZINONE, PYRIDINONE, PIPERIDINE AND PYRROLIDINE THROMBIN INHIBITORS

A compound which inhibits human thrombin and where has the structure and pharmaceutically acceptable salts thereof, wherein such as STR1 which are useful for inhibiting formation of blood platelet aggregates in blood in a mammal.

Antithrombotic diamides

This invention relates to a compound of the Formula IX--C(O)--Y--C(O)--NH--CH 2 --G--Im I(wherein X, Y, G and Im have the values defined in the description), or a pharmaceutically acceptable salt thereof, processes and intermediates for the preparation of such a compound or salt, pharmaceutical compositions comprising such a compound or salt and methods of their use as thrombin inhibitors, coagulation inhibitors and agents for the treatment of thromboembolic disorders.

Fibrinogen receptor antagonists

Novel fibrinogen receptor antagonists of the formula: are provided in which the claimed compounds exhibit fibrinogen receptor antagonist activity, inhibit platelet aggregation and are therefore useful in modulating thrombus formation.

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