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.
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-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.
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.
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.
Vibrational, NMR and quantum chemical investigations of acetoacetanilde, 2-chloroacetoacetanilide and 2-methylacetoacetanilide
Arjunan,Kalaivani,Senthilkumari,Mohan
, p. 154 - 174 (2013)
The vibrational assignment and analysis of the fundamental modes of the compounds acetoacetanilide (AAA), 2-chloroacetoacetanilide (2CAAA) and 2-methylacetoacetanilide (2MAAA) have been performed. Density functional theory studies have been carried out with B3LYP method utilising 6-311++G ** and cc-pVTZ basis sets to determine structural, thermodynamic and vibrational characteristics of the compounds and also to understand the influence of chloro and methyl groups on the characteristic frequencies of amide (-CONH-) group. intramolecular hydrogen bond exists in acetoacetanilide and o-substituted acetoacetanilide molecules and the N?O distance is found to be around 2.7 ?. The 1H and 13C nuclear magnetic resonance chemical shifts of the molecules were determined and the same have been calculated using the gauge independent atomic orbital (GiAO) method. The energies of the frontier molecular orbitals have been determined. in AAA, 2CAAA and 2MAAA molecules, the nN → pπ*co Interaction between the nitrogen lone pair and the amide C=O antibonding orbital gives strong stabilization of 64.75, 62.84 and 64.18 kJ mol 1, respectively. The blue shift in amide-ii band of 2MAAA is observed by 45-50 cm1 than that of AAA. The steric effect of ortho methyl group significantly operating on the N-H bond properties. The amide-iii, the C-N stretching mode of methyl and chloro substituted aceto-acetanilide compounds are not affected by the substitution while the amide-V band, the N-H out of plane bending mode of 2-chloroacetoacetanilide compound is shifted to a higher frequency than that of AAA. The substituent chlorine plays significantly and the blue shift in o-substituted compounds than the parent in the amide-V vibration is observed. The amide-Vi, C=O out of plane bending modes of 2MAAA and 2CAAA are significantly raised than that of AAA. A blue shift of amide-Vi, C=O out of plane bending modes of 2MAAA and 2CAAA than AAA is observed.
Tandem annulation and 1,2-alkyl migration reactions of α-bromo-β-oxoamides and amines: Access to polysubstituted pyrrolin-4-ones
Wang, Yu,Zhang, Rui,Li, Jiacheng,Bhujanga Rao, Chitturi,Ye, Xuebei,Dong, Dewen
, (2022/03/17)
-
Nickel-promoted oxidative domino Csp3-H/N-H bond double-isocyanide insertion reaction to construct pyrrolin-2-ones
Wen, Li-Rong,Wang, Ning-Ning,Du, Wu-Bo,Ma, Qiang,Zhang, Lin-Bao,Li, Ming
supporting information, p. 2895 - 2900 (2021/04/14)
The first nickel-catalyzed oxidative domino Csp3-H/N-H double isocyanide insertion reaction of acetamides with isocyanides has been developed for the synthesis of pyrrolin-2-one derivatives. A wide range of acetamides bearing various functional groups are compatible with this reaction system by utilizing Ni(acac)2as a catalyst. In this transformation, isocyanide could serve as a C1 connector and insert into the inactive Csp3-H bond, representing an effective way to construct heterocycles.
Design, synthesis, and molecular docking study of new monastrol analogues as kinesin spindle protein inhibitors
El-Hamamsy, Mervat H.,Sharafeldin, Nabaweya A.,El-Moselhy, Tarek F.,Tawfik, Haytham O.
, (2020/06/03)
Lung, colorectal, and breast cancers are the top three types of cancer by incidence and are responsible for one-third of the cancer incidence and mortality. A series of 18 3,4-dihydropyrimidine analogues bearing a 1,2-methylenedioxybenzene component at position 4 with diverse side chains at positions 5 and 6 was designed and synthesized as inhibitors of the Eg5 kinesin enzyme. Target compounds were screened for their anticancer activity according to the NCI-USA protocol toward a panel of 60 cancer cell lines. Compounds 12a and 12b displayed the best antiproliferation activity against many cell lines. Interestingly, compound 12a displayed lethal effects against non-small-cell lung cancer NCI-H522 cells (?42.26%) and MDA-MB-468 breast cancer cells (?1.10%) at a single-dose assay concentration of 10?5 M. Compounds 11c, 11d, 11g, 12a–d, 13, 15, and 18a were assayed against the kinesin enzyme, with IC50 values ranging from 1.2 to 18.71 μM, which were more potent compared with monastrol (IC50 = 20 μM). Cell cycle analysis of NCI-H522 cells treated with compound 12a showed cell cycle arrest at the G2/M phase. Furthermore, the expression levels of active caspase-3 and -9 were measured. A molecular docking study was performed for some demonstrative compounds as well as monastrol docked into the allosteric binding site of the kinesin spindle protein.