- A selective fluorescent sensor for Pb(II) in water
-
A new fluorescent sensor (1) containing bis(2-pyridylmethyl)amine group as a binding moiety for Pb2+ was developed. Compound 1 shows selective response to Pb2+ over other metal ions in pH 7.0 HEPES buffer solution. The fluorescence i
- Wu, Fang-Ying,Bae, Se Won,Hong, Jong-In
-
-
Read Online
- Discovery of novel 3-(hydroxyalkoxy)-2-alkylchromen-4-one analogs as interleukin-5 inhibitors
-
A series of novel chromen-4-one analogs 9a-d and 10a-u was designed, synthesized and evaluated for their IL-5 inhibitory activity. Most of the chromen-4-one analogs showed strong inhibitory activity in low micro molar potency. Among them, 5-(cyclohexylmet
- Boggu, Pulla Reddy,Venkateswararao, Eeda,Manickam, Manoj,Kim, Youngsoo,Jung, Sang-Hun
-
-
Read Online
- NaI-mediated oxidative amidation of benzyl alcohols/aromatic aldehydes to benzamides via electrochemical reaction
-
In this research, we have developed a mild electrochemical process for oxidative amidation of benzyl alcohols/aromatic aldehydes with cyclic amines into the corresponding benzamides. This electroorganic synthetic method proceeds using NaI as a redox mediator under ambient temperature in undivided cell, providing more than 25 examples of amide products in moderate to good yields. The benefits of this reaction include one-pot synthesis, open air condition, proceed in aqueous media and no requirement of external conducting salt, base and oxidant.
- Rerkrachaneekorn, Tanawat,Tankam, Theeranon,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
-
supporting information
(2021/04/15)
-
- Neuroregenerative Potential of Prenyl- And Pyranochalcones: A Structure-Activity Study
-
Loss of neuronal tissue is a hallmark of age-related neurodegenerative diseases. Since adult neurogenesis has been confirmed in the human brain, great interest has arisen in substances stimulating the endogenous neuronal regeneration mechanism based on ad
- Aigner, Ludwig,Bieler, Lara,Couillard-Despres, Sebastien,Priglinger, Eleni,Riepl, Herbert M.,Urmann, Corinna
-
supporting information
p. 2675 - 2682
(2021/10/12)
-
- Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction
-
A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.
- Carlet, Federica,Bertarini, Greta,Broggini, Gianluigi,Pradal, Alexandre,Poli, Giovanni
-
supporting information
p. 2162 - 2168
(2021/04/02)
-
- Flavanone compound as well as preparation method and application thereof
-
The invention belongs to the technical field of medicines, and particularly relates to a flavanone compound as well as a preparation method and application thereof. Specifically disclosed is a compound represented by formula (I) or a pharmaceutically acceptable salt thereof. The compound shown in the formula (I) can target hURAT1 and/or GLUT9, so that uric acid excretion is promoted, and the effect of reducing uric acid is achieved. The compound can be used for preparing medicines for treating and/or preventing and/or delaying and/or adjunctively treating and/or treating diseases related to hURAT1/GLUT9 activity, and has a good application prospect in preventing or treating diseases (such as gout, gouty arthritis, uric acid kidney stone and the like) related to hyperuricemia.
- -
-
Paragraph 0096-0099; 0106-0108
(2021/04/17)
-
- Microbial Transformation of Broussochalcones A and B by Aspergillus niger
-
Broussochalcones A (BCA, 1) and B (BCB, 2) are major bioactive constituents isolated from Broussonetia papyrifera, a polyphenol-rich plant belonging to the family Moraceae. Due to their low yields from natural sources, BCA (1) and BCB (2) were prepared sy
- Xiao, Yina,Han, Fubo,Kim, Myeong Ji,Lee, Kwang Youl,Lee, Ik-Soo
-
supporting information
p. 601 - 607
(2021/02/16)
-
- S1P1 AGONIST AND APPLICATION THEREOF
-
The present invention relates to a class of tricyclic compounds and an application thereof as a sphingosine 1-phosphate type 1 (S1P1) receptor agonist. The invention specifically relates to a compound represented by formula (II), and a tautomer and pharmaceutically acceptable salt of same.
- -
-
Paragraph 0345-0348
(2021/10/02)
-
- Analogues of 2′-hydroxychalcone with modified C4-substituents as the inhibitors against human acetylcholinesterase
-
A series of C4-substituted tertiary nitrogen-bearing 2′-hydroxychalcones were designed and synthesised based on a previous mixed type acetylcholinesterase inhibitor. Majority of the 2′-hydroxychalcone analogues displayed a better inhibition against acetyl
- Sukumaran, Sri Devi,Nasir, Shah Bakhtiar,Tee, Jia Ti,Buckle, Michael J. C.,Othman, Rozana,Rahman, Noorsaadah Abd.,Lee, Vannajan Sanghiran,Bukhari, Syed Nasir Abbas,Chee, Chin Fei
-
p. 130 - 137
(2020/12/03)
-
- COMBINATION TREATMENT OF BACTERIAL INFECTION
-
The present invention resides in the discovery that combined use of kuraridin (or any one of its analogs) and epicatechin gallate (ECG) can provide heightened level of antimicrobial activity, especially for the suppression of bacteria of the Staphylococcus aureus and Staphylococcal species. Compositions, kits, and methods for the combination use are disclosed.
- -
-
Paragraph 0153; 0154
(2020/06/08)
-
- Novel drug isolated from mistletoe (1: E,4 E)-1,7-bis(4-hydroxyphenyl)hepta-1,4-dien-3-one for potential treatment of various cancers: Synthesis, pharmacokinetics and pharmacodynamics
-
(1E,4E)-1,7-Bis(4-hydroxyphenyl)hepta-1,4-dien-3-one (DHDK) is a novel curcuminoid analogue isolated from mistletoe. DHDK exhibits better anti-tumour activity, higher bioavailability and superior stability than curcumin. DHDK is difficult to isolate from Viscum coloratum, but it can be synthesised. MTT (methylthiazolyldiphenyl tetrazolium bromide) assay was used to evaluate the in vitro cytotoxic activity of synthesised DHDK on 12 cancer cell lines. Results showed that DHDK exhibited excellent potential as an anticancer agent, especially for breast and lung cancer. Efficacy was further evaluated in vivo by using MCF-7 breast cancer models. DHDK showed a dose-dependent relationship without weight reduction, mortality growth inhibition or tissue toxicity. Pharmacokinetics and tissue distribution statistics were determined by LC-ESI-MS/MS. This work provided preliminary data on this natural compound and could open up new prospects for changing related parameters to improve drug efficacy.
- Hong, Jing,Meng, Lin,Qin, Feng,Yu, Peipei,Yu, Zhiguo,Zhang, Zhaoyan,Zhao, Yunli,Zhou, Ceng
-
p. 27794 - 27804
(2020/08/17)
-
- Synthesis method of isolicoflavonol
-
The invention provides a synthesis method of isolicoflavonol, which comprises the following steps: carrying out condensation reaction on 2,4-O-R1(protective group, the same below)-6-hydroxyacetophenone and 4-O-R2(protective group, the same below)-benzaldehyde to generate 2',4'-O-R1-6'-hydroxy-4-O-R2-chalcone; oxidizing the chalcone to generate flavonol; carrying out selective protection on 3-OH ofthe flavonol to obtain 3,5,7-O-R1-4'-O-R2-flavonol; removing the protecting group R2 from the 3,5,7-O-R1-4'-O-R2-flavonol to obtain 3,5,7-O-R1-4'-hydroxyflavonol; carrying out 1,1-dimethylpropargyl reaction on the 4,4'-OH site to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonol; carrying out partial hydrogenation on the alkynyl of the 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonolunder the action of a catalyst to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol and carrying out Claisen rearrangement on the 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol to obtain 3,5,7-O-R1-isolicoflavonol, and removing the protecting group R1 from the 3,5,7-O-R1-isolicoflavonol to obtain the isolicoflavonol.
- -
-
Paragraph 0111; 0188-0193
(2020/12/29)
-
- Synthesis of natural 3′-Prenylchalconaringenin and biological evaluation of ameliorating non-alcoholic fatty liver disease and metabolic syndrome
-
Non-alcoholic fatty liver disease (NAFLD) is the most common cause of chronic liver disease and important risk factor for cardiac diseases, diabetes and extrahepatic cancers. Natural 3′-geranylchalconaringenin (GC) and desmethylxanthohumol (DX) from hop w
- Zhang, Mengdi,Wang, Zhaoxin,Hao, Siyu,Hao, Lei,Zhang, Xinying,Yu, Peng,Sun, Hua
-
-
- 2-phenylchroman-4-one derivatives and antiviral composition comprising the same
-
The present invention relates to a 2-phenylchroman-4-one derivative or a pharmaceutically acceptable salt thereof, a method for manufacturing the same, and a therapeutic agent for MERS containing the same as an active component. A compound containing the
- -
-
Paragraph 0078- 0083
(2020/09/10)
-
- Synthesis and Pharmacological Characterization of Conformationally Restricted Retigabine Analogues as Novel Neuronal Kv7 Channel Activators
-
Kv7 K+ channels represent attractive pharmacological targets for the treatment of different neurological disorders, including epilepsy. In this paper, 42 conformationally restricted analogues of the prototypical Kv7 activator retigabine have been synthesized and tested by electrophysiological patch-clamp experiments as Kv7 agonists. When compared to retigabine (0.93 ± 0.43 μM), the EC50s for Kv7.2 current enhancements by compound 23a (0.08 ± 0.04 μM) were lower, whereas no change in potency was observed for 24a (0.63 ± 0.07 μM). In addition, compared to retigabine, 23a and 24a showed also higher potency in activating heteromeric Kv7.2/Kv7.3 and homomeric Kv7.4 channels. Molecular modeling studies provided new insights into the chemical features required for optimal interaction at the binding site. Stability studies evidenced improved chemical stability of 23a and 24a in comparison with retigabine. Overall, the present results highlight that the N5-alkylamidoindole moiety provides a suitable pharmacophoric scaffold for the design of chemically stable, highly potent and selective Kv7 agonists.
- Ostacolo, Carmine,Miceli, Francesco,Di Sarno, Veronica,Nappi, Piera,Iraci, Nunzio,Soldovieri, Maria Virginia,Ciaglia, Tania,Ambrosino, Paolo,Vestuto, Vincenzo,Lauritano, Anna,Musella, Simona,Pepe, Giacomo,Basilicata, Manuela Giovanna,Manfra, Michele,Perinelli, Diego Romano,Novellino, Ettore,Bertamino, Alessia,Gomez-Monterrey, Isabel M.,Campiglia, Pietro,Taglialatela, Maurizio
-
p. 163 - 185
(2020/01/09)
-
- Pyridoxine-resveratrol hybrids as novel inhibitors of MAO-B with antioxidant and neuroprotective activities for the treatment of Parkinson's disease
-
A series of pyridoxine-resveratrol hybrids were designed and synthesized as monoamine oxidase B inhibitors for the treatment of Parkinson's disease. Most of them exhibited potent inhibitory activities on MAO-B with high selectivity. Specifically, compounds 12a, 12g and 12l showed the most excellent inhibition to hMAO-B with the IC50 values of 0.01 μM, 0.01 μM and 0.02 μM, respectively. Further reversibility study demonstrated that 12a and 12l were reversible and 12g was irreversible MAO-B inhibitors. Molecular docking studies of MAO revealed the binding mode and high selectivity of these compounds with MAO-B. In addition, these three representative compounds also exhibited low cytotoxicity and excellent neuroprotective effect in the test on H2O2-induced PC-12 cell injury. Moreover, 12a, 12g and 12l showed good antioxidant activities and high blood-brain barrier permeability. Overall, all of these results highlighted 12a, 12g and 12l were potential and excellent MAO-B inhibitors for PD treatment.
- Cao, Zhongcheng,Deng, Yong,Li, Wei,Shi, Yichun,Song, Qing,Yang, Xia,Zhang, Li
-
-
- Visible light photoredox catalyzed deprotection of 1,3-oxathiolanes
-
An efficient visible light photoredox catalyzed aerobic deprotection of 1,3-oxathiolanes using organic dye Eosin Y as a photocatalyst is disclosed. The deprotection procedure features the use of a metal-free catalyst, mild conditions, a broad range of substrate scope, and good functional group tolerance. 35 examples were tested under the standard conditions and most of them afforded the deprotected products in modest to high yields.
- Yang, Mingyang,Xing, Zhimin,Fang, Bowen,Xie, Xingang,She, Xuegong
-
supporting information
p. 288 - 291
(2020/01/13)
-
- Design, synthesis, and evaluation of a water soluble C5-monoketone type curcumin analogue as a potent amyloid β aggregation inhibitor
-
A structure activity relationship study of curcumin analogues for the inhibition of amyloid β aggregation is described. Optimization of the o-phenol and olefin spacer resulted in the identification of the C5-monoketone type curcumin analogue AY1319, which
- Hotsumi, Mayumi,Tajiri, Misato,Nikaido, Yuri,Sato, Taki,Makabe, Koki,Konno, Hiroyuki
-
supporting information
p. 2157 - 2161
(2019/07/03)
-
- Method for synthesizing 1, 7-2-(4-hydroxy phenyl)-heptane-1, 4-diene-3-ketone
-
The invention relates to the field of pharmaceutical synthesis, in particular to a method for synthesizing 1,7-2-(4-hydroxy phenyl)-heptane-1,4-diene-3-ketone. The method, selecting 3-(4- hydroxy phenyl)propionic acid and 4-hydroxybenzaldehyde as raw materials, includes (1), subjecting the 3-(4-hydroxy phenyl)propionic acid to esterification, methyl protection, reduction and oxidation to obtain 3-(4-(methoxy methyl)phenyl)propionaldehyde; (2), subjecting the 4-hydroxybenzaldehyde to etherification and aldol reaction to obtain 4-(4-((methoxy methyl)phenyl)butyl-3-alkene-2-ketone; (3), subjecting the 4-(4-((methoxy methyl)phenyl) butyl-3-alkene-2-ketone and the 3-(4-(methoxy methyl)phenyl)propionaldehyde to aldol condensation, and allowing the reactor to react with hydrochloric acid to obtain 1, 7-2-(4-hydroxy phenyl)-heptane-1,4-diene-3-ketone. The method has the advantages of simplicity, easiness in operation, high yield and high purity.
- -
-
Paragraph 0043; 0053-0054; 0069-0070
(2018/04/03)
-
- A restorative Psoralea corylifolia active component in the synthesis of the key intermediate (by machine translation)
-
The invention relates to a fruit hyperuricemia active component in the synthesis of the key intermediate, comprising the following steps: (a) will be Paeonia suffruticosa Andr. (tree peony bark) phenol, 1 - bromo - 3 - methyl - 2 - butene and acetone mixe
- -
-
Paragraph 0016; 0020
(2018/09/13)
-
- Method for synthesizing active ingredient intermediate of traditional Chinese medicine fructus psoraleae
-
The invention relates to a method for synthesizing an active ingredient intermediate of a traditional Chinese medicine fructus psoraleae. The method comprises the following steps: (a) mixing paeonol,1-bromo-3-methyl-2-butene and acetone, and adding potass
- -
-
Paragraph 0018; 0022
(2018/11/22)
-
- Synthesis method of active component of Chinese herb psoralea corylifolia
-
The invention relates to a synthesis method of an active component of a Chinese herb psoralea corylifolia. The synthesis method comprises the following steps: (a), mixing paeonol, 1-bromo-3-methyl-2-butene and acetone, adding potassium carbonate, and then
- -
-
Paragraph 0020; 0024
(2018/11/22)
-
- Bioinspired Diastereoconvergent Synthesis of the Tricyclic Core of Palodesangrens via Diels-Alder Reaction, LiAlH4-Mediated Isomerization, and Acid-Mediated Cyclization
-
The cyclohexene moiety of the tricyclic 6,7-diaryl-tetrahydro-6H-benzo[c]chromene core of palodesangrens could be assembled in a biomimetic and step-economical fashion by the Diels-Alder reaction between the electron-rich (E)-1,3-butadienylarenes as the diene and the electron-deficient chalcones as the dienophile. During the reduction of ketone to the corresponding alcohol by LiAlH4, the mixture of endo and exo isomers underwent a novel diastereoconvergent LiAlH4-mediated isomerization to install the desired stereochemistry at C10a. Subsequent pyran ring closure under acidic conditions installed the stereochemistry at the remaining C6. Overall, the tricyclic core of palodesangrens could be prepared in three steps and up to 38% yield.
- Songthammawat, Poramate,Wangngae, Sirilak,Matsumoto, Koki,Duangkamol, Chuthamat,Ruchirawat, Somsak,Ploypradith, Poonsakdi
-
p. 5225 - 5241
(2018/05/07)
-
- Reduction of N,N-Dimethylcarboxamides to Aldehydes by Sodium Hydride–Iodide Composite
-
A new and concise protocol for selective reduction of N,N-dimethylamides into aldehydes was established using sodium hydride (NaH) in the presence of sodium iodide (NaI) under mild reaction conditions. The present protocol with the NaH-NaI composite allows for reduction of not only aromatic and heteroaromatic but also aliphatic N,N-dimethylamides with wide substituent compatibility. Retention of α-chirality in the reduction of α-enantioriched amides was accomplished. Use of sodium deuteride (NaD) offers a new step-economical alternative to prepare deuterated aldehydes with high deuterium incorporation rate. The NaH-NaI composite exhibits unique chemoselectivity for reduction of N,N-dimethylamides over ketones.
- Chan, Guo Hao,Ong, Derek Yiren,Yen, Zhihao,Chiba, Shunsuke
-
-
- A versatile platform for adding functional properties to amyloid fibrils
-
Herein we report the design, synthesis, and testing of prototype members of a family of amyloid-binding molecular tools that can manipulate the fibrils by giving them various new functional properties. Potential applications include manipulating disease-r
- Fontaine, Devon F. A.,Ivancic, Valerie A.,Reardon, Michael B.,Lazo, Noel D.,Jakobsche, Charles E.
-
supporting information
p. 8023 - 8027
(2017/10/10)
-
- A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine
-
Two consecutive Cu-catalyzed Ullmann-type C-O couplings permitted the first successful entry toward the curare alkaloids (±)-tubocurine and (±)-curine. Starting from vanillin, the synthetic sequence comprises 15 linear steps and includes a total of 24 transformations. In addition, the total synthesis of tubocurine represents a formal total synthesis of the famous arrow poison alkaloid tubocurarine.
- Otto, Nicola,Ferenc, Dorota,Opatz, Till
-
p. 1205 - 1217
(2018/06/18)
-
- Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers
-
Four ring-closed analogs of natural prenylated chalcone desmethylxanthohumol (1) and their dimers were synthesized from the commercially available 1-(2,4,6-trihydroxyphenyl)ethan-1-one in five and six linear steps, respectively. The structures of the eigh
- Teng, Yuou,Li, Xuzhe,Yang, Ke,Li, Xuehui,Zhang, Zijun,Wang, Luyao,Deng, Zhijie,Song, Binbin,Yan, Zhihong,Zhang, Yongmin,Lu, Kui,Yu, Peng
-
p. 335 - 345
(2016/10/03)
-
- Design, Synthesis, and Structure–Activity Relationships of Bavachinin Analogues as Peroxisome Proliferator-Activated Receptor γ Agonists
-
Peroxisome proliferator-activated receptor γ (PPARγ) agonists have been used for the treatment of diabetes with the effect of lowering blood glucose levels and improving insulin sensitivity. Natural compounds such as flavones, flavanones, and isoflavones
- Du, Guoxin,Zhao, Yuanyuan,Feng, Li,Yang, Zhuo,Shi, Jiye,Huang, Cheng,Li, Bo,Guo, Fujiang,Zhu, Weiliang,Li, Yiming
-
p. 183 - 193
(2017/02/05)
-
- Design, synthesis and evaluation of scutellarein-O-acetamidoalkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease
-
A series of scutellarein-O-acetamidoalkylbenzylamines derivatives were designed based on a multitarget-directed ligands strategy for the treatment of Alzheimer's disease. Among these compounds, compound T-22 demonstrated excellent acetylcholinesterase inhibitory, moderate inhibitory effects on self-induced Aβ1-42 aggregation, Cu2+-induced Aβ1-42 aggregation, human AChE-induced Aβ1-40 aggregation and disassembled Cu2+-induced aggregation of the well-structured Aβ1-42 fibrils, and also acted as potential antioxidant and biometals chelator. Both kinetic analysis of AChE inhibition and molecular modeling study suggested that T-22 interacted with both the catalytic active site and peripheral anionic site of AChE. Moreover, compound T-22 showed a good neuroprotective effect against H2O2-induced PC12?cell injury and low toxicity in SH-SY5Y cells. Furthermore, the step-down passive avoidance test indicated T-22 significantly reversed scopolamine-induced memory deficit in mice. Taken together, the data showed that T-22 was an interesting multifunctional lead compound worthy of further study for AD.
- Sang, Zhipei,Qiang, Xiaoming,Li, Yan,Xu, Rui,Cao, Zhongcheng,Song, Qing,Wang, Ting,Zhang, Xiaoyu,Liu, Hongyan,Tan, Zhenghuai,Deng, Yong
-
p. 307 - 323
(2017/05/01)
-
- Design, synthesis and bioactivity of chalcones and its analogues
-
The Vernohia anthelmintica L.'s extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and α, β-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a–15a, 20a and 1b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40?μg/mL.
- Niu, Chao,Tuerxuntayi, Adila,Li, Gen,Kabas, Madina,Dong, Chang-Zhi,Aisa, Haji Akber
-
p. 1533 - 1538
(2017/07/17)
-
- Synthesis, characterization, and antioxidant activity of Zn2+ and Cu2+ coordinated polyhydroxychalcone complexes
-
Four new metal complexes [Cu(ISO)2], [Cu(BUT)2] and [Zn(ISO)2], [Zn(BUT)2] of the polyhydroxychalcones (isoliquiritigenin and butein) are synthesized, structurally characterized and their antioxidant activity is investigated. The formation of the complexes [Cu(ISO)2] and [Zn(ISO)2] is followed by Job’s plot using NMR titration. The resulting compounds are characterized by mass spectrometry, IR spectroscopy, and elemental analysis. Studies on the radical scavenging activity are performed using DPPH as substrate. The results showed that the antioxidant activities of isoliquiritigenin and butein are enhanced after binding to copper or zinc. Graphical abstract: [Figure not available: see fulltext.]
- Sulpizio, Chiara,Müller, Simon T. R.,Zhang, Qi,Brecker, Lothar,Rompel, Annette
-
p. 1871 - 1881
(2016/10/22)
-
- Synthesis and biological evaluation of novel resveratrol-oxadiazole hybrid heterocycles as potential antiproliferative agents
-
A novel class of resveratrol-oxadiazole hybrid compounds was synthesized to screen for their in vitro antiproliferative activity against three human cancer cell lines. All the compounds showed superior antiproliferative activity than the reference compound resveratrol. The most promising active compounds in this series were 1g, 2g, 1c, 2c, 2i and 1a (GI50 0.1 μM), endowed with excellent antiproliferative activity. Thus, we believe that resveratrol-oxadiazole hybrid compounds may possibly be used as a good leads for the development of new antiproliferative agents. Structures of newly synthesized compounds were confirmed by NMR and IR spectral data.
- Murty,Penthala, Raju,Polepalli, Sowjanya,Jain
-
p. 627 - 643
(2016/03/08)
-
- Design and characterization of red fluorogenic push-pull chromophores holding great potential for bioimaging and biosensing
-
Fluorogenic chromophores have been used recently for fluorescence reporting and biosensing. Their ability to turn on upon specific interaction with a given target has been exploited in particular for the design of fluorogen-based reporters enabling biomol
- Li, Chenge,Plamont, Marie-Aude,Aujard, Isabelle,Le Saux, Thomas,Jullien, Ludovic,Gautier, Arnaud
-
p. 9253 - 9261
(2016/10/13)
-
- Divergent Total Syntheses of Flavonoid Natural Products Isolated from Rosa rugosa and Citrus unshiu
-
The concise and step-economical total syntheses of three hydroxyaurones and one polymethoxyflavone from readily available starting materials is described. A divergent synthetic strategy is employed, which centres on a common chalcone scaffold from which both the aurone and flavone frameworks can be accessed through the use of different oxidative cyclisation methods. These are the first reported total syntheses of these biologically interesting compounds.
- Sum, Tze Jing,Sum, Tze Han,Galloway, Warren R. J. D.,Spring, David R.
-
supporting information
p. 1725 - 1727
(2016/07/06)
-
- Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones
-
Allyl, dimethylallyl and prenyl ethers derived from o-acylphenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.
- Schmidt, Bernd,Riemer, Martin,Schilde, Uwe
-
supporting information
p. 7602 - 7611
(2016/01/25)
-
- Rational design of latent fluorophores from water-soluble hydroxyphenyltriazine dyes suitable for lipase sensing
-
Derivatives of 2-(2′-hydroxy-5′-dimethylaminobenzyl)-4,6-dimethylamino-1,3,5-triazine were synthesized by an original multistep protocol that afforded, after quaternization of the N,N-dimethylaminobenzyl moiety, water-soluble fluorescent dyes. These fluor
- Jacquemet, Alicia,Rihn, Sandra,Ulrich, Gilles,Renard, Pierre-Yves,Romieu, Anthony,Ziessel, Raymond
-
supporting information
p. 1664 - 1669
(2015/05/27)
-
- Separation and peroxisome proliferator-activated receptor-γ agonist activity evaluation of synthetic racemic bavachinin enantiomers
-
Abstract Bavachinin, isolated from Psoralea corylifolia seeds, has been reported to demonstrate peroxisome proliferator-activated receptor-γ (PPAR-γ) agonist activity. However, isolated bavachinin is actually a mixture of S and R configurations, with an e
- Du, Guoxin,Feng, Li,Yang, Zhuo,Shi, Jiye,Huang, Cheng,Guo, Fujiang,Li, Bo,Zhu, Weiliang,Li, Yiming
-
supporting information
p. 2579 - 2583
(2015/06/02)
-
- Synthesis of aminoalkyl-substituted aurone derivatives as acetylcholinesterase inhibitors
-
Alzheimer's disease (AD), a progressive and neurodegenerative disorder of the brain, is the most common cause of dementia among elderly people. To date, the successful therapeutic strategy to treat AD is maintaining the levels of acetylcholine by inhibiting acetylcholinesterase (AChE). In the present study, aurone derivatives were designed and synthesized as AChE inhibitors based on the lead structure of sulfuretin. Of those synthesized, compound 10d showed ca. 1700-fold and 6-fold higher AChE inhibitory activity than sulfuretin and galantamine, respectively. This compound also ameliorated scopolamine-induced memory deficit in mice when administered orally at the dose of 1 and 2 mg/kg.
- Lee, Young Hun,Shin, Min Cheol,Yun, Yong Don,Shin, Seo Young,Kim, Jong Min,Seo, Jeong Moo,Kim, Nam-Jung,Ryu, Jong Hoon,Lee, Yong Sup
-
p. 231 - 240
(2015/02/18)
-
- (E)-1-(5-METHOXY-2,2-DIMETHYL-2H-CHROMEN-8-YL)-3-(4-METHOXYPHENYL)PROP-2-EN-1-ONE AND ANALOGS THEREOF, AS WELL AS PREPARATION METHOD AND USE THEREOF
-
The present invention relates to millepachine ((E)-1-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(4-methoxyphenyl)prop-2-en-1-one) and its analogues. The present invention provides methods for preparing these compounds, pharmaceutical compositions includin
- -
-
Paragraph 0168; 0169
(2015/05/26)
-
- Synthesis and Characterization of 5-Hydroxy-2-(2-phenylethyl)chromone (5-HPEC) and Its Analogues as Non-nitrogenous 5-HT2B Ligands
-
The involvement of the neurotransmitter serotonin (5-HT) in numerous physiological functions is often attributed to the diversity of receptors with which it interacts. Ligands targeting serotonin receptor 2B (5-HT2B) have received renewed interest for their potential to help understand the role of 5-HT2B in migraines, drug abuse, neurodegenerative diseases, and irritable bowel syndrome. To date, most of the ligands targeting 5-HT2B have been nitrogen-containing compounds. The natural product 5-hydroxy-2-(2-phenylethyl)chromone (5-HPEC, 5) has been shown previously to act as a non-nitrogenous antagonist for the 5-HT2B receptor (pKi = 5.6). This report describes further progress on the study of the structure-activity relationship of both naturally occurring and synthetic compounds bearing the 2-(2-phenylethyl)chromone scaffold at the 5-HT2B receptor. The inhibitory activity of the newly synthesized compounds (at 10 μM) was tested against each of the 5-HT2 receptors. Following this assay, the binding affinity and antagonism of the most promising compounds were then evaluated at 5-HT2B. Among all the analogues, 5-hydroxy-2-(2-phenylpropyl)chromone (5-HPPC, 22h) emerged as a new lead compound, showing a 10-fold improvement in affinity (pKi = 6.6) over 5-HPEC with reasonable antagonist properties at 5-HT2B. Additionally, ligand docking studies have identified a putative binding pocket for 5-HPPC and have helped understand its improved affinity. (Figure Presented).
- Williams, Dwight A.,Zaidi, Saheem A.,Zhang, Yan
-
p. 1859 - 1867
(2015/09/08)
-
- Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure-activity relationship
-
To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells.
- Jiang, Wen-Jun,Ishiuchi, Kan'Ichiro,Furukawa, Megumi,Takamiya, Tomoko,Kitanaka, Susumu,Iijima, Hiroshi
-
p. 6922 - 6929
(2015/11/11)
-
- Synthesis of natural and non-natural curcuminoids and their neuroprotective activity against glutamate-induced oxidative stress in HT-22 cells
-
A strategy for the synthesis of natural and non-natural 5-deoxy-6,7-dihydrocurcuminoids (diarylheptanoids) was developed for the preparation of 14 compounds with varying aromatic substituent patterns and a different functionality in the aliphatic seven-carbon chain. The in vitro protective activity against glutamate-induced neuronal cell death was examined in the murine hippocampal cell line HT-22 to find structural motifs responsible for neuroprotective effects in vitro. Among the tested compounds the ferulic acid-like unit, present in the structures of (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-en-3-one (5) and (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hept-1-en-3-one (7), appeared to be an important feature for protection against glutamate-induced neurotoxicity. Both compounds demonstrated significant neuroprotective activity in a concentration range between 1 and 25 ~M without showing toxic effects in a cytotoxicity assay with HT-22 cells. Furthermore, (E)-1,7-bis(3,4-dihydroxyphenyl)hept-1-en-3-one (9), exhibiting a caffeic acid-like structural motif, displayed a neuroprotective activity at a nontoxic concentration of 25 ~M. In contrast, (1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione (4, di-O-demethylcurcumin) showed mainly cytotoxic effects. A corresponding single-ring analogue that contains the ferulic acid-like unit as an enone was not active.
- Jirsek, Petr,Amslinger, Sabine,Heilmann, J?rg
-
p. 2206 - 2217
(2014/12/11)
-
- New multi-target-directed small molecules against Alzheimer's disease: A combination of resveratrol and clioquinol
-
Alzheimer's disease (AD) is currently one of the most difficult and challenging diseases to treat. Based on the 'multi-target-directed ligands' (MTDLs) strategy, we designed and synthesised a series of new compounds against AD by combining the pharmacophores of resveratrol and clioquinol. The results of biological activity tests showed that the hybrids exhibited excellent MTDL properties: a significant ability to inhibit self-induced β-amyloid (Aβ) aggregation and copper(ii)-induced Aβ aggregation, potential antioxidant behaviour (ORAC-FL value of 0.9-3.2 Trolox equivalents) and biometal chelation. Among these compounds, (E)-5-(4-hydroxystyryl)quinoline-8-ol (10c) showed the most potent ability to inhibit self-induced Aβ aggregation (IC50 = 8.50 μM) and copper(ii)-induced Aβ aggregation and to disassemble the well-structured Aβ fibrils generated by self- and copper(ii)-induced Aβ aggregation. Note that 10c could also control Cu(i/ii)-triggered hydroxyl radical (OH) production by halting copper redox cycling via metal complexation, as confirmed by a Cu-ascorbate redox system assay. Importantly, 10c did not show acute toxicity in mice at doses of up to 2000 mg kg-1 and was able to cross the blood-brain barrier (BBB), according to a parallel artificial membrane permeation assay. These results indicate that compound 10c is a promising multifunctional compound for the development of novel drugs for AD. This journal is the Partner Organisations 2014.
- Mao, Fei,Yan, Jun,Li, Jianheng,Jia, Xian,Miao, Hui,Sun, Yang,Huang, Ling,Li, Xingshu
-
supporting information
p. 5936 - 5944
(2014/08/05)
-
- Stereoselective total synthesis of rhoiptelol B via prins cyclization
-
The stereoselective total synthesis of rhoiptelol B, a diaryl? heptanoid isolated from Rhoiptelea chiliantha is described. The tetrahydropyran ring was constructed by using Prins cyclization. The key steps involved in this synthesis are Prins cyclization,
- Yadav, Jhillu S.,Rahman, Md. Ataur,Reddy, N. Mallikarjuna,Prasad, Attaluri R.,Al Khazim Al Ghamdi, Ahmad
-
p. 661 - 664
(2014/04/03)
-
- METHODS OF TREATMENT USING ARYLCYCLOPROPYLAMINE COMPOUNDS
-
Described herein are methods of treating breast cancer using arylcyclopropylamine compounds.
- -
-
Paragraph 0291-0292
(2014/12/09)
-
- Development of a simple and efficient solution-phase parallel synthesis of flexible non-steroidal estradiol mimics
-
An efficient parallel synthesis was designed to provide libraries of estradiol mimics that can potentially interact with different biological targets associated with estradiol-related diseases. Two libraries of 75 members each were synthesized around a no
- Djigoué, Guy B.,Maltais, René,Poirier, Donald
-
p. 734 - 744
(2015/05/20)
-
- METHODS OF TREATMENT USING ARYLCYCLOPROPYLAMINE COMPOUNDS
-
Described herein are methods of treating Parkinson's disease using arylcyclopropylamine compounds.
- -
-
Paragraph 0209
(2013/07/19)
-
- Facile synthesis of diarylmethanes via quinone methides
-
A novel acid-mediated generation of quinone methides followed by nucleophilic addition of electronrich aromatic compounds to furnish diarylmethanes has been developed. A wide range of electronrich aromatic compounds including some heterocycles can be employed for this reaction to provide the corresponding diarylmethanes in good yields and regioselectivities.
- Tangdenpaisal, Kassrin,Phakhodee, Wong,Ruchirawat, Somsak,Ploypradith, Poonsakdi
-
p. 933 - 941
(2013/07/25)
-
- Phosphonium salts and aldehydes from the convenient, anhydrous reaction of aryl acetals and triphenylphosphine hydrobromide
-
The reactions of aryl acetals/ketals and triphenylphosphine hydrobromide gave the corresponding aldehydes/ketones and alkyl phosphonium bromides. This reaction was applied to convert acetals/ketals to the corresponding aldehydes/ketones under an anhydrous
- Ramanathan, Mani,Hou, Duen-Ren
-
-
- Synthesis and evaluation of 18F-labeled styryltriazole and resveratrol derivatives for β-amyloid plaque imaging
-
In the present study, a styryltriazole and four resveratrol derivatives were synthesized as candidates for β-amyloid (Aβ) plaque imaging. On the basis of their binding affinities to Aβ(1-42) aggregates, the styryltriazole (1, Ki = 12.8 nM) and one resveratrol derivative (5, Ki = 0.49 nM) were labeled with 18F. In normal mice, tissue distribution of [18F]5 showed good initial brain uptake (3.26% ID/g at 2 min) but slow wash-out from brains (2-to-60 min uptake ratio: 2.9). Furthermore, it underwent in vivo metabolic defluorination (1.88% ID/g at 2 min and 9.73% ID/g at 60 min). In contrast, [18F]1 displayed high initial brain uptake (5.38% ID/g at 2 min) with rapid wash-out from brains (0.52% ID/g at 60 min; 2-to-60 min uptake ratio: 10.3). These results indicate that [ 18F]1 has in vivo kinetics comparable to PET radiopharmaceuticals currently under commercial development, demonstrating that [18F]1 is a desirable PET radioligand for Aβ plaque imaging.
- Lee, Iljung,Choe, Yearn Seong,Choi, Joon Young,Lee, Kyung-Han,Kim, Byung-Tae
-
experimental part
p. 883 - 892
(2012/04/04)
-