22948-94-3Relevant articles and documents
Structure, electronic, spectroscopic and reactivity investigations of pharmacologically active compound 1–acetyl–3–indolecarboxaldehyde – An experimental and theoretical approach
Durgadevi,Arjunan,Thirunarayanan,Marchewka,Mohan
, p. 57 - 69 (2018)
The experimental and theoretical studies on the structure and vibrations of 1–acetyl–3–indolecarboxaldehyde (AIC) have been carried out by utilising FT–IR, FT–Raman, FT–NMR and quantum chemical density functional theory (DFT) method. The FT–IR and FT–Raman spectra are recorded in the region 4000–400 cm?1 and 4000–100 cm?1, respectively. The geometry of AIC is optimised by B3LYP method with 6–31G** 6–311++G** and cc–pVTZ basis sets. The more stable minimum energy conformer has been found by analyzing the potential energy profile. The fundamental vibrational frequencies, infrared intensities, Raman intensities and bonding features of this compound are determined. The HOMO and LUMO energy difference show that, the charge transfer occurs within the molecule. The electrostatic potential and thermodynamic properties of the compound at the different temperatures have been calculated. 1H and 13C NMR chemical shifts of the compound are determined by Gauge Invariant Atomic Orbital (GIAO) by using B3LYP/6–311++G** method. The electrostatic potential of AIC lie in the range +1.22e × 10?2 to ?1.22e × 10?2. The limits of total electron density of the complex is +4.906e × 10?2 to ?4.906e × 10?2.
Reactions of o-Alkenyloxyarenediazonium Fluoroborates and Related Species with Nitroxides
Beckwith, Athelstan L. J.,Meijs, Gordon F.
, p. 595 - 597 (1981)
Treatment of arenediazonium fluoroborates bearing suitable alkenyloxy- or alkenylamino-ortho-substituents affords ring-closed hydroxylamine derivatives via free-radical mechanism: similar treatment of o-alkynyloxy- or o-alkynylamino-arenediazonium salts gives aldehydes.
Spirocyclization reactions and antiproliferative activity of indole phytoalexins 1-methoxybrassinin and its 1-substituted derivatives
Budovská, Mariana,Pilátová, Martina Bago,Tischlerová, Viera,Moj?i?, Ján
, p. 198 - 234 (2016)
The effect of the reaction temperature and the solvent on the diastereoselectivity of the spirocyclization of 1-methoxybrassinin leading to 1-methoxyspirobrassinol methyl ether was studied. 1-Acyl derivatives of 1-methoxyspirobrassinol and 1-methoxyspirobrassinol methyl ether were prepared by the bromine-mediated spirocyclization reactions of derivatives of brassinin bearing an acyl group on the indole nitrogen with water or methanol as nucleophilic agents. The cyclization of 1-acyl derivatives of brassinin afforded the trans-diastereoisomer as the major product, whereas using 1-methoxybrassinin afforded the cis- and trans-isomers in a ratio near to 1:1. Bromospirocyclization of brassinin and 1-methylbrassinin in the presence of methanol resulted in the formation of spirobrassinin and 1-methylspirobrassinin. The newly synthesized analogues of indole phytoalexins exhibited more significant antiproliferative activity against human leukemia cell lines than the natural phytoalexins.
Computer-aided drug discovery: Novel 3,9-disubstituted eudistomin U derivatives as potent antibacterial agents
Dai, Jiangkun,Dan, Wenjia,Li, Na,Wang, Junru
, p. 333 - 338 (2018)
Thirty-two new 3,9-disubstituted eudistomin U derivatives were designed and synthesized based on computer-aided drug discovery (CADD). Sixteen 3,9-disubstituted eudistomin U derivatives (6a–6p) have exhibited potent antibacterial activity. Specially, the most active compound 6p displayed better activity than commercial drugs fosfomycin sodium, ciprofloxacin and propineb, with a peak minimum inhibitory concentration (MIC) of 1.5625 μmol/L. The antibacterial mechanism indicated that these compounds could exert bactericidal effect by damaging bacterial cell membrane and disrupting the function of DNA gyrase.
Selective Synthesis of Acylated Cross-Benzoins from Acylals and Aldehydes via N-Heterocyclic Carbene Catalysis
Onodera, Kou,Suzuki, Yumiko,Takashima, Ryo
supporting information, p. 4197 - 4202 (2021/06/27)
The utility of acylals as building blocks for selective cross-benzoin synthesis was explored in this study. The synthesis of α-acetoxyketones (O-acyl cross-benzoins) was achieved via selective N-heterocyclic carbene-catalyzed cross-benzoin reactions using acylals as aldehyde equivalents. Thus, the combination of ortho-substituted phenyl acylals and aromatic/aliphatic aldehydes as coupling substrates using bicyclic triazolium salts as precatalysts and potassium carbonate as a base in THF at reflux temperature selectively yielded O-acyl cross-benzoins.
Design and Synthesis of Pyrano[3,2-b]indolones Showing Antimycobacterial Activity
Monakhova, Natalia,Korduláková, Jana,Vocat, Anthony,Egorova, Anna,Lepioshkin, Alexander,Salina, Elena G.,Nosek, Jozef,Repková, Eva,Zemanová, Júlia,Jurdáková, Helena,Górová, Renáta,Roh, Jaroslav,Degiacomi, Giulia,Sammartino, José Camilla,Pasca, Maria Rosalia,Cole, Stewart T.,Miku?ová, Katarína,Makarov, Vadim
, p. 88 - 100 (2021/01/12)
Latent Mycobacterium tuberculosis infection presents one of the largest challenges for tuberculosis control and novel antimycobacterial drug development. A series of pyrano[3,2-b]indolone-based compounds was designed and synthesized via an original eight-step scheme. The synthesized compounds were evaluated for their in vitro activity against M. tuberculosis strains H37Rv and streptomycin-starved 18b (SS18b), representing models for replicating and nonreplicating mycobacteria, respectively. Compound 10a exhibited good activity with MIC99 values of 0.3 and 0.4 μg/mL against H37Rv and SS18b, respectively, as well as low toxicity, acceptable intracellular activity, and satisfactory metabolic stability and was selected as the lead compound for further studies. An analysis of 10a-resistant M. bovis mutants disclosed a cross-resistance with pretomanid and altered relative amounts of different forms of cofactor F420 in these strains. Complementation experiments showed that F420-dependent glucose-6-phosphate dehydrogenase and the synthesis of mature F420 were important for 10a activity. Overall these studies revealed 10a to be a prodrug that is activated by an unknown F420-dependent enzyme in mycobacteria.
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.
Spirocyclization reactions and antiproliferative activity of indole phytoalexins 1-methoxybrassinin and its 1-substituted derivatives
Budovská, Mariana,Pilátová, Martina Bago,Tischlerová, Viera,Moj?i?, Ján
, p. 198 - 234 (2017/09/25)
The effect of the reaction temperature and the solvent on the diastereoselectivity of the spirocyclization of 1-methoxybrassinin leading to 1-methoxyspirobrassinol methyl ether was studied. 1-Acyl derivatives of 1-methoxyspirobrassinol and 1-methoxyspirobrassinol methyl ether were prepared by the bromine-mediated spirocyclization reactions of derivatives of brassinin bearing an acyl group on the indole nitrogen with water or methanol as nucleophilic agents. The cyclization of 1-Acyl derivatives of brassinin afforded the trans-diastereoisomer as the major product, whereas using 1-methoxybrassinin afforded the cis-And trans-isomers in a ratio near to 1:1. Bromospirocyclization of brassinin and 1-methylbrassinin in the presence of methanol resulted in the formation of spirobrassinin and 1-methylspirobrassinin. The newly synthesized analogues of indole phytoalexins exhibited more significant antiproliferative activity against human leukemia cell lines than the natural phytoalexins.
Iron-Catalyzed Synthesis of C2 Aryl- and N-Heteroaryl-Substituted Tetrahydropyrans
Bosset, Cyril,Angibaud, Patrick,Stanfield, Ian,Meerpoel, Lieven,Berthelot, Didier,Guérinot, Amandine,Cossy, Janine
, p. 12509 - 12525 (2016/01/09)
An iron-catalyzed cyclization of hydroxy allylic derivatives into tetrahydropyrans possessing an N-heteroaryl at C2 is disclosed. The reaction proceeds with good yield and in high diastereoselectivity in favor of the more stable isomer. The diastereoselectivity results from an iron-induced reopening of the tetrahydropyrans, allowing a thermodynamic equilibration. The method allows access to a variety of 2,6-disubstituted as well as 2,4,6-trisubstituted tetrahydropyrans that could be considered as attractive scaffolds for the pharmaceutical industry.
Evaluation of (Z)-2-((1-benzyl-1H-indol-3-yl)methylene)-quinuclidin-3-one analogues as novel, high affinity ligands for CB1 and CB2 cannabinoid receptors
Madadi, Nikhil Reddy,Penthala, Narsimha Reddy,Brents, Lisa K.,Ford, Benjamin M.,Prather, Paul L.,Crooks, Peter A.
, p. 2019 - 2021 (2013/04/23)
A small library of N-benzyl indolequinuclidinone (IQD) analogs has been identified as a novel class of cannabinoid ligands. The affinity and selectivity of these IQDs for the two established cannabinoid receptor subtypes, CB1 and CB2, was evaluated. Compounds 8 (R = R2 = H, R1 = F) and 13 (R = COOCH3, R1 = R2 = H) exhibited high affinity for CB2 receptors with Ki values of 1.33 and 2.50 nM, respectively, and had lower affinities for the CB1 receptor (Ki values of 9.23 and 85.7 nM, respectively). Compound 13 had the highest selectivity of all the compounds examined, and represents a potent cannabinoid ligand with 34-times greater selectivity for CB2R over CB1R. These findings are significant for future drug development, given recent reports demonstrating beneficial use of cannabinoid ligands in a wide variety of human disease states including drug abuse, depression, schizophrenia, inflammation, chronic pain, obesity, osteoporosis and cancer.
