114657-35-1Relevant academic research and scientific papers
Synthesis of tetracyclic oxindoles and evaluation of their α-glucosidase inhibitory and glucose consumption-promoting activity
Dodd, Robert H.,Hao, Lei,Ma, Ying,Ma, Yujiao,Sun, Hua,Yu, Peng,Zhang, Xinying,Zhang, Yinan,Zhao, Lianbo
, (2020)
A series of tetracyclic oxindole derivatives was synthesized by asymmetric 1, 3-dipole reaction in 2–4 steps in 57–86% overall yields. These compounds were evaluated for α-glucosidase inhibitory and glucose consumption-promoting activity in vitro. Compound 4l competitively and reversibly inhibited α-glucosidase (IC50 = 3.64 μM) with activity 14-fold higher than that of acarbose. Docking analysis substantiated these findings. In addition, compound 4l exhibited significant glucose consumption promoting activity at 1 μM.
Synthesis and Cytotoxicity of Diarylpentanoids against Sensitive CCRF-CEM and Multidrug-Resistant CEM/ADR5000 Leukemia Cells
Di Chio, Carla,Efferth, Thomas,Ettari, Roberta,Schirmeister, Tanja,Zhou, Min,Zappalà, Maria
, (2022/01/04)
This article described the synthesis and biological investigation of a series of symmetric diarylpentanoids, characterized by a dienone moiety and by a different pattern of substitution on the two phenyl rings. The series of compounds 1a–p were tested aga
Base-catalyzed cross coupling of secondary alcohols and aryl-aldehydes with concomitant oxidation of alcohols to ketones: An alternative route for synthesis of the Claisen-Schmidt condensation products
Satrawala, Naveen,Sharma, Kamal N.,Matsinha, Leah C.,Maqeda, Latisa,Siangwata, Shepherd,Smith, Gregory S.,Joshi, Raj K.
supporting information, p. 2761 - 2764 (2017/06/23)
Base-catalyzed C–C cross coupling of secondary alcohols and aryl-aldehydes was achieved, when an alcoholic solution of an aryl-aldehyde was stirred under reflux for 45?h in the presence of a catalytic (20?mol%) amount of K2CO3. The consistent formation of α,α′-bis-(benzylidene) alkanones was obtained in moderate to good yields using various secondary alcohols and substituted aryl-aldehydes. Herein, α,α′-bis-(benzylidene)alkanones, which are the classical products of Claisen-Schmidt (cross aldol) condensation, have been synthesized via an alternative strategy using secondary alcohols. Bis-(benzylidene) alkanones are an integral part of various drug regimes and the production of bis-(benzylidene) alkanones without using any precious metal is a major outcome of the present reaction.
Mechanistically Inspired Route toward Hexahydro-2H-chromenes via Consecutive [4 + 2] Cycloadditions
Ashtekar, Kumar Dilip,Ding, Xinliang,Toma, Edmond,Sheng, Wei,Gholami, Hadi,Rahn, Christopher,Reed, Paul,Borhan, Babak
supporting information, p. 3976 - 3979 (2016/08/30)
Utilizing two robust C-C bond-forming reactions, the Baylis-Hillman reaction and the Diels-Alder reaction, we report a highly enantio-, regio-, and diastereoselective synthesis of hexahydro-2H-chromenes via two sequential [4 + 2] cycloadditions. These tandem and formal cycloadditions have also been performed as a "one-pot" sequence to access the corresponding heterocycles constituting up to five contiguous stereocenters in excellent yields and stereoselectivity.
Design, synthesis, and antiproliferative activity assessment of non-ATP-competitive fibroblast growth factor receptor 1 inhibitors
Ying,Wang, Jia,Xu,Kang,Zhang,Shi,Fan,Wang,Zhou,Wu,Wu,Li,Liang
, p. 2744 - 2751 (2017/03/22)
Fibroblast growth factor receptor 1 (FGFR1) is considered a therapeutic target for multiple cancers, including gastric cancer. FGFR1 inhibitors, being ATP competitors, can prevent the kinase domain and the downstream signaling cascade from phosphorylation
Tandem hydrogenation and condensation of fluorinated α,β-unsaturated ketones with primary amines, catalyzed by nickel
Castellanos-Blanco, Nahury,Flores-Alamo, Marcos,García, Juventino J.
supporting information, p. 15653 - 15663 (2015/09/07)
A simple homogeneous catalytic system based on nickel phosphine complexes has been developed for the transfer hydrogenation and condensation of α,β-unsaturated ketones to yield saturated ones and saturated imines using primary amines as hydrogen donors. Thus, a wide range of fluorinated 1,5-diaryl-1,4-pentadiene-3-ones were allowed to react with substituted benzylamines in the presence of [(dippe)Ni(μ-H)]2 (dippe = 1,2-bis-(diisopropylphosphino)-ethane) using ethanol as a solvent at 180 °C to give the corresponding saturated carbonyl compounds; here hydrogenation of the CC bond was preferred over the CO bond. Under the same reaction conditions but using an excess of benzylamine, a tandem process is then favoured, starting also with the reduction of the CC bond followed by a nucleophilic addition of the primary amine to yield valuable saturated imines with good to excellent yields (62%-91%).
Synthesis of novel curcumin analogues for inhibition of 11β-hydroxysteroid dehydrogenase type 1 with anti-diabetic properties
Yuan, Xiaohuan,Li, Hongzhi,Bai, He,Su, Zhijian,Xiang, Qi,Wang, Chaonan,Zhao, Binghai,Zhang, Yufei,Zhang, Qihao,Chu, Yanhui,Huang, Yadong
, p. 223 - 230 (2014/04/03)
In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which is responsible for the pharmacokinetic limitation of curcumin. We demonstrated that 4 of 9 curcumin an
Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors
Lin, Han,Hu, Guo-Xin,Guo, Jingjing,Ge, Yufei,Liang, Guang,Lian, Qing-Quan,Chu, Yanhui,Yuan, Xiaohuan,Huang, Ping,Ge, Ren-Shan
, p. 4362 - 4366 (2013/07/25)
A series of structurally novel mono-carbonyl curcumin analogues have been synthesized and biologically evaluated to test their inhibitory potencies and the structure-activity relationship (SAR) on human and rat 11β- hydroxysteroid dehydrogenase isoform (11β-HSD1) activities. 11β-HSD1 selective inhibitors have been discovered and compound A10 is discovered as a very potent with an IC50 value of 97 nM without inhibiting 11β-HSD2.
A novel monocarbonyl analogue of curcumin, (1E,4E)-1,5-Bis (2,3-dimethoxyphenyl)penta-1,4-dien-3-one, induced cancer cell H460 apoptosis via activation of endoplasmic reticulum stress signaling pathway
Wang, Yi,Xiao, Jian,Zhou, Huiping,Yang, Shulin,Wu, Xiaoping,Jiang, Chengxi,Zhao, Yunjie,Liang, Donglou,Li, Xiaokun,Liang, Guang
experimental part, p. 3768 - 3778 (2011/08/08)
Endoplasmic reticulum (ER) stress-induced cancer cell apoptosis has become a novel signaling target for development of cancer therapeutic drugs. Curcumin exhibits growth-suppressive activity against a variety of cancer cells. We previously synthesized a s
Synthesis and anti-bacterial properties of mono-carbonyl analogues of curcumin
Liang, Guang,Yang, Shulin,Jiang, Lijuan,Zhao, Yu,Shao, Lili,Xiao, Jian,Ye, Faqing,Li, Yueru,Li, Xiaokun
, p. 162 - 167 (2008/09/19)
The synthesis of three series of curcumin analogues with mono-carbonyl is described. Their in vitro antibacterial activities against seven Gram-positive and Gram-negative bacteria were tested and the effect of substituents on the aryl ring and the space structure of the linking strain were discussed. It was observed that part of the derivatives displayed significant activity when compared with curcumin and most of them exhibited activity against the ampicillin-resisted Enterobacter cloacae. Compounds A12, B09, B13, B14 and C09 show remarkable antibacterial activity in vitro. The result showed that heterocycle or long-chain substituents may enhance the activity of curcumin analogues.
