22/02/2023 - Page 5 of 66 - Indole Building Blocks

Pedras, M. Soledade C. et al. published their research in Journal of Agricultural and Food Chemistry in 2012 | CAS: 1016-47-3

N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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.Application In Synthesis of N-(2-(1H-Indol-3-yl)ethyl)acetamide

Metabolism and Metabolites of Dithiocarbamates in the Plant Pathogenic Fungus Leptosphaeria maculans was written by Pedras, M. Soledade C.;Sarma-Mamillapalle, Vijay K.. And the article was included in Journal of Agricultural and Food Chemistry in 2012.Application In Synthesis of N-(2-(1H-Indol-3-yl)ethyl)acetamide This article mentions the following:

Synthetic compounds containing a dithiocarbamate group are known to have a variety of biol. effects and applications including antifungal, herbicidal, and insecticidal application. Leptosphaeria maculans is a fungal pathogen of crucifers able to detoxify efficiently the only plant natural product containing a dithiocarbamate group, the phytoalexin brassinin. To evaluate the effects of dithiocarbamates on L. maculans, a number of structurally diverse S-Me dithiocarbamates containing indolyl, biphenyl, and benzimidazolyl moieties were synthesized, and their antifungal activities and metabolism by L. maculans were investigated. All dithiocarbamates were transformed by L. maculans through hydrolysis to the corresponding amines, which were less antifungal than the parent compounds Two dithiocarbonates were shown to be much less antifungal than the corresponding dithiocarbamates. Results of this investigation indicate that S-Me dithiocarbamates are not useful inhibitors of L. maculans and that their rates of transformation by L. maculans did not correlate with the antifungal activity of the particular compound In the experiment, the researchers used many compounds, for example, N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3Application In Synthesis 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

Garg, Neil K. et al. published their research in Tetrahedron Letters in 2005 | CAS: 18372-22-0

Methyl 2-(1H-indol-3-yl)-2-oxoacetate (cas: 18372-22-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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). COA of Formula: C11H9NO3

Synthesis of bis(indole)-1,2,4-triazinones was written by Garg, Neil K.;Stoltz, Brian M.. And the article was included in Tetrahedron Letters in 2005.COA of Formula: C11H9NO3 This article mentions the following:

A facile method for the synthesis of meta- and para-substituted bis(indole)-1,2,4-triazinones, e.g., I, is presented. To access these triazinones, a cyclocondensation reaction between amidrazone and ketoester functionalities was applied. The structures of these interesting compounds were established unambiguously by X-ray crystallog. In the experiment, the researchers used many compounds, for example, Methyl 2-(1H-indol-3-yl)-2-oxoacetate (cas: 18372-22-0COA of Formula: C11H9NO3).

Laezza, Antonio et al. published their research in Bioconjugate Chemistry in 2020 | CAS: 87276-51-5

tert-Butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate (cas: 87276-51-5) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application of 87276-51-5

Protecting Group Free Synthesis of Glyconanoparticles Using Amino-Oxy-Terminated Polymer Ligands was written by Laezza, Antonio;Georgiou, Panagiotis G.;Richards, Sarah-Jane;Baker, Alexander N.;Walker, Marc;Gibson, Matthew I.. And the article was included in Bioconjugate Chemistry in 2020.Application of 87276-51-5 This article mentions the following:

Glycomaterials display enhanced binding affinity to carbohydrate-binding proteins due to the nonlinear enhancement associated with the cluster glycoside effect. Gold nanoparticles bearing glycans have attracted significant interest in particular. This is due to their versatility, their highly tunable gold cores (size and shape), and their application in biosensors and diagnostic tools. However, conjugating glycans onto these materials can be challenging, necessitating either multiple protecting group manipulations or the use of only simple glycans. This results in limited structural diversity compared to glycoarrays which can include hundreds of glycans. Here we report a method to generate glyconanoparticles from unprotected glycans by conjugation to polymer tethers bearing terminal amino-oxy groups, which are then immobilized onto gold nanoparticles. Using an isotope-labeled glycan, the efficiency of this reaction was probed in detail to confirm conjugation, with 25% of end-groups being functionalized, predominantly in the ring-closed form. Facile post-glycosylation purification is achieved by simple centrifugation/washing cycles to remove excess glycan and polymer. This streamlined synthetic approach may be particularly useful for the preparation of glyconanoparticle libraries using automation, to identify hits to be taken forward using more conventional synthetic methods. Exemplar lectin-binding studies were undertaken to confirm the availability of the glycans for binding and show this is a powerful tool for rapid assessment of multivalent glycan binding. In the experiment, the researchers used many compounds, for example, tert-Butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate (cas: 87276-51-5Application of 87276-51-5).

Leino, Markku et al. published their research in Acta Ophthalmologica in 1984 | CAS: 20315-68-8

6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (cas: 20315-68-8) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application of 20315-68-8

Light microscopic autoradiography of rat retinae after intravitreal injection of [³H]6-methoxy-tetrahydro]尾-carboline was written by Leino, Markku;Markkanen, Seppo;Airaksinen, Mauno M.;Gynther, Jukka;Kari, Ilkka. And the article was included in Acta Ophthalmologica in 1984.Application of 20315-68-8 This article mentions the following:

The autoradiog. retinal distribution of intravitreally injected [³H]6-methoxy-tetrahydro-尾-carboline (6-MeO-THBC) in rats was studied. The synaptic and ganglion cell layers accumulate pronounced radioactivity, as do some intra- and extracellular locations in the inner nuclear layer and the outer segments of the photoreceptors. The pigment epithelium gradually accumulates a very dense band of radioactivity. The relation between 6-MeO-THBC, melatonin and other 5-methoxy-indoles is discussed. In the experiment, the researchers used many compounds, for example, 6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (cas: 20315-68-8Application of 20315-68-8).

Campanico, Andre et al. published their research in ChemMedChem in 2019 | CAS: 16800-68-3

1-Acetylindolin-3-one (cas: 16800-68-3) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Recommanded Product: 16800-68-3

Azaaurones as potent antimycobacterial agents active against MDR- and XDR-TB was written by Campanico, Andre;Carrasco, Marta P.;Njoroge, Mathew;Seldon, Ronnett;Chibale, Kelly;Perdigao, Joao;Portugal, Isabel;Warner, Digby F.;Moreira, Rui;Lopes, Francisca. And the article was included in ChemMedChem in 2019.Recommanded Product: 16800-68-3 This article mentions the following:

Herein we report the screening of a small library of aurones and their isosteric counterparts, azaaurones and N-acetylazaaurones, against Mycobacterium tuberculosis. Aurones were found to be inactive at 20 渭M, whereas azaaurones and N-acetylazaaurones emerged as the most potent compounds, with nine derivatives displaying MIC₉₉ values ranging from 0.4 to 2.0 渭M. In addition, several N-acetylazaaurones were found to be active against multidrug-resistant (MDR) and extensively drug-resistant (XDR) clin. M. tuberculosis isolates. The antimycobacterial mechanism of action of these compounds remains to be determined; however, a preliminary mechanistic study confirmed that they do not inhibit the mycobacterial cytochrome bc1 complex. Addnl., microsomal metabolic stability and metabolite identification studies revealed that N-acetylazaaurones are deacetylated to their azaaurone counterparts. Overall, these results demonstrate that azaaurones and their N-acetyl counterparts represent a new entry in the toolbox of chemotypes capable of inhibiting M. tuberculosis growth. In the experiment, the researchers used many compounds, for example, 1-Acetylindolin-3-one (cas: 16800-68-3Recommanded Product: 16800-68-3).

Pillaiyar, Thanigaimalai et al. published their research in Journal of Organic Chemistry in 2018 | CAS: 13544-43-9

6-(Trifluoromethyl)-1H-indole (cas: 13544-43-9) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Synthetic Route of C9H6F3N

General Synthesis of Unsymmetrical 3,3′-(Aza)diindolylmethane Derivatives was written by Pillaiyar, Thanigaimalai;Gorska, Ewelina;Schnakenburg, Gregor;Mueller, Christa E.. And the article was included in Journal of Organic Chemistry in 2018.Synthetic Route of C9H6F3N This article mentions the following:

Diindolylmethane (DIM) and its derivatives have recently been in the focus of interest due to their significant biol. activities, specifically in cancer prevention and therapy. Mol. targets of DIM have been identified, e.g., the immunostimulatory G protein-coupled receptor GPR84. However, most of the reported and investigated DIM derivatives are sym. because general methods for obtaining unsym. DIMs have been lacking. To optimize the interaction of DIM derivatives with their protein targets, unsym. substitution is required. In the present study we developed a new, mild and efficient access to unsym. substituted 3,3′-DIMs by reaction of (3-indolylmethyl)trimethylammonium iodides with a wide range of substituted indole derivatives 7-Azaindole also led to the 3,3′-connected DIM analog, while 4- and 5-azaindoles reacted at the N1-nitrogen atom as confirmed by X-ray crystallog. The reactions were performed in water without the requirement of a catalyst or other additives. Wide substrate scope, operational simplicity, environmentally benign workup, and high yields are further advantages of the new method. The synthetic protocol proved to be suitable for upscaling to yield gram amounts for pharmacol. studies. This procedure will allow the preparation of a broad range of novel, unsym. DIM derivatives to exploit their potential as novel drugs. In the experiment, the researchers used many compounds, for example, 6-(Trifluoromethyl)-1H-indole (cas: 13544-43-9Synthetic Route of C9H6F3N).

Shelar, Santosh V. et al. published their research in Organic & Biomolecular Chemistry in 2019 | CAS: 2971-31-5

2-(2-Oxoindolin-3-yl)acetic acid (cas: 2971-31-5) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Name: 2-(2-Oxoindolin-3-yl)acetic acid

Regioselective oxidation of indoles to 2-oxindoles was written by Shelar, Santosh V.;Argade, Narshinha P.. And the article was included in Organic & Biomolecular Chemistry in 2019.Name: 2-(2-Oxoindolin-3-yl)acetic acid This article mentions the following:

Facile regioselective oxidation of indoles to 2-oxindoles I [R = H, CH₂CO₂H, CH₂CO₂Me, etc.] promoted by sulfuric acid adsorbed on silica gel was reported. The demonstrated practical site-selective heterogeneous oxidation reactions conveniently took place with a broad substrate scope and functional group tolerances. The present oxidation strategy was also employed to accomplish the total synthesis of natural products donaxaridine and donaxarine. On the basis of anal. and spectral data it was evidenced that donaxarine stayed in equilibrium with its hydrated ring opened form. The structural features essential for this type of oxidation and plausible mechanism were discussed in brief. In the experiment, the researchers used many compounds, for example, 2-(2-Oxoindolin-3-yl)acetic acid (cas: 2971-31-5Name: 2-(2-Oxoindolin-3-yl)acetic acid).

Gallego-Gomez, Francisco et al. published their research in Advanced Functional Materials in 2011 | CAS: 109005-10-9

10,15-Dihydro-5H-diindolo[3,2-a:3′,2′-c]carbazole (cas: 109005-10-9) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C24H15N3

Very Large Photoconduction Enhancement Upon Self-Assembly of a New Triindole Derivative in Solution-Processed Films was written by Gallego-Gomez, Francisco;Garcia-Frutos, Eva M.;Villalvilla, Jose M.;Quintana, Jose A.;Gutierrez-Puebla, Enrique;Monge, Angeles;Diaz-Garcia, Maria A.;Gomez-Lor, Berta. And the article was included in Advanced Functional Materials in 2011.Electric Literature of C24H15N3 This article mentions the following:

A new carbazole-related small mol. exhibiting self-assembly into ordered nanostructures in solution-processed cast films has been synthesized and its charge-photogeneration and -transport properties have been investigated. Large photoconductivity was measured in the amorphous state while an enormous improvement in the photoconduction properties was observed when the mols. spontaneously organized. Photocurrents increased upon self-assembly by up to four orders of magnitude, mostly due to the drastic enhancement of the charge photogeneration. A greatly favorable arrangement of the aromatic cores in the resulting nanostructures, which were characterized by X-ray anal., may explain these improvements. Photocurrents of mA cm^-2, on/off ratios of 10⁴ and quantum efficiencies of unity at low field and light intensity, which are among the best values reported to date, along with the simplicity of fabrication, give this readily-available organic system great potential for use in plastic optoelectronic devices. In the experiment, the researchers used many compounds, for example, 10,15-Dihydro-5H-diindolo[3,2-a:3′,2′-c]carbazole (cas: 109005-10-9Electric Literature of C24H15N3).

Kawamura, Shuhei et al. published their research in Journal of Medicinal Chemistry in 2013 | CAS: 7432-21-5

(S)-2-(((Benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoic acid (cas: 7432-21-5) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.HPLC of Formula: 7432-21-5

Potent Proteasome Inhibitors Derived from the Unnatural cis-Cyclopropane Isomer of Belactosin A: Synthesis, Biological Activity, and Mode of Action was written by Kawamura, Shuhei;Unno, Yuka;List, Anja;Mizuno, Akirai;Tanaka, Motohiro;Sasaki, Takuma;Arisawa, Mitsuhiro;Asai, Akira;Groll, Michael;Shuto, Satoshi. And the article was included in Journal of Medicinal Chemistry in 2013.HPLC of Formula: 7432-21-5 This article mentions the following:

The natural product belactosin A (1) with a trans-cyclopropane structure is a useful prototype compound for developing potent proteasome (core particle, CP) inhibitors. To date, 1 and its analogs are the only CP ligands that bind to both the nonprimed S1 pocket as well as the primed substrate binding channel; however, these mols. harbor a high IC₅₀ value of more than 1 渭M. We have performed structure-activity relationship studies, thereby elucidating unnatural cis-cyclopropane derivatives of 1 that exhibit high potency to primarily block the chymotrypsin-like active site of the human constitutive (cCP) and immunoproteasome (iCP). The most active compound 3e reversibly inhibits cCP and iCP similarly with an IC₅₀ of 5.7 nM. X-ray crystallog. anal. of the yeast proteasome in complex with 3e revealed that the ligand is accommodated predominantly into the primed substrate binding channel and covalently binds to the active site threonine residue via its 尾-lactone ring-opening. In the experiment, the researchers used many compounds, for example, (S)-2-(((Benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoic acid (cas: 7432-21-5HPLC of Formula: 7432-21-5).

Huang, Liangbin et al. published their research in Angewandte Chemie, International Edition in 2017 | CAS: 1841512-58-0

1,3-Dioxoisoindolin-2-yl 4-phenylbutanoate (cas: 1841512-58-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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.Category: indole-building-block

Reductive Decarboxylative Alkynylation of N-Hydroxyphthalimide Esters with Bromoalkynes was written by Huang, Liangbin;Olivares, Astrid M.;Weix, Daniel J.. And the article was included in Angewandte Chemie, International Edition in 2017.Category: indole-building-block This article mentions the following:

A new method for the synthesis of terminal and internal alkynes from the Ni-catalyzed decarboxylative coupling of N-hydroxyphthalimide esters and bromoalkynes is presented. This reductive cross-electrophile coupling is the 1st to use a C(sp)-X electrophile, and appears to proceed via an alkynylnickel intermediate. The internal alkyne products were obtained in yields of 41-95% without the need for a photocatalyst, light, or a strong oxidant. The reaction displays a broad scope of carboxylic acid and alkyne coupling partners, and can tolerate an array of functional groups, including carbamate NH, halogen, nitrile, olefin, ketone, and ester moieties. Mechanistic studies suggest that this process does not involve an alkynylmanganese reagent and instead proceeds through Ni-mediated bond formation. In the experiment, the researchers used many compounds, for example, 1,3-Dioxoisoindolin-2-yl 4-phenylbutanoate (cas: 1841512-58-0Category: indole-building-block).