35241-61-3Relevant academic research and scientific papers
Discovery of novel dihydroartemisinin-cinnamic hybrids inducing lung cancer cells apoptosis via inhibition of Akt/Bad signal pathway
Hu, Yanping,Wang, Yujin,Li, Na,Chen, Li,Sun, Jianbo
, (2021/04/27)
A series of dihydroartemisinin-cinnamic acid hybrids were designed, synthesized and evaluated. Most of the tested compounds showed enhanced anti-proliferative activities than artemisinin and dihydroartemisinin, among which 16 g had the superior potency with IC50 values ranging from 5.07 μM to 7.88 μM against four tested cancer cell lines. The cell cycle arrest revealed that 16 g induced A549 cell cycle arrest at G0/G1 phase via regulation of G1-related protein expression (Cdk4). Further mechanism studies reveal that 16 g induced A549 cells apoptosis via inhibiting Akt/Bad pathway. Moreover, 16 g depolarized the mitochondria membrane potentials and induced ROS generation in A549. Additionally, 16 g blocked migration of A549 cells in a concentration-dependent manner. What's more, 16 g is barely nontoxic to zebrafish embryos. Overall, the cell cycle arrest, inhibition of Akt/Bad signal pathway, ROS generation and migration blocked might explain the potent anti-proliferative activities of these compounds.
TASTE-MODIFYING COMPOUNDS AND USES THEREOF
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Page/Page column 11, (2021/02/19)
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.
Microwave-Assisted Synthesis of 2-Substituted 2-Thiazolines and 5,6-Dihydro-4 H -1,3-thiazines
Bisceglia, Juan A.,Kilimciler, Natalia B.,Mancinelli, Michele,Mollo, María C.,Orelli, Liliana R.
, p. 1666 - 1679 (2020/06/01)
An efficient and general method for the synthesis of 2-substituted thiazolines and 5,6-dihydro-4 H -1,3-thiazines is developed via microwave-assisted ring closure of ω-thioamidoalcohols promoted by ethyl polyphosphate (PPE). The cyclization reaction involves an S N 2-type mechanism and features the advantages of very short reaction times, high yields and a predictable stereochemical outcome. The acyclic precursors are prepared in high overall yields by an improved diacylation-thionation-saponification sequence from commercially available ω-amino alcohols. The whole process is metal-free and operationally simple.
New Efficient Eco-Friendly Supported Catalysts for the Synthesis of Amides with Antioxidant and Anti-Inflammatory Properties
Charlet, Rogatien,Da?ch, Adam,Dufrénoy, Pierrick,Ghinet, Alina,Hechelski, Marie,Jawhara, Samir,Waterlot, Christophe
, (2020/02/20)
A new environmentally friendly approach for the synthesis of idrocilamide (1), a marketed myorelaxant and anti-inflammatory agent, is reported herein. The synthetic strategy involves a solvent-free aminolysis reaction catalyzed by zinc-containing species
Trimethylphosphine-Promoted Alcoholysis of α,β-Unsaturated Imides and α,β-Unsaturated Esters
Sato, Haruka,Hosokawa, Seijiro
supporting information, p. 1343 - 1349 (2018/01/27)
α,β-Unsaturated imides and α,β-unsaturated esters were found to undergo alcoholysis in the presence of trimethylphosphine. The reaction is initiated by nucleophilic addition of trimethylphosphine to the double bond of the α,β-unsaturated carbonyl compound. Saturated imides also undergo the alcoholysis in the presence of the corresponding α,β-unsaturated imide.
In Silico Discovery and Validation of Amide Based Small Molecule Targeting the Enzymatic Site of Shiga Toxin
Chauhan, Vinita,Chaudhary, Dilip,Pathak, Uma,Saxena, Nandita,Dhaked, Ram Kumar
, p. 10763 - 10773 (2016/12/16)
Shiga toxin (Stx), a category B biothreat agent, is a ribosome inactivating protein and toxic to human and animals. Here, we designed and synthesized small molecules that block the active site of the Stx A subunit. On the basis of binding energy, 20 molec
N-Heterocyclic carbene (NHC) catalyzed chemoselective acylation of alcohols in the presence of amines with various acylating reagents
Samanta, Ramesh C.,De Sarkar, Suman,Froehlich, Roland,Grimme, Stefan,Studer, Armido
, p. 2177 - 2184 (2013/05/21)
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.
Sodium carbonate mediated regioselective synthesis of novel N-(hydroxyalkyl)cinnamamides Dedicated to Dr. Sunita Dhingra on her 65th birthday
Garg, Parul,Milton, Marilyn Daisy
supporting information, p. 7074 - 7077 (2013/12/04)
A synthetic protocol for the direct synthesis of N-(hydroxyalkyl) cinnamamides from cinnamates and aminoalcohols in the presence of sodium carbonate as the base is presented. A wide variety of N-(hydroxyalkyl) cinnamamides were isolated in up to 99% yield
Synthesis and antidepressant-like action of N-(2-hydroxyethyl) cinnamamide derivatives in mice
Deng, Xian-Qing,Wu, Di,Wei, Cheng-Xi,Quan, Zhe-Shan
, p. 1273 - 1279 (2012/05/20)
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.
