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.
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.
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.
Pharmacologically active acetylene compounds. II. Propynyl-substituted indole derivatives.
Neumeyer,Moyer,Leonard
, p. 450 - 452 (1969)
-
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.
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.
Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines
Brandt, Simon D.,Tirunarayanapuram, Sri Subha,Freeman, Sally,Dempster, Nicola,Barker, Steven A.,Daley, Paul F.,Cozzi, Nicholas V.,Martins, Claudia P. B.
, p. 423 - 429 (2008)
A large number of N,N-dialkylated tryptamines are known to induce psychoactive effects in humans. This has resulted in their increased attention within clinical and forensic communities. Deuterated tryptamines are ideal for use as internal standards during MS bioanalysis or of use in biochemical NMR studies. The present study reports on a microwave-enhanced synthesis of 22 N,N-dialkylated-[α,α,β,β-d4]-tryptamines via the reduction with lithium aluminium deuteride of glyoxalylamide precursors obtained by the procedure of Speeter and Anthony. Syntheses were carried out using a single-mode system under elevated pressure conditions where anhydrous tetrahydrofuran was used as the solvent at 150°C. Good yields were obtained within 5 min. Copyright
The design and synthesis of novel 3-[2-indol-1-yl-ethyl]-1H-indole derivatives as selective inhibitors of CDK4
Aubry, Carine,Patel, Asma,Mahale, Sachin,Chaudhuri, Bhabatosh,Maréchal, Jean-Didier,Sutcliffe, Michael J.,Jenkins, Paul R.
, p. 1423 - 1425 (2005)
We present the design, synthesis and biological activity of novel 3-[2-indol-1-yl-ethyl]-1H-indole selective inhibitors of CDK4.
BMS Derivatives C7-Linked to β-Cyclodextrin and Hyperbranched Polyglycerol Retain Activity against R5-HIV-1NLAD8 Isolates and Can Be Deemed Potential Microbicides
Petit, Elena,Bosch, Lluís,Costa, Anna M.,Rodríguez-Izquierdo, Ignacio,Sepúlveda-Crespo, Daniel,Mu?oz-Fernández, M. Angeles,Vilarrasa, Jaume
, p. 2217 - 2222 (2021/05/06)
Amides from indole-3-glyoxylic acid and 4-benzoyl-2-methylpiperazine, which are related to entry inhibitors developed by Bristol-Myers Squibb (BMS), have been synthesized with aliphatic chains located at the C7 position of the indole ring. These spacers contain an azido group suitable for the well-known Cu(I)-catalyzed (3+2)-cycloaddition or an activated triple bond for the nucleophilic addition of thiols under physiological conditions. Reaction with polyols (β-cyclodextrin and hyperbranched polyglycerol) decorated with complementary click partners has afforded polyol-BMS-like conjugates that are not cytotoxic (TZM.bl cells) and retain the activity against R5-HIV-1NLAD8 isolates. Thus, potential vaginal microbicides based on entry inhibitors, which can be called of 4th generation, are reported here for the first time.
Fe-Catalyzed Pictet-Spengler-Type Cyclization via Selective Four-Electron Reductive Functionalization of CO2
Li, Wen-Duo,Chen, Jie,Zhu, Dao-Yong,Xia, Ji-Bao
supporting information, p. 614 - 620 (2021/02/12)
Herein, we describe a novel catalytic Pictet-Spengler-type cyclization using CO2 as a nontoxic and sustainable C1 feedstock with environmentally benign and non-precious-metal iron as catalyst. The reaction is achieved by selective four-electron reduction of CO2 into methylene level intermediate through carefully tuning the reaction parameters. A variety of tetrahydro-β-carbolines and other nitrogen-containing heterocycles can be easily obtained under mild conditions. Mechanistic studies have shown that tetrahydro-β-carbolines are probably obtained via spiroindolenine intermediates.
Synthesis and anti-tumor activity of marine alkaloids
Chen, Guangying,Huang, Gangliang,Zhou, Shiyang
, (2021/04/15)
Marine alkaloids were divided into five categories from the perspective of anti-tumor activity. The optimization process, chemical synthesis, anti-tumor activity evaluation and structure–activity relationship of various compounds were discussed.
