111480-86-5Relevant academic research and scientific papers
Biological activities of pyrazoline-indole based Re(I) carbonyls: DNA interaction, antibacterial, anticancer, ROS production, lipid peroxidation, in vivo and in vitro cytotoxicity studies
Bhatt, Bhupesh S.,Pandya, Juhee G.,Patel, Mohan N.,Pathak, Chandramani,Vaidya, Foram U.,Varma, Reena R.
, (2020)
Hetero mononuclear rhenium(I) metal complexes (I-V) using different substituted indole-pyrazoline based ligands were synthesized and characterized by spectroscopic and analytical methods. The binding of the rhenium complexes to Herring sperm DNA was monitored by UV spectroscopy, viscosity measurements, and molecular docking studies; groove binding was suggested as the most possible mode and the DNA-binding constants of the complexes were evaluated. In vivo and in vitro cytotoxicity of compounds were evaluated against the brine shrimp and S. cerevisiae cells. An antimicrobial study was carried out by estimating MIC (Minimum Inhibitory Concentration) against two Gram-positive and three Gram-negative bacteria. All synthesized complexes are biologically more active than the corresponding ligands. The anti-proliferation activity of complexes was evaluated on MCF-7, HCT116, and A549 cancer cells by MTT assay. The toxicity profile of synthesized compounds was confirmed by H2O2 production by reactive oxygen species. The increased concentration of lipid peroxidation end products increased free radicals, which enhancing the oxidative stress level in living organisms and results in cell death.
A copper-catalyzed domino radical cyclization route to benzospiro-indolizidinepyrrolidinones
Stevens, Christian V.,Van Meenen, Ellen,Masschelein, Kurt G.R.,Eeckhout, Yves,Hooghe, Wim,D'hondt, Bart,Nemykin, Victor N.,Zhdankin, Viktor V.
, p. 7108 - 7111 (2007)
In this Letter the synthesis of benzospiro-indolizidinepyrrolidinones is described by a domino atom transfer radical cyclization reaction using a copper catalyst. The structure of one of the products was established by single crystal X-ray diffraction. Th
Ultrasound-assisted synthesis and photophysical investigation of a heterocyclic alkylated chalcone: a sensitive and selective fluorescent chemosensor for Fe3+ in aqueous media
Asiri, Abdullah M.,Al-Amari, Mona Mohammad,Ullah, Qasim,Khan, Salman A.
, p. 2987 - 3002 (2020)
Alkylated pyridine chalcone (AIPO) has been synthesized by reaction of 1-allyl-1H-indole-3-carbaldehyde with 2-acetyl pyridine. The chalcone structure was characterized by spectral and elemental analysis. The absorption and emission in ten solvents with different polarities were used to calculate the photophysical parameters for this compound. This heterocyclic fluorescent compound serves as a selective probe for recognition of Fe3+. A 1:1 bonding stoichiometry between AIPO and Fe3+ has been detected by Benesi–Hildebrand, Stern–Volmer and Job-plot methods. The binding stoichiometric ratio was further confirmed by the density functional theory (DFT) calculations.
Novel [(N-alkyl-3-indolylmethylene)hydrazono]oxindoles arrest cell cycle and induce cell apoptosis by inhibiting CDK2 and Bcl-2: synthesis, biological evaluation and in silico studies
Abdel-Aziz, Hatem A.,Abo-Ashour, Mahmoud F.,Ahmed, Hanaa Y.,Al-Ansary, Ghada H.,Al-Sanea, Mohammad M.,Al-Warhi, Tarfah,Almahli, Hadia,Alotaibi, Ohoud J.,Elaasser, Mahmoud M.,Eldehna, Wagdy M.
, p. 1300 - 1309 (2020)
As a continuation for our previous work, a novel set of N-alkylindole-isatin conjugates (7, 8a–c, 9 and 10a–e) is here designed and synthesised with the prime aim to develop more efficient isatin-based antitumor candidates. Utilising the SAR outputs from the previous study, our design here is based on appending four alkyl groups with different length (ethyl and n-propyl), bulkiness (iso-propyl) and unsaturation (allyl) on N-1 of indole motif, with subsequent conjugation with different N-unsubstituted isatin moieties to furnish the target conjugates. As planned, the adopted strategy achieved a substantial improvement in the growth inhibitory profile for the target conjugates in comparison to the reported lead VI. The best results were obtained with N-propylindole –5-methylisatin hybrid 8a which displayed broad spectrum anti-proliferative action with efficient sub-panel GI50 (MG-MID) range from 1.33 to 4.23 μM, and promising full-panel GI50 (MG-MID) equals 3.10 μM, at the NCI five-dose assay. Also, hybrid 8a was able to provoke cell cycle disturbance and apoptosis in breast T-47D cells as evidenced by the DNA flow cytometry and Annexin V-FITC/PI assays. Furthermore, hybrid 8a exhibited good inhibitory action against cell cycle regulator CDK2 protein kinase and the anti-apoptotic Bcl-2 protein (IC50= 0.85 ± 0.03 and 0.46 ± 0.02 μM, respectively). Interestingly, molecular docking for hybrid 8a in CDK2 and Bcl-2 active sites unveiled that N-propyl group is involved in significant hydrophobic interactions. Taken together, the results suggested conjugate 8a as a promising lead for further development and optimisation as an efficient antitumor drug.
The Selective Nickel-Catalyzed N-Allylation of C3-Unprotected Indoles under Mild and Clean Conditions
Dumont, Clément,Karim, Abdallah,Mouhsine, Bouchaib,Saint Pol, Anthony,Sauthier, Mathieu,Suisse, Isabelle
supporting information, (2022/03/07)
A simple salt free and selective N-allylation of indoles with allylic alcohols has been developed. The protocol uses a catalytic amount of a nickel complex generated in situ from Ni(cod)2 and dppf as diphosphine. The use of DMSO as the reaction solvent is crucial to control the regioselectivity of the reaction with the exclusive formation of the N-allyl product among up to three possible products.
Discovery of unique thiazolidinone-conjugated coumarins as novel broad spectrum antibacterial agents
Geng, Rong-Xia,Kumar, Kannekanti Vijaya,Li, Shuo,Yang, Xun-Cai,Zhang, Peng-Li,Zhou, Cheng-He
, (2022/02/16)
Unique coumarin conjugates with thiazolidinone as novel structural antibacterial modulators were exploited to combat the lethal multidrug-resistant bacterial infections. Bioactivity evaluation identified that indole-incorporated coumarin thiazolidinone conjugate 14a with low cytotoxicity to mammalian cells showed a broad antibacterial spectrum and exerted potent inhibition efficiencies to the tested germs at low concentrations (0.25–2 μg/mL). Moreover, the favorable performance of 14a in eradicating bacterial biofilm was beneficial to avert developing drug resistance. Mechanistic explorations revealed that molecule 14a was able to destroy cell membrane, leading to the leakage of intracellular materials and metabolism inhibition. The accumulation of excess reactive oxygen species (ROS) mediated by compound 14a could impede glutathione (GSH) activity and induce lipid peroxidation to suppress bacteria growth. Furthermore, compound 14a could not only intercalate into DNA base pair but also take part in non-covalent interaction with DNA gyrase B to hinder their biological function. Quantum chemical study indicated that molecule 14a had low HOMO-LUMO energy gap, which resulted in more stabilizing interactions and was conducive to displaying better antibacterial activity. ADMET analysis manifested that 14a possessed promising pharmacokinetic properties.
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.
Rh(iii)-Catalyzed tandem indole C4-arylamination/annulation with anthranils: Access to indoloquinolines and their application in photophysical studies
Biswas, Aniruddha,Bera, Satabdi,Poddar, Puja,Dhara, Dibakar,Samanta, Rajarshi
supporting information, p. 1440 - 1443 (2020/02/11)
An efficient Rh(iii)-catalyzed straightforward strategy was developed for the tandem C4 arylamination/annulation of indole derivatives with anthranil to provide indoloquinoline moieties. This method is simple and regioselective with a wide scope and functional group tolerance. Mechanistic studies revealed the important role of the newly installed azacycle in the conversion of O-protected aldoximes to their cyano derivatives. Studies were carried out to explore the promising photophysical properties of the obtained indoloquinoline derivatives.
Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes
Yang, Liquan,Liu, Zhaoran,Li, Yujun,Lei, Ning,Shen, Yanling,Zheng, Ke
, p. 7702 - 7707 (2019/10/19)
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.
Method for synthesizing indole -3 - formaldehyde compounds (by machine translation)
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Paragraph 0041-0044; 0161-0164, (2018/08/28)
The invention relates to a synthetic indole - 3 - formaldehyde compounds, which belongs to the technical field of organic synthesis. The invention will be indole compound, hexamethylene tetramine, crystalline aluminum trichloride, N, N - dimethyl formamide in proportion in 120 °C reaction under the condition of 1 - 20 the H, then filtered, washing, filtering, concentrating, column chromatography purification and other after-treatment technology, make the refined indole - 3 - formaldehyde compound. The invention overcomes the indole - 3 - benzaldehyde compound of preparation need to use not stabilized peroxide, and for a long time under the high temperature reaction of the defect. And the invention uses the advantages of simple equipment, product yield is high, the resulting yield of a target product can be up to 94%. In addition, the invention relates to a low reaction conditions, less catalyst levels, low energy consumption, the post treatment process is simple and easy to use, without the need of using a high dosage of acid or alkali, post-processing the solvent can be recovered and recycled, industrial "three wastes" is discharged little, suitable for large-scale production. (by machine translation)
