22/02/2023 - Page 59 of 66 - Indole Building Blocks

Sguazzin, Matthew A. et al. published their research in Organic Letters in 2021 | CAS: 16502-01-5

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5) 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). Application In Synthesis of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole

Hexafluoroisopropyl Sulfamate: A Useful Reagent for the Synthesis of Sulfamates and Sulfamides was written by Sguazzin, Matthew A.;Johnson, Jarrod W.;Magolan, Jakob. And the article was included in Organic Letters in 2021.Application In Synthesis of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole This article mentions the following:

Sulfamates and sulfamides were most often synthesized from alcs. and amines with sulfamoyl chloride, which was an unstable reagent. Hexafluoroisopropyl sulfamate (HFIPS) as a bench-stable solid that reacts readily with a wide variety of alcs., amines, phenols, and anilines under mild reaction conditions was identified. The sole byproduct of the reaction was hexafluoroisopropanol (HFIP) and reaction products was often isolated in high purity after an aqueous workup (optional) and removal of solvents by evaporation In the experiment, the researchers used many compounds, for example, 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5Application In Synthesis of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole).

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

Tan, Yayu et al. published their research in Journal of Molecular Modeling in 2012 | CAS: 115956-12-2

rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate (cas: 115956-12-2) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Product Details of 115956-12-2

Predicting the potency of hERG K⁺ channel inhibition by combining 3D-QSAR pharmacophore and 2D-QSAR models was written by Tan, Yayu;Chen, Yadong;You, Qidong;Sun, Haopeng;Li, Manhua. And the article was included in Journal of Molecular Modeling in 2012.Product Details of 115956-12-2 This article mentions the following:

Blockade of the hERG K⁺ channel has been identified as the most important mechanism of QT interval prolongation and thus inducing cardiac risk. In this work, an ensemble of 3D-QSAR pharmacophore models was constructed to provide insight into the determinants of the interactions between the hERG K⁺ channel and channel inhibitors. To predict hERG inhibitory activities, the predicted values from the ensemble of models were averaged, and the results thus obtained showed that the predictive ability of the combined 3D-QSAR pharmacophore model was greater that those of the individual models. Also, using the same training and test sets, a 2D-QSAR model based on a heuristic machine-learning method was developed in order to analyze the physicochem. characters of hERG inhibitors. The models indicated that the inhibitors have certain key inhibitory features in common, including hydrophobicity, aromaticity, and flexibility. A final model was developed by combining the combined 3D-QSAR pharmacophore with the 2D-QSAR model, and this final model outperformed any other individual model, showing the highest predictive ability and the lowest deviation. This model can not only predict hERG inhibitory potency accurately, thus allowing fast cardiac safety evaluation, but it provides an effective tool for avoiding hERG inhibitory liability and thus enhanced cardiac risk in the design and optimization of new chem. entities. In the experiment, the researchers used many compounds, for example, rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate (cas: 115956-12-2Product Details of 115956-12-2).

Elsaman, Tilal et al. published their research in Pharma Chemica in 2016 | CAS: 15362-40-0

1-(2,6-Dichlorophenyl)-2-indolinone (cas: 15362-40-0) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Synthetic Route of C14H9Cl2NO

Synthesis and antiproliferative activity of some novel amides of flufenamic acid and diclofenac was written by Elsaman, Tilal;Aldeeb, Omar A. A.;Aboul-Fadl, Tarek;Al-Dhfyan, Abdullah. And the article was included in Pharma Chemica in 2016.Synthetic Route of C14H9Cl2NO This article mentions the following:

Coupling of the non-steroidal anti-inflammatory drugs (NSAIDs), flufenamic acid 2 and diclofenac 5 with the appropriate amino acid ester 6, using dicyclohexylcarbdiimide (DCC), afforded amides 7-17, resp. The structures of the newly synthesized amides 7-17 were confirmed on the basis of their spectral data and X-ray single crystal anal. All the synthesized compounds have been screened for anti-proliferative activity against A549 lung adenocarcinoma and HT-29 colon cancer cells. Compound 17 showed a good anti-proliferative activity IC50 = 25.82 μM compared with the chemotherapeutic agent 5-fluorouracil IC50 = 18 μM. Furthermore, compound 8 was more potent than the reference drug with IC50 = 15.4μM and cell cycle blockade activity at G0 and S-phase. Compounds 11, 12, 13 and 17 were more potent than the reference drug dichlorofluorescein diacetate (DCF) IC50 = 17.81 μM, while the IC50 for these compound ranges from 6.46-13.99 μM. In the experiment, the researchers used many compounds, for example, 1-(2,6-Dichlorophenyl)-2-indolinone (cas: 15362-40-0Synthetic Route of C14H9Cl2NO).

Clark, Robin D. et al. published their research in Synlett in 1990 | CAS: 129822-48-6

tert-Butyl 5-chloro-1H-indole-1-carboxylate (cas: 129822-48-6) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 129822-48-6

Synthesis of protected indoles from N-(tert-butoxycarbonyl)-2-alkylanilines was written by Clark, Robin D.;Muchowski, Joseph M.;Souchet, Michel;Repke, David B.. And the article was included in Synlett in 1990.Recommanded Product: 129822-48-6 This article mentions the following:

Lithiation of N-(tert-butoxycarbonyl)-2-alkylanilines and sequential condensation with Me₂NCHO and elimination gave N-(tert-butyoxycarbonyl)indoles I (R = H, Me, Ph; R¹ = H, 3-F, 3-Cl, 4-Cl, 4-F, 4-MeO, 4-Me). Lithiation of N-(tert-butoxycarbonyl)-2-methylaniline and reaction with (MeO)MeNCOR² (R² = Me, Ph) and sequential elimination gave 2-methyl- and 2-phenylindole, resp. In the experiment, the researchers used many compounds, for example, tert-Butyl 5-chloro-1H-indole-1-carboxylate (cas: 129822-48-6Recommanded Product: 129822-48-6).

Longeon, Arlette et al. published their research in Marine Drugs in 2011 | CAS: 18372-22-0

Methyl 2-(1H-indol-3-yl)-2-oxoacetate (cas: 18372-22-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Safety of Methyl 2-(1H-indol-3-yl)-2-oxoacetate

Bioactive indole derivatives from the South Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp was written by Longeon, Arlette;Copp, Brent R.;Quevrain, Elodie;Roue, Melanie;Kientz, Betty;Cresteil, Thierry;Petek, Sylvain;Debitus, Cecile;Bourguet-Kondracki, Marie-Lise. And the article was included in Marine Drugs in 2011.Safety of Methyl 2-(1H-indol-3-yl)-2-oxoacetate This article mentions the following:

Indole derivatives including bromoindoles were isolated from the South Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp. Their structures were established through anal. of mass spectra and 1- and 2-dimensional NMR spectroscopic data. Their potential inhibitory phospholipase A₂ (PLA₂), antioxidant and cytotoxic activities were evaluated. The new derivative 5,6-dibromo-L-hypaphorine (I) isolated from Hyrtios sp. revealed a weak bee venom PLA₂ inhibition (IC₅₀ 0.2 mM) and a significant antioxidant activity with an Oxygen Radical Absorbance Capacity (ORAC) value of 0.22. The sesquiterpene aureol, also isolated from Hyrtios sp., showed the most potent antioxidant activity with an ORAC value of 0.29. In the experiment, the researchers used many compounds, for example, Methyl 2-(1H-indol-3-yl)-2-oxoacetate (cas: 18372-22-0Safety of Methyl 2-(1H-indol-3-yl)-2-oxoacetate).

Abdelraheem, Eman et al. published their research in ACS Medicinal Chemistry Letters in 2022 | CAS: 61-54-1

2-(1H-Indol-3-yl)ethanamine (cas: 61-54-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 2-(1H-Indol-3-yl)ethanamine

Multicomponent Macrocyclic IL-17a Modifier was written by Abdelraheem, Eman;Lubberink, Max;Wang, Wenja;Li, Jingyao;Reyes Romero, Atilio;van der Straat, Robin;Du, Xiaochen;Groves, Matthew;Doemling, Alexander. And the article was included in ACS Medicinal Chemistry Letters in 2022.Recommanded Product: 2-(1H-Indol-3-yl)ethanamine This article mentions the following:

The design, discovery, synthesis and screening of macrocyclic compounds that bind to IL-17a was described. All currently described IL-17a modifiers belong to the same pharmacophore model, likely resulting in a similar receptor binding mode on IL-17a was found. A pipeline of pharmacophore anal., virtual screening, resynthesis and protein biophysics resulted in a potent IL-17a macrocyclic modifier. In the experiment, the researchers used many compounds, for example, 2-(1H-Indol-3-yl)ethanamine (cas: 61-54-1Recommanded Product: 2-(1H-Indol-3-yl)ethanamine).

Hewawasam, Piyasena et al. published their research in Journal of Medicinal Chemistry in 2002 | CAS: 18711-15-4

4,6-Dichloroisatin (cas: 18711-15-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Name: 4,6-Dichloroisatin

Synthesis and Structure-Activity Relationships of 3-Aryloxindoles: A New Class of Calcium-Dependent, Large Conductance Potassium (Maxi-K) Channel Openers with Neuroprotective Properties was written by Hewawasam, Piyasena;Erway, Matthew;Moon, Sandra L.;Knipe, Jay;Weiner, Harvey;Boissard, Christopher G.;Post-Munson, Debra J.;Gao, Qi;Huang, Stella;Gribkoff, Valentin K.;Meanwell, Nicholas A.. And the article was included in Journal of Medicinal Chemistry in 2002.Name: 4,6-Dichloroisatin This article mentions the following:

Aryloxindoles were prepared and evaluated as activators of the cloned maxi-K channel mSlo expressed in Xenopus laevis oocytes using electrophysiol. methods. The most promising maxi-K openers were (±)-(chlorohydroxyphenyl)dihydrohydroxy(trifluoromethyl)indolone I and its 3-des-hydroxy analog II. The individual enantiomers of (±)-I were prepared and the maxi-K channel-opening properties were shown to depend on the absolute configuration of the single stereogenic center with the efficacy of (-)-I superior to that of both (+)-I and (±)I at 20 μM. (±)-II exhibited greater efficacy than either (±)-I or the more active enantiomer in the electrophysiol. evaluation. In vitro metabolic stability studies conducted with (±)-I and (±)-II in rat liver S9 microsomal fractions revealed significant oxidative degradation with two hydroxylated metabolites observed by liquid chromatog./mass spectrometry for each compound in addition to the production of I from II. The pharmacokinetic properties of (±)-I and (±)-II were determined in rats as a prelude to evaluation in a rat model of stroke that involved permanent occlusion of the middle cerebral artery. In the MCAO model, conducted in the spontaneously hypertensive rat, the more polar 3-hydroxy derivative (±)-I did not demonstrate a significant reduction in cortical infarct volume when administered i.v. at doses ranging from 0.1 to 10 mg/kg as a single bolus 2 h after middle cerebral artery occlusion when compared to vehicle-treated controls. In contrast, i.v. administration of (±)-II at a dose of 0.03 mg/kg was found to reduce the measured cortical infarct volume by approx. 18% when compared to vehicle-treated control animals. I.p. administration of (±)-II at a dose of 10 mg/kg 2 h following artery occlusion was shown to reduce infarct volume by 26% when compared to vehicle-treated controls. To further probe the effects of compounds (±)-I and (±)-II on neurotransmitter release in vitro, both compounds were examined for their ability to reduce elec. stimulated [³H]-glutamate release from rat hippocampal slices that had been preloaded with [³H]-glutamate. Only (±)-II was able to demonstrate a significant inhibition [³H]-glutamate release in this assay at a concentration of 20 μM, providing concordance with the profile of these compounds in the MCAO model. Although (±)-II showed some promise as a potential developmental candidate for the treatment of the sequelae of stroke based on its efficacy in the rat MCAO model, the pharmacokinetic profile of this compound was considered to be less than optimal and was not pursued in favor of derivatives with enhanced metabolic stability. In the experiment, the researchers used many compounds, for example, 4,6-Dichloroisatin (cas: 18711-15-4Name: 4,6-Dichloroisatin).

Purgatorio, Rosa et al. published their research in Molecules in 2018 | CAS: 10601-19-1

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) 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.Computed Properties of C10H9NO2

Insights into structure-activity relationships of 3-arylhydrazonoindolin-2-one derivatives for their multitarget activity on β-amyloid aggregation and neurotoxicity was written by Purgatorio, Rosa;de Candia, Modesto;De Palma, Annalisa;De Santis, Francesco;Pisani, Leonardo;Campagna, Francesco;Cellamare, Saverio;Altomare, Cosimo Damiano;Catto, Marco. And the article was included in Molecules in 2018.Computed Properties of C10H9NO2 This article mentions the following:

A series of new 3-(2-arylhydrazono)indolin-2-one derivatives I [R = H, n-Bu, 5-MeO; R¹ = H; R² = H, Br; R³ = H, Me, cyclopropyl, Bn, (CH₂)₂C₆H₅, (CH₂)₃C₆H₅; R⁴ = H, Me; RR¹ = OCH₂O; Ar = 4-iPrC₆H₄, 4-NCC₆H₄, 1-naphthyl, etc.]was synthesized and assayed, investigating the effects of substitutions on both the indole core and arylhydrazone moiety. Compared with the reference we disclosed equipotent derivatives bearing alkyl substituents at the indole nitrogen and fairly tolerated bioisosteric replacements at the arylhydrazone moiety. For most of the investigated compounds, the inhibition of Aβ40 aggregation (expressed as pIC₅₀) was found to be correlated with lipophilicity, as assessed by a reversed-phase HPLC method, through a bilinear relationship. The compound I [R = MeO, R¹ = R² = H, R³ = cyclopropyl, R⁴ = H Ar = 4-iPrC₆H₄] was tested in cell-based assays of Aβ42 oligomer toxicity and oxidative stress induced by hydrogen peroxide, showing significant cytoprotective effects. This study confirmed the versatility of isatin in preparing multitarget small mols. affecting different biochem. pathways involved in Alzheimer’s disease. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1Computed Properties of C10H9NO2).

Romano, Keith P. et al. published their research in Proceedings of the National Academy of Sciences of the United States of America in 2010 | CAS: 924305-06-6

4-Fluoroisoindoline hydrochloride (cas: 924305-06-6) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.SDS of cas: 924305-06-6

Drug resistance against: HCV NS3/4A inhibitors is defined by the balance of substrate recognition versus inhibitor binding was written by Romano, Keith P.;Ali, Akbar;Royer, William E.;Schiffer, Celia A.. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2010.SDS of cas: 924305-06-6 This article mentions the following:

Hepatitis C virus infects an estimated 180 million people worldwide, prompting enormous efforts to develop inhibitors targeting the essential NS3/4A protease. Resistance against the most promising protease inhibitors, telaprevir, boceprevir, and ITMN-191, has emerged in clin. trials. In this study, crystal structures of the NS3/4A protease domain reveal that viral substrates bind to the protease active site in a conserved manner defining a consensus volume, or substrate envelope. Mutations that confer the most severe resistance in the clinic occur where the inhibitors protrude from the substrate envelope, as these changes selectively weaken inhibitor binding without compromising the binding of substrates. These findings suggest a general model for predicting the susceptibility of protease inhibitors to resistance: drugs designed to fit within the substrate envelope will be less susceptible to resistance, as mutations affecting inhibitor binding would simultaneously interfere with the recognition of viral substrates. In the experiment, the researchers used many compounds, for example, 4-Fluoroisoindoline hydrochloride (cas: 924305-06-6SDS of cas: 924305-06-6).

Chahdoura, Faouzi et al. published their research in Advanced Synthesis & Catalysis in 2013 | CAS: 118-12-7

1,3,3-Trimethyl-2-methyleneindoline (cas: 118-12-7) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Related Products of 118-12-7

Palladium Nanoparticles in Glycerol: A Versatile Catalytic System for C-X Bond Formation and Hydrogenation Processes was written by Chahdoura, Faouzi;Pradel, Christian;Gomez, Montserrat. And the article was included in Advanced Synthesis & Catalysis in 2013.Related Products of 118-12-7 This article mentions the following:

Palladium nanoparticles stabilized by tris(3-sulfophenyl)phosphine trisodium salt in neat glycerol have been synthesized starting from both Pd(II) and Pd(0) species and fully characterized. The versatility of this innovative catalytic colloidal solution has been proved by its efficient application in C-X bond formation processes (X = C, N, P, S) and C-C multiple bond hydrogenation reactions. The catalytic glycerol phase could be recycled more than ten times, preserving its activity and selectivity. The scope of each of these processes has demonstrated the power of the as-prepared catalyst, isolating the corresponding expected products in yields higher than 90%. The dual catalytic behavior of this glycerol phase, associated to the metallic nanocatalysts used in wet medium (mol.- and surface-like behavior), has allowed attractive applications in one-pot multi-step transformations catalyzed by palladium, such as C-C coupling followed by hydrogenation, without isolation of intermediates using only one catalytic precursor. In the experiment, the researchers used many compounds, for example, 1,3,3-Trimethyl-2-methyleneindoline (cas: 118-12-7Related Products of 118-12-7).