125334-52-3Relevant academic research and scientific papers
Synthesis of a novel N-nitroalkyl bisindolylmaleimide
Roy, Sudipta,Gribble, Gordon W.
, p. 1879 - 1886 (2007)
We describe the synthesis of the novel N-nitropropyl bisindolylmaleimide 6. Copyright Taylor & Francis Group, LLC.
Synthesis, molecular modelling and biological evaluation of novel heterodimeric, multiple ligands targeting cholinesterases and amyloid Beta
Hebda, Michalina,Bajda, Marek,Wieckowska, Anna,Szal?aj, Natalia,Pasieka, Anna,Panek, Dawid,Godyń, Justyna,Wichur, Tomasz,Knez, Damijan,Gobec, Stanislav,Malawska, Barbara
, (2016)
Cholinesterases and amyloid beta are one of the major biological targets in the search for a new and efficacious treatment of Alzheimer's disease. The study describes synthesis and pharmacological evaluation of new compounds designed as dual binding site
Substituent effects on photosensitized splitting of thymine cyclobutane dimer by an attached indole
Tang, Wenjian,Zhou, Hongmei,Wang, Jing,Pan, Chunxiao,Shi, Jingbo,Song, Qinhua
, p. 4180 - 4185 (2012)
In chromophore-containing cyclobutane pyrimidine dimer (CPD) model systems, solvent effects on the splitting efficiency may depend on the length of the linker, the molecular conformation, and the oxidation potential of the donor. To further explore the relationship between chromophore structure and splitting efficiency, we prepared a series of substituted indole-TT model compounds 2 a-2 g and measured their splitting quantum yields in various solvents. Two reverse solvent effects were observed: an increase in splitting efficiency in solvents of lower polarity for models 2 a-2 d with an electron-donating group (EDG), and vice versa for models 2 e-2 g with an electron-withdrawing group (EWG). According to the Hammett equation, the negative value of the slope of the Hammett plot indicates that the indole moiety during the TT-splitting reaction loses negative charge, and the larger negative value implies that the repair reaction is more sensitive to substituent effects in low-polarity solvents. The EDGs of the models 2 a-2 d can delocalize the charge-separated state, and low-polarity solvents make it more stable, which leads to higher splitting efficiency in low-polarity solvents. Conversely, the EWGs of models 2 e-2 g favor destabilization of the charge-separated state, and high-polarity solvents decrease the destabilization and hence lead to more efficient splitting in high-polarity solvents. Two reverse solvent effects were observed in a series of indole-cyclobutane pyrimidine dimer model systems with differently substituted indole moieties. Thus, the splitting quantum yield Φspl shows a normal relation with solvent polarity for compounds with an electron-donating group, and vice versa for those with an electron-withdrawing group (see picture; bet=back electron transfer). Copyright
Catalytic assay of Schiff base Co(II), Ni(II), Cu(II) and Zn(II) complexes for N-alkylation of heterocycles with 1,3-dibromopropane
Chavan, Sanjay,Gaikwad, Gautam,Hegade, Sujit,Jadhav, Yuvraj,Mulik, Ganpatrao
, (2020)
Abstract: N-alkylation of heterocycles with 1,3-dibromopropane using Schiff base Co(II), Ni(II), Cu(II) and Zn(II) transition metal complexes as a catalyst was studied in 1:1 and 2:1 coupling ratios under mild conditions. It was observed that all the complexes worked as efficient catalyst with product yield 78–92percent for coupling ratio 1:1 and product yield 63–78percent for coupling ratio 2:1. N-alkylation of heterocycles with 1,3-dibromopropane in 1:1 coupling ratio is easier with higher yields as compared with N-alkylation in 2:1 coupling ratio. Graphic abstract: N-Alkylation of heterocycles with 1,3-dibromopropane[Figure not available: see fulltext.]
Manganese(III) Acetate Catalyzed Aerobic Dehydrogenation of Tertiary Indolines, Tetrahydroquinolines and an N-Unsubstituted Indoline
Niu, Xiaokang,Yang, Lei
supporting information, p. 4209 - 4215 (2021/08/06)
A Mn(OAc)3 ? 2H2O-catalyzed aerobic dehydrogenation of five and six-membered N-heterocycles for the synthesis of N-heteroarenes is reported. Of note, this protocol can be applied to the dehydrogenation of tertiary indolines with various electron-deficient N-substituents. Preliminary mechanistic investigations support that a single-electron transfer pathway might be involved. (Figure presented.).
Synthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity
Nimbarte, Vijaykumar D.,Wirmer-Bartoschek, Julia,Gande, Santosh L.,Alshamleh, Islam,Seibert, Marcel,Nasiri, Hamid Reza,Schnütgen, Frank,Serve, Hubert,Schwalbe, Harald
supporting information, p. 1667 - 1679 (2021/03/24)
Lead-optimization strategies for compounds targeting c-Myc G-quadruplex (G4) DNA are being pursued to develop anticancer drugs. Here, we investigate the structure-activity- relationship (SAR) of a newly synthesized series of molecules based on the pyrrolidine-substituted 5-nitro indole scaffold to target G4 DNA. Our synthesized series allows modulation of flexible elements with a structurally preserved scaffold. Biological and biophysical analyses illustrate that substituted 5-nitroindole scaffolds bind to the c-Myc promoter G-quadruplex. These compounds downregulate c-Myc expression and induce cell-cycle arrest in the sub-G1/G1 phase in cancer cells. They further increase the concentration of intracellular reactive oxygen species. NMR spectra show that three of the newly synthesized compounds interact with the terminal G-quartets (5′- and 3′-ends) in a 2 : 1 stoichiometry.
Synthesis of Cyclopenta[b]indoles via a Formal [3+2] Cyclization of N-Sulfonyl-1,2,3-triazoles and Indoles
Duan, Shengguo,Zhang, Wan,Hu, Yuntong,Xu, Ze-Feng,Li, Chuan-Ying
supporting information, p. 3570 - 3575 (2020/08/05)
Annulation of benzoxy-tethered N-sulfonyl-1,2,3-triazoles and indoles has been developed in this paper, providing an efficient and convenient access to valuable cyclopenta[b]indoles in moderate to good yields. α,β-Unsaturated imine, which generated in situ from denitrogenation and 1,2-OBz migration of triazole, provided three carbons for the formal [3+2] cyclization reaction for the first time. (Figure presented.).
Bioconjugation with Thiols by Benzylic Substitution
Watanabe, Kenji,Ohshima, Takashi
supporting information, p. 3959 - 3964 (2018/02/22)
A benzylic substitution of 3-indolyl(hydroxyl)acetate derivatives with thiols proceeded specifically in the presence of amino, carboxy, and phosphate groups in weakly acidic aqueous solutions under nearly physiological condition, while no reaction occurred at pH over 7. Kinetic studies revealed that the reaction followed second-order kinetics (first-order in the reactant and first-order in thiol) in contrast with the SN1 mechanism of common benzylic substitution of alcohols. The utility of the present method for functionalization of biomacromolecules was demonstrated using several model proteins, such as lysozyme, insulin, trypsin, and serum albumin. The catalytic bioactivity of lysozyme in lysis of Micrococcus lysodeikticus cells was completely retained after the modification.
N-alkyl substituted indole-imidazolium salt compounds, and preparation method thereof
-
Paragraph 0013; 0014, (2017/08/31)
The invention discloses a series of N-alkyl substituted indole-imidazolium salt compounds having a structural formula (represented b figure I), and a preparation method thereof. The preparation method comprises the following steps: synthesizing N-alkyl su
Indole functionalization via photoredox gold catalysis
Kaldas, Sherif J.,Cannillo, Alexandre,McCallum, Terry,Barriault, Louis
supporting information, p. 2864 - 2866 (2015/06/16)
The use of photoredox catalyst [Au2(dppm)2]Cl2 to initiate free-radical cyclizations onto indoles is reported. Excitation of the dimeric Au(I) photocatalyst for the reduction of unactivated bromoalkanes and bromoarenes is used for the generation of carbon-centered radicals. Previous to this work, reduction processes leading to indole functionalization utilizing photoredox catalysts were limited to activated benzylic or α-carbonyl-positioned bromoalkanes. This method offers a mild and safe alternative to organostannanes and pyrophoric initiators for access to high energy radicals that were previously inaccessible through catalytic or stoichiometric means.
