- The ammonium-promoted formylation of indoles by DMSO and H2O
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DMSO and H2O is an efficient combination in the NH 4OAc-promoted formylation of indole, where DMSO serves as a C1 carbon source. The mechanism study reveals that the procedure involves a usual and unusual Pummerer reaction.
- Fei, Haiyang,Yu, Jintao,Jiang, Yan,Guo, Huan,Cheng, Jiang
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- Screening metal-free photocatalysts from isomorphic covalent organic frameworks for the C-3 functionalization of indoles
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The visible-light-driven organic transformation using two-dimensional covalent organic frameworks (2D-COFs) as metal-free heterogeneous photocatalysts is a green and sustainable approach, and it has gained a surge of interest by virtue of the photosensitizer's high crystallinity, abundant porosity, outstanding stability, excellent light-harvesting ability and tunable structure. However, the guiding principle for designing, constructing and selecting COF-based photocatalysts has not been put forward so far. Herein, we contribute a fascinating strategy to guide the acquisition of excellent framework photocatalysts, which is to screen them from a series of isomorphic COFs. As a proof of concept, three new isomorphic pyrene-based 2D-COFs (COF-JLU23, COF-JLU24 and COF-JLU25) with variable linkers were successfully synthesized. In addition to having similar crystallinity and porosity with the same pore size and shape, their absorption, emission, bandgap, energy level, transient photocurrent response and photocatalytic activity could be easily adjustedviaconfiguring different linkers in frameworks. Indeed, COF-JLU24 with electron donor-acceptor characteristics exhibited the best photocatalytic activity among the three isomorphic COFs for C-3 functionalization reactions of indoles, even better than that of the metal-free photocatalyst g-C3N4. More importantly, the screened COF-JLU24 as a metal-free photocatalyst still displayed extensive substrate adaptability and excellent recyclability. We anticipate that this strategy will become a robust rule of thumb for fast access to COF-based photocatalysts. In addition, we still highlight that the present study broadens the applied frontier of COF-based photocatalysts.
- Chen, Xiong,Feng, Xiao,Han, Songjie,Li, Chunzhi,Li, He,Li, Ziping,Liu, Xiaoming,Shao, Pengpeng,Xia, Hong
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- Eco-friendly synthesis and antimicrobial activities of substituted-5-(1H- indol-3-yl)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives
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l-Tyrosine is an efficient catalyst for the condensation of substituted indole-3-aldehydes 1(a-d), N-methyl indole-3-aldehydes 4(a-d), and N-ethyl indole-3-aldehydes 6(a-d) with meldrum's acid (2) containing a cyclic active methylene group to produce 3(a-d), 5(a-d), and 7(a-d), respectively, in water at room temperature for 30 min. The antimicrobial activities of 3(a-d), 5(a-d), and 7(a-d) have been studied.
- Thirupathi,Venkatanarayana,Dubey,Bharathi Kumari
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- I2-mediated C3-formylation of indoles by tertiary amine and H2O
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An I2-promoted 3-formylation of free (N-H) and N-substituted indoles with tetramethylethylenediamine (TMEDA) and H2O as the carbonyl source is achieved, providing 3-formylindole in moderate to excellent yields with good functional gr
- Zhang, Bo,Liu, Bin,Chen, Jianbin,Wang, Jiehui,Liu, Miaochang
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- Synthesis, biological evaluation and molecular docking studies of novel 1-(4,5-dihydro-1Hpyrazol-1-yl)ethanone-containing 1-methylindol derivatives as potential tubulin assembling inhibitors
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A series of novel compounds (6a-6v) containing 1-methylindol and 1-(4,5-dihydro-1H-pyrazol-1-yl) ethanone skeletons were designed, synthesized and biologically evaluated as potential tubulin polymerization inhibitors and anticancer agents. Among them, compound 6q showed the most potent tubulin polymerization inhibitory activity (IC50 = 1.98 mM) and in vitro growth inhibitory activity against A549, MCF-7 and HepG2 cell lines, with IC50 values of 0.15 mM, 0.17 mM, and 0.25 mM respectively, comparable to the positive control. Furthermore, compound 6q was a potent inducer of apoptosis in A549 cells and it had typical cellular effects for microtubule interacting agents, causing arrest of the cell cycle in the G2/M phase. Confocal microscopy assay and molecular docking results further demonstrated that 6q could bind tightly to the colchicine site of tubulin and act as an anti-tubulin agent. These studies, along with 3D-QSAR modeling provided an important basis for further optimization of compound 6q as a potential anticancer agent.
- Yang, Meng-Ru,Qin, Ya-Juan,Chen, Chen,Zhang, Ya-Liang,Li, Bo-Yan,Liu, Tian-Bao,Gong, Hai-Bin,Wang, Bao-Zhong,Zhu, Hai-Liang
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- Aerobic transition-metal-free visible-light photoredox indole C-3 formylation reaction
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An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs molecular oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups.
- Li, Xiang,Gu, Xiangyong,Li, Yongjuan,Li, Pixu
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- The copper-catalyzed C-3-formylation of indole C-H bonds using tertiary amines and molecular oxygen
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A copper-catalyzed formylation reaction has been developed by employing oxygen (O2) as the clean oxidant. The C-H bonds of indoles were C-3-formylated by tetramethylethylenediamine (TMEDA) and water (H2O; in situ formed and external added water) as the carbonyl source in moderate to good yields with good functional group tolerance. Thus, it represents a facile procedure leading to 3-formylindoles. Copyright
- Chen, Jianbin,Liu, Bin,Liu, Dongfang,Liu, Shan,Cheng, Jiang
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- 1,2,3-Thiadiazole substituted pyrazolones as potent KDR/VEGFR-2 kinase inhibitors
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KDR kinase inhibition is considered to play an important role in regulating angiogenesis, which is vital for the survival and proliferation of tumor cells. Recently we disclosed a structure-based kinase inhibitor design strategy which led to the identification of a new class of VEGFR-2/KDR kinase inhibitors bearing heterocyclic substituted pyrazolones as the core template. Instability in a rat S9 preparation and poor iv PK profiles for most of these inhibitors necessitated exploration of new pyrazolones to identify new analogs with improved metabolic stability. Optimization of the heterocyclic moiety led to the identification of the thiadiazole series of pyrazolones (D) as potent VEGFR-2/KDR kinase inhibitors. SAR modifications, kinase selectivity profiling, and structural elements for improved PK properties were explored. Oral bioavailability up to 29% was achieved in the rat. Modeling results based on the Glide XP docking approach supported our postulation regarding the interaction of the lactam segment of the pyrazolones with the hinge region of the KDR kinase.
- Tripathy, Rabindranath,Ghose, Arup,Singh, Jasbir,Bacon, Edward R.,Angeles, Thelma S.,Yang, Shi X.,Albom, Mark S.,Aimone, Lisa D.,Herman, Joseph L.,Mallamo, John P.
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- Total synthesis and antiproliferative activity screening of (±)-aplicyanins A, B and E and related analogues
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The first total synthesis of the indole alkaloids (±)-aplicyanins A, B, and E, plus 17 analogues, all in racemic form, is reported. Modifications to the parent compound included changing the number of bromine substituents on the indole, the nature of the substituents on the indole nitrogen (H, Me, or OMe), and/or the oxidation level of the heterocyclic core tetrahydropyrimidine. Each compound was screened against three human tumor cell lines, and 14 of the newly synthesized compounds showed considerable cytotoxicity. The assay results were used to establish structure-activity relationships. These results suggest that the presence of the bromine at position 5 of the indole is critical to activity, as well as the acetyl group on the imine nitrogen does in some compounds. 2009 American Chemical Society.
- ?í?a, Miroslav,Pla, Daniel,Altuna, Marta,Francesch, Andrés,Cuevas, Carmen,Albericio, Fernando,álvarez, Mercedes
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- Visible-Light-Mediated α-Oxygenation of 3-(N,N-Dimethylaminomethyl)-Indoles to Aldehydes
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The visible-light-mediated oxygenation of 3-N,N-(dimethylaminomethyl)-indoles bearing various substituents afforded a series of 3-carbaindole derivatives. Herein we describe the reaction scope, a plausible mechanism and a practical application of this transformation in the formal synthesis of (–)-vincorine is described as well.
- Stanek, Filip,Paw?owski, Robert,Mlynarski, Jacek,Stodulski, Maciej
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- Visible Light-Driven C-3 Functionalization of Indoles over Conjugated Microporous Polymers
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Metal-free and heterogeneous organic photocatalysts provide an environmentally friendly alternative to traditional metal-based catalysts. This paper reports a series of carbazole-based conjugated microporous polymers (CMPs) with tunable redox potentials and explores their photocatalytic performance with regard to C-3 formylation and thiocyanation of indoles. Conjugated polymers were synthesized through FeCl3 mediated Friedel-Crafts reactions, and their redox potentials were well regulated by simply altering the nature of the core (i.e., 1,4-dibenzyl, 1,3,5-tribenzyl, or 1,3,5-triazin-2,4,6-triyl). The resulting CMPs exhibited high surface areas, visible light absorptions, and tunable semiconductor-range band gaps. With the highest oxidative capability, CMP-CSU6 derived from 1,3,5-tri(9H-carbazol-9-yl)benzene showed the highest efficiency for C-3 formylation and thiocyanation of indoles at room temperature. Notably, the as-made catalysts can be easily recovered with good retention of photocatalytic activity and reused at least five times, suggesting good recyclability. These results are significant for constructing high-performance porous polymer catalysts with tunable photoredox potentials targeting an efficient material design for catalysis.
- Zhang, Weijie,Tang, Juntao,Yu, Wenguang,Huang, Qiao,Fu, Yu,Kuang, Guichao,Pan, Chunyue,Yu, Guipeng
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- Synthesis and biological evaluation of oxindole linked indolyl-pyrimidine derivatives as potential cytotoxic agents
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In our endeavor towards the development of effective cytotoxic agents, a series of oxindole linked indolyl-pyrimidine derivatives were synthesized and characterized by IR, 1H NMR, 13C NMR and Mass spectral analysis. All the newly synthesized target compounds were assessed against PA-1 (ovarian), U-87MG (glioblastoma), LnCaP (prostate), and MCF-7 (Breast) cancer cell lines for their cytotoxic potential, with majority of them showing inhibitory activity at low micro-molar concentrations. Significantly, compound 8e was found to be most potent amongst all the tested compounds with an IC50 value of (2.43 ± 0.29 μM) on PA-1 cells. The influence of the most active cytotoxic compound 8e on the cell cycle distribution was assessed on the PA-1 cell line, exhibiting a cell cycle arrest at the G2/M phase. Moreover, acridine orange/ethidium bromide staining and annexin V binding assay confirmed that compound 8e can induce cell apoptosis in PA-1 cells. These preliminary results persuade further investigation on the synthesized compounds aiming to the development of potential cytotoxic agents.
- Prajapti, Santosh Kumar,Nagarsenkar, Atulya,Guggilapu, Sravanthi Devi,Gupta, Keshav Kumar,Allakonda, Lingesh,Jeengar, Manish Kumar,Naidu,Babu, Bathini Nagendra
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- Synthesis, biological evaluation, and molecular docking studies of novel 1-benzene acyl-2-(1-methylindol-3-yl)-benzimidazole derivatives as potential tubulin polymerization inhibitors
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A series of 1-benzene acyl-2-(1-methylindol-3-yl)-benzimidazole derivatives were designed, synthesized and evaluated as potential tubulin polymerization inhibitors and for the cytotoxicity against anthropic cancer cell lines. Among the novel compounds, compound 11f was demonstrated the most potent tubulin polymerization inhibitory activity (IC50 = 1.5 μM) and antiproliferative activity against A549, HepG2 and MCF-7 (GI50 = 2.4, 3.8 and 5.1 μM, respectively), which was compared with the positive control colchicine and CA-4. We also evaluated that compound 11f could effectively induce apoptosis of A549 associated with G2/M phase cell cycle arrest. Docking simulation and 3D-QSAR model in these studies provided more information that could be applied to design new molecules with more potent tubulin inhibitory activity.
- Wang, Yan-Ting,Qin, Ya-Juan,Yang, Na,Zhang, Ya-Liang,Liu, Chang-Hong,Zhu, Hai-Liang
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- Simple and efficient Knoevenagel synthesis of (E)-2-((1H-indol-3-yl) methylene)-3-oxoindolylnitrile catalysed by PPh3
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Triphenylphosphine (TPP) is found to be an efficient catalyst for the Knoevenagel condensation of indole-3-carboxyaldehydes 1(a-e) and their N-substituted derivatives 4(a-e) with the active methylene compound, i.e., 3-cyanoacetylindole (2), affording novel substituted olefins 3(a-e) and 5(a-e) respectively. The latter products reacted with DMS in the presence of PEG-600 to afford the corresponding N, Nl dimethylated derivatives 6(a-e). Indian Academy of Sciences.
- Venkatanarayana,Dubey
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- Novel nicotinoyl pyrazoline derivates bearing N-methyl indole moiety as antitumor agents: Design, synthesis and evaluation
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In the present work, twenty-five nicotinoyl pyrazoline derivates bearing N-methyl indole moiety have been designed and synthesized. The biological evaluation of these compounds as tubulin assembly inhibitors revealed that most of them were potential antitumor agents. Among them, compound 28 exhibited most potency against cancer cell line panels (GI50 = 29–90 nM for HeLa, HepG2 and MCF-7 cells) without toxicity to non-tumor cells (CC50 > 300 μM for 293 T cell), bound to the colchicine site of tubulin and displayed excellent inhibitory activity in tubulin assembly assay (IC50 = 1.6 μM, better than CA-4). Molecular dynamics simulation was carried out to validate the docking pose of compound 28 with tubulin crystalline. Further investigation on HepG2 and HeLa cells demonstrated that compound 28 could cause mitosis arrest to G2/M phase, and subsequently induced cell apoptosis. The efficiency in vivo of compound 28 was also evaluated on HeLa-Xenograft nude mice, and the relative tumor inhibition ration was up to 61.52% without noticeable weight loss and tissue damage (examined by H&E staining), which was comparable to CA-4 (inhibited 59.92%). In brief, compound 28 is a promising candidate for tumor therapy as tubulin assembly inhibitor.
- Chen, Kun,Zhang, Ya-Liang,Fan, Jing,Ma, Xiang,Qin, Ya-Juan,Zhu, Hai-Liang
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- Facile synthesis and biological evaluation of substituted 5-(1H-Indol-3-ylmethylene) pyrimidine-2,4,6-trione derivatives using L-Tyrosine in aqueous medium
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L-Tyrosine as an efficient catalyst for the Knoevenagel condensation of substituted indole-3-aldehydes 1(a-d), N-methyl indole-3- aldehydes 4(a-d), N-ethyl indole-3-aldehydes 6(a-d) with barbituric acid (2) containing cyclic active methylene group to produce 3(a-d), 5(a-d) and 7(a-d), respectively in water at room temperature for 10 min. The antimicrobial activities of 3(a-d), 5(a-d) and 7(a-d) have been studied.
- Thirupathi,Dubey,Kumari, Y. Bharathi
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- PPh3-catalyzed knoevenagel condensation: A facile synthesis of 5-(1H-indol-3-yl)meth-ylene)-2, 2-dimethyl-1, 3-dioxane-4, 6-dione, and their N-alkyl derivatives by using peg-600 as the reaction medium
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Triphenylphosphine (TPP) has been utilized as a novel and efficient catalyst for the Knoevenagel condensation of indole-3-carboxaldehydes 1(a-e), 1-methyl-1H-indole-3-carboxaldehydes 4(a-e), and 1-ethyl-1H-indole-3- carboxaldehydes 6(a-e) with the active methylene compound, that is, meldrum's acid (2), to afford substituted derivatives 5-((1H-indol-3-yl) methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 3(a-e), 2,2-dimethyl-5-((1-methyl- 1H-indol-3-yl)methylene)-1,3-dioxane-4,6-dione 5(a-e), and 2,2-dimethyl-5-((1- ethyl-1H-indol-3-yl)methylene)-1,3-dioxane-4,6-dione 7(a-e), respectively, in ethanol medium at RT just within 1 h in excellent yields. The products 3(a-e) were reacted independently with alkylating agents, that is, DMS and DES in the presence of PEG-600 as an efficient and green solvent, to afford the corresponding N-substituted methyl and ethyl derivatives 5(a-e) and 7(a-e), respectively.
- Venkatanarayana, Muvvala,Kumar Dubey, Pramod
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- Pd(II)-Catalyzed asymmetric oxidative annulation of N-alkoxyheteroaryl amides and 1,3-dienes
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The first Pd(II)-catalyzed asymmetric oxidative annulation of N-alkoxyaryl amides and 1,3-dienes is reported, which features particular applicability for quick assembly of different types of chiral heterocycles with high yields and enantioselectivities. A novel chiral pyridine-oxazoline bearing a methoxyl group at the C-5 position and a gem-dimethyl group on the oxazoline moiety was found to be crucial for conversion.
- Zhang, Tao,Shen, Hong-Cheng,Xu, Jia-Cheng,Fan, Tao,Han, Zhi-Yong,Gong, Liu-Zhu
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- Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source
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A safe, practical and eco-friendly electrochemical methodology for the synthesis of 3-formylated indoles has been developed by the utilization of Me3N as a novel formylating reagent. Stoichiometric oxidants, metal catalysts, and activating agents were avoided in this method, and an aqueous biphasic system ofn-Bu4NBF4/PEG-400/H2O was used as a recyclable and reusable reaction medium, which made this electrosynthesis approach more sustainable and environmentally friendly. This process expanded the substrate scope and functional group tolerance for bothN-EDG andN-EWG indoles. Furthermore, late-stage functionalization and total/formal synthesis of drugs and natural products were realized by means of this route.
- Cheng, Didi,Li, Jingyi,Li, Yujin,Ling, Fei,Liu, Lei,Liu, Tao,Zhong, Weihui
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supporting information
p. 4107 - 4113
(2021/06/17)
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- Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes
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Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a well-known Mannich-type reaction and a C-N bond cleavage for carbonyl introduction. The key step - the C-N bond cleavage of the Mannich product - was enabled by electrochemistry. This strategy (with over 40 examples) ensures excellent functional-group tolerance as well as late-stage functionalization of pharmaceutical molecules.
- Yang, Liquan,Liu, Zhaoran,Li, Yujun,Lei, Ning,Shen, Yanling,Zheng, Ke
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supporting information
p. 7702 - 7707
(2019/10/19)
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- A Facile Synthesis of Novel (Z)-ethyl-3-(5-substituted-1-alkyl/aryl-1H-indol-3-yl)-2-(1H-tetrazol-5-yl)acrylate
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A novel route was developed for synthesis of high potential 1H-tetrazoles by using conventional method. Tetrazole scaffold is a promising pharmacophore fragment, frequently used in the development of various novel drugs. Here, the novel (Z)-3-(N-alkyl-indol-3-yl)-2-(1H-tetrazole-5-yl)acrylates 5 (a–i) have been synthesized from (Z)-ethyl-3-(1H-indol-3-yl)2-(1H-tetrazol-5-yl)acrylates 4 (a–c) by using various alkylating agents such as Dimethyl Sulphate (DMS), Diethyl Sulphate (DES), and benzyl chloride; 4 (a–c) were synthesized from sodium azide in the presence of copper sulfate in dimethylformamide; 3 (a–c) have been prepared by Knoevenagel condensation of indole-3-carbaldehyde 1 (a–c) and ethylcyanoacetate 2 in the presence of L-Proline as a catalyst at room temperature in ethanol for an hour. This is an efficient and clean click chemistry method that has various advantages such as easy workup, higher yields, shorter reaction times, and more economical.
- Bakkolla, Mahesh Goud,Taduri, Ashok Kumar,Bhoomireddy, Rama Devi
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- Indole-substituted hydrazide derivatives and uses thereof
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The invention discloses indole-substituted hydrazide derivatives and a use thereof, concretely relates to novel indole-substituted hydrazide derivatives and a medicinal composition including the abovecompounds, a use of the derivatives and the medicinal composition in the protection of nerve cells, and also relates to a method for preparing the compounds and the medicinal composition, and a use of the compounds and the medicinal composition in the preparation of drugs for treating diseases associated with glutamate excitotoxicity and oxidative stress damage or free radicals, or neurodegenerative diseases, especially the Alzheimer disease.
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Paragraph 0309; 0334-0337
(2018/11/03)
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- 2-Indolylmethylenebenzofuranones as first effective inhibitors of ABCC2
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ABC-transporters play a vital role in drugs bioavailability. They prevent intracellular accumulation of toxic compounds, rendering them a major defense mechanism against harmful substances. In this large family, ABCC2 is an apical efflux pump representing about 10% of all membrane proteins in liver and small intestine, and up to 25% in colon. In these tissues, ABCC2 plays a major role in the pharmacokinetics and pharmacodynamics of endo- and xenobiotics. To gain insight in the function of this crucial protein, we have investigated and developed the first effective inhibitors of this pump. Firstly, we set up a cellular flow cytometry assay for monitoring the drug efflux carried out by ABCC2, and used it for the screening of chemical libraries derived from several chemical classes. We found that 2-indolylmethylenebenzofuranone derivatives as promising candidates. Optimization of the hits provided new compounds that inhibit ABCC2 in the micromolar range, making them the first potent ABCC2 inhibitors reported so far. Such compounds would constitute valuable tools to further investigate the role of ABCC2 in the pharmacokinetics and pharmacodynamics of drugs.
- Baiceanu, Elisabeta,Nguyen, Kim-Anh,Gonzalez-Lobato, Lucia,Nasr, Rachad,Baubichon-Cortay, Hélène,Loghin, Felicia,Le Borgne, Marc,Chow, Larry,Boumendjel, Ahcène,Peuchmaur, Marine,Falson, Pierre
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p. 408 - 418
(2016/07/18)
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- Synthesis and Biological Evaluation of 1-Methyl-1H-indole–Pyrazoline Hybrids as Potential Tubulin Polymerization Inhibitors
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A series of 1-methyl-1H-indole–pyrazoline hybrids were designed, synthesized, and biologically evaluated as potential tubulin polymerization inhibitors. Among them, compound e19 [5-(5-bromo-1-methyl-1H-indol-3-yl)-3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide] showed the most potent inhibitory effect on tubulin assembly (IC50=2.12 μm) and in vitro growth inhibitory activity against a panel of four human cancer cell lines (IC50values of 0.21–0.31 μm). Further studies confirmed that compound e19 can induce HeLa cell apoptosis, cause cell-cycle arrest in G2/M phase, and disrupt the cellular microtubule network. These studies, along with molecular docking and 3D-QSAR modeling, provide an important basis for further optimization of compound e19 as a potential anticancer agent.
- Zhang, Ya-Liang,Qin, Ya-Juan,Tang, Dan-Jie,Yang, Meng-Ru,Li, Bo-Yan,Wang, Yan-Ting,Cai, Hong-Yu,Wang, Bao-Zhong,Zhu, Hai-Liang
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p. 1446 - 1458
(2016/07/16)
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- Synthesis of (Z)-5-[(5-(2-(Phenylsulfonyl-ethyl)-1H-indol-3-yl)methelene]- thiozolidine-2,4-dione of potential pharmacological interest
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Formylation of 5-bromoindole (1) under Vilsmeier-Hack formylation conditions using POCl3 and DMF as a reagents under cooling conditions (0-5 °C) followed by simple processing gave a 5-bromoindole-3- carboxyaldehyde (2) and condensation of (2) with thiazolidine-2,4-dione (3) in toluene as a solvent in the presence of PTSA and TBAB as a phase transfer catalyst under stirring at room temperature for 10-30 min, then slowly raise the temperature to 105 °C and maintained for 12-15 h, obtained a product(Z)-5-((5-bromo-1-alkyl-1H-indol-3-yl)methylene)thiazolidine-2,4-dione (4) later on condensation of (4) with phenylvinylsulfone (5) in the presence of palladium acetate as a catalyst in DMF as a solvent heating at 100-105 °C for 16 h gave (5Z)-5-((1-alkyl-5-((E)-2(-(phenylsulfonyl)vinyl)-1H-indol-3-yl) methelene)thiozolidine-2,4-dione (8) and on reduction of (8) in the presence of hydrogen gas, palladium-carbon by using catalytic amount acetic acid medium in methanol as a solvent heating at 45-50 °C for 8 h gave (Z)-5-((1-alkyl-5-(2- (-(phenylsulfonyl)ethyl)-1Hindol-3yl)methelene)thiozolidine-2,4-dione (11) and 11 could also be prepared by alternate methods structure of 11 has been established on the basis of its spectral and analytical data. Copyright
- Laxminarayana, Keetha,Rajendiran, Chinnapillai,Mukkanti, Khagga
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p. 1661 - 1665
(2013/05/09)
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- Copper-catalyzed aerobic methyl/methylene oxygenation and C-H formylation with a DABCO-DMSO system for the synthesis of carbonyl indoles and pyrroles
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Copper-catalyzed aerobic methyl/methylene oxygenation of substituted indoles and pyrroles was developed using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an additive in dimethyl sulfoxide (DMSO). Similar aerobic catalytic conditions could also be utilized for direct C-H formylation of C(3) on indoles and C(2) on pyrroles.
- Wang, Yi-Feng,Zhang, Feng-Lian,Chiba, Shunsuke
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experimental part
p. 1526 - 1534
(2012/06/18)
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- L-Proline-catalyzed Knoevenagel condensation: A facile, green synthesis of (E)-ethyl 2-cyano-3-(1H-indol-3-yl)acrylates and (E)-3-(1H-indol-3-yl) acrylonitriles
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L-Proline has been utilized as a novel and ecofriendly catalyst in ethanol medium for the Knoevenagel condensation of indole-3-carboxyaldehydes and their N-methyl derivatives 1(a-e) and 4(a-e) with the active methylene compound, ethyl cyanoacetate (2) to afford substituted (E)-ethyl 2-cyano-3-(1H-indol-3-yl) acrylates 3(a-e) and 5(a-e) respectively. These products were reacted with dimethyl sulfate in the presence of PEG-600 as an efficient and green solvent to afford the corresponding N-mthylated derivatives 5(a-e). These Knoevenagel products react with 5% NaOH, yielding (E)-3-(1H-indol-3-yl)acrylonitriles 6(a-e) and 7(a-e). Copyright Taylor & Francis Group, LLC.
- Venkatanarayana,Dubey
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scheme or table
p. 1746 - 1759
(2012/05/04)
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- Synthesis of Novel Indolyl-1,2,4-triazoles as Potent and Selective Anticancer Agents
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A diverse series of 22 indolyl-1,2,4-triazole congeners (6 and 7) have been synthesized from the reaction of indole-3-carbonitrile (4) or (5) with appropriate acid hydrazides in the presence of potassium carbonate. Synthesized compounds were evaluated for their cytotoxicity against six human cancer cell lines, and some of the compounds displayed promising activity. In particular, 3-(3',4',5'-trimethoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole (7i) and 3-(4'-piperidinyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole (7n) were the most promising and broadly active compounds against the tested cell lines. It was interesting to note that the trimethoxyphenyl analog 7i showed twofold selective cytotoxicity against PaCa2 cell line (IC50 0.8μm), whereas piperidinyl analog 7n was found to be selectively cytotoxic against MCF7 cell line (IC50 1.6μm). Notably, the 4-fluorophenyl derivative 7c exhibited selective cytotoxicity against PC3 cell line (IC50 4μm). The structure-activity relationship study revealed that substituents including 3,4,5-trimethoxyphenyl, 3,4-dimethoxyphenyl, 4-benzyloxy-3-methoxyphenyl, 4-piperidinyl, 4-fluorophenyl and N-methylindole are beneficial for the activity of indolyl-1,2,4-triazoles (6 and 7).
- Kumar, Dalip,Narayanam, Maruthi Kumar,Chang, Kuei-Hua,Shah, Kavita
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scheme or table
p. 182 - 188
(2012/01/03)
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- Reaction of 3/2-formylindoles with TOSMIC: Formation of indolyloxazoles and stable indolyl primary enamines
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3-Formylindole and its 1-substituted and 1,5-disubstituted derivatives react with TOSMIC in presence of potassium carbonate in methanol under reflux to furnish 5-(3′-indolyl)oxazoles, new stable E-2-(3′-indolyl)-2- tosylethenamines and two diastereomers of N-[2-(3′-indolyl)-1,2-dimethoxy] ethylformamides. In contrast, 2-formylskatole furnishes N-(1-tosyl-2-skatolyl) ethenylformamide.
- Chakrabarty, Manas,Basak, Ramkrishna,Harigaya, Yoshihiro,Takayanagi, Hiroaki
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p. 1793 - 1801
(2007/10/03)
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- THERAPEUTIC AGENTS I
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Compounds of formula(I), processes for preparing such compounds, their use in the treatment of obesity, psychiatric disorders, cognitive disorders, memory disorders, schizophrenia, epilepsy, and related conditions, and neurological disorders such as dementia, multiple sclerosis, Parkinson's disease, Huntington's chorea and Alzheimer's disease and pain related disorders, and pharmaceutical compositions containing them.
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Page/Page column 47
(2010/02/12)
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- N-Pyridinyl-indole-3-(alkyl)carboxamides and derivatives as potential systemic and topical inflammation inhibitors
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N-substituted-(indol-3-yl)carboxamides 10-15 and alkanamides 16-18 were prepared starting from the corresponding acids and submitted to screening for evaluation of their anti-inflammatory activity. None of the considered carboxamides exhibited significant inhibitory effect in the carrageenin-induced rat paw oedema after oral administration of 0.1 mM kg-1; nevertheless introduction of an alkyl chain, leading to alkanamides 16-18, induced moderate to high activity: 46-95% inhibition. The efficacy of these compounds in the inhibition of topical inflammation was confirmed by measuring reduction of ear thickness in the acute tetradecanoyl phorbol acetate (TPA)-induced mouse ear swelling assay. Preliminary pharmacomodulation brought to the fore that toxic effects induced, at 0.4 mM kg-1, by N-(pyridin-4-yl)(indol-3-yl)propanamide (17) could be attenuated or suppressed by 5-fluorination or introduction of a methoxycarbonylborane moiety, leading to 18 and 21.
- Duflos, Muriel,Nourrisson, Marie-Renee,Brelet, Jacques,Courant, Jacqueline,LeBaut, Guillaume,Grimaud, Nicole,Petit, Jean-Yves
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p. 545 - 553
(2007/10/03)
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- Structure-activity relationship for bromoindole carbaldehydes: Effects on the sea urchin embryo cell cycle
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Natural derivatives of indole-3-carbaldehyde were isolated from the tropical marine ascidian Stomoza murrayi. A series of 13 derivatives, three natural and 10 synthetic (brominated and N-methylated), were examined for their effects on cell division of sea urchin eggs. These derivatives were shown to inhibit the first mitotic cycle in a concentration-dependent manner. By comparing the IC50 values with the structure of the various molecules, we were able to determine that bromination increased the cytotoxicity of the compound with a maximum occurring when bromine was added to carbon number 2, while addition of N-methylation was shown to markedly reduce the cytotoxicity of these same compounds brominated at carbon 2 only. Biological activity of this family of compounds has been characterized, via detailed study of addition of the most active derivative, 2,5,6-tribromoindole-3-carbaldehyde, on macromolecule synthesis and cytoskeleton reorganization during the first mitotic cycle of fertilized sea urchin eggs. Fluorescence localization of chromatin and microtubules revealed that 2,5,6-tribromoindole-3-carbaldehyde allowed pronuclei migration and fusion but prevented the condensation of chromatin, nuclear envelope breakdown, and bipolar mitotic spindle assembly, inducing an arrest of sea urchin embryogenesis at the beginning of mitosis. It is postulated here that this phenotype is likely to be due to a strong inhibition of DNA replication and protein synthesis.
- Moubax, Isabelle,Bontemps-Subielos, Nathalie,Banaigs, Bernard,Combaut, Georges,Huitorel, Philippe,Girard, Jean-Pierre,Pesando, Danielle
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p. 589 - 596
(2007/10/03)
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