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102-01-2Relevant articles and documents
Protective Effect of a Novel (2S, 3R, 4S)-Chromene-3-Carboxamide Derivative, Z20 Against Sepsis-Induced Organ Injury
Chen, Peng,Li, Na,Niu, Mengwei,Wang, Yong,Wang, Yuhang,Zeng, Liyan
, (2020)
Sepsis, a systemic inflammatory response mediated by excessive production of diverse inflammatory cytokines, remains the vital cause of morality in the intensive care unit (ICU). TLR4-MD2 (toll-like receptor 4-myeloid differentiation factor 2) complex activated by LPS serves as an effective target to decrease the inflammation during sepsis. In this study, we evaluated the effects of a new small molecule Z20 structural based on (2S, 3R, 4S)-chromene-3-carboxamide on LPS-induced sepsis in mice. We found Z20 markedly improved the survival rate and attenuated the multiply organs injury after LPS administration?in mice. In addition, Z20 significantly alleviated organ inflammation as characterized by diminished inflammatory factors expression in vivo. Furthermore, by employing surface plasmon resonance (SPR) experiment, we identified that TLR4-MD2 complex?was the potential target for Z20. Finally, we performed the safety assessment experiment to confirm the safety of Z20 in vivo. In conclusion, Z20, as a potential TLR4-MD2 inhibitor, effectively attenuated LPS-induced organ injury and inflammation.
Phenothiazine and amide-ornamented dihydropyridines: Via a molecular hybridization approach: Design, synthesis, biological evaluation and molecular docking studies
Sivaramakarthikeyan, Ramar,Iniyaval, Shunmugam,Padmavathy, Krishnaraj,Liew, Hui-Shan,Looi, Chin-King,Mai, Chun-Wai,Ramalingan, Chennan
, p. 17046 - 17057 (2019)
A series of novel phenothiazinyldihydropyridine dicarboxamides 7a-7j was synthesized by adopting a multi-step synthetic strategy and characterized through physical and spectral techniques. Among them, the chemical entities with para-fluoro (7d), ortho-bromo and-fluoro (7f and 7i), ortho- A nd para-methyl (7e) and meta- A nd para-methoxy (7h) substituents exhibited either similar or superior anti-inflammatory activities with respect to the standard drug diclofenac sodium. Besides, the chemical entities with ortho-bromo and-fluoro substituents as well as meta-nitro substituents (7f, 7g and 7i) showed enhanced radical scavenging activities when compared to standard ascorbic acid. Furthermore, anticancer studies revealed that the meta- A nd para-chloro-substituted molecule 7a exerted the best activity against all the pancreatic cancer cells tested. Also, appreciable binding affinity (-8.10 kcal mol-1) was observed during molecular docking between B-cell lymphoma 2 and 7a. The structural diversifications of the potent chemical entities besides further exploration in connection with the biological profiles of the same are underway.
Synthesis of heterocyclic systems with carbohydrate fragment: 2. Stereoselective synthesis of tetrahydropyridones by reaction of levoglucosenone with amides of α-methylene-active acids
Samet,Kislyi,Chernyshova,Reznikov,Ugrak,Semenov
, p. 393 - 398 (1996)
The reactions of levoglucosenone with amides of several α-nitrocarboxylic acids and acetoacetic acid result in tetrahydropyridones fused with a carbohydrate fragment. In the case of acetoacetic acid amides, mixtures of keto and enol tautomers were obtained. The stereochemistry of cyclization is discussed in detail.
A facile and selective procedure for transesterification of β-keto esters promoted by yttria-zirconia based lewis acid catalyst
Kumar, Pradeep,Kumar Pandey, Rajesh
, p. 251 - 253 (2000)
An yttria-zirconia based strong Lewis acid efficiently catalyses the transesterification of β-keto esters under environmentally safe, heterogeneous reaction conditions with high selectivity and in good to excellent yields.
Microwave induced acetoacetylation of hetaryl and aryl amines
Suri,Satti,Suri
, p. 3709 - 3718 (2000)
Acetoacetylation of hetaryl and aryl amines by interaction with ethyl acetoacetate under microwave irradiation, without any catalyst and/or solvent, is reported.
Microwave-promoted direct amidation of unactivated esters catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions
Fu, Renzhong,Yang, Yang,Ma, Yunsheng,Yang, Fei,Li, Jingjing,Chai, Wen,Wang, Quan,Yuan, Rongxin
, p. 4527 - 4531 (2015)
Abstract A simple and efficient procedure for the synthesis of amides directly from unactivated esters and amines catalyzed by heteropolyanion-based ionic liquids under microwave-promoted and solvent-free conditions has been reported. The practical protocol was found to be compatible with different structurally diverse substrates. Moderate to excellent yields, solvent-free media, and operational simplicity are the main highlights. Furthermore, the heteropolyanion-based ionic liquids were easily reusable for this amidation.
Vinyl polymerizations of norbornene catalyzed by nickel complexes with acetoacetamide ligands
Feng, Qian,Chen, Dajun,Feng, Danyang,Jiao, Libin,Peng, Zhigang,Pei, Lixia
, p. 32 - 37 (2014)
On the basis of a remote effect, a series of acetoacetamide ligands and corresponding nickel complexes N-(R-phenyl) acetoacetamide Ni(CH2Ph) (PMe3) (R = H, 1; R = 2-methyl, 2; R = 2,6-dimethyl, 3; R = 2,6-diisopropyl, 4; R = 4-NO2, 5) were synthesized and characterized. The solid structure of complex 3 was confirmed by X-ray single-crystal analysis to be of cis form. 1H and 31P NMR spectroscopy confirmed that cis and trans isomers of nickel complexes were present in solution. Norbornene polymerizations with acetoacetamide nickel complexes activated with modified methylaluminoxane (MMAO) were investigated in detail. Remote steric and electronic effects of acetoacetamide ligand on catalytic activity and molecular weight of polynorbornenes (PNBs) were observed. Characterizations of the obtained PNBs show that the obtained polymer products are non-crystalline vinylic-addition polynorbornenes. Copyright
Mild and high-yielding synthesis of β-keto esters and β-ketoamides
Sridharan, Vellaisamy,Ruiz, Miriam,Menendez, J. Carlos
, p. 1053 - 1057 (2010)
In the presence of sodium acetate, the reaction between 2,2,6-trimethyl-4H-1,3-dioxin-4-one and secondary or tertiary alcohols (including chiral ones) or primary or secondary amines could be carried out in refluxing tetrahydrofuran, under much milder conditions than those described in the literature. In these new conditions, side products normally observed using the traditional protocol were avoided, and-keto esters and-ketoamides were normally obtained in quantitative yields.
Phenothiazine and amide-ornamented novel nitrogen heterocyclic hybrids: synthesis, biological and molecular docking studies
Iniyaval, Shunmugam,Karuppasamy, Ayyanar,Lim, Wei-Meng,Mai, Chun-Wai,Padmavathy, Krishnaraj,Ramalingan, Chennan,Sivaramakarthikeyan, Ramar
, p. 4049 - 4060 (2020)
The synthesis of novel hybrids, namely, phenothiazine and amide-ornamented nitrogen heterocycles (25-34) has been accomplished utilizing a multi-step synthetic protocol and the structures have been established based on physical and spectral techniques. Of these, the hybrids possessing meta-nitro (26), para-fluoro (28), meta- and para-methyl (31), ortho-bromo (33) and ortho- and para-dimethyl (34) phenyl carboxamide scaffolds exhibited superior anti-inflammatory profiles over the standard diclofenac sodium. A hybrid integrated with a para-fluorophenyl carboxamide moiety (28) showed the highest DPPH radical scavenging activity among the chemical entities synthesized. Furthermore, the results of anticancer evaluations implied that the hybrid tethered with a phenyl carboxamide structural unit (29) exerted superior activity when compared with other hybrids against the pancreatic cancer cells SW1990 and AsPC1. Molecular docking between the hybrid 29 and B-cell lymphoma 2 reflects its appreciable binding affinity (-8.84 kcal mol-1). The results revealed that these chemical entities can serve as potent biological agents and/or efficient intermediates for the construction of potent biological agents.
Palladium-catalyzed tandem diperoxidation/C - H activation resulting in diperoxy-oxindole in air
An, Guanghui,Zhou, Wei,Zhang, Guangqian,Sun, Hao,Han, Jianlin,Pan, Yi
, p. 4482 - 4485 (2010)
A highly efficient and facile palladium-catalyzed tandem diperoxidation and C - H activation process was reported, which provides a new pathway for the synthesis of biologically active diperoxides as well as oxindole derivatives from readily available starting materials in excellent chemical yields.