10511-51-0Relevant articles and documents
Novel [(3-indolylmethylene)hydrazono]indolin-2-ones as apoptotic anti-proliferative agents: design, synthesis and in vitro biological evaluation
Eldehna, Wagdy M.,Abo-Ashour, Mahmoud F.,Ibrahim, Hany S.,Al-Ansary, Ghada H.,Ghabbour, Hazem A.,Elaasser, Mahmoud M.,Ahmed, Hanaa Y. A.,Safwat, Nesreen A.
, p. 686 - 700 (2018)
On account of their significance as apoptosis inducing agents, merging indole and 3-hydrazinoindolin-2-one scaffolds is a logic tactic for designing pro-apoptotic agents. Consequently, 27 hybrids (6a–r, 9a–f and 11a–c) were synthesised and evaluated for their cytotoxicity against MCF-7, HepG-2 and HCT-116 cancer cell lines. SAR studies unravelled that N-propylindole derivatives were the most active compounds such as 6n (MCF-7; IC50=1.04 μM), which displayed a significant decrease of cell population in the G2/M phase and significant increase in the early and late apoptosis by 19-folds in Annexin-V-FTIC assay. Also, 6n increased the expression of caspase-3, caspase-9, cytochrome C and Bax and decreased the expression of Bcl-2. Moreover, compounds 6i, 6j, 6n and 6q generated ROS by significant increase in the level of SOD and depletion of the levels of CAT and GSH-Px in MCF-7.
Iodine-catalyzed C3-formylation of indoles using hexamethylenetetramine and air
Wang, Qing-Dong,Yang, Jin-Ming,Fang, Dong,Ren, Jiangmeng,Zeng, Bu-Bing
, p. 2877 - 2880 (2017)
An efficient iodine-catalyzed chemoselective 3-formylation of free (N–H) and N-substituted indoles was achieved by using hexamethylenetetramine (HMTA) in the presence of activated carbon under air atmosphere. This new method could provide 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this catalytic formylation of indoles procedure can be applied to gram-scale synthesis.
Synthesis, characterization, and biological evaluation of indole aldehydes containing N-benzyl moiety
Survase, Dattatray N.,Karhale, Shrikrishna S.,Khedkar, Vijay M.,Helavi, Vasant B.
, p. 3486 - 3497 (2019)
The present study describes the synthesis, characterization and biological evaluation of N-benzyl indole aldehydes. The biological activities of the newly synthesized compounds were examined by investigating their antioxidant and anti-inflammatory activities. The potential of these compounds as an antioxidant was determined by 2,2-diphenylpicrylhydrazyl, Nitric oxide, Superoxide, peroxide radical scavenging methods. We found that aldehydes 4a, 4b, 4c, and 4e and shows promising in vitro DPPH scavenging antioxidant activity while aldehyde 4b and 4e show good in vitro anti-inflammatory activity.
Solid-liquid phase alkylation of n-heterocycles: Microwave-assisted synthesis as an environmentally friendly alternative
Milen, Matyas,Gruen, Alajos,Balint, Erika,Dancso, Andras,Keglevich, Gyoergy
, p. 2291 - 2301 (2010)
The solid-liquid phase alkylation of a variety of five-membered N-heterocycles (carbazole, imidazole, benzimidazole, and indole-3-carbaldehyde) was carried out under different conditions. The use of alkali carbonate in dimethylformamide or in MeCN (in the latter case, in the presence of a phase-transfer catalyst) is a suitable method to prepare the corresponding N-alkylated products in an efficient way. In most cases, the solventless, microwave-assisted reaction is an environmentally friendly alternative to traditional methods. Copyrigh
Synthesis, crystal structures, and spectral properties of double N-alkylated dimethine cyanine dyes and their interactions with biomolecules and living cells
Jia, Hongliang,Lv, Ying,Wang, Shu,Sun, Dan,Wang, Lanying
, p. 4681 - 4692 (2015)
Six new double N-alkylated dimethine cyanine dyes were synthesized and the crystal structures of two of the dyes were analyzed by X-ray diffraction. The investigation of the spectral properties of the dyes in different solvents indicated that the absorption maxima of the dyes decreased with the increase of the basicity of the heterocyclic nucleus, and the increase of the solvent dielectric constants of the protonic solvents and non-protonic solvents. The six dyes all emitted fluorescence, and had a larger Stokes shift in water. The interaction between the dye molecules and the six biological molecules showed that one dye exhibited a larger enhancement of fluorescent quantum yield in the presence of DNA. Investigation of the cytotoxicity and cell staining of the selected dye showed that the dye had virtually no toxicity at the application dose and duration used and that it could stain cytoplasm, suggesting its potential application as a fluorescent reagent with which to observe and analyze the characteristics of living cells.
Synthesis of indolo[4,3-bc]phenanthridine-6,11(2H,12H)-diones using the schiff base–homophthalic anhydride cyclization reaction
Elsayed, Mohamed S. A.,Zeller, Matthias,Cushman, Mark
, p. 1902 - 1908 (2016)
A novel indolophenanthridine ring system has been synthesized via the Schiff base–homophthalic anhydride cyclization followed by thionyl chloride–mediated dehydrogenation and intramolecular Friedel–Crafts acylation. This adds to the array of heterocyclic systems that are available through the cycloaddition reaction of imines with cyclic dicarboxylic acid anhydrides. The cytotoxicities of the indolophenanthridines were investigated in human cancer cell cultures, and the results documented significant antitumor activity in a variety of human cancer cell lines. This provides a new heterocyclic scaffold for anticancer drug design.
Novel indole-thiazolidinone conjugates: Design, synthesis and whole-cell phenotypic evaluation as a novel class of antimicrobial agents
Abo-Ashour, Mahmoud F.,Eldehna, Wagdy M.,George, Riham F.,Abdel-Aziz, Marwa M.,Elaasser, Mahmoud M.,Abdel Gawad, Nagwa M.,Gupta, Antima,Bhakta, Sanjib,Abou-Seri, Sahar M.
, p. 49 - 60 (2018)
In connection with our research program on the development of novel anti-tubercular candidates, herein we report the design and synthesis of two different sets of indole-thiazolidinone conjugates (8a,b; 11a-d) and (14a-k; 15a-h). The target compounds were evaluated for their in vitro antibacterial and antifungal activities against selected human pathogens viz. Staphylococcus aureus (Gram positiveve), Pseudomonas aeruginosa, Escherichia coli (Gram negative), Mycobacterium tuberculosis (Acid-fast bacteria), Aspergillus fumigates and Candida albicans (fungi). Moreover, eukaryotic cell-toxicity was tested via an integrated ex vivo drug screening model in order to evaluate the selective therapeutic index (SI) towards antimicrobial activity when microbes are growing inside primary immune cells. Also, the cytotoxicity towards a panel of cancer cell lines and human lung fibroblast normal cell line, WI-38 cells, was explored to assure their safety. Compound 15b emerged as a hit in this study with potent broad spectrum antibacterial (MIC: 0.39–0.98 μg/mL) and antifungal (MIC: 0.49–0.98 μg/mL) activities, in addition to its ability to kill mycobacteria M. aurum inside an infected macrophage model with good therapeutic window. Moreover, compound 15b displayed promising activity towards resistant bacteria strains MRSA and VRE with MIC values equal 3.90 and 7.81 μg/mL, respectively. These results suggest compound 15b as a new therapeutic lead with good selectivity for further optimization and development.
Synthesis, spectral behaviour and photophysics of donor-acceptor kind of chalcones: Excited state intramolecular charge transfer and fluorescence quenching studies
Pannipara, Mehboobali,Asiri, Abdullah M.,Alamry, Khalid A.,Arshad, Muhammad N.,El-Daly, Samy A.
, p. 1893 - 1902 (2015)
The spectral and photophysical properties of two chalcones containing electron donating and accepting groups with intramolecular charge transfer characteristics were synthesized and characterized by 1H NMR, 13C NMR and X-ray crystall
Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air
Wang, Qing-Dong,Zhou, Bin,Yang, Jin-Ming,Fang, Dong,Ren, Jiangmeng,Zeng, Bu-Bing
, p. 2670 - 2674 (2017)
An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.
Synthesis and antimicrobial activities of new thiosemicarbazones and thiazolidinones in indole series
Benmohammed, Abdelmadjid,Djafri, Ayada,Kadiri, Mokhtaria,Khoumeri, Omar,Louail, Ahmed Amine,Rekiba, Nawel,Sehanine, Yassine,Terme, Thierry,Vanelle, Patrice
, p. 977 - 986 (2021)
Abstract: New thiosemicarbazones were synthesized in excellent yield reaction of indole derivatives with thiosemicarbazides. These thiosemicarbazones were reacted with ethyl bromoacetate to produce original heterocyclic-substituted indole derivatives possessing a 4-oxo-thiazolidine group. Analytical IR and NMR spectra and elemental analysis were performed to reveal their structures. The antimicrobial activity of all synthesized compounds was evaluated for antibacterial activity in vitro against Gram-positive and Gram-negative bacteria. Antibacterial screening data showed that two compounds demonstrated activity against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. These preliminary results indicate that some of these newly synthesized compounds show a promising antibacterial potency. Graphic abstract: [Figure not available: see fulltext.].
