- Mechanically induced solvent-free esterification method at room temperature
-
Herein, we describe two novel strategies for the synthesis of esters, as achieved under high-speed ball-milling (HSBM) conditions at room temperature. In the presence of I2 and KH2PO2, the reactions afford the desired esterification derivatives in 45% to 91% yields within 20 min of grinding. Meanwhile, using KI and P(OEt)3, esterification products can be obtained in 24% to 85% yields after 60 min of grinding. In addition, the I2/KH2PO2 protocol was successfully extended to the late-stage diversification of natural products showing the robustness of this useful approach. Further application of this method in the synthesis of inositol nicotinate was also discussed. This journal is
- Zheng, Lei,Sun, Chen,Xu, Wenhao,Dushkin, Alexandr V.,Polyakov, Nikolay,Su, Weike,Yu, Jingbo
-
p. 5080 - 5085
(2021/02/05)
-
- Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma
-
Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.
- Byrne, Andrew J.,Bright, Sandra A.,Fayne, Darren,McKeown, James P.,McCabe, Thomas,Twamley, Brendan,Williams, Clive,Meegan, Mary J.
-
p. 181 - 199
(2018/03/13)
-
- Rational design for multicolor flavone-based fluorophores with aggregation-induced emission enhancement characteristics and applications in mitochondria-imaging
-
Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted more attention in recent years. In order to realise more valuable applications, the different kinds of AIEE molecules are in serious need of further development. Therefore, a novel flavone-based AIEE system derived from restriction of intramolecular rotation (RIR) was designed and synthesized in this work. The results revealed that six of the compounds showed typical AIEE characteristics, with fluorescence emissions from purple, blue, cyan to green, tunable by changing substituent groups. This flavone-based AIEE system has never been reported before. The AIEE characteristics were investigated by optical spectroscopy, fluorescence photographs, scanning electron microscopy (SEM), fluorescence quantum yields (φF) and fluorescence lifetime in the CH3OH/H2O mixed solution. Moreover, benefiting from the simple structures and small molecular weight, they could permeate cells faster than current high-molecular-weight AIEE molecules. Furthermore, to examine possible biomedical applications, fluorescence imaging in living A549 lung cells and cell viabilities were examined, and the results displayed that these fluorophores showed good cellular uptake and low cytotoxicity within the experimental concentration range. In addition, these AIEE compounds possessed excellent specificity for mitochondrial targeting and mitochondrial morphological change tracking, besides, they displayed superior photostability, which indicated they are potential candidates for mitochondrial imaging.
- Liu, Liyan,Lei, Yaohui,Zhang, Jianhui,Li, Na,Zhang, Fan,Wang, Huaqiao,He, Feng
-
-
- Suppression of PGE2 production via disruption of MAPK phosphorylation by unsymmetrical dicarbonyl curcumin derivatives
-
Curcumin is an important molecule found in turmeric plants and has been reported to exhibit some profound anti-inflammatory activities by interacting with several important molecular targets found in the mitogen-activated protein kinase and NF-κβ pathways. As part of our continuing effort to search for new anti-inflammatory agents with better in vitro and in vivo efficacies, we have synthesized a series of new unsymmetrical dicarbonyl curcumin derivatives and tested their effects on prostaglandin E2 secretion level in interferon-γ/lipopolysaccharide-activated macrophage cells. Among those, five compounds exhibited remarkable suppression on prostaglandin E2 production with IC50 values ranging from 0.87 to 18.41 μM. The most potent compound 17f was found to down-regulate the expression of cyclooxygenase-2 mRNA suggesting that this series of compounds could possibly target the mitogen-activated protein kinase signal transduction pathway. Whilst the compound did not affect the expression of the conventional mitogen-activated protein kinases, the results suggest that it could disrupt the phosphorylation and activation of the proteins particularly the c-Jun N-terminal kinases. Finally, the binding interactions were examined using the molecular docking and dynamics simulation approaches.
- Mohd Aluwi, Mohd Fadhlizil Fasihi,Rullah, Kamal,Haque, Md. Areeful,Yamin, Bohari M.,Ahmad, Waqas,Amjad, Muhammad Wahab,Leong, Sze Wei,Fahmizar, Nurul Amira,Jalil, Juriyati,Abas, Faridah,Ismail, Nor Hadiani,Jantan, Ibrahim,Lam, Kok Wai
-
p. 3323 - 3335
(2017/10/06)
-
- A 7 - methoxy flavone preparation method (by machine translation)
-
The invention discloses a 7 - methoxy flavone preparation method, which belongs to the field of chemical synthesis, the method comprising: in order to Paeonia suffruticosa Andr. (tree peony bark) phenol and benzoyl chloride as the raw material, in the presence of triethylamine base to carry out the esterification reaction, the reaction mixture after the reaction is finished by carrying out simple suction filtering to eliminate triethylamine hydrochloride, potassium tertiary butanol filtrate directly the reaction at room temperature, after the reaction is finished adding dibutyl tin oxide and to the reaction mixture liquid to heating reflux dehydration, to obtain 7 - methoxy flavone. The technical route has the route is short, simple and convenient operation, pollution-free, the dehydrating agent can be used in circulation, and easy for industrial production characteristics, is a very economic, simple preparation of 7 - methoxy flavone method. (by machine translation)
- -
-
Paragraph 0030; 0031
(2017/02/02)
-
- Copper-catalyzed oxidative C-O bond formation of 2-acyl phenols and 1,3-dicarbonyl compounds with ethers: Direct access to phenol esters and enol esters
-
A copper-catalyzed oxidative coupling of 2-carbonyl-substituted phenols and 1,3-dicarbonyl compounds with a wide range of dibenzyl or dialkyl ethers is described. This protocol provides an efficient preparation of phenol esters and enol esters in good yields with high chemoselectivity. This method represents an alternative protocol for classical esterification reactions.
- Park, Jihye,Han, Sang Hoon,Sharma, Satyasheel,Han, Sangil,Shin, Youngmi,Mishra, Neeraj Kumar,Kwak, Jong Hwan,Lee, Cheong Hoon,Lee, Jeongmi,Kim, In Su
-
p. 4735 - 4742
(2014/06/09)
-
- Cu(II)-catalyzed oxidative esterification of 2-carbonyl substituted phenols from the alcohol oxidation level
-
A copper-catalyzed oxidative esterification of 2-carbonyl substituted phenols from the alcohol oxidation level is described. This protocol represents direct access to a range of 2-carbonylated aryl benzoate derivatives, which are important building blocks in the synthesis of natural and pharmacological compounds.
- Sharma, Satyasheel,Park, Jihye,Kim, Mirim,Kwak, Jong Hwan,Jung, Young Hoon,Kim, In Su
-
p. 9391 - 9397
(2013/10/08)
-
- Assessment of antiplatelet activity of 2-aminopyrimidines
-
A series of 4,6-diaryl-2-aminopyrimidines was developed as antiplatelet agents and their potency was evaluated by in vitro assay. Compound 14k was found to be two times more potent than aspirin. These encouraging results could be helpful for the development of new antiplatelet compounds.
- Giridhar, Rajani,Tamboli, Riyaj S.,Ramajayam,Prajapati, Dhaval G.,Yadav
-
scheme or table
p. 428 - 432
(2012/07/03)
-
- A new synthesis of flavones and pyranoflavone by intramolecular photochemical Wittig reaction in water
-
A new synthetic approach toward the synthesis of flavones and pyranoflavone has been developed by light induced intramolecular photochemical Wittig reaction in water onto aryloxycarbonyl groups and suitably substituted phosphonium bromides sans any phase transfer catalyst or promoter.
- Das, Jhantu,Ghosh, Somnath
-
supporting information; experimental part
p. 7189 - 7194
(2012/01/05)
-
- Design and synthesis of 3,5-diarylisoxazole derivatives as novel class of anti-hyperglycemic and lipid lowering agents
-
We have designed 1,3-disubstituted-5-membered heteroaromatic ring system as a common core motif from known anti-hyperglycemic agents. Designed compounds were synthesized and screened for in vivo anti-hyperglycemic activity in sucrose loaded model (SLM), sucrose-challenged streptozotocin-induced diabetic rat model (STZ-S) as well as db/db mice model. Some of the synthesized compounds showed promising in vivo anti-hyperglycemic as well as moderate lipid lowering activity. Synthesized Compounds were screened in various in vitro models of type-2 diabeties such as DPP-4, PTP1B and PPARγ to know the mechanism of their anti-hyperglycemic action. None of the synthesized compounds showed DPP-4 inhibitory as well as PPARγ activity. These compounds have shown promising PTP-1B inhibitory activity there by revealing that compounds exhibit anti-diabetic activity by PTP1B pathway.
- Kumar, Atul,Maurya, Ram Awatar,Sharma, Siddharth,Ahmad, Pervez,Singh,Tamrakar,Srivastava, Arvind K.
-
experimental part
p. 5285 - 5292
(2009/12/09)
-
- New synthesis of 3-bromoflavones via bromination of 1-(2-hydroxyphenyl)-3- arylpropane-1,3-dione by CuBr2, and conversion into 3-aminoflavones
-
A new synthesis of 3-bromoflavones from 1-(2-hydroxyphenyl)-3-arylpropane- 1,3-dione using CuBr2 is described. The usefulness of 3-bromoflavone as a precursor of 3-aminoflavone is also described. Copyright
- Miyake, Hideyoshi,Nishino, Shouko,Nishimura, Akinori,Sasaki, Mitsura
-
p. 522 - 523
(2008/02/10)
-
- A new metal complex promoted system for highly selective synthesis of 4H-chromen-4-ones (chromones)
-
Co(III)(salpr)(OH), a six coordinate cobalt Schiff base complex, promotes the highly selective conversion of 1-(o-hydroxyaryl)-1,3-diketones to 4H-chromen-4-ones under neutral conditions.
- Nishinaga,Ando,Maruyama,Mashino
-
p. 839 - 841
(2007/10/02)
-
- Synthesis of 2'-hydroxychalcone epoxides
-
Various preparations of some 2'-tetrahydropyran-2-yloxychalcone epoxides and removal of their tetrahydropyranyl (THP) protective groups in slightly aqueous acidic dioxane are described. So synthesised were 2'-hydroxy-6'-isopropoxy- and 2'-hydroxy-6'-methoxychalcone epoxide, as well as the 2-CF3, 4-Cl and 4-NO2 analogues of the latter. 2',4'-dihydroxy-6'-methoxychalcone epoxide was similarly prepared. In some other 6'-methoxy cases protective group removal was accompanied by epoxide solvolysis and the corresponding α,β-dihydroxydihydrochalcone was the only isolable product [2-OMe, 4-OMe, 3,4,5-(OMe)3 cases] or a byproduct [4-Me case]. Similarly prepared by THP removal were 2'-hydroxy-4'-methoxychalcone epoxide and 2',4'-dihydroxychalcone epoxide, whereas an attempt to convert 2',6'-ditetrahydropyranyloxychalcone epoxide into 2',6'-dihydroxychalcone epoxide gave the product of cyclisation of the latter, 3,5-dihydroxyflavanone.
- Adams,Main
-
p. 4959 - 4978
(2007/10/05)
-
- Epoxidation of Flavones by Dimethyldioxirane
-
The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported.These labile epoxides were isolated and completely characterized by UV, IR, 1H and 13C NMR, MS, and C,H analyses.Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n.Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f, as a mixture of cis and trans isomers.
- Adam, Waldemar,Golsch, Dieter,Hadjiarapoglou, Lazaros
-
p. 7292 - 7297
(2007/10/02)
-
- Structural Studies on Bio-active Compounds. Part 12. Tautomerism and Conformation of Aryl-substituted 1-(2-Hydroxyphenyl)-3-phenylpropane-1,3-diones in the Solid Phase and in Solution
-
The tautomerism of a series of aryl-substituted 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-diones has been studied in deuteriochloroform solution by 1H n.m.r. techniques and, in the case of 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione and 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione, in the solid state by X-ray crystallography.Of these compounds, most exist between 80 and 95percent in the enolised form in solution and 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione adopts this tautomer in the crystal.However, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione is present as the diketone in the solid phase and enolises very slowly in solution. 1-(6-Benzoyloxy-2-hydroxyphenyl)-3-hydroxy-3-phenylprop-2-en-1-one is shown by 1H n.m.r. spectroscopy possibly to adopt a 'coiled' conformation in solution in deuteriochloroform.
- Cunningham, Bernadette D. M.,Lowe, Philip R.,Threadgill, Michael D.
-
p. 1275 - 1284
(2007/10/02)
-