22980-09-2Relevant articles and documents
An 3-Indolyl-imidazol-4-one from the Tunicate Dendrodoa grossularia.
Guyot, Michele,Meyer, Michele
, p. 2621 - 2622 (1986)
A new compound, possessing an unususal 4H-imidazole ring was isolated; structure elucidation was performed using spectral analysis and confirmed by synthesis.
A general synthesis of tris-indole derivatives as potential iron chelators
Sears, R. Bryan,Carpenter, Russell A.,Whitlock, Christine R.
, p. 488 - 491 (2005)
The development of a novel route for the synthesis of a new class of compounds is described. The first tripodal, tris-indole amines are prepared by straightforward routes.
Rationally designed tri-armed imidazole–indole hybrids as naked eye receptors for fluoride ion sensing
Jain, Anshu,Gupta, Ragini,Agarwal, Madhu
, p. 1307 - 1318 (2017)
The present communication describes the design, synthesis, and characterization of unique tri-armed imidazole–indole hybrids RA-RE for naked eye detection of fluoride ion in 9:1 DMSO–water at concentration level of 1.5 ppm, which is recommended permissible limit of fluoride ion. Molecular structures of the receptors are so fabricated that both heterocyclic units, namely, indole and imidazole have been rationally used as chromophore and binding unit, respectively. Strategical introduction of nitro group(s) at the fifth position of indole ring remarkably enhances the binding ability of receptor RD making it highly selective toward fluoride ion (tetrabutylammonium salt) over other typical anionic species. The sensing event can be visualized by naked eyes swiftly with color change. This observation is well corroborated by a redshift of 80 nm in UV–visible spectroscopic studies. A peak at 16.1 ppm due to HF2- in 1H NMR titration validates the deprotonation of imidazolium N?H by fluoride ion.
N-1, C-3 substituted indoles as 5-LOX inhibitors - In vitro enzyme immunoaasay, mass spectral and molecular docking investigations
Singh, Palwinder,Pooja
, p. 1433 - 1437 (2013)
Based upon the structures of some known 5-LOX inhibitors, a set of five compounds carrying appropriate substituents at N-1 and C-3 of indole were synthesized and investigated for 5-LOX inhibitory activities. Fifty percent inhibitory concn (IC50) of these compounds ranges from 0.6 to 5 μM and found to be comparable to that of clinically used 5-LOX inhibitor, zileuton. The compounds under present investigations exhibited appreciable interactions with 5-LOX as apparent from their association constants calculated from the mass spectral data. Compound 5a with a tosyl group at N-1 and pyrolidinyl-1,2-dione substituent at C-3 of indole, exhibiting IC50 0.6 μM and stoichiometry of 1:7 in the enzyme-compound complex was identified as highly potent 5-LOX inhibitor and seems to be suitable for further investigations.
Rational modification of a lead molecule: Improving the antifungal activity of indole – triazole – amino acid conjugates
Mishra, Sahil,Kaur, Manpreet,Chander, Subhash,Murugesan, Sankaranarayanan,Nim, Lovedeep,Arora,Singh, Palwinder
, p. 658 - 669 (2018)
The modification of a molecule that was identified as highly efficacious in the previous studies could considerably improve the biological activity of the resulting compounds. While targeting lanosterol 14-α demethylase, the molecular modelling studies convinced that the extension of the phenyl ring of compound 1 deep into the hydrophobic pocket of the enzyme may increase the enzyme – ligand interactions and hence improve the anti-fungal profile of the molecules. As a result, the newly designed compounds 2 were synthesized and screened for their anti-microbial properties and these compounds were found to exhibit considerably better activity than the previous molecule 1. Some of the compounds in this series exhibited MIC90 16 μg mL?1 and 32 μg mL?1 against Candida albicans and Aspergillus niger, respectively as against 312 μg mL?1 for compound 1.
Total synthesis and bioactivity of the marine alkaloid pityriacitrin and some of its derivatives
Zhang, Puyong,Sun, Xiaofei,Xu, Bin,Bijian, Krikor,Wan, Shengbiao,Li, Guigen,Alaoui-Jamali, Moulay,Jiang, Tao
, p. 6089 - 6097 (2011)
We report herein the chemical synthesis and biological evaluation of β-carboline alkaloid pityriacitrin and some of its new derivatives. Using tryptophan or 5-hydroxytryptophan and 5-substituted indole-3-glyoxals as the starting materials, pityriacitrin and some of its derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by 1H and 13C NMR, mass spectroscopy and IR determinations. Biological studies revealed that pityriacitrin has a weak antiproliferative activity against a panel of breast and prostate cancer cell lines, whereas some of its derivatives exhibited stronger and potent activity, which was associated with induction of both cell apoptosis and necrosis.
N-(indol-3-ylglyoxylyl)piperidines: High affinity agonists of human GABA-A receptors containing the α1 subunit
Collins, Ian,Davey, William B.,Rowley, Michael,Quirk, Kathleen,Bromidge, Frances A.,McKernan, Ruth M.,Thompson, Sally-Anne,Wafford, Keith A.
, p. 1381 - 1384 (2000)
A new class of N-(indol-3-ylglyoxylyl)piperidines are high affinity agonists at the benzodiazepine binding site of human GABA-A receptor ion-channels, with modest selectivity for receptors containing the α1 subunit over α2 and α3. All three receptor subtypes discriminate substantially between the two enantiomers of the chiral ligand 10. (C) 2000 Elsevier Science Ltd. All rights reserved.
Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines
Cozzi, Nicholas V.,Daley, Paul F.
, p. 959 - 964 (2016)
N,N-Diallyltryptamine (DALT) and 5-methoxy-N,N-diallyltryptamine (5-MeO-DALT) are two tryptamines synthesized and tested by Alexander Shulgin. In self-experiments, 5-MeO-DALT was reported to be psychoactive in the 12-20 mg range, while the unsubstituted compound DALT had few discernible effects in the 42-80 mg range. Recently, 5-MeO-DALT has been used in nonmedical settings for its psychoactive effects, but these effects have been poorly characterized and little is known of its pharmacological properties. We extended the work of Shulgin by synthesizing additional 5-substituted-DALTs. We then compared them to DALT and 5-MeO-DALT for their binding affinities at 45 cloned receptors and transporter proteins. Based on in vitro binding affinity, we identified 27 potential receptor targets for the 5-substituted-DALT compounds. Five of the DALT compounds had affinity in the 10-80 nM range for serotonin 5-HT1Aand 5-HT2Breceptors, while the affinity of DALT itself at 5-HT1Areceptors was slightly lower at 100 nM. Among the 5-HT2subtypes, the weakest affinity was at 5-HT2Areceptors, spanning 250-730 nM. Five of the DALT compounds had affinity in the 50-400 nM range for serotonin 5-HT1D, 5-HT6, and 5-HT7receptors; again, it was the unsubstituted DALT that had the weakest affinity at all three subtypes. The test drugs had even weaker affinity for 5-HT1B, 5-HT1E, and 5-HT5Asubtypes and little or no affinity for the 5-HT3subtype. These compounds also had generally nanomolar affinities for adrenergic α2A, α2B, and α2Creceptors, sigma receptors σ1and σ2, histamine H1receptors, and norepinephrine and serotonin uptake transporters. They also bound to other targets in the nanomolar-to-low micromolar range. Based on these binding results, it is likely that multiple serotonin receptors, as well as several nonserotonergic sites are important for the psychoactive effects of DALT drugs. To learn whether any quantitative structure-affinity relationships existed, we evaluated correlations among physicochemical properties of the congeneric 5-substituted-DALT compounds. The descriptors included electronic (σp), hydrophobic (π), and steric (CMR) parameters. The binding affinity at 5-HT1A, 5-HT1D, 5-HT7, and κ opioid receptors was positively correlated with the steric volume parameter CMR. At α2A, α2B, and α2Creceptors, and at the histamine H1receptor, binding affinity was correlated with the Hammett substituent parameter σp; higher affinity was associated with larger σpvalues. At the σ2receptor, higher affinity was correlated with increasing π. These correlations should aid in the development of more potent and selective drugs within this family of compounds.
Synthesis of deuterium labeled tryptamine derivatives
Wang, Yu-Yun,Chen, Chinpiao
, p. 1363 - 1368 (2007)
The synthesis of deuterium labeled tryptamine derivatives, [2-(1H-indol-3-yl)-[2H4]-ethyl]-dimethylamine (DMT), [2H10]-diethyl-[2-(1H-indol-3-yl)-ethyl]-amine (DET), [2-(1H-indol-3-yl)-ethyl]-[2H6]-dipropyl-amine (DPT) and [2H2]-alpha-methyltryptamine (AMT) is described. The isotopically labeled compounds are used as internal standards in gas chromatography-mass spectrometry (GC-MS) assays.
Identification of an indole-triazole-amino acid conjugate as a highly effective antifungal agent
Pawar, Kalpana,Yadav, Anshuman,Prasher, Parteek,Mishra, Sahil,Singh, Balwinder,Singh, Palwinder,Komath, Sneha Sudha
, p. 1352 - 1359 (2015)
Compounds constructed by the grafting of amino acid and triazole with an indole moiety were synthesized and investigated for antifungal activities wherein one of the compounds gave highly promising results. Although the compound has a high MIC80 value in liquid medium, it shows significant antifungal activity against Candida albicans in solid plate assays. The compound is found to target chitin in the cell wall and lanosterol 14α-demethylase of the ergosterol biosynthesis pathway. The inhibitory effect of the compound becomes more pronounced in combination with azoles and CFW. The compound is also found to significantly affect chitin levels, cell morphology and cell viability in combination with ketoconazole.
