145695-69-8

Usage

Uses

Used in Pharmaceutical Industry:
α-AMino-N-Methyl-1-(triphenylMethyl)-1H-iMidazole-4-propanaMide is used as a key intermediate in the synthesis of carnosine derivatives. These derivatives have potential neuroprotective properties, making them valuable for the development of treatments and therapies for neurological disorders and conditions.
Used in Chemical Research:
As a unique chemical compound with distinct structural features, α-AMino-N-Methyl-1-(triphenylMethyl)-1H-iMidazole-4-propanaMide can be utilized in chemical research to explore its properties, reactivity, and potential for further modification. This may lead to the discovery of new compounds with novel applications in various industries.
Used in Material Science:
The compound's specific structural features and chemical properties may also make it a candidate for use in material science, where it could be explored for its potential to enhance or create new materials with specific properties for various applications.

Upstream product

• 74-89-5 methylamine 
• 32946-56-8 N(τ)-(triphenylmethyl)-L-histidine methyl ester hydrochloride 
• 109425-51-6 Fmoc-His(Trt)-OH 
• 1262323-28-3 C₄₁H₃₆N₄O₃ 
• 32946-56-8 N_im-trityl-L-histidine methyl ester dihydrochloride 

Downstream Products

• 145695-70-1 N-(2,2'-dimethylpropylidene)-N_im-trityl-L-histidine-N'-methylamide 
• 1262323-45-4 C₃₄H₃₉N₅O₄ 
• 1333228-14-0 [{[(S)-1-Methylcarbamoyl-2-(1-trityl-1H-imidazol-4-yl)-ethylcarbamoyl]-methyl}-(3-phenyl-propyl)-amino]-acetic acid methyl ester 
• 1333228-06-0 (Benzyl-{[(S)-1-methylcarbamoyl-2-(1-trityl-1H-imidazol-4-yl)-ethylcarbamoyl]-methyl}-amino)-acetic acid 
• 1333228-07-1 [{[(S)-1-Methylcarbamoyl-2-(1-trityl-1H-imidazol-4-yl)-ethylcarbamoyl]-methyl}-(3-phenyl-propyl)-amino]-acetic acid 
• 145695-72-3 (2R,4S)-3-benzoyl-2-(1,1-dimethylethyl)-1-methyl-4-<(N_im-tritylimidazol-4'-yl)methyl>-1,3-imidazolidin-5-one 
• 145695-73-4 (2R,4S)-3-benzoyl-2-(1,1-dimethylethyl)-4-(fluoromethyl)-4-<(N_im-tritylimidazol-4'-yl)methyl>-1-methyl-1,3-imidazolidin-5-one 
• 145695-76-7 (2R,4S)-3-benzoyl-2-(1,1-dimethylethyl)-4-(chloromethyl)-4<(N_im-tritylimidazol-4'-yl)methyl>-1-methyl-1,3-imidazolidin-5-one 
• 145695-77-8 (2R,4S)-3-benzoyl-2-(1,1-dimethylethyl)-4-(chloromethyl)-4-(4'-imidazolylmethyl)-1-methyl-1,3-imidazolidin-5-one 
• 145695-74-5 (2R,4S)-3-benzoyl-2-(1,1-dimethylethyl)-4-(fluoromethyl)-4-(4'-imidazolylmethyl)-1-methyl-1,3-imidazolidin-5-one 

Relevant academic research and scientific papers

Structure-activity relationships of imidazole-derived 2-[ N-carbamoylmethyl-alkylamino]acetic acids, dual binders of human insulin-degrading enzyme

Insulin degrading enzyme (IDE) is a zinc metalloprotease that degrades small amyloid peptides such as amyloid-a and insulin. So far the dearth of IDE-specific pharmacological inhibitors impacts the understanding of its role in the physiopathology of Alzheimer's disease, amyloid-a clearance, and its validation as a potential therapeutic target. Hit 1 was previously discovered by high-throughput screening. Here we describe the structure-activity study, that required the synthesis of 48 analogues. We found that while the carboxylic acid, the imidazole and the tertiary amine were critical for activity, the methyl ester was successfully optimized to an amide or a 1,2,4-oxadiazole. Along with improving their activity, compounds were optimized for solubility, lipophilicity and stability in plasma and microsomes. The docking or co-crystallization of some compounds at the exosite or the catalytic site of IDE provided the structural basis for IDE inhibition. The pharmacokinetic properties of best compounds 44 and 46 were measured in vivo. As a result, 44 (BDM43079) and its methyl ester precursor 48 (BDM43124) are useful chemical probes for the exploration of IDE's role.

Synthesis, physicochemical characterization, and biological activities of new carnosine derivatives stable in human serum as potential neuroprotective agents

The synthesis and the physicochemical and biological characterization of a series of carnosine amides bearing on the amido group alkyl substituents endowed with different lipophilicity are described. All synthesized products display carnosine-like properties differentiating from the lead for their high serum stability. They are able to complex Cu2+ ions at physiological pH with the same stoichiometry as carnosine. The newly synthesized compounds display highly significant copper ion sequestering ability and are capable of protecting LDL from oxidation catalyzed by Cu2+ ions, the most active compounds being the most hydrophilic ones. All the synthesized amides show quite potent carnosine-like HNE quenching activity; in particular, 7d, the member of the series selected for this kind of study, is able to cross the blood-brain barrier (BBB) and to protect primary mouse hippocampal neurons against HNE-induced death. These products can be considered metabolically stable analogues of carnosine and are worthy of additional investigation as potential neuroprotective agents.

A Novel Stereoselective Route to (S)-(+)-α-(Fluoromethyl)histidine: α-Halomethylation of (2R,4S)-3-Benzoyl-2-(1,1-dimethylethyl)-1-methyl-4--1,3-imidazolidin-5-one. Synthesis and 1H NMR Spectroscopy

A method is described for the α-enantioretentive methylation of L-histidine (S) to give (S)-(+)-α-(fluoromethyl)histidine (8).The synthesis involves the conversion of Nim-trityl-L-histidine methyl ester (1) to both the "trans"-(2S,4S)- and "cis