Day: February 23, 2023

In(OTf)₃-catalyzed chemoselective alkylation of tryptamines with 2-oxo-1-pyrrolidine derivatives was written by Zi, You;Chu, Xue-Qiang;Lu, Xin-Mou;Wang, Shun-Yi;Ji, Shun-Jun. And the article was included in RSC Advances in 2014.Safety of N-(2-(1H-Indol-3-yl)ethyl)acetamide This article mentions the following:

The chemoselective alkylation of tryptamine derivatives with 2-oxo-1-pyrrolidine compounds, catalyzed by In(OTf)₃, was investigated. A series of 2-alkyl and N-alkyl tryptamine derivatives were synthesized under mild conditions with good total yields (up to 99%) and chemoselectivity (up to 95 : 5). In the experiment, the researchers used many compounds, for example, N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3Safety of N-(2-(1H-Indol-3-yl)ethyl)acetamide).

N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Safety of N-(2-(1H-Indol-3-yl)ethyl)acetamide

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Database of free solution mobilities for 276 metabolites was written by Petrov, Alexander P.;Sherman, Lindy M.;Camden, Jon P.;Dovichi, Norman J.. And the article was included in Talanta in 2020.Synthetic Route of C10H10N2O This article mentions the following:

Although databases are available that provide mass spectra and chromatog. retention information for small-mol. metabolites, no publicly available database provides electrophoretic mobility for common metabolites. As a result, most compounds found in electrophoretic-based metabolic studies are unidentified and simply annotated as “features”. To begin to address this issue, the authors analyzed 460 metabolites from a com. library using capillary zone electrophoresis coupled with electrospray mass spectrometry. To speed anal., a sequential injection method was used wherein six compounds were analyzed per run. An uncoated fused silica capillary was used for the anal. at 20掳 with a 0.5% (volume/volume) formic acid and 5% (volume/volume) methanol background electrolyte. A Prince autosampler was used for sample injection and the capillary was coupled to an ion trap mass spectrometer using an electrokinetically-pumped nanospray interface. The authors generated mobility values for 276 metabolites from the library (60% success rate) with an average standard deviation of 0.01 脳 10^-8 m²V^-1s^-1. As expected, cationic and anionic compounds were well resolved from neutral compounds Neutral compounds co-migrated with electroosmotic flow. Most of the compounds that were not detected were neutral and presumably suffered from adsorption to the capillary wall or poor ionization efficiency. In the experiment, the researchers used many compounds, for example, Indole-3-acetamide (cas: 879-37-8Synthetic Route of C10H10N2O).

Indole-3-acetamide (cas: 879-37-8) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Synthetic Route of C10H10N2O

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Reductive Knoevenagel Condensation with the Zn-AcOH System was written by Ivanov, Konstantin L.;Melnikov, Mikhail Ya.;Budynina, Ekaterina M.. And the article was included in Synthesis in 2021.Related Products of 27421-51-8 This article mentions the following:

An efficient gram-scale one-pot approach to 2-substituted malonates and related structures were developed, starting from com. available aldehydes and active methylene compounds The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indole-2-carbaldehyde (cas: 27421-51-8Related Products of 27421-51-8).

1-Methyl-1H-indole-2-carbaldehyde (cas: 27421-51-8) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Related Products of 27421-51-8

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Daily Rhythm in Plasma N-acetyltryptamine was written by Backlund, Peter S.;Urbanski, Henryk F.;Doll, Mark A.;Hein, David W.;Bozinoski, Marjan;Mason, Christopher E.;Coon, Steven L.;Klein, David C.. And the article was included in Journal of Biological Rhythms in 2017.Quality Control of N-(2-(1H-Indol-3-yl)ethyl)acetamide This article mentions the following:

Normal physiol. undergoes 24-h changes in function that include daily rhythms in circulating hormones, most notably melatonin and cortical steroids. This study focused on N-acetyltryptamine, a little-studied melatonin receptor mixed agonist-antagonist and the likely evolutionary precursor of melatonin. The central issue addressed was whether N-acetyltryptamine is physiol. present in the circulation. N-acetyltryptamine was detected by LC-MS/MS in daytime plasma of 3 different mammals in subnanomolar levels (mean 卤 SEM: rat, 0.29 卤 0.05 nM, n = 5; rhesus macaque, 0.54 卤 0.24 nM, n = 4; human, 0.03 卤 0.01 nM, n = 32). Anal. of 24-h blood collections from rhesus macaques revealed a nocturnal increase in plasma N-acetyltryptamine (p < 0.001), which varied from 2- to 15-fold over daytime levels among the 4 animals studied. Related RNA sequencing studies indicated that the transcript encoding the tryptamine acetylating enzyme arylalkylamine N-acetyltransferase (AANAT) is expressed at similar levels in the rhesus pineal gland and retina, thereby indicating that either tissue could contribute to circulating N-acetyltryptamine. The evidence that N-acetyltryptamine is a physiol. component of mammalian blood and exhibits a daily rhythm, together with known effects as a melatonin receptor mixed agonist-antagonist, shifts the status of N-acetyltryptamine from pharmacol. tool to candidate for a physiol. role. This provides a new opportunity to extend our understanding of 24-h biol. In the experiment, the researchers used many compounds, for example, N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3Quality Control of N-(2-(1H-Indol-3-yl)ethyl)acetamide).

N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of N-(2-(1H-Indol-3-yl)ethyl)acetamide

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Pinoline may be used as a probe for CYP2D6 activity was written by Jiang, Xi-Ling;Shen, Hong-Wu;Yu, Ai-Ming. And the article was included in Drug Metabolism and Disposition in 2009.Category: indole-building-block This article mentions the following:

Pinoline, 6-methoxy-1,2,3,4-tetrahydro-尾-carboline, is a serotonin analog that selectively inhibits the activity of monoamine oxidase-A and shows antidepressant activity. Our previous study using a panel of recombinant cytochrome P 450 (P 450) enzymes suggests that pinoline O-demethylation may be selectively catalyzed by polymorphic CYP2D6. The current study, therefore, aimed to delineate the impact of CYP2D6 status on pinoline metabolism Enzyme kinetic studies using recombinant CYP2D6 allelic isoenzymes revealed that CYP2D6.2 exhibited 5-fold lower enzyme efficiency (V_max/K_m) toward pinoline compared with CYP2D6.1, and CYP2D6.10 did not show any catalytic activity. Inhibition study showed that quinidine (1 渭M) completely blocked pinoline O-demethylase activity in human liver microsomes, whereas other P 450 isoform-selective inhibitors had no or minimal effects. Pinoline O-demethylase activities in 10 human liver microsomes showed significantly strong correlation with bufuralol 1′-hydroxylase activities (R² = 0.93; p < 0.0001) and CYP2D6 contents (R² = 0.82; p = 0.005), whereas no appreciable correlations with enzymic activities of other P 450 enzymes were found. Furthermore, we compared pinoline urinary metabolic ratio (pinoline/6-hydroxy-1,2,3,4-tetrahydro-尾-carboline) between CYP2D6-humanized and wild-type control mice after i.p. injection of pinoline (30 mg/kg). Results indicated that the two genotyped mice were clearly distinguished by pinoline metabolic ratio (mean 卤 S.D.), which was much higher in wild-type mice (0.29 卤 0.19, n = 4) than in CYP2D6-humanized transgenic mice (0.0070 卤 0.0048, n = 4). Our findings suggest that pinoline O-demethylation is governed by CYP2D6 status, and pinoline, at a proper concentration or dose, may be a good probe to evaluate CYP2D6 activity. In the experiment, the researchers used many compounds, for example, 6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (cas: 20315-68-8Category: indole-building-block).

6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (cas: 20315-68-8) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis, Conformational Analysis, and Biological Evaluation of 1-Hexylindolactam-V10 as a Selective Activator for Novel Protein Kinase C Isozymes was written by Yanagita, Ryo C.;Nakagawa, Yu;Yamanaka, Nobuhiro;Kashiwagi, Kaori;Saito, Naoaki;Irie, Kazuhiro. And the article was included in Journal of Medicinal Chemistry in 2008.COA of Formula: C8H6N2O2 This article mentions the following:

Conventional and novel protein kinase C (PKC) isoenzymes are the main targets of tumor promoters. We developed 1-hexylindolactam-V10 (I) as a selective activator for novel PKC isoenzymes that play important roles in various cellular processes related to tumor promotion, ischemia-reperfusion injury in the heart, and Alzheimer’s disease. The compound existed as a mixture of three conformers. The trans-amide restricted analogs of I hardly bound to PKC isoenzymes, suggesting that the active conformation of I could be that with a cis-amide. Compound I selectively translocated novel PKC isoenzymes over conventional PKC isoenzymes in HeLa cells at 0.1-1 渭M. These results suggest that I could be useful for the functional anal. of novel PKC isoenzymes. In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5COA of Formula: C8H6N2O2).

4-Nitroindole (cas: 4769-97-5) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.COA of Formula: C8H6N2O2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Salicylaldehyde-Promoted Cobalt-Catalyzed C-H/N-H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue was written by Huang, Mao-Gui;Shi, Shuai;Li, Ming;Liu, Yue-Jin;Zeng, Ming-Hua. And the article was included in Organic Letters in 2021.Category: indole-building-block This article mentions the following:

A cobalt-catalyzed annulation of the C(sp²)-H/N-H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C-H activation step. The synthetic applications are proven by the gram-scale reaction and one-step construction of the multicyclic 5-HT3 receptor antagonist. In the experiment, the researchers used many compounds, for example, 5-Bromo-1-methyl-1H-indole-3-carboxylic acid (cas: 400071-95-6Category: indole-building-block).

5-Bromo-1-methyl-1H-indole-3-carboxylic acid (cas: 400071-95-6) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Crystal structure, infrared and EPR spectra and anticancer activity in vitro of the novel manganese(II) complexes of indolecarboxylic acids was written by Morzyk-Ociepa, Barbara;Kokot, Mariusz;Rozycka-Sokolowska, Ewa;Gielzak-Kocwin, Krystyna;Filip-Psurska, Beata;Wietrzyk, Joanna;Michalska, Danuta. And the article was included in Polyhedron in 2014.Related Products of 4382-54-1 This article mentions the following:

The new complexes of 5-methoxyindole-2-carboxylic acid (5-MeOI2CAH) and indole-2-carboxylic acid (I2CAH) with manganese(II): catena-poly[diaquamanganese(II)-bis(渭²-5-methoxyindole-2-carboxylato-O:O’)], [Mn(5-MeOI2CA)₂(H₂O)₂]_n (1) and catena-poly[diaquamanganese(II)-bis(渭²-indole-2-carboxylato-O:O’)], [Mn(I2CA)₂(H₂O)₂]_n (2) have been prepared A single crystal x-ray anal. of 1 shows that the complex crystallizes in the monoclinic system, space group P2₁/c. The 5-MeOI2CA anion acts as a bidentate bridging ligand coordinated to Mn(II) in an abnormal non-planar skew-skew mode, which differs from the coplanar syn-syn, syn-anti and anti-anti bridging modes commonly occurring in metal carboxylates. The FTIR and EPR spectroscopic studies of Mn(II) complexes are reported. In vitro cytotoxicities of 1, 2, 5-MeOI2CAH, I2CAH and their Zn(II) complexes have been evaluated by an MTT assay against the selected human leukemia cell lines: HL-60, MV-4-11, U937, Jurkat, KG-1, U2932 and murine melanoma B16-F0. The two manganese(II) complexes are cytotoxic and their antiproliferative activity against some cell lines (e.g. Jurkat derived from an acute T cell leukemia) is similar to that of cisplatin. In the experiment, the researchers used many compounds, for example, 5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1Related Products of 4382-54-1).

5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Related Products of 4382-54-1

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

A simple two-step synthesis of indoles was written by Walkington, Andrew;Gray, Matthew;Hossner, Frank;Kitteringham, John;Voyle, Martyn. And the article was included in Synthetic Communications in 2003.SDS of cas: 13544-43-9 This article mentions the following:

A two-step synthesis of indoles that is suitable for use on a large scale is described. The general applicability of this methodol. was also briefly explored. In the experiment, the researchers used many compounds, for example, 6-(Trifluoromethyl)-1H-indole (cas: 13544-43-9SDS of cas: 13544-43-9).

6-(Trifluoromethyl)-1H-indole (cas: 13544-43-9) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.SDS of cas: 13544-43-9

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles