10102-94-0Relevant articles and documents
The ammonium-promoted formylation of indoles by DMSO and H2O
Fei, Haiyang,Yu, Jintao,Jiang, Yan,Guo, Huan,Cheng, Jiang
, p. 7092 - 7095 (2013)
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.
Eco-friendly synthesis and antimicrobial activities of substituted-5-(1H- indol-3-yl)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives
Thirupathi,Venkatanarayana,Dubey,Bharathi Kumari
, p. 1569 - 1580 (2014)
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.
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
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
, p. 30412 - 30424 (2016)
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.
The copper-catalyzed C-3-formylation of indole C-H bonds using tertiary amines and molecular oxygen
Chen, Jianbin,Liu, Bin,Liu, Dongfang,Liu, Shan,Cheng, Jiang
, p. 2438 - 2442 (2012)
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
Total synthesis and antiproliferative activity screening of (±)-aplicyanins A, B and E and related analogues
?í?a, Miroslav,Pla, Daniel,Altuna, Marta,Francesch, Andrés,Cuevas, Carmen,Albericio, Fernando,álvarez, Mercedes
, p. 6217 - 6223 (2009)
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.
Visible Light-Driven C-3 Functionalization of Indoles over Conjugated Microporous Polymers
Zhang, Weijie,Tang, Juntao,Yu, Wenguang,Huang, Qiao,Fu, Yu,Kuang, Guichao,Pan, Chunyue,Yu, Guipeng
, p. 8084 - 8091 (2018)
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.
Synthesis, biological evaluation, and molecular docking studies of novel 1-benzene acyl-2-(1-methylindol-3-yl)-benzimidazole derivatives as potential tubulin polymerization inhibitors
Wang, Yan-Ting,Qin, Ya-Juan,Yang, Na,Zhang, Ya-Liang,Liu, Chang-Hong,Zhu, Hai-Liang
, p. 125 - 137 (2015)
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.
Novel nicotinoyl pyrazoline derivates bearing N-methyl indole moiety as antitumor agents: Design, synthesis and evaluation
Chen, Kun,Zhang, Ya-Liang,Fan, Jing,Ma, Xiang,Qin, Ya-Juan,Zhu, Hai-Liang
, p. 722 - 737 (2018)
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.
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
Venkatanarayana, Muvvala,Kumar Dubey, Pramod
, p. 41 - 48 (2012)
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.
Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source
Cheng, Didi,Li, Jingyi,Li, Yujin,Ling, Fei,Liu, Lei,Liu, Tao,Zhong, Weihui
supporting information, p. 4107 - 4113 (2021/06/17)
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.
A Facile Synthesis of Novel (Z)-ethyl-3-(5-substituted-1-alkyl/aryl-1H-indol-3-yl)-2-(1H-tetrazol-5-yl)acrylate
Bakkolla, Mahesh Goud,Taduri, Ashok Kumar,Bhoomireddy, Rama Devi
, p. 92 - 98 (2018/11/30)
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.
