- New thiazole-2(3H)-thiones containing 4-(3,4,5-trimethoxyphenyl) moiety as anticancer agents
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A new series of thiazole-2(3H)-thiones containing 4-(3,4,5-trimethoxyphenyl) moiety were synthesized as diaryl-heterocylic analogs of combretastatin A-4 with anticancer activity. The cytotoxicity evaluation of synthesized compounds against cancer cell lin
- Ansari, Mahsa,Shokrzadeh, Mohammad,Karima, Saeed,Rajaei, Shima,Fallah, Marjan,Ghassemi-Barghi, Nasrin,Ghasemian, Majid,Emami, Saeed
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Read Online
- Identification of novel non-toxic and anti-angiogenic α-fluorinated chalcones as potent colchicine binding site inhibitors
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α-Fluorinated chalcones were prepared and evaluated for their cell growth inhibitory properties against six human cancer cell lines. The most potent chalcone 4c demonstrated excellent selective toxicity against cancer cells versus normal human cells, with
- Sun, Moran,Yuan, Minghua,Kang, Yingying,Qin, Jinling,Zhang, Yixin,Duan, Yongtao,Wang, Longfei,Yao, Yongfang
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p. 339 - 354
(2022/01/10)
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- Antiproliferative Activity of Diarylnaphthofurans through Microtubule Destabilization
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The present communication deals with pharmacophore designing based on “Fragment-Based Drug Discovery” approach. Two series of compounds were synthesized and evaluated against human cancer cell lines by sulforhodamine assay, target studies through tubulin
- Bhukya, Balakishan,Chanda, Debabrata,Kaushal, Tanu,Khan, Feroz,Khan, Sana,Konwar, Rituraj,Kumar, Deepak,Kumar, Shailesh,Luqman, Suaib,Meena, Abha,Negi, Arvind S.,Parveen, Shahnaz,Singh, Diksha
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p. 443 - 455
(2021/11/22)
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- Alkylation of monomeric, dimeric, and polymeric lignin models through carbon-hydrogen activation using Ru-catalyzed Murai reaction
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In this study, we have assessed directed carbon-hydrogen activation (CHA) for alkylation of monomeric, dimeric, and polymeric lignin models using Murai's catalyst [RuH2(CO)(PPh3)3]. Based on related work from our laboratory showing that isolated organosolv lignin bears benzylic directing groups ideal for CHA reactions, this approach could offer new methodology for the valorization of biorefinery lignin. Monomeric and dimeric models bearing a keto group at the benzylic position undergo Ru-catalyzed alkylation in good to excellent yield. Similarly, models bearing a benzylic OH group also undergo alkylation via a tandem oxidation/alkylation process enabled by the Ru catalyst. Polymeric models show low levels of functionalization as a result of the poor solubility of the starting polymer. With unsymmetrical models, functionalization occurs first at the least sterically hindered ortho-site, but a subsequent alkylation, leading to disubstituted products can occur at the more sterically hindered site, leading to hexasubstituted arenes. The reaction shows sensitivity to free phenolic OH groups, which appears to reduce the yield in some reactions, and is also a contributing factor to the low yields observed with polymeric lignin models. Combining CHA methodology with lignin isolation technology able to introduce appropriate directing groups for catalytic functionalization will form the basis for improved conversion of lignin to high value chemical products.
- Zuleta, Ernesto C.,Bozell, Joseph J.
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- 1,3,4-thiadiazine compound and application thereof
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The invention relates to a 1,3,4-thiadiazine compound, and the chemical structure of the compound is shown as a formula (I). The provided compound has a remarkable inhibition effect on human cervicalcancer cells Hela and human colon cancer cells HCT116, a
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Paragraph 0023-0025; 0031; 0039-0040
(2020/08/06)
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- In(OTf)3-catalyzed intramolecular hydroarylation of α-phenylallyl β-ketosulfones - synthesis of sulfonyl 1-benzosuberones and 1-tetralones
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In(OTf)3-catalyzed intramolecular hydroarylation of α-phenylallyl β-ketosulfones provides sulfonyl 1-benzosuberones and 1-tetralones in moderate to good yields in refluxing (CH2Cl)2under open-vessel and easy-operation reaction conditions. A plausible mechanism is proposed and discussed. This highly regioselective protocol provides an atom-economic ring-closure route.
- Chang, Meng-Yang,Chang, Yu-Lun,Lai, Kai-Xiang
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p. 18231 - 18244
(2020/06/08)
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- Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study
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Based on our prior work, we reported the design, synthesis, and biological evaluation of fifty-two new triazolothiadiazine-based analogues of CA-4 and their preliminary structure-activity relationship. Among synthesized compounds, Iab was found to be the most potent derivative possessing IC50 values ranging from single-to double-digit nanomolar in vitro, and also exhibited excellent selectivity over the normal human embryonic kidney HEK-293 cells (IC50 > 100 μM). Further mechanistic studies revealed that Iab significantly blocked tubulin polymerization and disrupted the intracellular microtubule network of A549 cells. Moreover, Iab induced G2/M cell cycle arrest by regulation of p-cdc2 and cyclin B1 expressions, and caused cell apoptosis through up-regulating cleaved PARP and cleaved caspase-3 expressions, and down-regulating of Bcl-2. Importantly, in vivo, Iab effectively suppressed tumor growth of A549 lung cancers in a xenograft mouse model without obvious signs of toxicity, confirming its potential as a promising candidate for cancer treatment.
- Ma, Weifeng,Chen, Peng,Huo, Xiansen,Ma, Yufeng,Li, Yanhong,Diao, Pengcheng,Yang, Fang,Zheng, Shengquan,Hu, Mengjin,You, Wenwei,Zhao, Peiliang
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- Highly Selective Oxidation and Depolymerization of α,γ-Diol-Protected Lignin
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Lignin oxidation offers a potential sustainable pathway to oxygenated aromatic molecules. However, current methods that use real lignin tend to have low selectivity and a yield that is limited by lignin degradation during its extraction. We developed stoichiometric and catalytic oxidation methods using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively deprotect the acetal and oxidize the α-OH into a ketone. The oxidized lignin was then depolymerized using a formic acid/sodium formate system to produce aromatic monomers with a 36 mol % (in the case of stoichiometric oxidation) and 31 mol % (in the case of catalytic oxidation) yield (based on the original Klason lignin). The selectivity to a single product reached 80 % (syringyl propane dione, and 10–13 % to guaiacyl propane dione). These high yields of monomers and unprecedented selectivity are attributed to the preservation of the lignin structure by the acetal.
- Lan, Wu,de Bueren, Jean Behaghel,Luterbacher, Jeremy S.
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p. 2649 - 2654
(2019/02/01)
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- Design, synthesis and biological evaluation of flexible and rigid analogs of 4H-1,2,4-triazoles bearing 3,4,5-trimethoxyphenyl moiety as new antiproliferative agents
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Several flexible and rigid analogs of 4H-1,2,4-triazoles (compounds 8a-g and 9a-g) bearing trimethoxyphenyl pharmacophoric unit, were designed and synthesized as potential anticancer agents. The in vitro cytotoxic assay indicated that both flexible and rigid analogs (8 and 9, respectively) can potentially inhibit the growth of cancerous cells (A549, MCF7, and SKOV3), with IC50 values less than 5.0 μM. Furthermore, compounds 10a-l as regional isomers of compounds 9 exhibited remarkable cytotoxic activity with IC50 values ranging from 0.30 to 5.0 μM. The rigid analogs 9a, 10h and 10k were significantly more potent than etoposide against MCF7, SKOV3 and A549 cells, respectively. These compounds showed high selectivity towards cancer cells over normal cells, as they had no significant cytotoxicity against L929 cells. In addition, the representative compounds 9a and 10h could inhibit the tubulin polymerization at micro-molar levels. By determining changes in the colchicine-tubulin fluorescence, it was suggested that compound 10h could bind to the tubulin at the colchicine pocket. The molecular docking study further confirmed the inhibitory activity of promising compounds 9a, 10h and 10k on tubulin polymerization through binding to the colchicine-binding site.
- Ansari, Mahsa,Shokrzadeh, Mohammad,Karima, Saeed,Rajaei, Shima,Hashemi, Seyedeh Mahdieh,Mirzaei, Hassan,Fallah, Marjan,Emami, Saeed
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- N,N,N coordinated trivalent bicyclophosphide, synthetic method and catalytic application thereof
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The invention provides a N,N,N coordinated trivalent bicyclophosphide as an organic catalyst. The chemical structural formula of the compound is shown in the description. The final N,N,N coordinated trivalent bicyclophosphide is synthesized by adopting ketone as a raw material and multiple steps of bromination, ammoniation, reduction, imidization, hydrogenation and cyclization and the like in sequence. The N,N,N coordinated trivalent bicyclophosphide is characterized by synthesis of the N,N,N coordinated trivalent bicyclophosphide with an all-new structure and all-new synthetic route for preparing the phosphorus compound; simultaneously, the effective application of the N,N,N coordinated trivalent bicyclophosphide is successfully obtained, i.e., intramolecular aza Wittig reaction can be effectively catalyzed. Compared with the traditional transitional metal catalyst, the rare N,N,N coordinated trivalent bicyclophosphide has an obvious action in catalyzing an organic reaction system, and provides an all-new idea for the existing organic catalytic reaction. Compared with the traditional phosphine catalyst, the N,N,N coordinated trivalent bicyclophosphide has an obvious action in catalyzing the organic reaction system.
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Paragraph 0047; 0048; 0049; 0050; 0053; 0059-0061; 0064
(2018/07/30)
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- 7H-[1,2,4]triazole[3,4-b][1,3,4]thiadiazine-phenylhydrazone compound
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The invention discloses a 7H-[1,2,4]triazole[3,4-b][1,3,4]thiadiazine-phenylhydrazone compound as well as a preparation method and application thereof. The method comprises the following steps: adding3,4,5-trimethoxy acetophenone, N-bromo-succinimide and
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Paragraph 0013; 0021-0022
(2018/09/08)
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- Fe-Catalyzed Cycloisomerization of Aryl Allenyl Ketones: Access to 3-Arylidene-indan-1-ones
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A cycloisomerization of aryl allenyl ketones to 3-arylidene-indan-1-ones using a cationic Fe-complex as a catalyst is reported. The catalyst opens a synthetically interesting reaction pathway to this surprisingly underrepresented class of indanones that are not accessible using alternative catalytic systems.
- Teske, Johannes,Plietker, Bernd
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supporting information
p. 2257 - 2260
(2018/04/27)
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- O,O,N-ligand trivalent bicyclic phosphide, synthetic method and catalysis application
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The invention relates to an O,O,N-ligand trivalent bicyclic phosphide as an organic catalyst, and a chemical structural formula of the above compound is shown as the specification, substituent R1 andR2 can be any one of alkyl or nitro group such as hydrogen or methyl or ethyl or isopropyl or t-butyl, nitro group, cyano group, carbonyl group, and trifluoromethyl group, and the substituent position, number and conjugate position are not fixed. The synthetic method takes conventional ketone as a raw material, the multiple steps of bromination, ammonification, reduction, and cyclisation are carried out, and the O,O,N-ligand trivalent bicyclic phosphide can be finally synthesized. The method is used for synthesizing the O,O,N-ligand trivalent bicyclic phosphide with a novel structure, and provides a novel synthesis route for the type of the phosphor compound, and successfully achieves the effective application of the O,O,N-ligand trivalent bicyclic phosphide, which can effectively catalyzean intermolecular Wittig reaction. The rear O,O,N-ligand trivalent bicyclic phosphide has obvious effect in catalysis of an organic reaction system, can effectively catalyze the intermolecular Wittigreaction, increases the reaction rate, and shortens the reaction time.
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Paragraph 0043; 0047; 0049; 0051; 0052; 0056; 0061; 0064
(2018/07/30)
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- NOVEL BRIDGED BICYCLOALKYL-SUBSTITUTED AMINOTHIZOLES AND THEIR METHODS OF USE
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The present invention includes novel bridged bicycloalkyl-substituted aminothiazole compounds useful in preventing or treating cancer in a subject in need thereof. The present invention also includes methods of preventing or treating cancer in a subject i
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Paragraph 0322; 0323
(2018/08/20)
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- Synthesis and cytotoxic evaluation of combretastatin A-4 analogues of benzo[b]furans
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Abstract: A series of benzo[b]furans was synthesized with modification at the 5-position of the benzene ring by introducing different aryl acetylenyl and acrylic acid moiety as combretastatin A-4 analogues. The compounds were evaluated by MTT assay for cy
- Fan, Ye,Luo, Yang,Ma, Cheng
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p. 1823 - 1832
(2017/09/26)
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- Design, synthesis and in vitro cytotoxicity studies of novel β-carbolinium bromides
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A series of novel β-carbolinium bromides has been synthesized from easily accessible β-carbolines and 1-aryl-2-bromoethanones. The newly synthesized compounds were evaluated for their in vitro anticancer activity. Among the synthesized derivatives, compounds 16l, 16o and 16s exhibited potent anticancer activity with IC50values of 50= 3.16–7.93 μM). In order to test the mechanism of cell death, we exposed castration resistant prostate cancer cell line (C4-2) to compounds 16l and 16s, which resulted in increased levels of cleaved PARP1 and AO/EB staining, indicating that β-carbolinium salts induce apoptosis in these cells. Additionally, the most potent β-carbolines 16l and 16s were found to inhibit tubulin polymerization.
- Venkataramana Reddy,Mishra, Shriprada,Tantak, Mukund P.,Nikhil, Kumar,Sadana, Rachna,Shah, Kavita,Kumar, Dalip
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supporting information
p. 1379 - 1384
(2017/03/08)
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- Synthesis and bioevaluation of N,4-diaryl-1,3-thiazole-2-amines as tubulin inhibitors with potent antiproliferative activity
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A series of N,4-diaryl-1,3-thiazole-2-amines containing three aromatic rings with an amino linker were designed and synthesized as tubulin inhibitors and evaluated for their antiproliferative activity in three human cancer cell lines. Most of the target compounds displayed moderate antiproliferative activity, and N-(2,4-dimethoxyphenyl)-4-(4-methoxyphenyl)-1,3-thiazol-2-amine (10s) was determined to be the most potent compound. Tubulin polymerization and immunostaining experiments revealed that 10s potently inhibited tubulin polymerization and disrupted tubulin microtubule dynamics in a manner similar to CA-4. Moreover, 10s effectively induced SGC-7901 cell cycle arrest at the G2/M phase in both concentrationand time-dependent manners. The molecular docking results revealed that 10s could bind to the colchicine binding site of tubulin.
- Sun, Maolin,Xu, Qile,Xu, Jingwen,Wu, Yue,Wang, Yueting,Zuo, Daiying,Guan, Qi,Bao, Kai,Wang, Jian,Wu, Yingliang,Zhang, Weige
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- Stereoselective synthesis of cis-2,6-disubstituted morpholines and 1,4-oxathianes by intramolecular reductive etherification of 1,5-diketones
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A simple and efficient, Lewis acid catalysed reductive etherification strategy for the stereoselective synthesis of cis-2,6- disubstituted morpholines and 1,4-oxathianes starting from readily available 1,5-diketones has been developed. The strategy is used in the total synthesis of morpholine-based natural products (±)-chelonin A and formal total synthesis of (±)-chelonin C.
- Gharpure, Santosh J.,Anuradha, Dandela,Prasad, Jonnalagadda V. K.,Rao, Pidugu Srinivasa
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supporting information
p. 86 - 90
(2015/01/16)
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- Stereoselective Synthesis of Lignans of Three Structural Types from a Common Intermediate, Enantioselective Synthesis of (+)-Yangambin
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Enantioselective total synthesis of (+)-yangambin was achieved. The key transformation is one-pot conjugate addition/aldol reaction that involves an enantioenriched benzyl tert-butyl sulfoxide, an enone, and gaseous formaldehyde to construct the bis(pheny
- Syed, Majid Khalil,Murray, Cian,Casey, Mike
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p. 5549 - 5556
(2014/10/15)
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- Synthesis, biological evaluation, and structure-activity relationships of tri- and tetrasubstituted olefins related to isocombretastatin A-4 as new tubulin inhibitors
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The synthesis and structure-activity relationships associated with a series of 1,1-diarylethylene tubulin polymerization inhibitors 3 and 4 are described. The key step for their preparation involves a palladium-catalyzed coupling of N-arylsulfonylhydrazon
- Aziz, Jessy,Brachet, Etienne,Hamze, Abdallah,Peyrat, Jean-Fran?ois,Bernadat, Guillaume,Morvan, Estelle,Bignon, Jér?me,Wdzieczak-Bakala, Joanna,Desravines, Déborah,Dubois, Joelle,Tueni, Marie,Yassine, Ahmad,Brion, Jean-Daniel,Alami, Mouad
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p. 430 - 442
(2013/02/23)
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- Efficient cobalt-catalyzed oxidative conversion of lignin models to benzoquinones
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Phenolic lignin model monomers and dimers representing the primary substructural units of lignin were successfully oxidized to benzoquinones in high yield with molecular oxygen using new Co-Schiff base catalysts bearing a bulky heterocyclic nitrogen base as a substituent. This is the first example of a catalytic system able to convert both S and G lignin model phenols in high yield, a process necessary for effective use of lignin as a chemical feedstock.
- Biannic, Berenger,Bozell, Joseph J.
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supporting information
p. 2730 - 2733
(2013/07/26)
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- LUMINOPHORES
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There is described a non-planar iridium-ligand complex with accessible triplet states and a molecular structure that confers liquid-crystal like properties.
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Page/Page column
(2013/06/05)
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- Synthesis and biological evaluation of a new series of N-ylides as protein farnesyltransferase inhibitors
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A new family of 30 benzoylated N-ylides 4 and 5 was synthesized and evaluated for the inhibitory activity on human protein farnesyltransferase. Most of these novel compounds possessed in vitro inhibition potencies in the micromolar range. The nature of th
- Abuhaie, Cristina-Maria,Ghinet, Alina,Farce, Amaury,Dubois, Jo?lle,Rigo, Beno?t,B?cu, Elena
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p. 5887 - 5892
(2013/10/22)
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- Substituted 3-(5-imidazo[2,1- b ]thiazolylmethylene)-2-indolinones and analogues: Synthesis, cytotoxic activity, and study of the mechanism of action(1)
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The synthesis of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2- indolinones and analogues is reported. Their cytotoxic activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. The action of selected compounds was examined for potential inhibition of tubulin assembly in comparison with the potent colchicine site agent combretastatin A-4. The most potent compounds also strongly and selectively inhibited the phosphorylation of the oncoprotein kinase Akt in cancer cells. The effect of the most interesting compounds was examined on the growth of HT-29 colon cancer cells. These compounds caused the cells to arrest in the G2/M phase of the cell cycle, as would be expected for inhibitors of tubulin assembly.
- Andreani, Aldo,Granaiola, Massimiliano,Locatelli, Alessandra,Morigi, Rita,Rambaldi, Mirella,Varoli, Lucilla,Calonghi, Natalia,Cappadone, Concettina,Farruggia, Giovanna,Stefanelli, Claudio,Masotti, Lanfranco,Nguyen, Tam L.,Hamel, Ernest,Shoemaker, Robert H.
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supporting information; experimental part
p. 2078 - 2088
(2012/05/05)
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- Emissive metallomesogens based on 2-phenylpyridine complexes of iridium(III)
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Preparation of IrIII complexes using anisotropic 2,5-di(4-alkoxyphenyl)pyridine ligands leads to emissive, liquid-crystalline complexes containing bound Cl and dimethyl sulfoxide. Using analogous poly(alkoxy) ligands allows the preparation of bis(2-phenylpyridine)iridium(III) acac complexes, which are also mesomorphic. The observation of liquid crystallinity in octahedral complexes of this type is without precedent.(Figure Presented)
- Santoro, Amedeo,Prokhorov, Anton M.,Kozhevnikov, Valery N.,Whitwood, Adrian C.,Donnio, Bertrand,Williams, J. A. Gareth,Bruce, Duncan W.
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supporting information; experimental part
p. 5248 - 5251
(2011/06/10)
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- Design, synthesis, and SAR studies of 4-substituted methoxylbenzoyl-aryl- thiazoles analogues as potent and orally bioavailable anticancer agents
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In a continued effort to improve upon the previously published 4-substituted methoxybenzoyl-aryl-thiazole (SMART) template, we explored chemodiverse "B" rings and "B" to "C" ring linkage. Further, to overcome the poor aqueous solubility of this series of agents, we introduced polar and ionizable hydrophilic groups to obtain water-soluble compounds. For instance, based on in vivo pharmacokinetic (PK) studies, an orally bioavailable phenyl-amino-thiazole (PAT) template was designed and synthesized in which an amino linkage was inserted between "A" and "B" rings of compound 1. The PAT template maintained nanomolar (nM) range potency against cancer cell lines via inhibiting tubulin polymerization and was not susceptible to P-glycoprotein mediated multidrug resistance in vitro, and markedly improved solubility and bioavailability compared with the SMART template (45a-c (PAT) vs 1 (SMART)).
- Lu, Yan,Li, Chien-Ming,Wang, Zhao,Chen, Jianjun,Mohler, Michael L.,Li, Wei,Dalton, James T.,Miller, Duane D.
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experimental part
p. 4678 - 4693
(2011/09/14)
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- COMPOUNDS FOR TREATMENT OF CANCER
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The present invention relates to novel compounds having anti-cancer activity, methods of making these compounds, and their use for treating cancer and drug-resistant tumors, e.g. melanoma, metastatic melanoma, drug resistant melanoma, prostate cancer and drug resistant prostate cancer.
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Paragraph 0037; 00311
(2011/10/03)
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- Synthesis and Biological Evaluation of New Quinoxaline Derivatives as Antioxidant and Anti-Inflammatory Agents
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We report the synthesis, anti-inflammatory, and antioxidant activities of novel quinoxaline and quinoxaline 1,4-di-N-oxide derivatives. Microwave-assisted methods have been used to optimize reaction times and to improve yields. The tested compounds presented important scavenging activities and promising in vitro inhibition of soybean lipoxygenase (LOX). Two of the best LOX inhibitors (compounds 7b and 8f) were evaluated as invivo anti-inflammatory agents using the carrageenin-induced edema model. One of them (compound 7b) showed important in vivo anti-inflammatory effect (41%) similar to that of indomethacin (47%) used as the reference drug. Synthesis and Biological Evaluation of New Quinoxaline Derivatives as Antioxidant and Anti-Inflammatory Agents Asuncion Burguete, Eleni Pontiki, Dimitra Hadjipavlou-Litina*, Saioa Ancizu, Raquel Villar, Beatriz Solano, Elsa Moreno, Enrique Torres, Silvia Perez, Ignacio Aldana and Antonio Monge The synthesis, anti-inflammatory and antioxidant activities of new quinoxaline derivatives are reported. The new compounds exhibit important scavenging activities and promising values of in vitro inhibition of soybean LOX, One of them shows strong in vivo anti-inflammatory effect similar to that of indomethacin used as the reference drug.
- Burguete, Asuncion,Pontiki, Eleni,Hadjipavlou-Litina, Dimitra,Ancizu, Saioa,Villar, Raquel,Solano, Beatriz,Moreno, Elsa,Torres, Enrique,Perez, Silvia,Aldana, Ignacio,Monge, Antonio
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scheme or table
p. 255 - 267
(2012/01/13)
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- Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity
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The α-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G2/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 μM; CA4, 0.10 μM) and compete with [3H]colchicine for binding to tubulin (8% [3H]colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity.
- Ducki, Sylvie,Rennison, David,Woo, Meiko,Kendall, Alexander,Chabert, Jeremie Fournier Dit,McGown, Alan T.,Lawrence, Nicholas J.
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experimental part
p. 7698 - 7710
(2010/03/24)
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- Synthesis and anticancer activity of novel 3,4-diarylthiazol-2(3H)-ones (imines)
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A series of 3,4-diarylthiazol-2(3H)-ones and three 3,4-diarylthiazol-2(3H)-imines were synthesized and evaluated for their cytotoxicity in a panel of human cancer cell lines. Compounds 21 and 22 showed potential anticancer activity against human CEM cells
- Liu, Zong-Ying,Wang, Yue-Ming,Li, Zhuo-Rong,Jiang, Jian-Dong,Boykin, David W.
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scheme or table
p. 5661 - 5664
(2010/04/30)
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- Effects of α-substitutions on structure and biological activity of anticancer chalcones
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Chalcones are known to exhibit antimitotic properties caused by inhibition of tubulin polymerisation. We describe here the effects of different α-substitutions, in particular α-fluorination, on the structure and biological activity of a series of chalcones.
- Lawrence, Nicholas J.,Patterson, Richard P.,Ooi, Li-Ling,Cook, Darren,Ducki, Sylvie
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p. 5844 - 5848
(2007/10/03)
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- HEXAHYDRO-PYRROLO-ISOQUINOLINE COMPOUNDS
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Certain hexahydro-pyrrolo-isoquinoline compounds are histamine H3 receptor and serotonin transporter modulators useful in the treatment of histamine H3 receptor- and serotonin-mediated diseases.
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Page/Page column 32
(2010/11/25)
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- Five-membered heterocyclic compounds as inhibitors of SRC family protein kinase.
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The present invention refers to novel substituted aromatic heteroaryl derivatives of formula (I). with the definitions of A, L1, L2, G, J, X and Y according to claim 1. These novel compounds are useful for the inhibition of protein kinases, particularly of the inhibition of Src family protein kinases. Methods for inhibiting kinases by contacting kinases with these novel compounds are disclosed. In another embodiment the present invention refers to pharmaceutical compositions containing these novel compounds and their use for the preparation of medicaments for treating diseases or disorders associated with unphysiological activity of kinases in the body, particularly for the treatment of cancer, immunosuppression, and osteoporosis.
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Page/Page column 16
(2008/06/13)
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- BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS GNRH ANTAGONISTS
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A subject of the present application is new benzimidazole derivatives of formula in which A, Y, R1, R2, R3 and R4 represent different variable groups. These products have an antagonist activity of GnRH (Gonadotropin-Releasing Hormone). The invention also relates to pharmaceutical compositions containing said products and their use for the preparation of a medicament.
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Page/Page column 33
(2008/06/13)
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- Generation and reactivity of ketyl radicals with lignin related structures. On the importance of the ketyl pathway in the photoyellowing of lignin containing pulps and papers
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(Chemical Equation Presented) Ketyl radicals with lignin related structures have been generated by means of radiation chemical and photochemical techniques. In the former studies ketyl radicals are produced by reaction of α-carbonyl-β-aryl ether lignin models with the solvated electron produced by pulse radiolysis of an aqueous solution at pH 6.0. The UV-vis spectra of ketyl radicals are characterized by three main absorption bands. The shape and position of these bands slightly change when the spectra are recorded in alkaline solution (pH 11.0) being now assigned to the ketyl radical anions and a pKa = 9.5 is determined for the 1-(3,4,5-trimethoxyphenyl)-2- phenoxyethanol-1-yl radical. Decay rates of ketyl radicals are found to be dose dependent and, at low doses, lie in the range (1.7-2.7) × 103 s-1. In the presence of oxygen a fast decay of the ketyl radicals is observed (k2 = 1.8-2.7 × 109 M-1 s -1) that is accompanied by the formation of stable products, i.e., the starting ketones. In the photochemical studies ketyl radicals have been produced by charge-transfer (CT) photoactivation of the electron donor-acceptor salts of methyl viologen (MV2+) with α-hydroxy-α- phenoxymethylaryl acetates. This process leads to the instantaneous formation of the reduced acceptor (methyl viologen radical cation, MV+?), as is clearly shown in a laser flash photolysis experiment by the two absorption bands centered at 390 and 605 nm, and an acyloxyl radical [ArC(CO 2?)(OH)CH2(OC6H5)], which undergoes a very fast decarboxylation with formation of the ketyl radicals. Steady-state photoirradiation of the CT ion pairs indicates that 1-aryl-2-phenoxyethanones are formed as primary photoproducts by oxidation of ketyl radicals by MV2+ (under argon) or by molecular oxygen. Small amounts of acetophenones are formed by further photolysis of 1-aryl-2-phenoxyethanones and not by β-fragmentation of the ketyl radicals. The high reactivity of ketyl radicals with oxygen coupled with the low rates of β-fragmentation of the same species have an important bearing in the context of the photoyellowing of lignin containing pulps and papers.
- Fabbri, Claudia,Bietti, Massimo,Lanzalunga, Osvaldo
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p. 2720 - 2728
(2007/10/03)
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- 2-Arylimino-2,3-dihydrothiazoles, and their use thereof as somatostatin receptor ligands
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The invention concerns novel 2-arylimino-2,3-dihydrothiazole derivatives of general formula (I), their preparation methods and their use as medicines, in particular for treating pathological conditions or diseases wherein one (or several) somatostatin receptors is/are involved. Said pathological conditions include in particular acromegaly, pituitary adenoma or endocrine gastroenteropanceatic tumors including the carcinoid syndrome, and gastrointestinal bleeding. In general formula (I), R1 represents in particular an alkyl, aralkyl, cyclohexyl radical optionally substituted by an amino radical or R1 represents a —C(R11)(R12)—CO—R10 radical wherein R11 represents H, R12 represents in particular H, carbocyclic or heterocyclic alkyl, cycloalkyl or aralkyl and R10 represents in particular an aminoalkylamino radical; R2 represents a carcyclic or heterocyclic aryl radical optionally substituted; R3 represents in particular COR5 or a carbocyclic or heterocyclic alkyl, adamantyl, aryl radical optionally substituted, carbocyclic or heterocyclic aralkyl optionally substituted on the aryl group; and R5 represents a radical fixed by a nitrogen atom to the group CO.
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Page column 46
(2010/02/06)
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- Combretoxazolones: Synthesis, cytotoxicity and antitumor activity
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Two series of combretoxazolones including 3,4-diaryloxazolones (6) and 4,5-diaryloxazolones (7) were synthesized and evaluated for cytotoxicity and antitumor activity. Both series showed strong cytotoxicities against a variety of tumor cell lines. Compound 6g exhibited a significant antitumor activity in BDF1 mice bearing B16 murine melanoma cells with inhibition rates of 67 and 61% at 100 and 30 mg/kg/day, respectively.
- Nam, Nguyen-Hai,Kim, Yong,You, Young-Jae,Hong, Dong-Ho,Kim, Hwan-Mook,Ahn, Byung-Zun
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p. 3073 - 3076
(2007/10/03)
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- New 2-sulfonamidothiazoles substituted at C-4: Synthesis of polyoxygenated aryl derivatives and in vitro evaluation of antifungal activity
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Polymethoxylated and polyhydroxylated derivatives of 2-amino-4- arylthiazoles bearing a halogenobenzenesulfonamide moiety at position 2 were synthesized as azole antifungal analogues. X-ray crystallography studies revealed the predominance of the 2-imino-2,3-dihydrothiazole form in the amino/imino tautomerism. In vitro assays against various pathogenic fungal strains (Candida and Trichophyton species) showed no activity in comparison to econazole as reference. These results are discussed on the basis of the estimated global lipophilicity of the molecules (Rekker's method) and the π- electron distribution (Mulliken population analysis, AM1 method) within the five-membered heterocycle.
- Beuchet, Pierre,Varache-Lembege, Martine,Neveu, Arlette,Leger, Jean-Michel,Vercauteren, Joseph,Larrouture, Stephane,Deffieux, Gerard,Nuhrich, Alain
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p. 773 - 779
(2007/10/03)
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- Propenone derivatives
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The present invention relates to propenone derivatives represented by the following formula (I): STR1 wherein R1 represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, or YR5 (wherein Y represents S or O; and R5 represents substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a substituted or unsubstituted cyclic ether residue); R2 and R3 independently represent hydrogen, lower alkyl, or substituted or unsubstituted aralkyl, or alternatively R2 and R3 are combined to form substituted or unsubstituted methylene or ethylene; R4 represents hydrogen, hydroxy, lower alkyl, substituted or unsubstituted aralkyl, lower alkoxy, substituted or unsubstituted aralkyloxy, or halogen; and X represents substituted or unsubstituted indolyl; or pharmaceutically acceptable salts thereof.
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- PROPENONE DERIVATIVES
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The present invention relates to propenone derivatives represented by the following formula (I): wherein R1represents substituted lower alkyl or YR5(wherein Y represents S or O, and R5represents substituted or unsubstitute
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- Pharmaceutically active bicyclic-heterocyclic amines
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The pharmaceutically active bicyclic heterocyclic amines (XXX) STR1 where W1 is --N= or --CH=; W3 is --N= or --CH=; W5 is --N= or --CR5 -- with the proviso that W5 is --CR5 -- when both W1 and W3 are --N= which are useful as pharmaceuticals in treating mild and/or moderate to severe head injury, subarachnoid hemorrhage and subsequent ischemic stroke, asthma and reduction of mucous formation/secretion in the lung and other diseases and injuries.
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