- A new family of 1D exchange biased heterometal single-molecule magnets: Observation of pronounced quantum tunneling steps in the hysteresis loops of quasi-linear {Mn2Ni3} clusters
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First members of a new family of heterometallic Mn/Ni complexes [Mn 2Ni3X2L4(LH)2(H 2O)2] (X = Cl: 1; X = Br: 2) with the new ligand 2-{3-(2-hydroxyphenyl)-1H-pyrazol-1-yl}ethanol (H2L) have been synthesized, and single crystals obtained from CH2Cl2 solutions have been characterized crystallographically. The molecular structures feature a quasi-linear MnIII-NiII-NiII-Ni II-MnIII core with six-coordinate metal ions, where elongated axes of all the distorted octahedral coordination polyhedra are aligned parallel and are fixed with respect to each other by intramolecular hydrogen bonds. 1 and 2 exhibit quite strong ferromagnetic exchange interactions throughout (JMn-Ni ≈ 40 K (1) or 42 K (2); JNi-Ni ≈ 22 K (1) or 18 K (2)) that lead to an Stot = 7 ground state, and a sizable uniaxial magnetoanisotropy with Dmol values -0.55 K (1) and -0.45 K (2). These values are directly derived also from frequency- and temperature-dependent high-field EPR spectra. Slow relaxation of the magnetization at low temperatures and single-molecule magnet (SMM) behavior are evident from frequency-dependent peaks in the out-of-phase ac susceptibilities and magnetization versus dc field measurements, with significant energy barriers to spin reversal Ueff = 27 K (1) and 22 K (2). Pronounced quantum tunnelling steps are observed in the hysteresis loops of the temperature- and scan rate-dependent magnetization data, but with the first relaxation step shifted above (1) or below (2) the zero crossing of the magnetic field, despite the very similar molecular structures. The different behavior of 1 and 2 is interpreted in terms of antiferromagnetic (1) or ferromagnetic (2) intermolecular interactions, which are discussed in view of the subtle differences of intermolecular contacts within the crystal lattice.
- Das, Animesh,Gieb, Klaus,Krupskaya, Yulia,Demeshko, Serhiy,Dechert, Sebastian,Klingeler, Ruediger,Kataev, Vladislav,Buechner, Bernd,Mueller, Paul,Meyer, Franc
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- Analogues of Dehydroacetic Acid as Selective and Potent Agonists of an Ectopic Odorant Receptor through a Combination of Hydrophilic and Hydrophobic Interactions
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Identification of potent agonists of odorant receptors (ORs), a major class of G protein-coupled receptors, remains challenging due to complex receptor–ligand interactions. ORs are present in both olfactory and non-chemosensory tissues, indicating roles beyond odor detection that may include modulating physiological functions in non-olfactory tissues. Selective and potent agonists specific for particular ORs can be used to investigate physiological functions of ORs in non-chemosensory tissues. In this study, we designed and synthesized novel synthetic dehydroacetic acid analogues as agonists of odorant receptor 895 (Olfr895) expressed in bladder. Among the synthesized analogues, (E)-3-((E)-1-hydroxy-3-(piperidin-1-yl)allylidene)-6-methyl-2H-pyran-2,4(3H)-dione (10) exhibited extremely high agonistic activity for Olfr895 in Dual-Glo luciferase reporter (EC50=9 nm), Ca2+ imaging, and chemotactic migration assays. Molecular docking and site-directed mutagenesis studies suggested that a combination of hydrophilic and hydrophobic interactions is central to the selective and specific binding of 10 to Olfr895. The design of agonists armed with both hydrophilic and hydrophobic portions could therefore lead to highly potent and selective ligands for ectopic ORs.
- Park, Bernie Byunghoon,Lee, NaHye,Kim, YunHye,Jae, YoonGyu,Choi, Seunghyun,Kang, NaNa,Hong, Yu Ri,Ok, Kiwon,Cho, Jeonghee,Jeon, Young Ho,Lee, Eun Hee,Byun, Youngjoo,Koo, JaeHyung
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- Chromenone-rhodamine conjugate for naked eye detection of Al3+ and Hg2+ ions in semi aqueous medium
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Chromenone-rhodamine conjugate 1 has been synthesized and its metal ion binding properties have been studied in CH3CN/water (3:1, v/v; 10?mM HEPES buffer; pH?=?6.85). Compound 1 senses multiple metal ions such as Al3+ and Hg2+/
- Mondal, Subhendu,Bandyopadhyay, Chandrakanta,Ghosh, Kumaresh
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- Reusable manganese compounds containing pyrazole-based ligands for olefin epoxidation reactions
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We describe the synthesis of new manganese(ii) and manganese(iii) complexes containing the bidentate ligands 2-(3-pyrazolyl)pyridine, pypz-H, and 3(5)-(2-hydroxyphenyl)pyrazole, HOphpz-H, with formula [MnX2(pypz-H)2] (X = Cl-, 1, CF3SO3-, 2, OAc-, 3 or NO3- (4)), [MnCl2(pypz-H)(H2O)2], 5, or [MnCl(Ophpz-H)2], 6. All the complexes have been characterized through analytical, spectroscopic and electrochemical techniques. Single X-ray structure analysis revealed a six-coordinated Mn(ii) ion in complexes 1-5, and a five-coordinated Mn(iii) ion in complex 6. Compound 5 is the first co-crystal of Mn(ii) containing Cl and H2O ligands together with bidentate nitrogen ligands. The catalytic activity of complexes 1-6 has been tested with regard to the epoxidation of styrene and, in the case of 1, 5 and 6, other alkenes have been epoxidized using peracetic acid as oxidant in different media, among which glycerol, a green solvent never used in epoxidation reactions using peracetic acid as oxidant. The catalysts show moderate to high conversions and selectivities towards the corresponding epoxides. For complexes 1, 5 and 6, a certain degree of cis → trans isomerization is observed in the case of cis-β-methylstyrene. These observations have been explained through computational calculations. The reutilization of catalysts 1 and 6 for the epoxidation of alkenes has been evaluated in [bmim]:acetonitrile mixture (bmim = 1-butyl-3-methylimidazolium), allowing the effective recyclability of the catalytic system and keeping high conversion and selectivity values up to 12 successive runs, in all cases.
- Manrique, Ester,Poater, Albert,Fontrodona, Xavier,Solà, Miquel,Rodríguez, Montserrat,Romero, Isabel
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- A Convenient and Practical Synthesis of Aminopyrazoles
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A selective methodology for preparing highly substituted aminopyrazoles has been demonstrated. Starting with an acetophenol core, the corresponding substituted isoxazole is prepared in two steps. The isoxazole is transformed into a benzopyran. Alkylation
- Mitchell, David,Luo, Yumei,Mcnulty, Lu Anne M.,Buser, Jonas Y.,Mcfarland, Adam D.
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- Selectfluor-Mediated Tandem Cyclization of Enaminones for the Synthesis of 3-Fluorochromones
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An efficient synthesis of various 3-fluorochromones (3-fluoro-4 H -chromene-4-ones) from enamino ketones by using Selectfluor is described. The key step in the synthesis involves tandem fluorination and cyclization to form 3-fluorochromones in good yields. The significant features of this method include simple operational procedures, a high purity of the product, and excellent regioselectivity.
- Behera, Manoranjan,Chatterjee, Anindita,Kandula, Venu,Mallesham, Poosa,Raghavulu, K.,Thota, Pradeep Kumar,Yennam, Satyanarayana
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- 2-Azolylchromone derivatives as potent and selective inhibitors of monoamine oxidases A and B
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A series of 2-azolylchromone derivatives were synthesized and their monoamine oxidase (MAO) A and B inhibitory activities were evaluated. Of the synthesized compounds, compounds 1b, 2b, 4a-c, 5b and 7b showed potent inhibitory activities against MAO-A (IC50 values, 1b: 0.32 μM; 2b: 0.14 μM; 4a: 0.11 μM; 4b: 0.023 μM; 4c: 0.15 μM; 5b: 0.59 μM; 7b: 0.19 μM) and 4a, c, 5a, c, 6c and 8c for MAO-B (IC50 values, 4a: 0.028 μM; 4c: 0.019 μM; 5a: 0.73 μM; 5c: 0.28 μM; 6c: 0.28 μM; 8c: 0.27 μM). These data suggest that 6-methoxy substitution favors MAO-A inhibition and 7-methoxy substitution favors MAO-B inhibition. In addition, compound 4b was the most potent inhibitor for MAO-A, and compound 4c for MAO-B. This is the first report identifying 2-azolylchromone derivatives as potent monoamine oxidase inhibitors. These results suggest that the 2-triazolylchromone structure may be a useful scaffold for the design and development of novel monoamine oxidase inhibitors, as evidenced by the activities of 4a-c and 5a-c.
- Takao, Koichi,Saito, Takayuki,Chikuda, Daisuke,Sugita, Yoshiaki
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- Synthesis and antitubercular activity evaluation of 4-furano-coumarins and 3-furano-chromones
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The synthesis of novel 4-furano-coumarins and 3-furano-chromones has been achieved using silver-mediated oxidative C–H/C–H functionalization of 4-ethynylcoumarin/3-ethynylchromone with ethyl acetoacetate in 80%–90% and 82%–90% yields, respectively. The st
- Singh, Ankita,Bimal, Devla,Kumar, Rajesh,Maikhuri, Vipin K.,Thirumal,Senapati, Nihar Nalini,Prasad, Ashok K.
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- Visible Light-Promoted Selenylation/Cyclization of Enaminones toward the Formation of 3-Selanyl-4H-Chromen-4-Ones
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A simple and efficient visible-light-promoted selenylation/cyclization of enaminones have been realized for the practical synthesis of 3-selanyl-4H-chromen-4-ones. This reaction is performed in the mild conditions, no transition metal catalyst or photocatalysts and no additional oxidants are required. In addition, the 3-selanyl-4H-chromen-4-ones could be easily converted to selanyl-functionalized pyrimidines by reacting with benzamidine substrates. (Figure presented.).
- Liu, Hao-Yang,Zhang, Jia-Rong,Huang, Guo-Bao,Zhou, Yi-Huan,Chen, Yan-Yan,Xu, Yan-Li
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- Synthesis of new hybrid heterocyclic compounds having 1,2,3-triazole and isoxazole via click chemistry
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A simple and highly efficient method for the regioselective synthesis of isoxazolyl-1,4-disubstituted-1,2,3-triazoles 6a-l in good to excellent yields from terminal alkynes having isoxazole scaffold 4a-c and various azides through Cu(I)-catalyzed 1,3-dipolar cycloaddition is described. The reaction proceeds smoothly in 1:1 mixture of t-BuOH and water at RT. The structures of all newly synthesized hybrid heterocycles are established on the basis of spectral data ir, 1H nmr, mass, and elemental analysis.
- Jayaprakash Rao,Srinivas
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- Synthesis of 3-thiophenchromone by stille cross-coupling palladium on charcoal-catalyzed ligand-free
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A new concise, facile, and efficient method for synthesis of 3-thiophenchromone was accomplished in more than over 80% yield starting from formation of the substituted 3-iodochromones and tetrathiophentins by Stille cross-coupling reaction in the presence of palladium on charcoal-catalyzed ligand-free under mild conditions.
- Yang, Qian,Zhang, Zunting,Liang, Bo
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- Chiral FLP-catalyzed asymmetric hydrogenation of 3-fluorinated chromones
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The asymmetric hydrogenation of fluorinated olefins is an efficient pathway towards the synthesis of chiral fluorine-containing compounds. This paper described metal-free asymmetric hydrogenation of 3-fluorinated chromones with the use of readily availabl
- Dai, Yun,Du, Haifeng,Feng, Xiangqing,Meng, Wei
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supporting information
p. 1558 - 1560
(2022/02/11)
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- CuI/Cu(OSO2CF3)2 catalysed convenient approach to dichromenopyridines and triazole-thiazole appended chromone derivatives
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A variety of new pentacyclic dichromenopyridines have been synthesized from 2-amino chromone and O-propargyloxy salicilaldehydes through intramolecular Povarov reaction using CuI/Cu(OSO2CF3)2 as a Lewis acid catalyst. The
- Yerrabelly, Jayaprakash Rao,Porala, Subbanarasimhulu,Kasireddy, Venkateshwar Reddy,Ghojala, Venkat Reddy,Rebelli, Pradeep
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p. 3781 - 3790
(2021/11/01)
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- Structure-Based Discovery of Pyrimidine Aminobenzene Derivatives as Potent Oral Reversal Agents against P-gp- And BCRP-Mediated Multidrug Resistance
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Overexpression of ATP binding cassette (ABC) transporters, including P-glycoprotein (P-gp) and breast cancer resistance protein (BCRP), is an important factor leading to multidrug resistance (MDR) in cancer treatments. Three subclasses of dual inhibitors of P-gp and BCRP were designed based on the active moieties of BCRP inhibitors, tyrosine kinase inhibitors, and P-gp inhibitors, of which compound 21 possessed low cytotoxicity, high reversal potency, and good lipid distribution coefficient. 21 also increased the accumulation of Adriamycin (ADM) and Mitoxantrone (MX), blocked Rh123 efflux, and made no change in the protein expression of P-gp and BCRP. Importantly, coadministration of 21 can significantly improve the oral bioavailability of paclitaxel (PTX). It was also demonstrated that 21 significantly inhibited the growth of K562/A02 xenograft tumors by increasing the sensitivity of ADM in vivo. In summary, 21 has the potential to overcome MDR caused by P-gp and BCRP and to improve the oral bioavailability of PTX.
- Qiu, Qianqian,Zou, Feng,Li, Huilan,Shi, Wei,Zhou, Daoguang,Zhang, Ping,Li, Teng,Yin, Ziyu,Cai, Zilong,Jiang, Yuxuan,Huang, Wenlong,Qian, Hai
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p. 6179 - 6197
(2021/06/01)
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- Synthesis of 2H-benzo[g]furo/thieno/pyrrolo[2,3-e]indazoles via Intramolecular Dehydrogenation Photocyclization
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A catalyst-, acid- and base-free, environmental-friendly method for synthesis of 2H-benzo[g]furo[2,3-e]indazoles, 2H-benzo[g]thieno[2,3-e]indazoles and 2H-benzo[g]pyrrolo[2,3-e]indazoles via UV light irradiation of 3-phenyl-4-(2-heteroaryl)pyrazoles (aryl
- Liu, Zhicun,Wang, Ping,Wang, Rui,Wang, Tao,Zhang, Wei,Zhang, Xi,Zhang, Zunting
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supporting information
p. 2213 - 2219
(2021/07/26)
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- Drug discovery of acetophenone derivatives as BRD4 inhibitors
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Background: The bromodomain and extra-terminal proteins (BET), in particular BRD4, has recently emerged as a potential therapeutic target for the treatment of many human disorders such as cancer, inflammation, obesity and cardiovascular disease, which draw more and more attention to discover potent BRD4 inhibitors in the past years. In this article, we described the discovery process of an entirely new chemotype of BRD4 inhibitors. Methods: A fragment-based drug discovery strategy was employed in attempting to find a novel chemotype of BRD4 inhibitors. Thus, the potential hits were firstly identified by docking study with KAc binding pocket and AlphaScreen assay. Then the elected hit was further structurally optimized based on the interaction revealed by the docking study and the Structure-Activity Relationship (SAR). Results: A 1-(2-hydroxyphenyl)ethan-1-one fragment was first identified as an efficient hit to BRD4 with a weak inhibition activity and high ligand efficiency (IC50 = 8.9 μM,LE > 0.5) based on virtual screening and biochemical assay. Then, two-rounds optimization of the hit by a fragment-based drug discovery approach enabled the discovery of a potent BRD4 inhibitor 9, which exhibit nanomolar potency in biochemical assays (IC50 = 0.18 μM). Conclusion: The title compounds displayed potent inhibitory activity to BRD4, implying acetophenone core is an effective KAc residue mimic, suggesting acetophenone derivatives as a new chemotype may be promising for developing novel BRD4 inhibitors. 9.
- Huang, Wenhai,Li, Chuansheng,Shen, Zhengrong,Zhang, Zhimin,Zheng, Xiaoliang
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p. 323 - 329
(2020/04/17)
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- Synthetic method and application of indolizine compounds
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A synthetic method of the indolizine compound comprises the following steps: mixing a benzopyrone derivative, a bromopyridinium salt derivative, alkali and a solvent in a 10ml round-bottom flask, andstirring the mixture for 2-48 hours at the temperature of 25 DEG C and 100 DEG C; after the reaction is finished, purifying the crude product through silica gel chromatography to obtain a target compound with a structural formula shown as the formula I.
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Paragraph 0034-0037
(2020/11/26)
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- Preparation method and application of N-(pyrimidine-2-yl) coumarin-7-amine derivative as protein kinase inhibitor
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The invention discloses a cyclin-dependent kinase inhibitor. The cyclin-dependent kinase inhibitor comprises an N-(pyrimidine-2-yl) coumarin-7-amine derivative shown as a general formula (I). In-vitropharmacodynamic tests prove that the compound has a high-selectivity inhibition effect on CDK9 kinase, and can be applied to reducing or inhibiting the activity of CDK9 kinase in cells. The inventionalso discloses a preparation method of the inhibitor and application of the inhibitor in drugs for CDK family kinase mediated diseases, especially hyperproliferative diseases, virus-induced infectious diseases and cardiovascular diseases.
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Paragraph 0297; 0305-0306; 0480; 0483-0485
(2020/12/14)
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- T3P mediated domino C(sp2)-H sulfenylation/annulation of enaminones and methylsulfinyls for the synthesis of chromone thioether derivatives
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A new regioselective method for the synthesis of 3-(methylthio)-4H-chromen-4-one and 3-(phenylthio)-4H-chromen-4-one derivatives has been developed. The reaction between o-hydroxy-phenyl-functionalized enaminones and methylsulfinyl derivatives using T3P gave good yields of chromone thioether derivatives. The reaction proceeds via domino chromone ring construction and C(sp2)-H bond sulfenylation under transition-metal-free conditions.
- Balakrishna,Gudipati, Ramakrishna,Kandula, Venu,Yennam, Satyanarayana,Uma Devi,Behera, Manoranjan
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supporting information
p. 2458 - 2463
(2019/02/14)
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- Synthesis of 3-HCF2S-Chromones through Tandem Oxa-Michael Addition and Oxidative Difluoromethylthiolation
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A simple protocol for the synthesis of difluoromethylthiolated chromen-4-ones using elemental sulfur and ClCF2CO2Na as the difluoromethylthiolating agent is described. Three-component reactions of 2′-hydroxychalcones, ClCF2CO2Na, and sulfur under basic conditions using TEMPO as the oxidant afforded HCF2S-containing 4H-chromen-4-one and 9H-thieno[3,2-b]chromen-9-one derivatives in good yield. The protocol is practical and efficient, and the starting materials are cheap and readily available.
- Zhang, Pingshun,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
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supporting information
p. 9326 - 9329
(2019/12/24)
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- METHODS FOR PRECISION THERAPEUTIC TARGETING OF HUMAN CANCER CELL MOTILITY AND KITS THEREOF
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Disclosed are methods for identifying an agent of interest that alters binding or activity of a client protein to a chaperone and kits thereof.
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Page/Page column 53
(2019/08/29)
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- A Benazepine isoprenoid flavone compound and its preparation method and application
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The invention relates to a piperazine ring-containing isoflavone-like compound as well as a preparation method and application thereof. The preparation method comprises the following steps: dissolving2-hydroxyacetophenone and N,N-dimethylformamide dimethy
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Paragraph 0049; 0050; 0051; 0052
(2019/06/24)
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- Zn(OTf)2-Catalyzed Formal [3 + 3] Cascade Annulation of Propargylic Alcohols with 2-Aminochromones: Accessing the Chromeno[2,3- b]pyridines
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A Zn(OTf)2-catalyzed formal [3 + 3] cascade annulation strategy for the synthesis of functionalized chromeno[2,3-b]pyridines has been developed using propargylic alcohols and 2-aminochromones as the substrates. The protocol provides a convenien
- Tong, Pei,Sun, Zhou,Wang, Shutao,Zhang, Yuan,Li, Ying
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p. 13967 - 13974
(2019/10/16)
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- Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides
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A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.
- Jin, Can,Sun, Bin,Xu, Tengwei,Yan, Zhiyang,Zhang, Xun
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supporting information
p. 1585 - 1591
(2019/08/07)
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- Synthesis of unsymmetrical 4-oxo-2-vinyl-4H-chromene-3-carbonitrile dyes via Knoevenagel reaction
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New 4-oxo-2-vinyl-4H-chromene-3-carbonitrile derivatives have been synthesized by the Knoevenagel reaction of 2-methyl-4-oxo-4H-chromene-3-carbonitrile with aromatic and heteroaromatic aldehydes. Spectral properties of the obtained compounds have been studied.
- Levchenko,Chudov,Zinoviev,Lyssenko,Demin,Poroshin,Shmelin,Grebennikov
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supporting information
p. 2788 - 2792
(2018/06/08)
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- Precision therapeutic targeting of human cancer cell motility
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Increased cancer cell motility constitutes a root cause of end organ destruction and mortality, but its complex regulation represents a barrier to precision targeting. We use the unique characteristics of small molecules to probe and selectively modulate cell motility. By coupling efficient chemical synthesis routes to multiple upfront in parallel phenotypic screens, we identify that KBU2046 inhibits cell motility and cell invasion in vitro. Across three different murine models of human prostate and breast cancer, KBU2046 inhibits metastasis, decreases bone destruction, and prolongs survival at nanomolar blood concentrations after oral administration. Comprehensive molecular, cellular and systemic-level assays all support a high level of selectivity. KBU2046 binds chaperone heterocomplexes, selectively alters binding of client proteins that regulate motility, and lacks all the hallmarks of classical chaperone inhibitors, including toxicity. We identify a unique cell motility regulatory mechanism and synthesize a targeted therapeutic, providing a platform to pursue studies in humans.
- Xu, Li,Gordon, Ryan,Farmer, Rebecca,Pattanayak, Abhinandan,Binkowski, Andrew,Huang, Xiaoke,Avram, Michael,Krishna, Sankar,Voll, Eric,Pavese, Janet,Chavez, Juan,Bruce, James,Mazar, Andrew,Nibbs, Antoinette,Anderson, Wayne,Li, Lin,Jovanovic, Borko,Pruell, Sean,Valsecchi, Matias,Francia, Giulio,Betori, Rick,Scheidt, Karl,Bergan, Raymond
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- A flavonoid compound and its preparation method and application (by machine translation)
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A flavonoid compound and its preparation method and application, relates to an anti-tumor compound. The class flavone compounds for the treatment of cancer (including liver cancer, cervical cancer and lung cancer) in the medicament of the application. The compounds are new compounds of structure, creative and obviously the practicability of the anti-tumor effect, can be used as a potential drug development application. (by machine translation)
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Paragraph 0042; 0047-0049
(2018/03/26)
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- An Efficient Microwave-Assisted Propylphosphonic Anhydride (T3P )-Mediated One-Pot Chromone Synthesis via Enaminones
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An efficient synthesis of 4 H -chromene-4-ones via enamino ketones, with cyclization by using T3P under microwave heating is described. This is the first report for the synthesis of chromones by using T3P . Significant features of this method include short reaction times and high-purity products.
- Balakrishna,Kandula, Venu,Gudipati, Ramakrishna,Yennam, Satyanarayana,Devi, P. Uma,Behera, Manoranjan
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supporting information
p. 1087 - 1091
(2018/04/30)
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- Convenient and Rapid Synthesis of 3-Selenocyanato-4 H -chromen-4-ones
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A sequential one-pot, simple and convenient method is described for the synthesis of 3-selenocyanato-4 H -chromen-4-ones by addition, first of DMF-DMA and then of triselenodicyanide as electrophile.
- Kosso, Anne Roly Obah,Broggi, Julie,Redon, Sébastien,Vanelle, Patrice
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supporting information
p. 1215 - 1218
(2018/03/26)
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- Expedient chemoselective and catalyst-free synthesis of 3,3-difluorochroman-4-ones from o-hydroxyarylenaminones and Selectfluor
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An expedient and mild strategy for the synthesis of unconventional 2-(dimethylamino)-3,3-difluorochroman-4-one derivatives from o-hydroxyarylenaminones and Selectfluor was developed at room temperature under catalyst-free conditions. This method showed excellent chemoselectivity and great functional groups tolerance.
- Xu, Jian,Kuang, Zhijie,Song, Qiuling
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supporting information
p. 963 - 966
(2017/11/27)
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- Copper-catalyzed C-S direct cross-coupling of thiols with 5-arylpenta-2,4-dienoic acid ethyl ester
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A selective copper (Cu)-catalyzed C-S bond direct cross-coupling of thiols with 5-arylpenta-2,4-dienoic acid ethyl ester was developed. Notably, various biologically active 5-phenyl-3-phenylsulfanylpenta-2,4-dienoic acid ethyl ester derivatives were efficiently synthesized under moderate conditions. Finally, a plausible Cu(i)/Cu(iii) reaction mechanism was proposed.
- Cai, Rongrong,Zhou, Zhuoda,Chai, Qianqian,Zhu, Yueer,Xu, Runsheng
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p. 26828 - 26836
(2018/08/07)
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- 1-phenyl-3-benzenemethylamido-2-propylene-1-ketone compounds and preparation method and use thereof
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The invention provides 1-phenyl-3-benzenemethylamido-2-propylene-1-ketone compounds and a preparation method and use thereof. The compounds are a series of compounds with brand-new structures, have a very good inhibitory effect on aggregation of A beta protein, meanwhile, can also be used for inhibiting the aggregation of Tau proteins and can be used for developing drugs for treating neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease.
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Paragraph 0036; 0037; 0038
(2017/08/30)
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- Amberlyst-15 in PEG-400: Green synthesis of 3-benzoyl-5-hydroxy benzofuran and naphtho[1,2-b]furan derivatives at room temperature
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Background: Oxygen heterocycles exhibit diverse biological and pharmacological activities. In particular, benzofurans are available in a wide number of natural products and have drawn considerable attention over the last few years due to their profound physiological and biological properties. The aim of this paper describes a green methodology to synthesize this potent molecule with high selectivity by using ionic resin in PEG at room temperature. Methods: The methodology is very simple and easily accessible at room temperature. It uses low catalyst loadings and is recycled subsequently. In addition, detailed experimental procedure for the selected compounds including the spectral data are provided. Results: Among the various ionic resins attempted, Amberlyst-15 in PEG-400 was the choice of selection for the synthesis of 3-benzoyl-5-hydroxy benzofuran and naphtho[1,2-b]furan derivatives at room temperature in an environmentally friendly method. This catalyst system resulted in excellent yields in short reaction times and high selectivity. Conclusion: We have developed a green highly efficient and environmentally friendly protocol for the facile synthesis of 3-benzoyl-5-hydroxy benzofuran and naphtho[1,2-b]furan derivatives at room temperature in high yields (>90-95%) using nontoxic and inexpensive ion exchange resin Amberlyst-15. The notable advantages of the catalyst approach enables the reactions with high selectivity, short reactions time and excellent yields without generating any waste and was reused.
- Bathula, Surendra Bose,Khagga, Mukkanti,Venkatasubramanian, Hariharakrishnan
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p. 353 - 360
(2017/07/26)
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- INHIBITION OF CANCER CELL MOTILITY
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Provided herein are compositions and methods for inhibiting cancer cell motility and/or metastasis. In particular embodiments, KBU2046 (or an analog thereof) and one or more additional therapies (e.g., cancer therapies (e.g., hormone therapies and chemotherapies) are provided to inhibit cancer cell motility, inhibit metastasis, and/or treat cancer (e.g., prostate cancer, lung cancer, breast cancer, colon cancer, etc.).
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Page/Page column 29; 30
(2016/06/01)
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- Metal-Free Route for the Synthesis of 4-Acyl-1,2,3-Triazoles from Readily Available Building Blocks
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Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of α-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means.
- Thomas, Joice,Goyvaerts, Vince,Liekens, Sandra,Dehaen, Wim
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supporting information
p. 9966 - 9970
(2016/07/19)
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- Development of a general approach to the synthesis of a library of isoflavonoid derivatives
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Isoflavonoids are a class of organic compounds that act primarily as antioxidants. They are produced almost exclusively by various members of the bean family including soybeans, tofu, peanuts, chick peas, and alfalfa. The antioxidant characteristics that isoflavonoids exhibit help hinder the progression of certain cancers, primarily breast, prostate, and colon cancer. We have developed a three-five step synthesis for obtaining a suite of isoflavonoid derivatives. The synthesis involves an enamine formation, a ring closure and halogenation, a Suzuki coupling, and finally a global deprotection to obtain the respective isoflavonoid derivatives.
- Biegasiewicz, Kyle F.,Gordon, James S.,Rodriguez, Deana A.,Priefer, Ronny
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p. 5210 - 5212
(2014/12/11)
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- Synthesis and bioactivities of some new 1H-pyrazole derivatives containing an aryl sulfonate moiety
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A new series of 1H-pyrazole derivatives 5a-j bearing an aryl sulfonate moiety have been synthesized by a one-pot cyclo-condensation reaction of 2-(3-(dimethylamino)acryloyl)phenyl-4-methyl benzene sulfonates 4a-e and hydrazine hydrate or phenyl hydrazine
- Kendre, Babasaheb V.,Landge, Mahadev G.,Jadhav, Wamanrao N.,Bhusare, Sudhakar R.
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p. 325 - 328
(2013/07/11)
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- Facile syntheses of 2-substituted 3-cyanochromones
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A simple and general route to 3-cyanochromones containing various substituents on position 2 of the ring is developed. The method is based on condensation of 3-(2-hydroxyphenyl)-3-oxopropionitrile with acid chlorides or anhydrides in pyridine at room temp
- Levchenko,Semenova,Yarovenko,Shmelin,Krayushkin
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scheme or table
p. 3630 - 3632
(2012/09/22)
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- Synthesis of novel disubstituted pyrazolo[1,5-a]pyrimidines, imidazo[1,2-a]pyrimidines, and pyrimido[1,2-a]benzimidazolescontaining thioether and aryl moieties
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A series of novel 6-[(1,3,4-thiadiazol-2-yl)sulfanyl]-7-phenylpyrazolo[1,5- a]pyrimidines, 5-phenyl-6-[(1,3,4-thiadiazol-2-yl)sulfanyl]imidazo[1,2-a] pyrimidines, and 2-phenyl-3-[(1,3,4-thiadiazol-2-yl)sulfanyl] pyrimido[1,2-a]benzimidazoles have been synthesized in four steps starting with 2-hydroxyacetophenone. The intermediate 3-[(1,3,4-thiadiazol-2-yl)sulfanyl]-4H- 1-benzopyran-4-ones reacted with pyrazol-3-amines, 5-methylpyrazol-3-amine, and 1H-imidazol-2-amine, 1H-benzimidazol-2-amine via a cyclocondensation to give the title compounds in the presence of MeONa as base, respectively. The approach affords the target compounds in acceptable-to-good yields. The new compounds were characterized by their IR, NMR, and HR mass spectra.
- Li, Gang,Zhang, Zun-Ting,Dai, Li-Yan,Du, Yin-Li,Xue, Dong
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experimental part
p. 989 - 997
(2012/08/08)
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- Regioselective copper(I)-catalyzed C-H hydroxylation/C-S coupling: Expedient construction of 2-(styrylthio)phenols
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Regioselective copper(I)-catalyzed C-H hydroxylation/C-S coupling of aryl thiols with vinyl halides was developed. Starting from substituted aryl thiols and vinyl halides, various 2-(styrylthio)phenol derivatives were efficiently prepared. The application of the synthetic methodology to generate the bioactive organic intermediate was also exemplified.
- Xu, Run-Sheng,Yue, Lei,Pan, Yuan-Jiang
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experimental part
p. 5046 - 5052
(2012/08/07)
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- Efficient synthesis of chromones with alkenyl functionalities by the heck reaction
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The usefulness of the Heck reaction in the field of chromones has been demonstrated. Bromochromones with the halogen atom in their rings A and B were reacted with various terminal alkenes to give hitherto unknown alkenyl-substituted chromones. Reactivity of the substrates was found to markedly depend on the position of the bromine atom. Under phosphine-free conditions using a phase-transfer catalyst additive (tetrabutylammonium bromide), shorter reaction periods and usually higher yields were obtained.
- Patonay, Tams,Vasas, Attila,Kiss-Szikszai, Attila,Silva, Artur M. S.,Cavaleiro, Jos A. S.
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scheme or table
p. 1582 - 1593
(2011/08/04)
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- Efficient Synthesis of Ratiometric Fluorescent Nucleosides Featuring 3-Hydroxychromone Nucleobases
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The synthesis of a novel class of fluorescent nucleosides featuring 2-aryl-3-hydroxychromones (3-HC) as base analogues is described. Nucleoside 1a bearing the 2-thienyl-3-HC nucleobase was prepared using sequential aryl-aldol condensation/cycloetherificat
- Spadafora, Marie,Postupalenko, Victoria Y.,Shvadchak, Volodymyr V.,Klymchenko, Andrey S.,Mély, Yves,Burger, Alain,Benhida, Rachid
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supporting information; experimental part
p. 7809 - 7816
(2009/12/26)
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- Catalytic asymmetric alkylation of substituted isoflavanones
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The asymmetric alkylation of isoflavanones (3-aryl-chroman-4-ones) and protected 3-phenyl-2,3-dihydroquinolin-4(1H)-ones catalyzed by a novel cinchonidine-derived phase transfer catalyst E is reported. This functionalization occurs at the unactivated C3 methine to afford novel products that can easily be functionalized to generate more complex fused ring systems. The process accommodates a variety of isoflavanones and activated electrophiles and installs a stereogenic quaternary center in high yield and with good-to-excellent selectivity. Isoflavanones are a privileged class of natural products with a broad spectrum of biological activities including insecticidal, antimicrobial, antibacterial, estrogenic, antitumor, and anti-HIV activity. 1 Isoflavanones are also precursors for more complex natural products such as pterocarpans and rotenones.1 Given their therapeutic promise, selective strategies to access new classes of isoflavanones and related structures has high value.2 The functionalization of the C3 position could promote beneficial interactions with biological targets of interest. Specifically, an alkylation at C3 can rapidly access new members of the general class of biologically active homoisoflavanones.3
- Nibbs, Antoinette E.,Baize, Amanda-Lauren,Herter, Rachel M.,Scheidt, Karl A.
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supporting information; experimental part
p. 4010 - 4013
(2009/12/05)
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- A facile access to a novel bidentate enantiomerically pure P,N-donor ligand
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The synthesis of a new chiral P,N-donor ligand containing a phosphite and a pyrazole site and its coordination chemistry with transition metals are described. The Royal Society of Chemistry 2009.
- Seubert, Christoph K.,Sun, Yu,Thiel, Werner R.
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scheme or table
p. 4971 - 4977
(2009/09/30)
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