670-80-4Relevant articles and documents
Design, synthesis, and evaluation of semi-conservative mono-carbonyl analogs of curcumin as anti-inflammatory agents against lipopolysaccharide-induced acute lung injury
Dong, Lili,Zheng, Suqing,Zhang, Yali,Jiang, Xin,Wu, Jianzhang,Zhang, Xiaoqin,Shan, Xiaoou,Liang, Dandan,Ying, Shilong,Feng, Jianpeng,Liang, Guang
, p. 1544 - 1553 (2015)
Acute lung injury (ALI), one of a few severe diseases with high mortality, cannot be tackled by any effective therapies so far. Pro-inflammatory cytokines play an essential role in the pathogenesis of ALI. In order to discover novel anti-inflammatory agents against ALI, 37 semi-conservative mono-carbonyl analogs of curcumin (ScMACs) were designed, synthesized and screened for anti-inflammatory activities. The majority of these compounds exhibited remarkable inhibition of the expression of inflammatory cytokines in LPS-stimulated macrophages. Among them, compounds 6, 7, 10 and 18, efficiently inhibited the secretion of TNF-α and IL-6 in a dose-dependent manner. The most potent analog, compound 6, prevented the LPS-induced elevation of inflammatory gene expression, and alleviated the lung inflammatory cell infiltration and histopathological changes in vivo. Therefore, compound 6 is a potential lead for developing new anti-inflammatory candidate drugs against LPS-induced ALI.
Thermal [2 + 2] cycloaddition of morpholinoenamines with C60 via a single electron transfer
Mikie, Tsubasa,Asahara, Haruyasu,Nagao, Kazuaki,Ikuma, Naohiko,Kokubo, Ken,Oshima, Takumi
, p. 4244 - 4247 (2011)
The thermal reaction of C60 with five- and six-membered morpholinocycloalkenes in refluxing toluene exclusively gave the [2 + 2] cycloadducts in high yields. However, a seven-membered homologue sluggishly reacted with C60 because of the increasing steric hindrance. This cycloaddition reaction is likely to proceed via a single electron transfer (SET), a radical-coupling, and subsequent ion cyclization rather than the prior proton transfer between the radical ions.
Reaction of enamines with semicarbazone-based amidoalkylating reagents: A straightforward synthesis of annulated 1-aminopyrimidin-2-one derivatives
Fesenko, Anastasia A.,Shutalev, Anatoly D.
, (2021)
An efficient synthesis of 1-arylideneamino-substituted hexahydro-1H-cyclopenta[d]pyrimidin-2-ones and octahydroquinazolin-2-ones has been developed. The synthesis involves a stereo- and regioselective cascade reaction of the corresponding 4-(tosylmethyl)semicarbazones with 1-morpholinocyclopentene or 1-morpholinocyclohexene to give predominantly bicyclic pyrimidines with an exocyclic C[dbnd]C double bond (80–97%). The later undergo rapid isomerization when heated in THF in the presence of TsOH to form bicyclic pyrimidines with a significant predominance of those with an endocyclic C[dbnd]C double bond (90–97%).
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Dutt,Samyal
, p. 651 (1972)
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A newly designed curcumin analog Y20 mitigates cardiac injury via anti-inflammatory and anti-oxidant actions in obese rats
Qian, Yuanyuan,Zhong, Peng,Liang, Dandan,Xu, Zheng,Skibba, Melissa,Zeng, Chunlai,Li, Xiaokun,Wei, Tiemin,Wu, Lianpin,Liang, Guang
, (2015)
Obesity is strongly associated with the cause of structural and functional changes of the heart in both human and animal models. Oxidative stress and inflammation play a critical role in the development of obesity-induced cardiac disorders. Curcumin is a natural product from Curcuma Longa with multiple bioactivities. In our previous study, in order to reach better anti-inflammatory and anti-oxidant dual activities, we designed a new mono-carbonyl curcumin analog, Y20, via the structural modification with both trifluoromethyl and bromine. This study was designed to investigate the protective effects of Y20 on obesity-induced cardiac injury and its underlying mechanisms. In high fat diet-fed rats, oral administration of Y20 at 20 mg/kg or curcumin at 50 mg/kg significantly decreased the cardiac inflammation and oxidative stress and eventually improved the cardiac remodeling by mitigating cardiac disorganization, hypertrophy, fibrosis and apoptosis. Y20 at 20 mg/kg showed comparable and even stronger bioactivities than curcumin at 50 mg/kg. The beneficial actions of Y20 are closely associated with its ability to increase Nrf2 expression and inhibit NF-κB activation. Taken together, these results suggest that Y20 may have a great therapeutic potential in the treatment of obesity-induced cardiac injury using Nrf2 and NF-κB as the therapeutic targets for treating obesity-related disorders.
Three-Step One-Pot Process of 3-Methyl-5-Benzofuranol from Amine, Aldehydes, and p-Benzoquinone
Liang, Chaoming,Sun, Maolin,Shen, Xinyuan,Shan, Chao,Wang, Weijuan,Cheng, Ruihua,Ye, Jinxing
, p. 810 - 816 (2021/04/05)
3-Methyl-5-benzofuranol was prepared by a one-pot process from morpholine, propionaldehyde, and p-benzoquinone in 85-87% isolated yields. Avoiding the tedious multistep isolation and purification operations, this practical and efficient process dramatically enhanced the production efficiency as well as reduced the amount of chemical wastes of reaction. The scale-up results showed that the performance was maintained, suggesting potential large-scale applications. Furthermore, the synthesis strategy showed high efficiency for a wide range of aliphatic aldehydes and ketone derivatives.
Discovery of quinolone derivatives as antimycobacterial agents
Gao, Chao,Li, Xiao,Liu, Kun-Lin,Teng, Fei,Xiong, Lu,Yu, Luo-Ting
, p. 24095 - 24115 (2021/07/29)
Tuberculosis (TB), an infectious disease caused byMycobacterium tuberculosis(M. tuberculosis), is an important public health issue. Current first-line drugs administered to TB patients have been in use for over 40 years, whereas second-line drugs display strong side effects and poor compliance. Additionally, designing effective regimens to treat patients infected with multi- and extremely-drug-resistant (MDR and XDR) strains of TB is challenging. In this report, we screened our compound library and identified compound1with antituberculosis activity and a minimal inhibitory concentration (MIC) againstM. tuberculosisof 20 μg mL?1. Structure optimization and the structure-activity relationship of1as the lead compound enabled the design and synthesis of a series of quinolone derivatives,6a1-6a2,6b1-6b36,6c1,6d1-6d14,7a1-7a2,7b1-7b2,7c1,8a1-8a5,9a1-9a4and10a1-10a6. These compounds were evaluatedin vitrofor anti-tubercular activity against theM. tuberculosisH37Rv strain. Among them, compounds6b6,6b12and6b21exhibited MIC values in the range of 1.2-3 μg mL?1and showed excellent activity against the tested MDR-TB strain (MIC: 3, 2.9 and 0.9 μg mL?1, respectively). All three compounds were non-toxic toward A549 and Vero cells (>100 and >50 μg mL?1, respectively). In addition, an antibacterial spectrum test carried out using compound6b21showed that this compound specifically inhibitsM. tuberculosis. These can serve as a new starting point for the development of anti-TB agents with therapeutic potential.
