Indoles. Medical search. Frequent questions

Substituted indoles are structural elements of (and for some compounds, the synthetic precursors for) the tryptophan-derived tryptamine alkaloids, which includes the neurotransmitter serotonin and the hormone melatonin, as well as the naturally occurring psychedelic drugs dimethyltryptamine and psilocybin. (wikipedia.org)
In the 1930s, interest in indole intensified when it became known that the indole substituent is present in many important alkaloids, known as indole alkaloids (e.g., tryptophan and auxins), and it remains an active area of research today. (wikipedia.org)
"Indole alkaloids in plant hallucinogens" Planta Med . (erowid.org)
Ten indole alkaloids were obtained from the marine sponge-associated fungus Neosartorya siamensis KUFA 0017. (nih.gov)

Certain indole derivatives were important dyestuffs until the end of the 19th century. (wikipedia.org)
A number of indole derivatives have important cellular functions, including neurotransmitters such as serotonin. (wikipedia.org)
Indole and its derivatives can also be synthesized by a variety of methods. (wikipedia.org)
Furthermore, indole and its derivatives are viewed as potential antivirulence compounds against antibiotic-resistant pathogens because of their ability to inhibit quorum sensing and virulence factor production. (nih.gov)
This review presents current knowledge regarding indole and its derivatives, their biotechnological applications and their role in prokaryotic and eukaryotic systems. (nih.gov)
Indole derivatives are obtained as single regioisomers in high yields. (organic-chemistry.org)
Various 2-phenyl-1H-indoles and benzimidazole derivatives have been tested for total antioxidant capacity by phosphomolybednum reduction method and 2,2-diphenyl-1-picrylhydrazide free radical scavenging activity. (ijpsonline.com)
The present study was focused on evaluating substituted indole and benzimidazole derivatives ( Table 1 ) for total antioxidant capacity (TAC), free radical scavenging and antimicrobial activity. (ijpsonline.com)
Indole derivatives, microbiome and graft versus host disease. (stembook.org)
Indole derivatives have been mostly reported to demonstrate significant activities such as analgesics, anti-inflammatory agents, antifungals, antiarrhythmic agents, and inhibitors of nitric oxide synthase. (civilica.com)
The metabolites of note included small fatty acids such as decanoic and octanoic acid, amino acids such as serine and 1H-indole-3-acetic acid, and sugar derivatives such as glycerol. (medscape.com)

A Br nsted acid-catalyzed one-pot synthesis of indoles from o -aminobenzyl alcohols and furans via in situ formation of aminobenzylfuran followed by its recyclization into the indole core proved to be efficient for a wide range of substrates. (organic-chemistry.org)
The development of a long-term manufacturing route to a potent and selective KDR kinase inhibitor has led to the discovery of several novel methodologies for the general synthesis of indoles. (chimia.ch)

Then, in 1866, Adolf von Baeyer reduced oxindole to indole using zinc dust. (wikipedia.org)
Så, i 1866 reduserte Adolf von Baeyer oxindol til indol ved hjelp av sinkstøv . (wikipedia.org)

A series of 1-pentyl-1H-indol-3-yl-(1-naphthyl)methanes (9-11) and 2-methyl-1-pentyl-1H-indol-3-yl-(1-naphthyl)methanes (12-14) have been synthesized to investigate the hypothesis that cannabimimetic 3-(1-naphthoyl)indoles interact with the CB(1) receptor by hydrogen bonding to the carbonyl group. (erowid.org)
Hydrogen peroxide-dependent oxidation of indole producing indigo has been catalyzed by engineered myoglobins (Mbs). (rsc.org)
The hydrogen bond increases the cyclopropane's electrophilicity permitting indole nucleophiles to open the ring. (uwo.ca)
Hydrogen bond activation of donor-acceptor cyclopropanes was successful in generating a multitude of functional indole products in high yields. (uwo.ca)
This method incorporates a two-tube system, whereupon, one tube tests for hydrogen sulfide production, phenylalanine deaminase, lysine decarboxylase, lactose utilization, and gas production from glucose, and the other tube tests for indole production, ornithine decarboxylase, and motility. (cdc.gov)

Indole is widely distributed in the natural environment and can be produced by a variety of bacteria. (wikipedia.org)
A number of bacteria, and some plants, produce large quantities of indole, which is widespread in animal intestinal tracts and in the rhizosphere. (nih.gov)

One of the oldest and most reliable methods for synthesizing substituted indoles is the Fischer indole synthesis, developed in 1883 by Emil Fischer. (wikipedia.org)

Cruciferous vegetables contain an active compound known as indole-3-carbinol. (frysfood.com)

The amino acid tryptophan is an indole derivative and the precursor of the neurotransmitter serotonin. (wikipedia.org)
Indole-3-carbinol (I3C) is the precursor to diindolylmethane (DIM) - to which it is rapidly metabolized in vivo . (ultimatefatburner.com)
Method one involves radicals to cyclize an additional ring to an indole precursor. (uwo.ca)

These included decanoic acid, octanoic acid, glycerol serine, and 1H-Indole-3-acetic acid. (medscape.com)

Synthesis of only benzene ring functionalized indoles and poly-substituted carbazoles is reported via a one-pot triple cascade benzannulation protocol. (rsc.org)
Application of this methodology has led to the synthesis of highly functionalized pharmacophores including other KDR kinase inhibitors, biindoles and tjipanazole natural products, indolo[2,3-a]pyrrolo [3,4-c]carbazoles, indole-4-carboxylic amides, N-hydroxyindoles, and 2,3-dihydrobenzofurans. (chimia.ch)

En av de eldste og mest pålitelige metoder for å syntetisere substituerte indoler er Fischer indolsyntese som ble utviklet i 1883 av Emil Fischer . (wikipedia.org)

Indoles also present in naturally occurring compounds like dimethyltryptamine (hallucinogen), tryptophan (amino acid) and melatonin [ 16 ] (antioxidant as free radical scavenger). (ijpsonline.com)

Indole is an aromatic, heterocyclic, organic compound with the formula C8H7N. (wikipedia.org)
A three-component synthesis of substituted indoles starts from ortho -dihaloarenes through the use of a multicatalytic system consisting of an N -heterocyclic carbene palladium complex and CuI. (organic-chemistry.org)

Deltakelsen av et enslig elektronpar av nitrogen i den aromatiske ringen medfører at indol ikke er en base , og det oppfører seg ikke som et usammensatt amin . (wikipedia.org)
Indoles and benzimidazoles are very popular nitrogen containing heterocycles. (ijpsonline.com)

The name indole is a portmanteau of the words indigo and oleum, since indole was first isolated by treatment of the indigo dye with oleum. (wikipedia.org)
Navnet indol er avledet fra en kombinasjon av ordene ind igo og ol eum fordi indol til å begynne med ble isolert gjennom behandling av indigofargestoff med oleum. (wikipedia.org)

The catalytic activity of mutants depends on the amino acids at 68 and 107 positions and the H64D/V68I/I107A mutant gave the highest catalytic activity, suggesting that the side chains of Ile-68 and Ala-107 provide a hydrophobic environment suitable for indole binding. (rsc.org)

Indole, as an interspecies and interkingdom signaling molecule, plays important roles in bacterial pathogenesis and eukaryotic immunity. (nih.gov)
Important as a component of many pharmaceuticals, indole is a biological molecule found throughout the natural world. (uwo.ca)

In 1869, he proposed a formula for indole. (wikipedia.org)
[1] I 1869 foreslo han formelen til indol (til venstre) som i dag er akseptert. (wikipedia.org)

Figure 1: Indole test results with sulfur-indole-motility (SIM) agar. (asm.org)
Figure 2: Results of the indole test using sulfur-indole-motility medium. (asm.org)
Figure 6: Reactions on sulfide-indole-motility (SIM) medium. (asm.org)

Isatin is an indole derivative first obtained by Erdman and Laurent in 1841 as an oxidation product of Indigo dye with nitric acid and chromic acids. (drugbank.com)

Chapter 3 outlines the application of single electron transfer agent, Mn(OAc) 3 , to isolate 1,2-annulated indoles in a one-pot procedure. (uwo.ca)

"3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB(1) cannabinoid receptor" Bioorg Med Chem . (erowid.org)
Molecular modeling and receptor docking studies of naphthoylindole 16, its 2-methyl congener (19) and indolyl-1-naphthylmethanes 11 and 14, combined with the receptor affinities of these cannabimimetic indoles, strongly suggest that these cannabinoid receptor ligands bind primarily by aromatic stacking interactions in the transmembrane helix 3-4-5-6 region of the CB(1) receptor. (erowid.org)

Common classical methods applied for the detection of extracellular and environmental indoles, are Salkowski, Kovács, Ehrlich's reagent assays and HPLC. (wikipedia.org)
The basis of the preference of indole-3-tetrazole for TIR1 was revealed to be a single residue substitution using molecular docking, and assays using tir1 and afb5 mutant lines confirmed selectivity in vivo. (whiterose.ac.uk)

Cp*Co III =a Co III complex with one Cp* ligand and other coordinating ligand(s), such as C 6 H 6 , a base (OAc), or a substrate (imine or a pyrimidine unit in indoles). (wiley.com)

Indole chemistry began to develop with the study of the dye indigo. (wikipedia.org)

Indole is biosynthesized in the shikimate pathway via anthranilate. (wikipedia.org)
The focus was on two particular enzymes, nitrilase and nitrile hydratase which participate in the indole-3-acetonitrile pathway. (uwaterloo.ca)

Toxicologic analysis of product samples and clinical specimens (available from seven cases) identified a fluorinated SC previously unreported in synthetic marijuana products: (1-(5-fluoropentyl)-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl) methanone, also known as XLR-11, in four of five product samples and four of six patients' clinical specimens. (cdc.gov)

For intracellular indole detection and measurement genetically encoded indole-responsive biosensor is applicable. (wikipedia.org)
Various analytical procedures for the measurement of indole are evaluated. (nofima.no)

The effect of various process parameters on the presence of indole in shrimps is reviewed in relation to the FDA action levels for indole in shrimps of 25 mu g/100 g and 50 mu g/100 g, respectively. (nofima.no)

Originally disclosed in a patent in 1976, this method is high-yielding and can generate substituted indoles. (wikipedia.org)
Metoden som opprinnelig ble avslørt i en patent i 1976 gir høy avkastning og kan generere substituerte indoler. (wikipedia.org)

Indoles of commercial importance include drugs such as indomethacin (antiinflammatory, an antipyretic and an analgesic) and indoxole (an antiinflammatory and antipyretic drug). (ijpsonline.com)

Indoles 9-11 have significant (K(i)=17-23nM) receptor affinity, somewhat less than that of the corresponding naphthoylindoles (5, 15, 16). (erowid.org)
2-Methyl-1-indoles 12-14 have little affinity for the CB(1) receptor, in contrast to 2-methyl-3-(1-naphthoyl)indoles 17-19, which have affinities comparable to those of 5, 15, 16. (erowid.org)

The research in this thesis outlines two new methods for the synthesis of further functionalized indole products. (uwo.ca)

The SAR shows that 3-piperidin-4-yl-1H-indole is intolerant to most N-piperidinyl modifications. (unl.pt)

Many psychoactive plants owe their activity to structures containing an indole nucleus. (erowid.org)

Tube 2: Indole production. (asm.org)
One of the most prominent and important of these mechanisms is the production of the plant hormone indole-3-acetic acid. (uwaterloo.ca)

Indole can still be synthesized, however, using the Fischer indole synthesis by reacting phenylhydrazine with pyruvic acid followed by decarboxylation of the formed indole-2-carboxylic acid. (wikipedia.org)
An indole-3-carboxylic acid carrying a carboxy group at position 3. (mcw.edu)
IAA (Indole-3-Acetic Acid) is the abundant and well known plant hormone of the auxin class. (goldbio.com)
In this study, four different levels of Indole-3- Butyric Acid (IBA) concentration (0, 1000, 1500 and 2000 mg L-1) and three rooting media ( sphagnum moss , vermicompost and garden soil ) were applied after removal of bark ( phloem ) on the shoot to determine the effect on rooting and survivability of the wax apple air layer under field conditions. (bvsalud.org)

In this paper, harmonic vibrational frequencies, molecular structure, NBO and HOMO, LUMO analysis and detonation properties of (E)-2-Bromo-1-[2-(2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl] ethanone is calculated. (civilica.com)
Then the same calculations are done for the indole structure and are compared with the (E)-2-Bromo-1-[2-(2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl]ethanone calculations. (civilica.com)

The Leimgruber-Batcho indole synthesis is an efficient method of synthesizing indole and substituted indoles. (wikipedia.org)
This method is especially popular in the pharmaceutical industry, where many pharmaceutical drugs are made up of specifically substituted indoles. (wikipedia.org)
High pressure liquid chromatography (HPLC) with fluorescence detection seems to be the most effective analytical method for the determination of indole. (nofima.no)
Method two functionalizes indoles by reacting them with strained three-membered ring molecules called cyclopropanes. (uwo.ca)

High indole levels in frozen shrimp can be considered an indicator of poor product quality prior to freezing and thus of hygienic practices far away from Good Hygienic Practice (GHP). (nofima.no)

Temperature abuse is an important critical process parameter for the formation of indole. (nofima.no)

Indole modulates oxidative stress, intestinal inflammation, and hormone secretion in animals, and it controls plant defense systems and growth. (nih.gov)

By applying bio-isosteric replacement we discovered that indole-3-tetrazole was active by surface plasmon resonance (SPR) spectrometry, showing that the tetrazole could initiate assembly of the TIR1 auxin co-receptor complex. (whiterose.ac.uk)

A randomized, placebo-controlled, double-blinded pilot trial was conducted, comparing the effects of Brassica consumption and indole-3-carbinol supplements on PSA among prostate cancer patients with PSA recurrence following prostectomy. (aicr.org)

Oxyphenisatin acetate is the pro-drug of oxyphenisatin (3,3-bis(4-hydroxyphenyl)-1H-indol-2-one). (drugbank.com)

However, a low content of indole does not necessarily imply a good quality. (nofima.no)

Indoles exhibited better antibacterial activity compared to benzimidazoles. (ijpsonline.com)

In this paper the processing of shrimp is described and microbial formation of indole is discussed. (nofima.no)

Anatomy1

Organisms23

Chemicals and Drugs64

Analytical, Diagnostic and Therapeutic Techniques and Equipment13

Phenomena and Processes23

Disciplines and Occupations1

Technology, Industry, Agriculture4

Information Science2

Alkaloids4

Derivatives11

Synthesis of Indoles2

Adolf von Ba2

Hydrogen5

Bacteria2

Synthesizing substituted1

Cruciferous vegetables1

Precursor3

Serine1

Carbazoles2

Emil Fischer1

Compounds1

Heterocyclic2

Nitrogen2

Oleum2

Amino1

Molecule2

18692

Motility3

Derivative1

Isolate1

Aromatic2

Assays2

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Chemistry1

Pathway2

Synthetic1

Measurement2

Presence1

19762

Indomethacin1

Affinity2

Methods1

Modifications1

Plants1

Production2

Acid4

Structure2

Method4

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Plant1

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