- Novel 4,5-dihydro-1H-pyrazole derivatives as potential succinate dehydrogenase inhibitors: design, synthesis, crystal structure, biological activity and molecular modeling
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Twenty-eight new 4, 5-dihydro-1H-pyrazole derivatives were designed, synthesized and characterized by IR, 1H NMR, 13C NMR and HRMS. The crystal structure of compound 2j was characterized by single crystal X-ray diffraction. Their ant
- Cheng, Wei,Jiang, Wenjing,Liu, Hui,Lu, Tong,Tang, Xiaorong,Wang, Jingwen,Xiao, Tingting,Zhang, Guilan,Zhang, Tingting
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- Design, synthesis, and antifungal activity evaluation of novel 2-cyano-5-oxopentanoic acid derivatives as potential succinate dehydrogenase inhibitors
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Two series of novel 2-cyano-5-oxopentanoic acid derivatives (1a?l, 2a?l) were designed, synthesized, and characterized by IR, 1H NMR, 13C NMR, and HRMS. Their in vitro antifungal activity against five plant pathogenic fungi were then
- Mai, Yong-zhan,Peng, Mi-jun,Tang, Xiao-rong,Wang, Xue-song
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- Design, synthesis and insecticidal activity of novel semicarbazones and thiosemicarbazones derived from chalcone
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Thirty semicarbazone and thiosemicarbazone derivatives (2a–w and 4a–g) from chalcones containing furan and thiophene ring were designed and synthesized. They were characterized by IR, 1H NMR, 13C NMR and HRMS. The crystal structure o
- Cheng, Wei,Xiao, Tingting,Qian, Weifeng,Lu, Tong,Zhang, Tingting,Tang, Xiaorong
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p. 3801 - 3809
(2020/03/23)
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- 6-methoxypyridine derivative and application thereof in pesticide
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The invention relates to a 6-methoxypyridine derivative and application thereof in pesticides, which belong to the technical field of pesticides. The structural formula of the 6-methoxyl pyridine derivative is shown as a formula (I), and in the formula (I
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Paragraph 0060-0062
(2021/06/22)
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- Transition metal-free domino aryl-aryl coupling/phospha-Michael addition of diarylphosphinite to α,β-unsaturated ketones triggered by alkaline hydrolysis of (4-(2-alkenoyl)phenyl)triarylphosphonium salts
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Alkaline hydrolysis of a variety of (4-(2-alkenoyl)phenyl)triarylphosphonium bromides is reported. This hydrolysis triggers coupling of 4-(2-alkenoyl)phenyl with one aryl via phosphorus(V). Both diarylphosphinite and an α,β-unsaturated ketone are in situ generated and then undergo phospha-Michael addition to provide β-diarylphosphoryl ketones bearing a biaryl moiety in 27–70% yields in the absence of a transition metal.
- Huang, Wenhua,Xue, Jing-Yu
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- 4, 5-dihydropyrazole compound and application thereof in pesticides
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The invention relates to a 4, 5-dihydropyrazole compound and an application thereof in pesticides, which belong to the technical field of pesticides. The technical problem to be solved by the invention is to provide a new compound which can be used as an
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Paragraph 0055-0057
(2020/05/14)
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- Studies of NMR Chemical Shifts of Chalcone Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
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A series of the chalcone derivatives of the five-membered monoheterocyclic compounds, (E)-1-aryl-3-heteroarylpropen-1-ones, were prepared by aldol condensation of the corresponding aldehydes of thiophene, pyrrole, and furan with m- and p-substituted acetophenones. Similar condensation of the acetyl compounds of the heterocycles with m- and p-substituted benzaldehydes gave another series of the chalcone derivatives, (E)-1-heteroaryl-3-arylpropen-1-ones. The 13C chemical shift values (δC) of the chalcone derivatives were determined in order to find if they correlated with the Hammett σ values. A good correlation, especially for the β-C for both series, was found for the 13C chemical shift values (δC) of the chalcone derivatives with the Hammett σ values. The chemical shift values of the β-C of the heterocyclic compounds were plotted against those of the benzene derivatives. The resulting slopes were found to be close to the values of the aromaticity indices.
- Jeong, Eun Jeong,Lee, In-Sook Han
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p. 668 - 673
(2019/07/12)
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- 1-(2-furyl)-3-(4-substituted phenyl)propylene derivative as well as preparation method and application thereof
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The invention provides a 1-(2-furyl)-3-(4-substituted phenyl)propylene derivative as well as a preparation method and application thereof. The derivative has a structural formula (I) shown in the following description; in the structural formula (I), R is
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Paragraph 0047; 0048
(2016/10/07)
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- 3-(2-furyl)propenol derivative as well as preparation method and application thereof
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The invention provides a 3-(2-furyl)propenol derivative as well as a preparation method and application thereof. The derivative has a structural formula (I) shown in the following description; in the structural formula (I), R is a fluorine atom, a chlorin
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Paragraph 0046; 0047
(2016/10/09)
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- Semicarbazone compound and preparation method and application thereof
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The invention provides a semicarbazone compound and a preparation method and application thereof. The structural general formula of the compound is shown in the description, wherein the R represents fluorine atoms, chlorine atoms, bromine atoms, iodine at
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Paragraph 0047; 0048
(2016/10/31)
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- Study of Regiochemical Trends During the Synthesis of Furan and 5-(p-chlorophenyl)Furan Containing Novel Spiropyrrolidine Library Through 1,3-dipolar Cycloaddition Reactions
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A new class of functionalized furan and 5-(p-chlorophenyl)furan containing spiropyrrolidines has been synthesized in moderate to excellent yields by the one-pot, three-component 1,3-dipolar cycloaddition reaction of in situ generated azomethine ylides with various furan/aryl furan-substituted chalcones as dipolarophiles. The effect of electron deficient substituents at the fifth position of the furan ring in the chalcone on the regiochemistry of the cycloaddition formed was studied. The structures of the newly synthesized cycloaddicts were proved by analytical and spectral data.
- Mallya, Sahana,Kalluraya, Balakrishna,Jois, H. S. Vidyashree
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p. 1859 - 1865
(2016/11/23)
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- Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents
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The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.
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Page/Page column 218
(2015/11/16)
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- A general, mild and efficient palladium-catalyzed 2,2,2-trifluoroethoxylation of activated aryl bromides and bromo-chalcones: Bromo-chalcones a new coupling partner in cross-coupling reaction
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An efficient protocol for Pd-catalyzed 2,2,2-trifluoroethoxylation of activated aryl bromides and bromo-chalcones has been developed. We unveil a fascinating insight into the Pd-catalyzed C-O cross-coupling reaction. Pd/tBuXPhos (L1) ligand system facilitates the C-O cross-coupling reaction between 2,2,2-trifluoroethanol and activated aryl bromides at both higher (115 °C) and lower temperatures (40 °C). Unprecedentedly, this catalyst system facilitates the C-O cross-coupling reaction in short span of reaction times, generally 5-25 min (at 115 °C). The structurally simple analogue of tBuXPhos ligand so called JohnPhos (L2) ligand is also facilitated the C-O bond formation with activated aryl bromides and bromo-chalcones. Interestingly, under the optimal conditions (L1), methanol is also coupled rapidly with activated aryl bromides. These catalyst systems (L1 and L2) fail to couple electron rich aryl bromides with 2,2,2-trifluoroethanol, thus these catalyst systems allow the reductive elimination through an electronic pathway of reductive elimination. The unusual reactivity of 2,2,2-trifluoroethanol in Pd-catalyzed C-O cross-coupling reaction makes that the chemistry of fluorinated molecules is unique than that of non-fluorinated analogues. The bromo-chalcones can be used as a new coupling partner in the cross-coupling reaction.
- Rangarajan,Devi, Kavita,Ayushee,Prasad, Ashok K.,Pal Singh, Rishi
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p. 8307 - 8314
(2015/10/05)
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- Iron-catalyzed aerobic oxidative aromatization of 1,3,5-trisubstituted pyrazolines
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A simple and high yielding method for the synthesis of tri-substituted pyrazoles via iron(III) catalyzed aerobic oxidative aromatization of pyrazolines has been reported. The process demonstrates a variety of functional group tolerance.
- Ananthnag, Guddekoppa S.,Adhikari, Adithya,Balakrishna, Maravanji S.
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p. 240 - 243
(2013/12/04)
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- 1-Acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles: Exhibiting anticancer activity through intracellular ROS scavenging and the mitochondria-dependent death pathway
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A series of 17 analogs of 1-acetyl-4,5-dihydro(1H)pyrazoles (JP-1 to JP-17) bearing two aromatic rings at positions 3 and 5, either of which ought to be heterocyclic, were synthesized and evaluated for their anti-proliferative potential against breast cancer (MCF-7 and T-47D) and lung cancer (H-460 and A-549) cell lines for the first time. JP-1-7, -10, -11, -14, and -15 were observed to exhibit significant anti-proliferative activity against MCF-7 cells. Some notions about structure-activity relationships are reported. The investigated compounds were found to lower the intracellular reactive oxygen species in the H2DCFDA assay and also caused mitochondria-dependent cell death in the MCF-7 cell line, indicating a plausible mechanism of their anticancer effect. Analogs of 1-acetyl-4,5-dihydro(1H)pyrazoles (JP-1-17) were synthesized and evaluated for their anti-proliferative activity in four cancer cell lines and for their intracellular ROS scavenging properties. An attempt was made to determine the mitochondrial membrane potential of MCF-7 cells treated with JP-1 and -14, aiming to elucidate the mechanism by which proliferation was curbed.
- Alex, Jimi M.,Singh, Sandeep,Kumar, Raj
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p. 717 - 727
(2016/02/18)
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- Synthesis and biological evaluation of some new 4-aryl-1-(4,6-diaryl pyrimidine)-2-azetidinone by conventional and microwave methods and their biological activities
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4-Aryl-1-(4,6-diaryl pyrimidine)-2-azetidinone/4-aryl-3-chloro-1-(4,6- diaryl pyrimidine)-2-azetidinone were prepared by reaction of appropriate 2-(methoxy phenylideneamino)-4-diaryl pyrimidine (Schiff base) and acetyl chloride/chloroacetylchloride in dim
- Sharma, Sharda,Jain, Renuka,Sharma, Vikas,Chawla, Chetali
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p. 221 - 229
(2013/06/04)
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- Microwave assisted synthesis and antibacterial activity of chalcone derivatives
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Chalcone derivatives have been synthesized by equimolar reactions between substituted aldehydes and substituted acetophenones in basic medium by using conventional and microwave assisted technique. These compounds are characterized by FTIR and 1H NMR spectra. Before characterization purity of these compounds has been checked by thin-layer chromatography method. These synthesized compounds have been screened for their antibacterial (E. coli, S. aureus) activities in different concentrations. The results showed that the chalcone derivatives are better at inhibiting growth of both types of bacteria (Gram negative and Gram positive) compared to chloramphenicol.
- Yadav, Khushbu,Sharma, Abha,Srivastava, J. N.
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p. 5779 - 5781,3
(2020/09/14)
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- Structure-activity relationship of pyrrole based S-nitrosoglutathione reductase inhibitors: Carboxamide modification
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The enzyme S-nitrosoglutathione reductase (GSNOR) is a member of the alcohol dehydrogenase family (ADH) that regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). GSNO and SNOs are implicated in the pathogenesis of many diseases including those in respiratory, gastrointestinal, and cardiovascular systems. The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious GSNOR inhibitor which is currently in clinical development for acute asthma. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogs of N6022 focusing on carboxamide modifications on the pendant N-phenyl moiety. We have identified potent and novel GSNOR inhibitors that demonstrate efficacy in an ovalbumin (OVA) induced asthma model in mice.
- Sun, Xicheng,Qiu, Jian,Strong, Sarah A.,Green, Louis S.,Wasley, Jan W.F.,Blonder, Joan P.,Colagiovanni, Dorothy B.,Stout, Adam M.,Mutka, Sarah C.,Richards, Jane P.,Rosenthal, Gary J.
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scheme or table
p. 2338 - 2342
(2012/04/18)
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- Discovery and modification of sulfur-containing heterocyclic pyrazoline derivatives as potential novel class of β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors
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A series of sulfur-containing heterocyclic pyrazoline derivatives (C1-C18; D1-D9) have been synthesized and purified (all are new except one) to screen for FabH inhibitory activity. Compound C14 showed the most potent biological activity against Escherich
- Yang, Yu-Shun,Zhang, Fei,Gao, Chao,Zhang, Yan-Bin,Wang, Xiao-Liang,Tang, Jian-Feng,Sun, Jian,Gong, Hai-Bin,Zhu, Hai-Liang
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supporting information; experimental part
p. 4619 - 4624
(2012/08/07)
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- Design, synthesis, and bioactivities screening of a diaryl ketone-inspired pesticide molecular library as derived from natural products
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Three natural products, 1,5-diphenylpentan-1-one, 1,5-diphenylpent-2-en-1-one, and 3-hydroxy-1,5-diphenylpentan-1-one, with good insecticidal activities were extracted from Stellera chamaejasme L. Based on their shared diaryl ketone moiety as 'pharmacophores', a series of diaryl ketones were synthesized and tested for insecticidal activity, acetylcholinesterase inhibitory activity, and antifungal activity. All synthesized compounds showed poor insecticidal and acetylcholinesterase inhibitory activities. Compound III with a furyl ring showed strong activities against plant pathogenic fungi. The IC50 of compound (E)-1-(2,4-dichlorophenyl)-3-(furan-2-yl)- -prop-2-en-1-one (III2) was 1.20mg/L against Rhizoctonia solani, suggesting its strong potential as a novel antifungal drug.
- Zhang, Hong,Jin, Hong,Ji, Lan-Zhu,Tao, Ke,Liu, Wei,Zhao, Hao-Yu,Hou, Tai-Ping
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experimental part
p. 94 - 100
(2012/06/01)
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- Synthesis and anti-bacterial activity of some heterocyclic chalcone derivatives bearing thiofuran, furan, and quinoline moieties
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36 Novel heterocyclic chalcone derivatives were synthesized and tested for their anti-bacterial activity. Some compounds presented good anti-microbial activities against Gram-positive bacteria (including the multidrug-resistant clinical isolates). This cl
- Zheng, Chang-Ji,Jiang, Sheng-Ming,Chen, Zhen-Hua,Ye, Bai-Jun,Piao, Hu-Ri
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experimental part
p. 689 - 695
(2012/06/01)
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- Potassium-tertiary butoxide-assisted addition of thioglicolic acid to chalcone derivatives under solvent-free conditions
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A series of chalcone derivatives containing thioglicolic acid (4a-j) was prepared by addition of thioglicolic acid to the chalcones (3a-j) in the presence of KOt-Bu under solvent-free conditions. The mechanistic pathway of the reaction can be explained by
- Ceylan, Mustafa,Guerdere, Meliha Burcu,Gezegen, Hayreddin,Budak, Yakup
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experimental part
p. 2598 - 2606
(2010/10/03)
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- Synthesis and biological activity of 4,6-substituted aryl-1-acetyl pyrimidine-2-ols
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The synthesis of 4-(4'-bromophenyl)-6-substituted aryl-1-acetyl-pyrimidine-2-ols have been reported. The synthesized derivatives were characterized by elemental analysis and spectral data (IR and 1H NMR). All the synthesized derivatives have been evaluated for their antimicrobial and anthelmintic activities against microbes and helminthes.
- Bamnela, Rita,Shrivastava
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experimental part
p. 6553 - 6558
(2010/12/25)
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- Screening of biological activities of a series of chalcone derivatives against human pathogenic microorganisms
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In an effort to develop new antimicrobial agents, a series of chalcone derivatives, 3-60, were prepared by Claisen-Schmidt condensation of appropriate acetophenones and 2-furyl methyl ketones with appropriate aromatic aldehydes, furfural, and thiophene-2-carbaldehyde in an aqueous solution of NaOH and EtOH at room temperature. The synthesized compounds were characterized by means of their IR- and NMR-spectral data, and elemental analysis. All compounds were tested for their antibacterial and antifungal activities by the disc diffusion method. For the most active compounds, also minimum inhibitory concentrations (MICs) were determined.
- Karaman, Isa,Gezegen, Hayreddin,Guerdere, M. Burcu,Dingil, Alparslan,Ceylan, Mustafa
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experimental part
p. 400 - 408
(2010/09/04)
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