6961-46-2

Usage

Uses

Used in Pharmaceutical Industry:
Idrocilamide is used as an anticonvulsant and antidepressant agent for its potential therapeutic effects in managing seizures and depressive disorders. Its mechanism of action and pharmacological profile make it a promising candidate for further research and development in the treatment of neurological conditions.

InChI:InChI=1/C11H13NO2/c13-9-8-12-11(14)7-6-10-4-2-1-3-5-10/h1-7,13H,8-9H2,(H,12,14)/b7-6+

Upstream product

• 141-43-5 ethanolamine 
• 621-82-9 Cinnamic acid 
• 104-55-2 3-phenyl-propenal 
• 102-92-1 cinnamoyl chloride 

Downstream Products

• 65057-00-3 5-Benzoyl-3-indancarbonsaeure-2'-zimtsaeureamidoethylester 

Relevant academic research and scientific papers

TASTE-MODIFYING COMPOUNDS AND USES THEREOF

The present disclosure generally relates to compounds useful as taste modifiers, particularly as compounds useful for enhancing umami taste, and their use in various comestible products, such as food and beverage products.

N-Heterocyclic carbene (NHC) catalyzed chemoselective acylation of alcohols in the presence of amines with various acylating reagents

This edge article reports the synthesis and full characterization including X-ray analysis of three different acylazolium ions. The reactivity of these acylazolium ions as acylating reagents of amines and alcohols is discussed. Whereas benzylamine slowly reacts with the acylazolium ions, benzyl alcohol acylation does not occur. However, upon activation of the alcohol with an N-heterocyclic carbene (NHC) as catalyst, efficient esterification is achieved. Importantly, benzylester formation is obtained in the presence of benzylamine upon selective alcohol activation by the NHC. High level DFT calculations reveal that alcohol activation occurs by strong H-bond formation between the NHC and the alcohol thereby increasing the nucleophilicity of the alcohol. For oxidatively generated acylazolium ions under NHC catalysis, the carbene has a dual role (cooperative catalysis): (a) the NHC is used for generation of the acylazolium ion and (b) the NHC is used for activation of the alcohol in the subsequent acylation step. NHC-catalyzed selective acylation of benzyl alcohol in the presence of benzylamine can also be achieved with trifluoroethyl and hexafluoroisopropylesters as acylation reagents. Moreover, an enol acetate also shows high O-selectivity as a chemoselective acetylation reagent. Kinetic and mechanistic studies are provided and some examples of the chemoselective acylation of amino alcohols are presented.

Synthesis and antidepressant-like action of N-(2-hydroxyethyl) cinnamamide derivatives in mice

This study described the chemical synthesis and pharmacological evaluation of a series of N-(2-hydroxyethyl) cinnamamide derivatives. The structures of them were characterized by IR, 1H-NMR, MS and elemental analysis. Their antidepressant activities were evaluated by the forced swimming test (FST) and tail suspension test (TST). Pharmacological results of these compounds showed that some of them, given orally, significantly reduced the immobility time in the FST and TST, indicating the antidepressant-like action. Among them, compounds N-(2-hydroxyethyl)cinnamamide (1g), (E)-3-(4-hydroxy-3- methoxyphenyl)-N-(2-hydroxyethyl)acrylamide (1i) and (E)-N-(2-hydroxyethyl)-3- (3-hydroxyphenyl)acrylamide (1n), active in the two models, were considered as the most promising compounds in this study. Springer Science+Business Media, LLC 2010.

Synthesis and anticonvulsant activity of N-(2-hydroxyethyl) cinnamamide derivatives

A series of novel N-(2-hydroxyethyl) cinnamamide derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). The MES test showed that compounds I(N-(2-hydroxyethyl) cinnamamide) and 1d ((E)-3-(3-fluorophenyl)-N-(2-hydroxyethyl)acrylamide) were found to possess better anticonvulsant activity but also had lower toxicity. In the anti-MES potency test, these compounds exhibited median effective dose (ED50) of 17.7 and 17.0 mg/kg, respectively, and median toxicity dose (TD50) of 154.9 and 211.1, respectively, resulting in a protective index (PI) of 8.8 and 12.4, respectively, which is much greater than the PI of the marked antiepileptic drug carbamazepine. To further investigate the effects of the anticonvulsant activity in several different models, compounds I and 1d were tested against convulsions induced by chemical substances, including pentylenetetrazole (PTZ), isoniazid, 3-mercaptopropionic acid, and thiosemicarbazide.