67478-50-6

Usage

Uses

Used in Organic Synthesis:
1-TRITYLIMIDAZOLE-2-CARBOXALDEHYDE is used as a protective group in organic synthesis for [application reason]. The trityl group provides a means to protect certain functional groups during chemical reactions, allowing for selective reactions to occur at other sites on a molecule.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-TRITYLIMIDAZOLE-2-CARBOXALDEHYDE is used as a building block or intermediate for the synthesis of pharmaceutical compounds. Its imidazole structure and functional groups can be incorporated into drug molecules to modulate their biological activity and pharmacokinetic properties.
Used in Chemical Research:
1-TRITYLIMIDAZOLE-2-CARBOXALDEHYDE is also utilized in chemical research as a model compound to study the reactivity and properties of imidazole derivatives and trityl-protected compounds. This can provide insights into the development of new synthetic methods and the understanding of reaction mechanisms.
Used in Specialty Chemicals Industry:
1-TRITYLIMIDAZOLE-2-CARBOXALDEHYDE may find applications in the specialty chemicals industry, where it can be used as a reagent or catalyst in specific chemical transformations. Its unique structure and functional groups can offer advantages in selectivity and efficiency for certain types of reactions.

InChI:InChI=1/C23H18N2O/c26-18-22-24-16-17-25(22)23(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-18H

Upstream product

• 107-31-3 Methyl formate 
• 15469-97-3 N-tritylimidazole 
• 68-12-2 N,N-dimethyl-formamide 
• 596-43-0 bromo-triphenyl-methane 
• 10111-08-7 2-imidazolecarbaldehyde 
• 76-83-5 trityl chloride 
• 3034-50-2 4⁽⁵⁾formylimidazole 
• 96797-15-8 N-trityl-4⁽⁵⁾-iodoimidazole 

Downstream Products

• 10111-08-7 2-imidazolecarbaldehyde 
• 76-84-6 triphenylmethyl alcohol 
• 102152-03-4 2-(hydroxymethyl)-1-tritylimidazole 
• 558441-71-7 ethyl (2E)-3-(1-triphenylmethyl-1H-imidazol-2-yl)acrylate 
• 277328-05-9 benzyl((1-(triphenylmethyl)imidazol-2-yl)methyl)amine 
• 317335-10-7 3-hydroxy-1-(5-phenethylthiophen-2-yl)-3-(1-trityl-1H-imidazol-2-yl)propan-1-one 
• 1174192-08-5 1-trityl-2-vinyl-1H-imidazole 
• 1174192-09-6 3-(1-trityl-1H-imidazole-2-yl)acrylonitrile 

Relevant academic research and scientific papers

OGA INHIBITOR COMPOUNDS

The present invention relates to O-GIcNAc hydrolase (OGA) inhibitors of formula (I). The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which inhibition of OGA is beneficial, such as tauopathies in particular Alzheimer's disease or progressive supranuclear palsy; and neurodegenerative diseases accompanied by a tau pathology, in particular amyotrophic lateral sclerosis or frontotemporal lobe dementia caused by C90RF72 mutations.

Optimization of diarylpentadienones as chemotherapeutics for prostate cancer

Our earlier studies indicate that (1E,4E)-1,5-bis(1-alkyl-1H-imidazol-2-yl)penta-1,4-diene-3-ones and (1E,4E)-1,5-bis(1-alkyl-1H-benzo[d]imidazol-2-yl)penta-1,4-diene-3-ones exhibit up to 121-fold greater antiproliferative potency than curcumin in human p

Synthesis and Biological Evaluation of Imidazole-Bearing α-Phosphonocarboxylates as Inhibitors of Rab Geranylgeranyl Transferase (RGGT)

Rab geranylgeranyl transferase (RGGT) is an interesting therapeutic target, as it ensures proper functioning of Rab GTPases, a class of enzymes responsible for the regulation of vesicle trafficking. Relying on our previous studies, we synthesized a set of new α-phosphonocarboxylic acids as potential RGGT inhibitors, with emphasis on the elaboration of imidazole-containing analogues. We identified two compounds with activity similar to that of previously reported RGGT inhibitors, showing structural similarity to imidazo[1,2-a]pyridine-containing analogues in terms of their substitution pattern. Interestingly, analogues of the N-series, derived from another phosphonocarboxylate RGGT inhibitor, 2-fluoro-3-(1H-imidazol-1-yl)-2-phosphonopropanoic acid, turned out to be inactive in our model, indicating that an additional substituent localized at positions C2 or C4 of the imidazole ring, may adversely affect the potency against the targeted enzyme.

Identification of a novel class of covalent modifiers of hemoglobin as potential antisickling agents

Aromatic aldehydes and ethacrynic acid (ECA) exhibit antipolymerization properties that are beneficial for sickle cell disease therapy. Based on the ECA pharmacophore and its atomic interaction with hemoglobin, we designed and synthesized several compounds-designated as KAUS (imidazolylacryloyl derivatives)-that we hypothesized would bind covalently to βCys93 of hemoglobin and inhibit sickling. The compounds surprisingly showed weak allosteric and antisickling properties. X-ray studies of hemoglobin in complex with representative KAUS compounds revealed an unanticipated mode of Michael addition between the β-unsaturated carbon and the N-terminal αVal1 nitrogen at the α-cleft of hemoglobin, with no observable interaction with βCys93. Interestingly, the compounds exhibited almost no reactivity with the free amino acids, l-Val, l-His and l-Lys, but showed some reactivity with both glutathione and l-Cys. Our findings provide a molecular level explanation for the compounds biological activities and an important framework for targeted modifications that would yield novel potent antisickling agents.

Synthesis, structure-activity relationship studies, and identification of novel 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine derivatives as dual orexin receptor antagonists. Part 1

A novel series of non-peptidic OX1R/OX2R orexin receptor antagonists was prepared by heterocyclic replacement of the dimethoxyphenyl moiety contained in the tetrahydroisoquinoline core skeleton of almorexant. Introduction of substituted imidazole moieties delivered potent dual orexin receptor antagonists with nanomolar potency for hOX1R and hOX2R suitable for further fine-tuning. The preparation of these novel orexin receptor antagonists and the outcome of preliminary structure-activity relationship studies are described in this communication.

Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors

A new series of potential GABA uptake inhibitors starting from of 1H-imidazol-4-ylacetic acid with the carboxylic acid side chain originating from different positions and varying in length have been synthesized and tested for the inhibitory potency at the

Asymmetric Copper(II)-catalysed nitroaldol (Henry) reactions utilizing a chiral C1-symmetric dinitrogen ligand

A series of stable chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensation of chiral amines [(-)-exo-bornylamine or (+)-(1S,2S,5R)-menthylamine] with various substituted imidazolecarbaldehydes. With the assistance of base, the ligand L1 in combination with CuCl2·2H2O (2.5 mol-% or 5.0 mol-%) can efficiently promote nitroaldol (Henry) reactions between a variety of aldehydes and nitromethane. Both aromatic and aliphatic aldehydes were tolerated in our catalytic system, affording the expected nitroalcohol products in high yields (up to 97%) and with good enantioselectivities (up to 96%) under mild reaction conditions. A series of chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensations of chiralamines with various substituted imidazolecarbaldehydes. The ligand L1 in conjunction with CuCl2·2H2O can efficiently promote nitroaldol (Henry) reactions between various aldehydes and nitromethane in high yields (up to 97%) and with good enantioselectivities (up to 96%).

5,6,7,8-TETRAHYDRO-IMIDAZO[1,5-A]PYRAZINE DERIVATIVES

The invention relates to 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine derivatives of formula (I),wherein X represents CH2 or O; R1 represents a phenyl group, which group is independently mono-, di-, or tri-substituted wherein the substituents are independently selected from the group consisting of (C1-4)alkyl, (C1-4)alkoxy, halogen, cyano, trifluoromethoxy and trifluoromethyl; R2 represents (C1-4)alkyl, (C1-4)alkoxy, (C2-4)alkenyl, halogen, cyano, hydroxymethyl, trifluoromethyl, C(O)NR5R6 or cyclopropyl; R3 represents (C1-4)alkyl, (C1-4)alkoxy-methyl or halogen; R4 represents (C1-4)alkyl; R5 represents hydrogen or (C1-4)alkyl; and R6 represents hydrogen or (C1-4)alkyl. The invention also relates to pharmaceutically acceptable salts of such compounds; and to the use of such compounds as medicaments; especially as orexin receptor antagonists.

Chemokine receptor binding heterocyclic compounds with enhanced efficacy

The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

Chemokine receptor binding heterocyclic compounds with enhanced efficacy

The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).