Category: indole-building-block

Dittmann, Juergen published the artcileSeparation of phenols and phenol carboxylic acids by thin-layer chromatography on cellulose, Formula: C8H6KNO4S, the publication is Journal of Chromatography (1968), 32(4), 764-8, database is CAplus.

The Rf values and the detection limits are tabulated for the separation of 42 phenols and phenol carboxylic acids for 4 different developing systems by thin-layer chromatog. on cellulose. The use of 4 detection reagents is discussed. 42 references.

Journal of Chromatography 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, 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

Matsuda, Kazuhiro published the artcileIndican as a feeding stimulant to the strawberry leaf beetle, Galerucella vittaticollis Baly attacking polygonaceous plants, Computed Properties of 2642-37-7, the publication is Applied Entomology and Zoology (1983), 18(4), 552-4, database is CAplus.

Feeding by G. vittaticollis was stimulated by indicans and K 3-indoxylsulfate at 0.001-0.1M, but not by indoxyl acetate, IAA, indigo, indole, or isatin. Indican was detected in Polygonum tinctorium leaves but not in leaves of other polygonaceous plants or strawberry leaves. Other beetles which feed on polygonaceous plant were not stimulated to feed by indican or related compounds

Applied Entomology and Zoology 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, Computed Properties of 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

Melzer, Marvin S. published the artcileApplicability of the Hammett equation to the indole system: acidity of indole-3-carboxylic acids, SDS of cas: 10242-03-2, the publication is Journal of Organic Chemistry (1962), 496-9, database is CAplus.

The acidities of six 5- and 6-substituted indole-3-carboxylic acids were determined in aqueous alc. and their pK plotted against the Hammett substituent constants of the resp. substituents. A good correlation was obtained using the one-term Hammett equation (log K/K° = ρσ) using σ_m for groups in the 5-position and σ_p for groups in the 6-position. These results were taken to indicate thai electronic effects were transmitted to the acid center through the C pare to the 6-position and that virtually no transmission occurred through the indole N atom. It was also found that the 5-bromoindole-3-carboxylic acid (I) was somewhat less acidic than expected, an effect attributed to steric and electronic factors. Infrared data indicated that whereas the 6-aminoindole-3-carboxylic acid (II) existed as the free acid, the 5-amino isomer (III) existed in its zwitterionic form. All pK measurements were made in 50% and 95% alc. and the pH measured using a Beckmann meter. Indole treated with MeMgI then CO₂ gave indote-3-carboxylic acid (IV), m. 214° (decomposition). 5-Nitroindote (.5 g.) treated 1 day in a refrigerator with excess (COCl)₂ gave 5 g. 5-nitroindole-3-glyoxylyl chloride (V), m. 310° (decomposition). V refluxed with KOH gave 3.5 g. 5-nitroindole 3-carboxylic acid (VI), m. 270-2° (decomposition). VI (3.5 g.) refluxed 3 hrs. in refluxing 30% H₂O₂, filtered hot, and the solid further purified gave 2.5 g. 5-nitroindole-3-carboxylic acid (VII), m. 276-8° (decomposition). A portion of V treated directly with 30% H₂O₂ gave 47% VII. V failed to undergo decarboxylation in refluxing tetrachloroethane. VII failed to undergo cleavage on treatment with Pb(OAc)₄ in refluxing AcOH. 5-Bromoindole treated with MeMgl and carbonated gave I, m. 238-40° (decomposition). IV in AcOH treated with HNO₃ gave 6-nitroimtole-3-carboxylic acid (VIII), m. 280-1°. Reduction of VIII in MeOH with Raney Ni under 35 lb./sq. in. H pressure gave II. Another preparation using the same procedure gave a small amount of material, m. 197-9°. VI (500 mg.) in MeOH shaken 8 hrs. with Raney Ni under 50 lb./sq. in. H pressure gave 65 mg. III, m. 177-9° (decomposition). The pK of indole-3-carboxylic acids at 26° were obtained (compound, pK in 50% alc., number of determinations, pK in 95% alc., no of determinations, a used, NH (cm.^-1 given): IV, 7.00, 9, 8.92, 3, 0.00, 3247; VIII, 6.45, 3, 8.06, 2, 0.78, 8425; VI, 6.50, 6, 8.15, 3, 0.71, 3338; I, 6.96, 7, 8.72, 3, 0.391, 3310; 5-ethoxyindote-3-carboxylic acid, 6.98, 6, 8.91, 2, 0.10, 3226; II, 7.43, 2, -, -, -0.66, 3312. Reaction constants and precision of correlation of pK of indole-3-carboxylic acids with Hammett substituent constants were given in a table.

Journal of Organic 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, SDS of cas: 10242-03-2.

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

Mueting, Dieter published the artcileDisturbances in protein metabolism in renal insufficiency, Recommanded Product: Potassium 1H-indol-3-yl sulfate, the publication is Protides of the Biological Fluids (1962), 148-54, database is CAplus.

Studies were conducted in 129 patients with renal insufficiency resulting from glomerulonephritis and pyelonephritis. Total serum protein and albumin were decreased and α₁-, α₂– and γ-globulins were increased to an extent proportional to the degree of uremia. Tyrosine and tryptophan were elevated in serum, as well as their phenolic and indolyl catabolites. Increased concentrations of the latter were due not only to decreased urinary excretion but also to decrease oxidative processes. Impairment of oxidation reactions in uremia was also reflected by elevation of sulfate esters. Detoxication processes involving glucuronic acid, as well as sulfate conjugation, are impaired which further aggravates the toxic conditions produced by uremia. The most sensitive criteria of incipient renal insufficiency appeared to be the retention of creatinine and indican, obtained by analyses of their serum and urinary levels.

Protides of the Biological Fluids 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

Sprince, Herbert published the artcileA modified Ehrlich benzaldehyde reagent for detection of indoles on paper chromatograms, Name: Potassium 1H-indol-3-yl sulfate, the publication is Journal of Chromatography (1960), 97-8, database is CAplus.

Indole chromatograms, sprayed first with a 2% solution of p-dimethylaminobenzaldehyde in 12.1N HCl, and, after 2-3 min., with 1% aqueous NaO₂, show deep-blue spots which appear immediately. Indican appears as an orange-brown spot and urea as a large deep-yellow spot. Colors developed with this reagent often persist for at least a month without fading.

Journal of Chromatography 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 C65H82N2O18S2, Name: 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

Tahata, Eiichi published the artcileMetabolism of indole, Product Details of C8H6KNO4S, the publication is Fukuoka Igaku Zasshi (1959), 4751-67, database is CAplus.

Isolated rabbit liver was perfused with heparinized blood containing indole. After 2-hrs. the perfuzate was deproteinized and treated with an aldehyde reagent. The BuOH extract of the colored substance was subjected to paper chromatography in a isoPrOH-H₂O system. The presence of indole, isatin, indican, anthranilic acid, and urochrome in the perfuzate was demonstrated by comparing their values with those of pure compounds The addition of flavine adenine dinucleotide to the perfuzate enlarged the size of the spots of these compounds except indole.

Fukuoka Igaku 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 C12H14IN, 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

Murakami, Yasuoki published the artcileFischer indolization of ethyl pyruvate 2-bis(2-methoxyphenyl)hydrazone and new insight into the mechanism of Fischer indolization. Fischer indolization and its related compounds. XXVII., Formula: C12H13NO3, the publication is Chemical & Pharmaceutical Bulletin (1995), 43(8), 1287-93, database is CAplus.

In connection with studies on the direction of cyclization in the Fischer indolization of substituted diphenylhydrazones, the Fischer indolization of Et pyruvate 2-bis(2-methoxyphenyl)hydrazone was carried out. The result showed that cyclization in Fischer indolization of diphenylhydrazone does not always proceed to the electron-richer nucleus, but depends on the conformation of the enehydrazine. Thus, the Fischer indolization should proceed via a [3,3] sigmatropic route, with an electronic effect.

Chemical & Pharmaceutical Bulletin 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, Formula: C12H13NO3.

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

Murakami, Yasuoki published the artcileA novel method for the debenzylation of protected indole nitrogen, Related Products of indole-building-block, the publication is Synthesis (1984), 738-40, database is CAplus.

The AlCl₃-catalyzed deprotection of indoles I (R = H, OMe, Cl, COMe; R¹ = OEt, Me) gave the resp. II. I (R = 7-Cl, R¹ = OEt) was stirred with AlCl₃ in C₆H₆ 30 min to give 66% II (R = 7-Cl, R¹ = OEt).

Synthesis 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, Related Products of 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

Zhang, Yan-Yan published the artcileDual-role of PtCl₂ catalysis in the intramolecular cyclization of (hetero)aryl-allenes for the facile construction of substituted 2,3-dihydropyrroles and polyheterocyclic skeletons, Safety of 5-Fluoro-1H-indole-2-carbaldehyde, the publication is Chemical Communications (Cambridge, United Kingdom) (2017), 53(44), 5966-5969, database is CAplus and MEDLINE.

A Pt(II)-catalyzed cyclization of (hetero)aryl-allenes were developed, providing controllable synthesis of substituted 2,3-dihydropyrroles and polyheterocyclic skeletons. Another notable feature of this method was the dual-role of the Pt(II) catalyst: initiation of the migration of the (hetero)arylmethylene group and the subsequent Friedel-Crafts type annulation.

Chemical Communications (Cambridge, United Kingdom) published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C5H5F3O2, Safety of 5-Fluoro-1H-indole-2-carbaldehyde.

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

Remers, William A. published the artcileSynthesis of indoles from 4-oxo-4,5,6,7-tetrahydroindoles. III. Introduction of substituents by electrophilic substitution, Recommanded Product: 2-Bromo-6,7-dihydro-1H-indol-4(5H)-one, the publication is Journal of Organic Chemistry (1971), 36(9), 1241-7, database is CAplus.

The general method of indole synthesis by way of 4-oxo-4,5,6,7-tetrahydroindoles (I) was extended by a variety of electrophilic substitution reactions, including bromination, nitration, acylation, and formylation. An order of selective substitution was established as follows: C-2 > C-3 > C-5, except in certain Vilsmeier-Haack formylations of 2-substituted compounds. When the pyrrole ring of a I was substituted with a strong electron-withdrawing group, electrophilic substitution was diverted to C-5. Most of the 6,7-dihydroindoles prepared in this investigation could be dehydrogenated to the fully aromatic indoles, but many of the new I were resistant to dehydrogenation. Vilsmeier-Haack formylation of certain I led directly to fully aromatic indoles which had a 4-chloro-5-(dimethylaminomethyl) pattern of substitution.

Journal of Organic Chemistry published new progress about 27784-79-8. 27784-79-8 belongs to indole-building-block, auxiliary class Other Aromatic Heterocyclic,Bromide,Ketone, name is 2-Bromo-6,7-dihydro-1H-indol-4(5H)-one, and the molecular formula is C8H8BrNO, Recommanded Product: 2-Bromo-6,7-dihydro-1H-indol-4(5H)-one.

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