Category: indole-building-block

Bowden, Keith published the artcileThe transmission of polar effects. IV. The kinetics of esterification with diazodiphenylmethane of substituted heterocyclic carboxylic acids, Safety of 6-Nitro-1H-indole-3-carboxylic acid, the publication is Canadian Journal of Chemistry (1966), 44(13), 1493-9, database is CAplus.

cf. CA 64, 12480h. The rate coefficients for the reaction with diazodiphenylmethane, in EtOH at 30.0°, of a number of substituted indole-2-carboxylic acids, indole-3-carboxylic acids, coumarin-3-carboxylic acids, coumarilic acids, and N-phenylglycines have been determined The effect of substitution is assessed by use of adapted Hammett and Dewar-Grisdale relations. The relations give good correlations for oxygen-ring heterocyclic systems, and the relative ability of the systems to transmit π-electron effects has been determined An anomalous perturbing effect appears to operate in the indolecarboxylic acid systems.

Canadian Journal of Chemistry published new progress about 10242-03-2. 10242-03-2 belongs to indole-building-block, auxiliary class Indole,Nitro Compound,Carboxylic acid,Indole, name is 6-Nitro-1H-indole-3-carboxylic acid, and the molecular formula is C9H6N2O4, Safety of 6-Nitro-1H-indole-3-carboxylic acid.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Sharma, S. K. published the artcileUrinary Indican in healthy Indian subjects, Product Details of C8H6KNO4S, the publication is Indian Journal of Physiology and Pharmacology (1977), 21(4), 342-6, database is CAplus and MEDLINE.

The average urinary excretion of indican was 40.4 mg/day in healthy Indian subjects. The average bacterial count in jejunal fluid was 1.96 × 10³/mL. There was a significant correlation between the indican excretion and total bacterial count.

Indian Journal of Physiology and Pharmacology published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C14H10O4, Product Details of C8H6KNO4S.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Holt, Sandra published the artcileInhibition of fatty acid amide hydrolase, a key endocannabinoid metabolizing enzyme, by analogues of ibuprofen and indomethacin, Product Details of C23H23ClN2O4, the publication is European Journal of Pharmacology (2007), 565(1-3), 26-36, database is CAplus and MEDLINE.

There is evidence in the literature that the nonsteroidal anti-inflammatory drugs indomethacin and ibuprofen can interact with the cannabinoid system both in vitro and in vivo. In the present study, a series of analogs of ibuprofen and indomethacin have been investigated with respect to their ability to inhibit fatty acid amide hydrolase, the enzyme responsible for the hydrolysis of the endogenous cannabinoid anandamide. Of the compounds tested, the 6-methyl-pyridin-2-yl analog of ibuprofen (“ibu-am5”) was selected for further study. This compound inhibited rat brain anandamide hydrolysis in a non-competitive manner, with IC₅₀ values of 4.7 and 2.5 μM being found at pH 6 and 8, resp. By comparison, the IC₅₀ values for ibuprofen were 130 and 750 μM at pH 6 and 8, resp. There was no measurable N-acylethanolamine hydrolyzing acid amidase activity in rat brain membrane preparations In intact C6 glioma cells, ibu-am5 inhibited the hydrolysis of anandamide with an IC₅₀ value of 1.2 μM. There was little difference in the potencies of ibu-am5 and ibuprofen towards cyclooxygenase-1 and -2 enzymes, and neither compound inhibited the activity of monoacylglycerol lipase. Ibu-am5 inhibited the binding of [³H]-CP55,940 to rat brain CB₁ and human CB₂ cannabinoid receptors more potently than ibuprofen, but the increase in potency was less than the corresponding increase in potency seen for inhibition of FAAH activity. It is concluded that ibu-am5 is an analog of ibuprofen with a greater potency towards fatty acid amide hydrolase but with a similar cyclooxygenase inhibitory profile, and may be useful for the study of the therapeutic potential of combined fatty acid amide hydrolase-cyclooxygenase inhibitors.

European Journal of Pharmacology published new progress about 2854-32-2. 2854-32-2 belongs to indole-building-block, auxiliary class GPCR/G Protein,Cannabinoid Receptor, name is 2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-1-morpholinoethanone, and the molecular formula is C23H23ClN2O4, Product Details of C23H23ClN2O4.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Chowdhury, Rajdip published the artcileN-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C-H alkylation of indoles, Safety of 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, the publication is Chemical Communications (Cambridge, United Kingdom) (2021), 57(37), 4532-4535, database is CAplus and MEDLINE.

Despite the extensive studies on the reactions between conventional diazocompounds and indoles, these are still limited by the independent synthesis of the carbene precursors, the specific catalysts, and the required multi-step manipulation of the products. In this work, use of redox-active carbenes in the expedited and divergent synthesis of functionalized indoles is reported. NHPI-DA displays unusual efficiency and selectivity to yield insertion products that can be swiftly elaborated into boron and carbon substituents that are particularly problematic in carbene-mediated reactions.

Chemical Communications (Cambridge, United Kingdom) published new progress about 1206163-56-5. 1206163-56-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, and the molecular formula is C21H24BNO2, Safety of 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Elkin, Samuel published the artcileSynthesis and local anesthetic activity of several dialkylaminoalkyl esters of indolecarboxylic acids, Category: indole-building-block, the publication is Journal of Pharmaceutical Sciences (1963), 79-81, database is CAplus.

By the method of Burtner and Cusic (CA 37, 1711³), compounds having the general formulas I and II were prepared (compound, R, n, % yield, and m.p. given): I, H, 2, 25, 174-5°; I, H, 3, 21.8, 165-7°; I, NO₂, 2, 15.6, 210-12°; I, NO₂, 3, 15.1, 208-10°; II, –, 2, 6.2, 178-80°; II, –, 3, 17.5, 170-1°. All compounds were effective as topical anesthetics but had no action on unbroken skin. Nitrated indole-3-carboxylic acid and the esters of indole-2-carboxylic acid showed a marked decrease in duration of local anesthetic activity.

Journal of Pharmaceutical Sciences published new progress about 10242-03-2. 10242-03-2 belongs to indole-building-block, auxiliary class Indole,Nitro Compound,Carboxylic acid,Indole, name is 6-Nitro-1H-indole-3-carboxylic acid, and the molecular formula is C9H6N2O4, Category: indole-building-block.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Baek, Hye Suk published the artcileAnti-Inflammatory Effects of the Novel PIM Kinase Inhibitor KMU-470 in RAW 264.7 Cells through the TLR4-NF-κB-NLRP3 Pathway, Category: indole-building-block, the publication is International Journal of Molecular Sciences (2020), 21(14), 5138, database is CAplus and MEDLINE.

PIM kinases, a small family of serine/threonine kinases, are important intermediates in the cytokine signaling pathway of inflammatory disease. In this study, we investigated whether the novel PIM kinase inhibitor KMU-470, a derivative of indolin-2-one, inhibits lipopolysaccharide (LPS)-induced inflammatory responses in RAW 264.7 cells. We demonstrated that KMU-470 suppressed the production of nitric oxide and inducible nitric oxide synthases that are induced by LPS in RAW 264.7 cells. Furthermore, KMU-470 inhibited LPS-induced up-regulation of TLR4 and MyD88, as well as the phosphorylation of IκB kinase and NF-κB in RAW 264.7 cells. Addnl., KMU-470 suppressed LPS-induced up-regulation at the transcriptional level of various pro-inflammatory cytokines such as IL-1β, TNF-α, and IL-6. Notably, KMU-470 inhibited LPS-induced up-regulation of a major component of the inflammasome complex, NLRP3, in RAW 264.7 cells. Importantly, PIM-1 siRNA transfection attenuated up-regulation of NLRP3 and pro-IL-1β in LPS-treated RAW 264.7 cells. Taken together, these findings indicate that PIM-1 plays a key role in inflammatory signaling and that KMU-470 is a potential anti-inflammatory agent.

International Journal of Molecular Sciences published new progress about 837392-64-0. 837392-64-0 belongs to indole-building-block, auxiliary class Indoline,Boronic acid and ester,Amide,Boronate Esters, name is 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one, and the molecular formula is C14H18BNO3, Category: indole-building-block.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Sano, Isamu published the artcileIndican and analogs in human urine. I. Millon’s reaction of indoxylsulfate at room temperature, SDS of cas: 2642-37-7, the publication is Seikagaku (1955), 153-6, database is CAplus.

Human urine showed pink red color with Millon’s reagent at room temperature The color tone was apparently different from that of phenols. To sep. a compound which showed the reaction, 200 l. urine was treated with C, the C extracted with a mixture of H₂O-NH₄OH-BuOH-MeOH (8:1:1:0.5). The extract was taken to dryness and extracted with 60% EtOH to remove uric acid. The residue was further extracted with BuOH, the extract was chromatographed on cellulose powder, and the fraction showing the Millon’s reaction was collected and purified by Amberlite IR-4B to yield 167 mg. of crystals. The crystals showed the Millon’s reaction and were identified to be K indoxylsulfate. 8-Quinolinol and 7-hydroxyindoleacetic acid (I) also showed the Millon’s reaction, but the presence of I was not detected in urines of 50 individuals when examined by paper chromatography.

Seikagaku published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C8H6KNO4S, SDS of cas: 2642-37-7.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Matsumoto, Satoshi published the artcileChemicals inhibiting the growth of HeLa cells. II. Indole, anthranilic acid, and the related compounds, Recommanded Product: Potassium 1H-indol-3-yl sulfate, the publication is Nippon Yakurigaku Zasshi (1959), 1065-8, database is CAplus.

The min. growth-inhibiting concentrations were: L-tryptophan 100 γ/mL., DL-5-hydroxytryptophan 200, K 3-indoleacetate 1000, 3-indolebutyric acid 250, indoxyl acetate 10, indican 500, dihydroxyindole 50, K indigodisulfonate >1000, K indigotetrasulfonate >1000, anthranilic acid 1000, 2-ureidobenzoic acid 500, 2-(thioureido)benzoic acid 200, 2-(carboxymethylamino)benzoic acid 500, 2,4-quinazolinediol 100, 2-amino-4-quinazolinol 10, 2-mercapto-4-quinazolinol 10, 5-hydroxyanthranilic acid 200, 5-hydroxy-2-ureidobenzoic acid 50, 2,4,6-quinazolinetriol 50, and 3-hydroxyanthranilic acid 200.

Nippon Yakurigaku Zasshi published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C8H6KNO4S, Recommanded Product: Potassium 1H-indol-3-yl sulfate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Fassbender, Svenja I. published the artcileGeometric E→Z Isomerisation of Alkenyl Silanes by Selective Energy Transfer Catalysis: Stereodivergent Synthesis of Triarylethylenes via a Formal anti-Metallometallation, Category: indole-building-block, the publication is Angewandte Chemie, International Edition (2019), 58(51), 18619-18626, database is CAplus and MEDLINE.

An efficient geometrical E→Z isomerization of alkenyl silanes is disclosed via selective energy transfer using an inexpensive organic sensitizer. Characterized by operational simplicity, short reaction times (2 h), and broad substrate tolerance, the reaction displays high selectivity for trisubstituted systems (Z/E up to 95:5). In contrast to thermal activation, directionality results from deconjugation of the π-system in the Z-isomer due to A^1,3-strain thereby inhibiting re-activation. The structural importance of the β-substituent logically prompted a study of mixed bis-nucleophiles (Si, Sn, B). These versatile linchpins also undergo facile isomerization, thereby enabling a formal anti-metallometalation. Mechanistic interrogation, supported by a theor. study, is disclosed together with application of the products to the stereospecific synthesis of biol. relevant target structures.

Angewandte Chemie, International Edition published new progress about 1256359-23-5. 1256359-23-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester,, name is 1-(Phenylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C20H22BNO4S, Category: indole-building-block.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Swann, Elizabeth published the artcileRates of reductive elimination of substituted nitrophenols from the (indol-3-yl)methyl position of indolequinones, Recommanded Product: 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, the publication is Journal of the Chemical Society, Perkin Transactions 2 (2001), 1340-1345, database is CAplus.

A series of indolequinones bearing substituted nitrophenols on the (indol-3-yl)methyl position (I;R¹,R²,R³,R⁴,R⁵ given: H,NO₂,H,NO₂,H; H,MeO,H,H,NO₂;H,MeO,H,NO₂,H; Me,F,H,NO₂,H; H,CHO,H,NO₂,H; etc. )was synthesized. The nitrophenol leaving groups were appropriately substituted to give a wide range (4 units) in phenolic pK_a value. The rate of reductive elimination of phenoxide anions from the (indol-3-yl)methyl position of semiquinone radicals was dependent upon this pK_a, with a decrease in 3.8 pK units shortening the half-life from 28 to 1.5 ms. Only 2,4-dinitrophenol (pK_a = 3.9) was eliminated from an unsubstituted (indol-3-yl)methyl position at a rate that would compete with reoxidation of the radical by oxygen. A nitrothiophenol leaving group was eliminated comparatively slowly and only from the hydroquinone. These studies demonstrate the dependence upon leaving group pK_a of the rate of reductive elimination from the (indol-3-yl)methyl position of indolequinones.

Journal of the Chemical Society, Perkin Transactions 2 published new progress about 192820-78-3. 192820-78-3 belongs to indole-building-block, auxiliary class Fused/Partially Saturated Cycles,Dihydroindoles, name is 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, and the molecular formula is C13H17BO2, Recommanded Product: 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles