5465-06-5Relevant academic research and scientific papers
Flavonoid analogues as urease inhibitors: Synthesis, biological evaluation, molecular docking studies and in-silico ADME evaluation
Liu, Honghui,Wang, Yan,Lv, Mingxia,Luo, Yi,Liu, Bu-Ming,Huang, Yan,Wang, Mian,Wang, Jianyi
, (2020/10/23)
A series of novel flavonoid analogues were designed and synthesized. The aimed compounds for urease inhibitory activities were clearly superior to the control drug thiourea (more than 10 times). Among these compounds, L2 (IC50 = 1.343 μM) and L12 (IC50 = 1.207 μM) exhibited the most excellent urease inhibitory activity in vitro. The molecular dockings of L2, L12 and L22 into urease were performed to explore the binding modes and their structure-activity relationship. Furthermore, these aimed compounds showed good druggable properties.
Synthesis and biological evaluation of flavone-8-acrylamide derivatives as potential multi-target-directed anti Alzheimer agents and investigation of binding mechanism with acetylcholinesterase
Shaik, Jeelan Basha,Yeggoni, Daniel Pushparaju,Kandrakonda, Yelamanda Rao,Penumala, Mohan,Zinka, Raveendra Babu,Kotapati, Kasi Viswanath,Darla, Mark Manidhar,Ampasala, Dinakara Rao,Subramanyam, Rajagopal,Amooru, Damu Gangaiah
, (2019/05/17)
In a search for novel multifunctional anti-Alzheimer agents, a congeneric set of seventeen flavone-8-acrylamide derivatives (8a─q)were synthesized and evaluated for their cholinesterase inhibitory, antioxidant, neuroprotective and modulation of Aβ aggregation activities. The target compounds showed effective and selective inhibitory activity against the AChE over BuChE. In addition, the target compounds also showed moderate anti-oxidant activity and strong neuroprotective capacities, and accelerated dosage-dependently the Aβ aggregation. Also, we presented here a complete study on the interaction of 8a, 8d, 8e, 8h and 8i with AChE. Through fluorescence emission studies, the binding sites number found to be 1, binding constants were calculated as 2.04 × 104, 2.22 × 104, 1.18 × 104, 9.8 × 103 and 3.2 × 104 M?1 and free energy change as ?5.83, ?5.91, ?5.51, ?5.41 and ?6.12 kcal M?1 at 25 °C which were well agreed with the computational calculations indicating a strong binding affinity of flavones and AChE. Furthermore, the CD studies revealed that the secondary structure of AChE became partly unfolded upon binding with 8a, 8d, 8e, 8h and 8i.
New Flavone-Cyanoacetamide Hybrids with a Combination of Cholinergic, Antioxidant, Modulation of β-Amyloid Aggregation, and Neuroprotection Properties as Innovative Multifunctional Therapeutic Candidates for Alzheimer's Disease and Unraveling Their Mechanism of Action with Acetylcholinesterase
Basha, Shaik Jeelan,Mohan, Penumala,Yeggoni, Daniel Pushparaju,Babu, Zinka Raveendra,Kumar, Palaka Bhagath,Rao, Ampasala Dinakara,Subramanyam, Rajagopal,Damu, Amooru Gangaiah
, p. 2206 - 2223 (2018/05/23)
In line with the modern multi-target-directed ligand paradigm of Alzheimer's disease (AD), a series of 19 compounds composed of flavone and cyanoacetamide groups have been synthesized and evaluated as multifunctional agents against AD. Biological evaluation demonstrated that compounds 7j, 7n, 7o, 7r, and 7s exhibited excellent inhibitory potency (AChE, IC50 of 0.271 ± 0.012 to 1.006 ± 0.075 μM) and good selectivity toward acetylcholinesterase, significant antioxidant activity, good modulation effects on self-induced Aβ aggregation, low cytotoxicity, and neuroprotection in human neuroblastoma SK-N-SH cells. Further, an inclusive study on the interaction of 7j, 7n, 7o, 7r, and 7s with AChE at physiological pH 7.2 using fluorescence, circular dichroism, and molecular docking methods suggested that these derivatives bind strongly to the peripheral anionic site of AChE mostly through hydrophobic interactions. Overall, the multifunctional profiles and strong AChE binding affinity highlight these compounds as promising prototypes for further pursuit of innovative multifunctional drugs for AD.
An Efficient One-Pot Synthesis and Anticancer Activity of 4'-Substituted Flavonoids
Wang,Liu,Zhang
, p. 1036 - 1041 (2018/07/06)
A number of 4'-substituted (R = H, Me, Cl, F) flavone derivatives is synthesized from 2-hydroxyacetophenones using the modified Baker–Venkataraman reaction. Compound [3-(4-fluorobenzoyl)-5- hydroxy-4'-fluoroflavone] was synthesized for the first time with the yield of 12%. Antiproliferative assays indicate that the synthesized flavones with F substituent at the 4' position demonstrate higher activity than the other flavone derivatives, particularly against HeLa and MCF-7 with the IC50 9.5 and 2.7 μM, respectively.
Synthesis and biological evaluation of Complex I inhibitor R419 and its derivatives as anticancer agents in HepG2 cells
Huang, Yaping,Sun, Geng,Wang, Pengfei,Shi, Rui,Zhang, Yanchun,Wen, Xiaoan,Sun, Hongbin,Chen, Caiping
supporting information, p. 2957 - 2960 (2018/07/21)
In this study, Complex I inhibitor R419 was firstly revealed to have significant anticancer activity against HepG2 cells (IC50 = 5.2 ± 0.9 μM). Based on this finding, a series of R419 derivatives were synthesized and biologically evaluated. As results, 9 derivatives were found to have obvious anticancer activity. Among them, H20 exhibited the most potent activity (IC50 = 2.8 ± 0.4 μM). Mechanism study revealed that H20 caused severe depletion of cellular ATP, dose-dependently activated AMPK, decreased Bcl-2/Bax ratio and induced necrotic cell death. Most importantly, H20 displayed definite inhibitory activity against Complex I.
Crystal structure and luminescence properties of 4-(4-benzoyloxy-2- hydroxyphenyl)-2,2-difluoro-6-phenyl-1,3,2-dioxaborine
Bukvetskii,Fedorenko,Mirochnik
, p. 1991 - 1998 (2014/07/07)
The crystal structure of 4-(4-benzoyloxy-2-hydroxyphenyl)-2,2- difluoro6phenyl-1,3,2-dioxaborine (1) was determined by X-ray diffraction analysis. π-π-Stacking interaction between the molecules results in joining the molecules into a threedimensional laye
Design, synthesis and biological evaluation of new arylpiperazine derivatives bearing a flavone moiety as α1-adrenoceptor antagonists
Jin, Jing,Wang, Xiao-Bing,Kong, Ling-Yi
scheme or table, p. 909 - 911 (2011/03/20)
Elaborate study on the three-dimensional model of α1- adrenoceptor (α1-AR) antagonists led to the development of a series of new arylpiperazine derivatives bearing a flavone nucleus as α1-AR antagonists. The in vitro activities were evaluated and compounds 1, 4, 10, 13 and 15 showed activities close to the reference compound (Prazosin).
Synthesis of flavonoid 7-O-β-D-glycosides by phase transfer catalysis
Wu, Zheng,Jiang, Ling,Chen, He,Wang, Qiu-An
experimental part, p. 195 - 197 (2009/11/30)
Six flavonoid 7-O-β-D-glycosides 1a-3a and 1b-3b were synthesised from the flavones 7a and 7b by glycosidation and deacetylation with the corresponding a-acetylglycosyl bromides. 7a and 7b were prepared in high yield by an improved Baker-Venkataraman rearrangement using 2, 4- dihydro×yacetophenone as starting material and tetrabutylammonium bromide (TBAB) as a phase transfer catalyst. The glycosidation procedure was modified by using anhydrous K2CO3 in a solvent mixture of DMF/acetone (3:2v/v) and TBAB as a phase transfer catalyst.
Facile synthesis of 7-methoxy-2-aryl-3-phenyl/or-H-8-[2-(4,6-dimethyl-3,5- dicarbethoxy-pyridyl)]-4H-1-benzopyran-4-ones
Soni, Anil Kumar,Krupadanam, G. L. David,Srimannarayana
, p. 795 - 804 (2007/10/03)
Condensation of 8-formyl-7-methoxy-2-phenyl-4H-1-benzopyran-4-ones (5a-f) with ethyl-3-aminocrotonate (6) in glacial acetic acid under Hantzsch conditions afforded 7-methoxy-2-aryl-3-phenyl/or-H-8-[2-(4,6-dimethyl-3,5-dicarbethoxy- pyridyl)]-4H-1-benzopyran-4-ones (7a-f) in good yields. Copyright Taylor & Francis Group, LLC.
