- New pentadienone oxime ester derivatives: synthesis and anti-inflammatory activity
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To develop novel anti-inflammatory agents, a series of new pentadienone oxime ester compounds were designed and synthesized. The structures were determined by IR, 1H NMR, 13C NMR, and HRMS. All compounds have been screened for their anti-inflammatory activity by evaluating their inhibition against LPS-induced nitric oxide (NO) release in RAW 264.7 cell. Among them, compound 5j was found to be one of the most potent compounds in inhibiting NO and IL-6 (IC50 values were 6.66 μM and 5.07 μM, respectively). Preliminary mechanism studies show that title compound 5j could significantly suppress expressions of nitric oxide synthase, COX-2, and NO, IL-6 through Toll-like receptor 4/mitogen-activated protein kinases/NF-κB signalling pathway. These data support further studies to assess rational design of more efficient pentadienone oxime ester derivatives with anti-inflammatory activity in the future.
- Li, Qin,Zhang, Juping,Xue, Wei,Chen, Liu Zeng,Wang, Jie Quan,Tang, Wen Jian,Liu, Xin Hua,Zhou, Hai Ping
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Read Online
- Novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments: Design, synthesis and bioactivity
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A series of novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether moieties were designed and synthesized. Their anticancer activities were evaluated by MTT assay, the results showed that most compounds exhibited extremely inhibitory effects against hepatoma SMMC-7721 cells. In particular, compounds Q2 and Q8 displayed the more potent inhibitory activity with IC50 values of 0.64 and 0.63 μM, which were better than that of gemcitabine (1.40 μM). Further mechanism studies indicated that compounds Q2, Q8, Q13 and Q19 could control the migration of SMMC-7721 cells effectively, and inhibit the proliferation of cancer cells by inhibiting the DNA replication. Western-blot results showed that compounds Q2 and Q8 induced irreversible apoptosis of SMMC-7721 cells by regulating the expression level of apoptose-related proteins. Those studies demonstrated that the penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments merited further research as potential anticancer agents.
- Su, Shijun,Chen, Mei,Li, Qin,Wang, Yihui,Chen, Shuai,Sun, Nan,Xie, Chengwei,Huai, Ziyou,Huang, Yinjiu,Xue, Wei
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Read Online
- Organocatalytic diastereo- And enantioselective oxa-hetero-Diels-Alder reactions of enones with aryl trifluoromethyl ketones for the synthesis of trifluoromethyl-substituted tetrahydropyrans
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Tetrahydropyran derivatives are found in bioactives, and introduction of the trifluoromethyl group into molecules often improves biofunctions. Here we report diastereo- and enantioselective oxa-hetero-Diels-Alder reactions catalyzed by amine-based catalyst systems that afford trifluoromethyl-substituted tetrahydropyranones. Catalyst systems and conditions suitable for the reactions to provide the desired diastereomer products with high enantioselectivities were identified, and various trifluoromethyl-substituted tetrahydropyranones were synthesized with high diastereo- and enantioselectivities. Mechanistic investigation suggested that the reactions involve a [4 + 2] cycloaddition pathway, in which the enamine of the enone acts as the diene and the ketone carbonyl group of the aryl trifluoromethyl ketone acts as the dienophile. In this study, tetrahydropyran derivatives with the desired stereochemistry that are difficult to synthesize by previously reported methods were concisely obtained, and the range of tetrahydropyran derivatives that can be synthesized was expanded. This journal is
- Pasha, Maira,Tanaka, Fujie
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supporting information
p. 9242 - 9250
(2021/11/16)
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- Dopamine D2 receptor selective agonist and application thereof
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The invention relates to a dopamine D2 receptor selective agonist and application thereof. Specifically, the invention discloses an agonist with selectivity to DRD2 and discloses a potential application value of the agonist in disease treatment. The invention discloses an agonist with DRD2 selectivity for the first time, and the specific targeting DRD2 of the agonist can play a role in treating low dopamine related diseases such as Parkinson's disease, attention deficit hyperactivity disorder, pituitary adenoma, hyperprolactinemia, hyperactivity leg syndrome, negative schizophrenia and the like while side effects are reduced to the maximum extent.
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Paragraph 0203-0204
(2020/12/29)
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- Synthesis and biological evaluation of myricetin-pentadienone hybrids as potential anti-inflammatory agents in vitro and in vivo
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Some important pro-inflammatory cytokines such as interleukin-6, tumor necrosis factor-α and nitric oxide are thought to play key roles in the destruction of cartilage and bone tissue in joints affected by rheumatoid arthritis. In the present study, a series of new myricetin-pentadienone hybrids were designed and synthesized. Majority of them effectively inhibited the expressions liposaccharide-induced secretion of IL-6, TNF-α and NO in RAW264.7. The most prominent compound 5o could significantly decrease production of above inflammatory factors with IC50 values of 5.22 μM, 8.22 μM and 9.31 μM, respectively. Preliminary mechanism studies indicated that it could inhibit the expression of thioredoxin reductase, resulting in inhibiting of cell signaling pathway nuclear factor (N-κB) and mitogen-activated protein kinases. Significantly, compound 5o was found to effectively inhibit Freund's complete adjuvant induced rat adjuvant arthritis in vivo.
- Chen, Liu Zeng,Han, Xu,Liu, Chao,Liu, Xin Hua,Xue, Wei,Yu, Pei Jing
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supporting information
(2020/02/04)
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- Dehydrozingerone derivative and preparation method and application thereof
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The invention provides a dehydrozingerone derivative as shown in the description. R-R are each independently selected from hydrogen or halogen or a nitro group or an alkyl group or a substitutedalkoxy group or an alkoxy group or a hydroxyl group; the substituent in the substituted alkoxy group is selected from one or multiple of halogen, a nitro group and a hydroxyl group; R and R areeach independently selected from hydrogen or halogen or nitrogen-containing heterocycle; R is selected from an alkyl group or an alkoxy group or a substituted alkoxy group; the substituent in thesubstituted alkyl group is selected from one or multiple of halogen, a nitro group and a hydroxyl group; X is selected from a hetero atom or a hydroxylamine group. The dehydrozingerone derivative hasbroad-spectrum activity against plant pathogenic fungi and bacteria, and has certain nematicidal activity, and is a lead compound with the broad biological activity.
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Paragraph 0084-0087; 0088; 0096
(2019/11/20)
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- Quinoxaline-containing pentadiene ketone oxime ester compound and production method and application thereof
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The invention relates to a quinoxaline-containing pentadiene ketone oxime ester compound and a production method and application thereof. The compound is as shown in a formula A, wherein X is selectedfrom O, R1 is one of phenyl, substituted phenyl and substituted heterocyclyl, R2 is one of phenyl, substituted phenyl, substituted heterocyclyl and substituted benzyl, and R3 is a hydrogen atom or achlorine atom or the like. The compound has a good control effect on tobacco mosaic viruses.
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Paragraph 0071; 0072
(2019/10/01)
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- Quinoxaline-containing 1,4-pentadiene-3-ketones derivative, preparation method and application thereof
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The invention discloses a quinoxaline-containing 1,4-pentadiene-3-ketones derivative, a preparation method and an application thereof. The ketones derivative is as shown in the general structure (I) in the specification, wherein R1 is phenyl, substituted phenyl or substituted aromatic heterocyclic group; R is more than one hydrogen atom, methoxy group, nitro group, methyl group, trifluoromethyl group or halide atom on the 5,6,7 or 8 sites in the quinoxaline structure. The derivative has excellent inhibitory activity on liver cancer SMMC-7721 cells, shows relatively high anti-tumor activity andcan be used as a potential anti-tumor medicament.
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Paragraph 0015
(2018/10/11)
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- Boehmite - An efficient and recyclable acid-base bifunctional catalyst for aldol condensation reaction
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In this work boehmite was used as an acid-base bifunctional catalyst for aldol condensation reactions of aromatic aldehydes and ketones. The catalyst was prepared by simple sol-gel method using Al(NO3)3 · 9H2O and NH4OH as precursors. The catalyst has been characterized by X-ray diffraction (XRD), Fourier Transform Infrared (FTIR), Scanning Electron Microscopy (SEM), UV-visible spectroscopy (DRS), BET surface area analyses. Boehmite is successfully applied as catalyst for the condensation reaction between 4-nitrobenzaldehyde and acetone as a model substrate giving α,β-unsaturated ketones without any side product. The scope of the reaction is extended for various substituted aldehydes. A probable mechanism has been suggested to explain the cooperative behavior of the acidic and basic sites. The catalyst is environmentally friendly and easily recovered from the reaction mixture. Also the catalyst is reusable up to 3 catalytic cycles.
- Reshma, P.C. Rajan,Vikneshvaran, Sekar,Velmathi, Sivan
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p. 4270 - 4275
(2018/01/11)
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- Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin
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Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose-response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues.
- Deck, Lorraine M.,Hunsaker, Lucy A.,Vander Jagt, Thomas A.,Whalen, Lisa J.,Royer, Robert E.,Vander Jagt, David L.
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supporting information
p. 854 - 865
(2017/12/13)
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- Evaluation of sulphonamide derivatives acting as inhibitors of human carbonic anhydrase isoforms I, II and Mycobacterium tuberculosis β-class enzyme Rv3273
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A series of novel sulphonamide derivatives was obtained from sulphanilamide which was N4-alkylated with ethyl bromoacetate followed by reaction with hydrazine hydrate. The hydrazide obtained was further reacted with various aromatic aldehydes. The novel sulphonamides were characterised by infrared, mass spectrometry, 1H- and 13C-NMR and purity was determined by high-performance liquid chromatography (HPLC). Human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and II and Mycobacterium tuberculosis β-CA encoded by the gene Rv3273 (mtCA 3) inhibition activity was investigated with the synthesised compounds which showed promising inhibition. The KIs were in the range of 54.6 nM–1.8 μM against hCA I, in the range of 32.1 nM–5.5 μM against hCA II and of 127 nM–2.12 μM against mtCA 3.
- Wani, Tanvi V.,Bua, Silvia,Khude, Pravin S.,Chowdhary, Abdul H.,Supuran, Claudiu T.,Toraskar, Mrunmayee P.
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p. 962 - 971
(2018/05/29)
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- Design, synthesis and biological evaluation of tricyclic pyrazolo[1,5-c][1,3]benzoxazin-5(5H)-one scaffolds as selective BuChE inhibitors
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Based on the structural analysis of tricyclic scaffolds as butyrylcholinesterase (BuChE) inhibitors, a series of pyrazolo[1,5-c][1,3]benzoxazin-5(5H)-one derivatives were designed, synthesized and evaluated for their acetylcholinesterase (AChE) and BuChE inhibitory activity. Compounds with 5-carbonyl and 7- or/and 9-halogen substitutions showed potential BuChE inhibitory activity, among which compounds 6a, 6c and 6g showed the best BuChE inhibition (IC50 = 1.06, 1.63 and 1.63 μM, respectively). The structure–activity relationship showed that the 5-carbonyl and halogen substituents significantly influenced BuChE activity. Compounds 6a and 6g were found nontoxic, lipophilic and exhibited remarkable neuroprotective activity and mixed-type inhibition against BuChE (Ki = 7.46 and 3.09 μM, respectively). Docking studies revealed that compound 6a can be accommodated into BuChE via five hydrogen bonds, one Pi–Sigma interaction and three Pi–Alkyl interactions.
- Qiu, Guo-Liang,He, Shao-Sheng,Chen, Shi-Chao,Li, Bo,Wu, Hui-Hui,Zhang, Jing,Tang, Wen-Jian
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p. 1506 - 1515
(2018/10/15)
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- Tricyclic pyrromonazole [1,5-c][1,3] benzoxazinone derivative as well as preparation method and purpose thereof
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The invention discloses a tricyclic pyrromonazole [1,5-c][1,3] benzoxazinone derivative, which has the following structure general formula I shown in the description, wherein R1 is halogen, C1-C6-alkyl or C1-C6-alkoxy; R2 is halogen, C1-C6-alkyl or C1-C6-alkoxy; R3 is halogen, C1-C6-alkyl or C1-C6-alkoxy; R4 is halogen, C1-C6-alkyl or C1-C6-alkoxy. The invention provides a reversible and selectiveBuChE inhibitor; good cholinesterase inhibitory activity is realized; selectivity is realized on the BuChE inhibitory activity, wherein the partial preferred tricyclic pyrromonazole [1,5-c][1,3] benzoxazinone derivative has better BuChE inhibitory activity; the BuChE inhibitory activity of the partial tricyclic pyrromonazole [1,5-c][1,3] benzoxazinone derivative is superior to positive control medicine donepezil.
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Paragraph 0037; 0045-0047; 0051-0052
(2019/06/22)
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- Are triazole amide-containing 1, 4 - pentadiene - 3 - ketone compound and its preparation method and application
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The invention discloses 1,4-pentadiene-3-ketone compounds containing triazole amide, which has a structure general formula (I) shown in the specification. The invention relates to the technical fields of chemicals and pesticides. The invention also discloses a preparation method of the triazole amide 1,4-pentadiene-3-amide ketone compounds. The compounds disclosed by the invention are good in stability, has good insecticidal activity, and is used for preparing pesticides or agents for crops.
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Paragraph 0097; 0098; 0099
(2017/08/25)
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- [...] propoxycyclohexyl the pentadiene ketone compound, preparation method and application
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The invention discloses a compound of resisting plant viruses: a pentadienone compound containing quinazolinone aryloxy and a preparation method and biological activity. The invention introduces a series of novel pentadienone derivatives containing quinazolinone aryloxy which are synthesized by six steps by taking substituted o-aminobenzoic acid, formamide, 35% formalin, 1, 4-dioxane, thionyl chloride, hydroxyl benzaldehyde, acetone, sodium hydroxide, hydrochloric acid, potassium carbonate, potassium iodide, substituted aromatic aldehyde, substituted heterocyclic aldehyde and the like as raw materials. The compound disclosed by the invention further has higher treating, protecting and passivating and inhibiting effects to cucumber mosaic virus (CMV), tobacco mosaic virus (TMV), southern rice black streaked dwarf virus (SRBSDV) and rice stripe virus (RSV), shows higher anti-plant virus activity, and can be used for preparing anti-plant virus pesticides.
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Paragraph 0072-0073
(2017/01/12)
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- Discovery of New Monocarbonyl Ligustrazine-Curcumin Hybrids for Intervention of Drug-Sensitive and Drug-Resistant Lung Cancer
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The elevation of oxidative stress preferentially in cancer cells by inhibiting thioredoxin reductase (TrxR) and/or enhancing reactive oxygen species (ROS) production has emerged as an effective strategy for selectively targeting cancer cells. In this study, we designed and synthesized 21 ligustrazine-curcumin hybrids (10a-u). Biological evaluation indicated that the most active compound 10d significantly inhibited the proliferation of drug-sensitive (A549, SPC-A-1, LTEP-G-2) and drug-resistant (A549/DDP) lung cancer cells but had little effect on nontumor lung epithelial-like cells (HBE). Furthermore, 10d suppressed the TrxR/Trx system and promoted intracellular ROS accumulation and cancer cell apoptosis. Additionally, 10d inhibited the NF-κB, AKT, and ERK signaling, P-gp-mediated efflux of rhodamine 123, P-gp ATPase activity, and P-gp expression in A549/DDP cells. Finally, 10d repressed the growth of implanted human drug-resistant lung cancer in mice. Together, 10d acts a novel TrxR inhibitor and may be a promising candidate for intervention of lung cancer.
- Ai, Yong,Zhu, Bin,Ren, Caiping,Kang, Fenghua,Li, Jinlong,Huang, Zhangjian,Lai, Yisheng,Peng, Sixun,Ding, Ke,Tian, Jide,Zhang, Yihua
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p. 1747 - 1760
(2016/03/25)
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- Dihydropyrazole derivatives as telomerase inhibitors: Structure-based design, synthesis, SAR and anticancer evaluation in vitro and in vivo
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It is of our interest to generate and identify novel compounds with regulation telomerase for cancer therapy. In order to carry out more rational design, based on structure-based drug design, several series of N-substituted-dihydropyrazole derivatives, totally 78 compounds as potential human telomerase inhibitors were designed and synthesized. The results demonstrated that some compounds had potent anticancer activity against four tumor cell lines, and showed good selectivity on tumor cells over somatic cells. By the modified TRAP assay, compound 13i exhibited the most potent inhibitory activity against telomerase with an IC50 value of 0.98 μM. In vivo evaluation results indicated that compound 13i could inhibit growth of S180 and HepG2 tumor-bearing mice, and it also significantly enhanced the survival rate of EAC tumor-bearing mice. The further results in vivo confirmed that it could significantly improve pathological changes of N,N-diethylnitrosamine (DEN)-induced rat hepatic tumor. These data support further studies to assess rational design of more efficient telomerase inhibitors in the future.
- Wang, Yang,Cheng, Fei Xiong,Yuan, Xiao Long,Tang, Wen Jian,Shi, Jing Bo,Liao, Chen Zhong,Liu, Xin Hua
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p. 231 - 251
(2016/05/02)
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- Identification of human telomerase inhibitors having the core of N-acyl-4,5-dihydropyrazole with anticancer effects
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Eight human telomerase inhibitors (5a–5h) having the core of N-acyl-4,5-dihydropyrazole with anticancer effects were identified in this study. Biological results revealed that a few compounds had potent anticancer activities against three common tumor cell lines (SGC-7901, HepG2 and MGC-803). Among them, compound 5c, with a molecular weight of only 272.2?Da, had antiproliferative activities against SGC-7901 and MGC-803 with EC50values of 2.06?±?0.17 and 2.89?±?0.62?μM, respectively, better than 5-Fluorouracil. Compound 5c inhibited the enzyme of telomerase with an IC50value of 1.86?±?0.51?μM, surpassing the control compound, ethidium bromide. Modeling study showed that this compound can reside in the binding pocket of the telomerase/TNA:DNA hairpin complex. When the moiety of N-acyl was changed to N-sulfonyl, the gotten compounds (8a–8i) had deteriorative activities against both these three cancer cell lines and the enzyme of telomerase.
- Xiao, Xuan,Ni, Yong,Jia, Ying-Ming,Zheng, Min,Xu, Han-Fei,Xu, Jun,Liao, Chenzhong
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p. 1508 - 1511
(2016/07/27)
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- Compound and application of compound in preparation of medicines
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The invention discloses a compound and its application in a medicine. the invention specifically provides a compound as shown in the formula (I) or a stereisomer, a geometrical isomer, a tautomer, a racemate, nitric oxide, hydrate, a solvate, a metabolite, pharmaceutically acceptable salts or a prodrug of the compound as shown in the formula (I). The invention also discloses an application of the compound in preparation of a medicine. The medicine is used in treating cancers.
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Paragraph 0154; 0155; 0292
(2016/10/08)
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- ZrCl4-catalysed synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridine derivatives
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In the presence of a catalytic amount of zirconium(IV) chloride, an efficient synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridines has been developed by the reaction 2-hydroxychalcones with 3-methyl-1-phenyl-1H-pyrazol-5-amine in refluxing ethanol. All these novel compounds have been characterised by 1H NMR, 13C NMR, HRMS, IR spectra and X-ray crystallographic analysis.
- Liu, Meilin,Yin, Guodong
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p. 236 - 266
(2015/06/02)
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- Effect of phosphorus amount on the particle size and catalytic performance of heterogeneous nickel(ii) schiff-base complex in aldol condensation reaction
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The organic-inorganic hybrid of citric acid, tetraethoxysilane (TEOS), and triethylphosphate (TEP) doped by a nickel Schiff-base complex was prepared by sol-gel method. The prepared composites were characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), transmittance electron microscopy (TEM), scanning tunnelling microscopy (STM), and infrared spectroscopy (IR). In order to determine the phosphorus amount effect on the catalytic activity of the prepared composites, the aldol condensation was used as a model reaction. The results revealed that the composite with 10% phosphorus is a better catalyst in comparison with other composites.
- Eshtiagh-Hosseini, Hossein,Tabari, Taymaz
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p. 1778 - 1791
(2013/11/06)
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- Design and synthesis of novel 2-methyl-4,5-substitutedbenzo[f]-3,3a,4,5- tetrahydro-pyrazolo[1,5-d][1,4]oxazepin-8(7H)-one derivatives as telomerase inhibitors
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Eight novel 4,5-tetrahydropyrazolo[1,5-d][1,4]oxazepine derivatives have been synthesized and purified to be screened for anticancer activity. By a modified TRAP assay, some titled compounds were tested against telomerase, and compound 4a showed the most potent inhibitory activity with IC50 value at 0.78 ± 0.22 μM. Western blot assays showed that compounds 4a and 4b could inhibit expression of Cyclin D1, TERT, phospho-AKT and PI3K/AKT pathway.
- Liu, Xin-Hua,Jia, Ying-Ming,Song, Bao-An,Pang, Zhi-Xiang,Yang, Song
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p. 720 - 723
(2013/03/13)
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- Organocatalyzed michael-michael cascade reaction: Asymmetric synthesis of polysubstituted chromans
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An enantioselective cascade Michael-Michael reaction between chalcones enolates and nitromethane catalyzed by a bifunctional thiourea is developed. This reaction provides a mild but efficient approach to chiral benzopyrans bearing three consecutive stereocenters in high yields with excellent stereoselectivities, and the benzopyrans can be easily transformed to the corresponding tricyclic product.
- Jia, Zhen-Xin,Luo, Yong-Chun,Cheng, Xi-Na,Xu, Peng-Fei,Gu, Yu-Cheng
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p. 6488 - 6494
(2013/07/26)
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- Pd(II)-catalyzed asymmetric Wacker-type cyclization for the preparation of 2-vinylchroman derivatives with biphenyl tetraoxazoline ligands
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This article describes an efficient method for the preparation of chiral chroman derivatives by the Pd(II)-catalyzed asymmetric Wacker-type cyclization using a chelation-induced axially chiral tetraoxazoline ligand. Under the optimized conditions, up to 80% yield and up to 92% ee were obtained. This is the first example to utilize o-trisubstituted 3-butenylphenols as substrates in such transformation.
- Liu, Qingchuan,Wen, Ke,Zhang, Zhenfeng,Wu, Zhengxing,Zhang, Yong Jian,Zhang, Wanbin
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p. 5209 - 5215
(2012/08/08)
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- Design and synthesis of novel 5-phenyl-N-piperidine ethanone containing 4,5-dihydropyrazole derivatives as potential antitumor agents
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A series of novel 5-phenyl-N-piperidine ethanone-4,5-dihydropyrazole derivatives as potential telomerase inhibitors were synthesized. The bioassays demonstrated that compounds 4d, 4f, 7a and 7b occupied high antiproliferative activities against SGC-7901, MGC-803 and Bcap-37 cell lines. By a modified TRAP assay, some titled compounds were tested against telomerase, and compound 7b showed the most potent inhibitory activity with IC50 value at 2.00 ± 0.40 μM. The active compound 4d was also docked into the telomerase TERT active site to determine the probable binding model. The results indicated that conserved residues Lys189, Asp254 and Gln308 were important for ligand binding via hydrogen bond interactions.
- Liu, Xin-Hua,Li, Jun,Shi, Jing Bo,Song, Bao-An,Qi, Xing-Bao
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scheme or table
p. 294 - 299
(2012/07/14)
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- 2-Hydroxycurcuminoid induces apoptosis of human tumor cells through the reactive oxygen species-mitochondria pathway
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2-Hydroxycinnamaldehyde (HCA) and curcumin have been reported to have antitumor effects against various human tumor cells in vitro and in vivo by generation of ROS. Aldehyde-free HCA analogs were synthesized based on the structure of curcumin, which we have called 2-hydroxycurcuminoids. The hydroxyl group of curcuminoids enhances the ability to generate ROS. 2-Hydroxycurcuminoid (HCC-7) strongly inhibited the growth of SW620 colon tumor cells with a GI 50 value of 7 μM, while the parent compounds, HCA and curcumin, displayed GI50 values of 12 and 30 μM, respectively. HCC-7 was found to induce apoptosis through the reactive oxygen species-mitochondria pathway and cell cycle arrest at G2/M phase.
- Han, Young-Min,Shin, Dae-Seop,Lee, Yu-Jin,Ismail, Ismail Ahmed,Hong, Su-Hyung,Han, Dong Cho,Kwon, Byoung-Mog
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scheme or table
p. 747 - 751
(2011/03/18)
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- Design and synthesis of N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential antitumor agents
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A series of novel N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential telomerase inhibitors were synthesized. The bioassay tests show that compound 4a exhibited high activity against human gastric cancer cell SGC-7901, liver cancer Hep-G2 and human prostate PC-3 cell lines with IC 50 values of 21.23 ± 0.99, 29.43 ± 0.32 and 30.89 ± 1.07 μM, respectively. All title compounds were assayed for telomerase inhibition by a modified TRAP assay, the results show that compound 4a can inhibit telomerase with IC50 value of 4.0 ± 0.32 μM. Docking simulation was performed to position compound 4a into the telomerase (3DU6) active site to determine the probable binding model.
- Liu, Xin-Hua,Ruan, Ban-Feng,Liu, Jing-Xin,Song, Bao-An,Jing, Ling-Hong,Li, Jun,Yang, Yang,Zhu, Hai-Liang,Qi, Xing-Bao
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scheme or table
p. 2916 - 2920
(2011/06/26)
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- A simple and efficient synthesis of pyrazoles in water
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A simple, highly efficient, and environmentally friendly method for the synthesis of substituted 1H-pyrazoles by one-pot condensation reaction of α,β-unsaturated carbonyl compounds with tosyl hydrazide in water was developed. The reaction system exhibited tolerance with various functional groups, Aromatic moiety with both electron-rich and electron-deficient substituents could give desired products in good to excellent yields.
- Wen, Jun,Fu, Yun,Zhang, Ruo-Yi,Zhang, Ji,Chen, Shan-Yong,Yu, Xiao-Qi
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supporting information; experimental part
p. 9618 - 9621
(2011/12/14)
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- Di(ortho-hydroxybenzylidene)acetone as a new acid-base indicator and a chromogenic receptor for anions and guanidine
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The development of a new simple acid-base indicator di(o- hydroxybenzylidene)acetone (1) is reported as a possible alternative to phenolphthalein and its performance has been compared with those of o-hydroxybenzylideneacetone (2) and p-hydroxybenzylideneacetone (3), two synthetic compounds, and curcumin (4), a natural product occurring in turmeric. Among the four compounds, 1 is found to be the best. It may also be used in the titration of guanidine in non-aqueous solvents (e.g. in dry alcohol). It is also shown to be a chemosensor for anions.
- Goswami, Shyamaprosad,Chakrabarty, Rinku
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experimental part
p. 547 - 557
(2012/03/26)
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- Novel 2-(benzo[d]thiazol-2-yl)-1-(3-methyl-5-substituted-phenyl-4,5- dihydropyrazol-1-yl)ethanone Derivatives: Synthesis and antibacterial activity
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A series of novel 2-(benzo[d]thiazol-2-yl)-1-(3-methyl-5-substituted- phenyl-4,5-dihydropyrazol-1-yl)ethanone derivatives were synthesized and characterized by NMR, ESI-MS. Biological activity tests results show that compounds 4a, 4b, 4d and 4g displayed activity with MIC of 1.562 ?g/mL against B. subtilis ATCC 6633, compound 4d displayed significant activity with MIC of 1.562 μg/mL against S. aureus ATCC 6538. Compound 4a with potent antibacterial activities strongly inhibited S. aureus DNA gyrase and B. subtilis DNA gyrase with IC50s of 0.5 μg/ml against S. aureus DNA gyrase and B. subtilis DNA gyrase.
- Pan, Chun-Xiu,Lia, Jun,Liu, Xin-Hua
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scheme or table
p. 459 - 463
(2012/06/15)
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- Molecular iodine mediated intramolecular cyclization: An efficient method for the synthesis of benzoxepine derivatives
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A simple, efficient and cost effective method for a divergent synthesis of benzoxepine derivatives using a hitherto unreported, highly regioselective, tandem iodocyclization procedure is described.
- Majumdar,Sinha, Biswajit,Ansary, Inul,Chakravorty, Santanu
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supporting information; experimental part
p. 1407 - 1411
(2010/07/20)
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- Synthesis and molecular docking studies of novel 2-chloro-pyridine derivatives containing flavone moieties as potential antitumor agents
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A series of novel 2-chloro-pyridine derivatives containing flavone, chrome or dihydropyrazole moieties as potential telomerase inhibitors were synthesized. The bioassay tests showed that compounds 6e and 6f exhibited some effect against gastric cancer cell SGC-7901 with IC50 values of 22.28 ± 6.26 and 18.45 ± 2.79 μg/mL, respectively. All title compounds were assayed for telomerase inhibition by a modified TRAP assay, the results showed that compound 6e can strongly inhibit telomerase with IC50 value of 0.8 ± 0.07 μM. Docking simulation was performed to position compound 6e into the active site of telomerase (3DU6) to determine the probable binding model.
- Liu, Xin-Hua,Liu, Hui-Feng,Shen, Xu,Song, Bao-An,Bhadury, Pinaki S.,Zhu, Hai-Liang,Liu, Jin-Xing,Qi, Xing-Bao
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scheme or table
p. 4163 - 4167
(2010/08/20)
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- Synthesis and molecular docking study of novel coumarin derivatives containing 4,5-dihydropyrazole moiety as potential antitumor agents
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A series of novel coumarin derivatives containing 4,5-dihydropyrazole moiety as potential telomerase inhibitors were synthesized. The bioassay tests show that compound 3d exhibited potentially high activity against human gastric cancer cell SGC-7901 with IC50 value of 2.69 ± 0.60 μg/mL. All title compounds were assayed for telomerase inhibition by a modified TRAP assay, the results show that compounds 3d and 3f can strongly inhibit telomerase with IC50 values of 2.0 ± 0.07 and 1.8 ± 0.35 μM, respectively. Docking simulation was performed to position compound 3d into the telomerase (3DU6) active site to determine the probable binding model.
- Liu, Xin-Hua,Liu, Hui-Feng,Chen, Jin,Yang, Yang,Song, Bao-An,Bai, Lin-Shan,Liu, Jing-Xin,Zhu, Hai-Liang,Qi, Xing-Bao
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scheme or table
p. 5705 - 5708
(2010/11/17)
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- Direct catalytic asymmetric synthesis of highly functionalized 2-methylchroman-2,4-diols via Barbas-list aldol reaction
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A study was conducted to demonstrate the organocatalytic approach to the asymmetric synthesis of functionalized 2-methylchroman-2,4-diol products through 'Barbas-List aldol (BLA) reactions'. Investigations were conducted on the BLA reactions by screening
- Ramachary, Dhevalapally B.,Sakthidevi, Rajasekar
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scheme or table
p. 4516 - 4522
(2010/02/16)
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- Enantioselective synthesis of chromanes by iridium-catalyzed asymmetric hydrogenation of 4H-chromenes
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Iridium complexes of chiral oxazoline-based P,N-ligands proved to be efficient catalysts for the enantioselective hydrogenation of 2-aryl- and 2-alkyl-4H-chromenes. The best results were obtained with a ligand derived from threonine (ThrePHOX), which induced ee values of 95% to >99% in the hydrogenation of 2-methyl-, 2-cyclohexyl- and various 2-aryl-substituted chromenes. Georg Thieme Verlag Stuttgart.
- Valla, Carine,Baeza, Alejandro,Menges, Frederik,Pfaltz, Andreas
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experimental part
p. 3167 - 3171
(2009/06/17)
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- HETEROCYCLIC COMPOUNDS USEFUL AS ANABOLIC AGENTS FOR LIVESTOCK ANIMALS
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Compounds of formula (I) and pharmaceutically acceptable salts thereof are agonists at the beta-2 adrenoceptor. They are useful as feed additives for livestock animals.
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Page/Page column 97
(2008/06/13)
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- Method and compounds for cancer treatment utilizing NFkB as a direct or ultimate target for small molecule inhibitors
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A method is described for cancer treatment through NFκB inhibition. NFκB is a direct or ultimate target for small molecule inhibitors. These small molecule inhibitors are aimed at suppression of NFκB directly or by indirect suppression of IKK, SFK kinases, or other upstream kinases. The present invention includes small molecule inhibitors comprising three, five, and seven carbon unsaturated spacers having one or two carbonyls, flanked by substituted aryl rings. The small molecule inhibitors can be symmetrical or unsymmetrical.
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Page/Page column 4; sheet 2
(2008/06/13)
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- Benzoyl 2-methyl indoles as selective PPARγ modulators
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A series of selective PPARγ modulators (SPPARγMs) and their development from hPPARγ active screening leads 1 and 2 is described. SPPARγM 24 displayed robust anti-diabetic activity with an improved therapeutic window in comparison to a PPARγ full agonist in a rodent efficacy model. Routine screening for human PPAR ligands yielded compounds 1 and 2, both of which were sub-micromolar hPPARγ agonists. Synthetic modifications of these leads led to a series of potent substituted 3-benzyl-2-methyl indoles, a subset of which were noted to be selective PPARγ modulators (SPPARγMs). SPPARγM 24 displayed robust anti-diabetic activity with an improved therapeutic window in comparison to a PPARγ full agonist in a rodent efficacy model.
- Acton III, John J.,Black, Regina M.,Jones, A. Brian,Moller, David E.,Colwell, Lawrence,Doebber, Thomas W.,MacNaul, Karen L.,Berger, Joel,Wood, Harold B.
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p. 357 - 362
(2007/10/03)
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- POLYMETHINE DYES BASED ON BENZOPYRYLIUM IONS
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A method is described for the synthesis of a series of benzopyrylium polymethine dyes by the acid cyclization of 2-hydroxystyryl polyenyl ketones, obtained by the successive crotonic condensation of aliphatic or alicyclic ketones initially with salicylaldehyde and its alkyl or halogen derivatives and then with aromatic aldehydes containing a p-methoxyphenyl or 9-alkylcarbazole fragment.The electronic absorption spectra of the new benzopyrylium dyes were studied.
- Makin, S. M.,Markina, T. A.,Boiko, I. I.
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p. 2182 - 2187
(2007/10/02)
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