Tag: M.W=250-300

Masuda, Minoru published the artcileUrinary aromatic metabolites in schizophrenia, Category: indole-building-block, the publication is J. Nervous Mental Disease (1960), 125-33, database is CAplus.

The studies were carried out on 50 acute schizophrenic and 53 nonpsychotic subjects. Overnight urine specimens were prepared as recommended by Dalgleish (CA 51, 3715b) and analyzed by paper chromatography. In the schizophrenics the increased excretion of aromatic compounds was due to indolic, but not phenolic, substances, especially indoleacetic acid, 5-hydroxyindoleacetic acid, and indican. There was also increased excretion of urea. No metabolite was found regularly which would characterize the schizophrenic group.

J. Nervous Mental Disease 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, 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

Han, Xu published the artcileRational Design and Development of Novel CDK9 Inhibitors for the Treatment of Acute Myeloid Leukemia, Formula: C14H18BNO3, the publication is Journal of Medicinal Chemistry (2021), 64(19), 14647-14663, database is CAplus and MEDLINE.

CDK9 is an essential drug target correlated to the development of acute myeloid leukemia (AML). Starting from the hit compound 10, which was discovered through a screening of our inhouse compound library, the structural modifications were carried out based on the bioisosterism and scaffold hopping strategies. Consequently, compound 37 (I) displayed the optimal CDK9 inhibitory activity with an IC₅₀ value of 5.41 nM, which was nearly 1500-fold higher than compound 10. In addition, compound 37 exhibited significant antiproliferative activity in broad cancer cell lines. Further investigation of in vivo properties demonstrated that compound 37 could be orally administrated with an acceptable bioavailability (F = 33.7%). In MV-4-11 s.c. xenograft mouse model, compound 37 (7.5 mg/kg) could significantly suppress the tumor progression with a T/C value of 27.80%. Compound 37 represents a promising lead compound for the development of a novel class of CDK9 inhibitors for the treatment of acute myeloid leukemia.

Journal of Medicinal Chemistry 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, Formula: C14H18BNO3.

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

Haustein, Catherine published the artcileRoom-temperature phosphorescence of 3- and 5-substituted indoles, Safety of Potassium 1H-indol-3-yl sulfate, the publication is Talanta (1989), 36(11), 1065-8, database is CAplus and MEDLINE.

The room-temperature phosphorescence of indole and 13 substituted indoles on filter paper is reported. Cesium and iodide ions increase the emission intensity. In the presence of iodide, the excitation and emission wavelengths of indole are 279 and 440 nm, resp. The excitation and emission wavelengths of indoles with aliphatic groups in the 3-position are 288-289 and 443-449 nm, resp. Indoles with 3,5-substitution have excitation and emission wavelengths of 300-308 and 448-460 nm, resp. Indoxylsulfate and indoxyl-β-D-glucoside were the only indoles surveyed for which variations in the excitation and emission wavelengths depended on the heavy-atom ion present. These compounds had excitation wavelengths ranging from 288 to 388 nm, depending on which heavy-atom perturber was used. Emission wavelengths were 460-500 nm. Log-log plots of intensity vs. concentration were linear between 0.05 and 700 μg/mL for all the compounds studied, with detection limits in the nanogram range.

Talanta 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, Safety of 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

Ravula, Suchitra published the artcileLead Optimization of 5-Aryl Benzimidazolone- and Oxindole-Based AMPA Receptor Modulators Selective for TARP γ-8, Category: indole-building-block, the publication is ACS Medicinal Chemistry Letters (2018), 9(8), 821-826, database is CAplus and MEDLINE.

Glutamate mediates fast excitatory neurotransmission via ionotropic α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors. The trafficking and gating properties of AMPA receptors (AMPARs) can be amplified by transmembrane AMPAR regulatory proteins (TARPs), which are often expressed in localized brain regions. Herein, the authors describe the discovery, lead optimization, and preclin. characterization of 5-arylbenzimidazolone and oxindole-based neg. modulators of AMPARs associated with TARP γ-8, the primary TARP found in hippocampus. High-throughput screen lead 4 (5-(o-tolyl)indolin-2-one) was optimized for potency and brain penetration to provide benzimidazolone 3, JNJ-55511118. Replacement of the benzimidazolone core in 3 with an oxindole mitigated reactive metabolite formation and led to the identification of 18 (5-[2-chloro-6-(trifluoromethoxy)phenyl]-7-methylindolin-2-one) (GluA1/γ-8 pIC₅₀ = 9.7). Following oral dosing in rats, 18 demonstrated robust target engagement in hippocampus as assessed by ex vivo autoradiog. (ED₅₀ = 0.6 mg/kg, plasma EC₅₀ = 9 ng/mL).

ACS Medicinal Chemistry Letters 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

Van Rheenen, D. L. published the artcileQuantitative determination of urinary indoxyl sulfate (indican) and the total content of basic compounds in the feces of cattle in relation to hypomagnesemia, Quality Control of 2642-37-7, the publication is Nature (London, United Kingdom) (1966), 212(5067), 1269-70, database is CAplus and MEDLINE.

For the determination of indican, FeCl3 in concentrated HCl was used as oxidant. The method could detect 5 γ of indican. To 1 mL. of diluted urine or standard were added 2 mL. of 20% Cl3CCO2H, 1 mL. of 0.5% thymol, and 3 mL. of 0.34% FeCl3 in concentrated HCl. After incubation in boiling water for 20 min., the tubes were centrifuged at 4000 rpm. for 10 min. The yellow supernatant (0.4 mL.) was made up to 4 mL. with CHCl3 and the color intensity determined at 540 mμ. The total amount of amines and basic amino acids in extracts of feces were determined with ninhydrin. Urinary indican increased when feed was changed from hay to grain. This was an indication of increased bacterial metabolism in the gastrointestinal tract. After treatment resulting in hypomagnesemia, the total content of basic compounds in the feces decreased. This was due to absorption during passage through the gut. Under normal conditions, indican and basic amines normally formed in the colon are partly removed in the faces, partly detoxicated in the tissues and removed in the urine. In abnormal gastrointestinal function, larger amounts are absorbed. Hypomagnesemia may affect the destruction of these compounds in the tissues.

Nature (London, United Kingdom) 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 C7H13NO2, Quality Control 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

Palani, Vignesh published the artcileA pyrone remodeling strategy to access diverse heterocycles: application to the synthesis of fascaplysin natural products, Name: 5-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Chemical Science (2021), 12(4), 1528-1534, database is CAplus and MEDLINE.

The synthesis of diverse N-fused heterocycles, including the pyrido[1,2-a]indole scaffold, e.g., I, using an efficient pyrone remodeling strategy was described. The pyrido[1,2-a]indole core was demonstrated to be a versatile scaffold that could be site-selectively functionalized. The utility of this novel annulation strategy was showcased in a concise formal synthesis of three fascaplysin congeners.

Chemical Science published new progress about 683229-62-1. 683229-62-1 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Ether,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 5-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C15H20BNO3, Name: 5-Methoxy-2-(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

Yates, C. G. published the artcileNew intermediates and dyes. X. Preparation and reactions of 2-n-alkylquinizarins, SDS of cas: 2642-37-7, the publication is Journal of the Chemical Society (1965), 626-9, database is CAplus.

2-Methylquinizarin was prepared by hydrolysis of 4-chloro-l-hydroxy-2 methylanthraquinone, or better, from 1,4-diamino-2-methylanthraquinone and aqueous alk. dithionite. 2-Propyl-, 2-butyl-, 2- hexyl-, 2-heptyl-, and 2-octylquinizarin were derived by the interaction of leucoquinizarin and an aliphatic aldehyde: this reaction appeared to be limited, as the use of decyl- and dodecylaldehyde gave quinizarin only. Inhibiting effects of the 2-n-alkyl groups in reactions with amines were examined Thus, 2-methyl-, propyl-, and butylquinizarin and aqueous NH₃ gave some disubstitution of the hydroxy groups, but with derivatives of longer alkyl chain, only monosubstitution occurred; MeNH₂ afforded yellow fluorescent products, probably formed by loss of water from 2-alkyl-1,4-bis(methylamino)anthraquinones. Whereas cyclohexylamine gave excellent yields of 2-alkyl-1,4-bis(cyclohexylamino)anthraquinones, disubstitution was inhibited in reactions with PhNH₂, which gave monoanilino derivatives

Journal of the Chemical Society 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 C9H9ClN2, 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

Nakamura, Hiroshi published the artcileSensitive and specific detection of tryptophan, tryptamine and N-terminal tryptophan peptides on thin-layer plates using a unique fluorogenic reaction with fluorescamine, Recommanded Product: Potassium 1H-indol-3-yl sulfate, the publication is Journal of Chromatography (1978), 152(1), 153-65, database is CAplus.

Two sensitive and sp. methods were developed for the detection of tryptophan, tryptamine, N-terminal tryptophan peptides and other 3-(2-aminoethyl)-indoles on thin-layer plates in which the reaction is based on the unique fluorescence of the fluorescamine derivatives after treatment with HClO₄. The 1st method the compounds are separated on plates and reacted by dipping in acetone-n-hexane (1:4) containing fluorescamine, whereas in the 2nd method the compounds are first derivatized with fluorescamine at the origin of the plates by dipping in the solution and then separated When sprayed with 40% HClO₄, the fluorescamine derivatives appear as yellow-orange fluorescent spots. Certain 3,4-dihydroxyphenylethylamines and 3-methoxy-4-hydroxyphenylethylamines that have a free amino group in the side-chain also react, but they give a bluish fluorescence. Depending on the compounds, amounts of 1-800 pmole could be detected.

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, 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

Nakamura, Hiroshi published the artcilePerchloric acid, a fluorogenic spray reagent for tryptophan, tryptamine, peptides containing tryptophan and other 3-substituted indoles, Application In Synthesis of 2642-37-7, the publication is Journal of Chromatography (1978), 152(1), 167-74, database is CAplus.

When silica gel plates containing 3-substituted indoles (e.g., 3-methylindole, indole-3-acetic acid), tryptophan derivatives, tryptamine, and tryptophan-containing peptides (e.g., H-Trp-Gly-OH, H-Pro-Trp-OH, H-Lys-Trp-Lys-OH) were sprayed with 70% HClO₄, a strong yellow-orange fluorescence developed. Other indole derivatives did not give this fluorescence when sprayed with 70% HClO₄. 3-Substituted indoles can be detected at 40-850 pmole by this method.

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, Application In Synthesis 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

Li, Hua published the artcileModified metabolites mapping by liquid chromatography-high resolution mass spectrometry using full scan/all ion fragmentation/neutral loss acquisition, Safety of Potassium 1H-indol-3-yl sulfate, the publication is Journal of Chromatography A (2019), 80-87, database is CAplus and MEDLINE.

Modified metabolites play important roles in diagnostic monitoring, oxidative response and physiol. regulation. Comprehensive anal. methods are greatly needed for improving the coverage of modified metabolites and studying their physiol. function. Here, a novel nontargeted profiling method for mapping modified metabolites was developed by liquid chromatog.-high resolution mass spectrometry with full scan/all ion fragmentation/neutral loss (FS/AIF/NL) data acquisition. Modified metabolites were unbiasedly defined with less false pos. results by mixed standards verification. Thirteen types of modified metabolites in urine were analyzed at the same time, and 198 of 307 modified metabolites at pos. mode and 166 of 366 modified metabolites at neg. mode were putatively identified. The modified metabolites profiling method was applied for investigating the metabolic differences between the patients with breast cancer and health controls. As a result, many modified metabolites with glucuronidation, ribosylation and indole acetylation modification were significantly up-regulated in breast cancer and four modified metabolites including 7-methylguanosine, N₄-acetylcytidine, dihyroxy-1H-indole glucuronide I and indole-3-acetic acid-O-glucuronide were identified as potential biomarkers for the diagnose of breast cancer.

Journal of Chromatography A 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, Safety of 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