19005-93-7Relevant articles and documents
Molecular Structure and Photochemistry of (E)- and (Z)-Ethyl 3-(2-Indolyl)propenoate. Ground State Conformational Control of Photochemical Behavior and One-Way E -> Z Photoisomerization
Lewis, Frederick D.,Yang, Jye-Shane
, p. 14560 - 14568 (1996)
The molecular structure, electronic spectra, and photoisomerization of (E)- and (Z)-ethyl 3-(2-indolyl)propenoate, two methylated indole derivatives, and their N,N-dimethylamide analog have been investigated.The E ester exists in the ground state as a mixture of anti and syn rotational isomers.The spectroscopic and photochemical behaviors of the individual anti and syn conformers were characterized with the assistance of comparisons with the behavior of the methylated indole derivatives.The major anti conformer of the E ester absorbs and emits at shorter wavelength than the minor syn conformer.The rate constant for singlet state isomerization of the anti conformer is substantially larger than that of the syn conformer, resulting in a shorter singlet lifetime and smaller fluorescence quantum yield for the anti conformer.The behavior of the E amide in both the ground and excited states is similar to that of the ester.The Z isomers of the ester and amide possess a relatively strong intramolecular hydrogen bond.Their singlet states are weakly fluoroscent and photoisomerize ineffeciently in nonpolar solvents.Thus photostationary states highly enriched in the Z isomers are obtained in nonpolar solvents.The red-shifted, structureless emission observed upon irradiating the Z amide in an EPA or methylcyclohexane glass at 77 K is attributed to an excited state tautomer formed via intramolecular hydrogen transfer.
Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains
Akunuri, Ravikumar,Veerareddy, Vaishnavi,Kaul, Grace,Akhir, Abdul,Unnissa, Tanveer,Parupalli, Ramulu,Madhavi,Chopra, Sidharth,Nanduri, Srinivas
supporting information, (2021/08/27)
Infections caused due to multidrug resistant organisms have emerged as a constant menace to human health. Even though numerous antibiotics are currently available for treating infectious diseases, a great number of bacterial strains have acquired resistance to many of them. Among these, infections caused due to Staphylococcus aureus are predominant in adult and paediatric population. Indole is a prominent chemical scaffold found in many pharmacologically active natural products and synthetic drugs. A number of oxime ether containing compounds have attracted attention of researchers owing to their interesting biological properties. Current work details the synthesis of indole containing oxime ether derivatives and their evaluation for antimicrobial activity against a panel of bacterial and mycobacterial strains. Synthesized compounds demonstrated good to moderate activity against drug-resistant S. aureus including resistant to vancomycin. Among all, compound 5h was found to possess potent activity against susceptible as well as MRSA and VRSA strains of S. aureus with MIC of 1 μg/mL and 2–4 μg/mL respectively. In addition, compound 5h was found to be non-toxic to Vero cells and exhibited good selectivity index of >40. Further, 5h, E-9a and E-9b possessed good biofilm inhibition against S. aureus. With these assuring biological properties, synthesized compounds could be potential prospective antimicrobial agents.
Au(I)-Catalyzed Pictet-Spengler Reactions All around the Indole Ring
Milcendeau, Pierre,Zhang, Zhenhao,Glinsky-Olivier, Nicolas,Van Elslande, Elsa,Guinchard, Xavier
, p. 6406 - 6422 (2021/05/29)
Au(I) complexes catalyze iso-Pictet-Spengler reactions. Ethylamine or methylamine chains were introduced at C2, C4, or the nitrogen atom of the indole ring, and the corresponding substrates were reacted in the presence of aldehydes and catalytic amounts of Au(I) complexes, leading to a variety of polycyclic scaffolds. Selectivity could be achieved in the course of a double iso-Pictet-Spengler reaction involving two successive aldehydes, leading to highly complex molecules.
Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics
Buijs, Ned,Campagna, Roberto,Emanuelli, Monica,Gao, Yongzhi,Innocenti, Paolo,Jespers, Willem,Martin, Nathaniel I.,Parsons, Richard B.,Sartini, Davide,Van Haren, Matthijs J.,Van Westen, Gerard J. P.,Zhang, Yurui,Gutiérrez-De-Terán, Hugo
, p. 12938 - 12963 (2021/09/11)
Nicotinamide N-methyltransferase (NNMT) methylates nicotinamide (vitamin B3) to generate 1-methylnicotinamide (MNA). NNMT overexpression has been linked to a variety of diseases, most prominently human cancers, indicating its potential as a therapeutic target. The development of small-molecule NNMT inhibitors has gained interest in recent years, with the most potent inhibitors sharing structural features based on elements of the nicotinamide substrate and the S-adenosyl-l-methionine (SAM) cofactor. We here report the development of new bisubstrate inhibitors that include electron-deficient aromatic groups to mimic the nicotinamide moiety. In addition, a trans-alkene linker was found to be optimal for connecting the substrate and cofactor mimics in these inhibitors. The most potent NNMT inhibitor identified exhibits an IC50 value of 3.7 nM, placing it among the most active NNMT inhibitors reported to date. Complementary analytical techniques, modeling studies, and cell-based assays provide insights into the binding mode, affinity, and selectivity of these inhibitors.