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.
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.
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Savel'eva et al.
, (1973)
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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.
