Day: November 28, 2022

Ishii, H. published the artcileFischer indolization and its related compounds. VII. Development of abnormal Fischer indolization of o-methoxyphenylhydrazone to provide a synthetic method for useful indole derivatives possessing an active methine group at C-6 and novel 3,6′-biindole derivatives, SDS of cas: 20538-12-9, the publication is Tetrahedron (1973), 29(14), 1991-2003, database is CAplus.

o-MeOC6H4NHN:CMeCO2Et (I) with p-MeC6H4SO3H in C6H6 in the presence of MeCOCH2COR (R = Me and OEt) gave Et 6-(1-acetyl-2-oxopropyl)indole-2-carboxylate (II, R = Me) and Et α-acetyl-2-(ethoxycarbonyl)indole-6-acetate (II, R = OEt), resp. Under similar conditions, I with Et 6-chloroindole-2-carboxylate gave di-Et 6-chloro-3,6′-biindole-2,2′-dicarboxylate (III, R = Cl, R1 = OH) and Et 5-(p-tolylsulfonyloxy)indole-2-carboxylate. Similarly, I with Et 7-methoxyindole-2-carboxylate gave di-Et 7-methoxy-4,6′-biindole-2,2′-dicarboxylate and III (R = H, R1 = OMe).

Tetrahedron published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, SDS of cas: 20538-12-9.

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

Kitazaki, Hirotaro published the artcileA colorimetric assay of protein kinase activity based on peptide-induced coagulation of gold nanorods, Synthetic Route of 330161-87-0, the publication is Colloids and Surfaces, B: Biointerfaces (2012), 7-11, database is CAplus and MEDLINE.

The authors succeeded in applying gold nanorods (NRs) for the detection of protein kinase (PK) activity based on a substrate-induced coagulation mechanism. Because NRs have cationic surface charges due to surface-adsorbed cetyltrimethylammonium bromide (CTAB), phosphorylated substrate peptides, which gain augmented anionic charges by phosphorylation, induce coagulation of the NRs, resulting in a red-to-blue color change of the corresponding NR dispersion. A large absorption coefficient of the NRs at the near-IR region enabled clear-cut detection of the peptide-induced coagulation. IC₅₀ values of several inhibitors of c-Src kinase determined by the present assay are consistent with reported values.

Colloids and Surfaces, B: Biointerfaces published new progress about 330161-87-0. 330161-87-0 belongs to indole-building-block, auxiliary class Protein Tyrosine Kinase/RTK,Src, name is SU6656, and the molecular formula is C19H21N3O3S, Synthetic Route of 330161-87-0.

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

Wellers, Georges published the artcileExchange between S³⁵ of ammonium sulfate and S³² of indoxylsulfate in aqueous solution, Formula: C8H6KNO4S, the publication is Compt. rend. (1960), 1140-2, database is CAplus.

A solution of indoxylsulfate, isolated from the urine of rabbits fed indole and methionine, was added to a solution of (NH₄)₂S³⁵O₄, and after 48 hrs. the mixture was chromatographed for 15 hrs. The radioactivity on the paper was determined before and after spraying with Ehrlich’s reagent. The radioactivity appeared only in the indoxylsulfate spot. The authors believed that the transfer of radioactivity takes place between the sulfate ions rather than between the S atoms. Although direct esterification of phenols by mineral sulfates would explain the appearance of radioactivity in the conjugated sulfates of the urine of animals administered Na₂S³⁵O₄, the fact that exchange between (NH₄)₂SO₄ and indoxylsulfate does occur would indicate that the former may not be the full explanation.

Compt. rend. 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 C6H10O7, Formula: 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

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

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

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

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

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

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

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