Tag: M.W=250-300

Yamashita, Mitsuaki published the artcileOne-pot synthesis of polyhydropyrido[1,2-a]indoles and tetracyclic quinazolinones from 2-arylindoles using copper-mediated oxidative tandem reactions, COA of Formula: C15H20BNO3, the publication is Tetrahedron (2016), 72(27-28), 4123-4131, database is CAplus.

We developed facile one-pot methods for the transformation of 2-arylindoles to polyhydropyrido[1,2-a]indoles and tetracyclic quinazolinones. The copper-catalyzed oxidation of 2-arylindoles to C-acylimines followed by aza-Diels-Alder reactions or oxidative ring-expansion reactions afforded significant polycyclic heterocycles, e. g., I.

Tetrahedron 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 C8H13N5O, COA of Formula: C15H20BNO3.

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

Hong, Fang-Tsao published the artcileSmall Molecule Disruptors of the Glucokinase-Glucokinase Regulatory Protein Interaction: 4. Exploration of a Novel Binding Pocket, Safety of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one, the publication is Journal of Medicinal Chemistry (2014), 57(14), 5949-5964, database is CAplus and MEDLINE.

Structure-activity relationship investigations conducted at the 5-position of the N-pyridine ring of a series of N-arylsulfonyl-N’-2-pyridinyl-piperazines led to the identification of a novel bis-pyridinyl piperazine sulfonamide I that was a potent disruptor of the glucokinase-glucokinase regulatory protein (GK-GKRP) interaction. Anal. of the x-ray cocrystal of compound I bound to hGKRP revealed that the 3-pyridine ring moiety occupied a previously unexplored binding pocket within the protein. Key features of this new binding mode included forming favorable contacts with the top face of the Ala27-Val28-Pro29 (“shelf region”) as well as an edge-to-face interaction with the Tyr24 side chain. Compound I was potent in both biochem. and cellular assays (IC₅₀ = 0.005 μM and EC₅₀ = 0.205 μM, resp.) and exhibited acceptable pharmacokinetic properties for in vivo evaluation. When administered to db/db mice (100 mg/kg, po), compound I demonstrated a robust pharmacodynamic effect and significantly reduced blood glucose levels up to 6 h postdose.

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, Safety of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-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

King, L. J. published the artcileThe metabolism of indole-2-¹⁴C in the rat, HPLC of Formula: 2642-37-7, the publication is Biochemical Journal (1966), 98(1), 266-77, database is CAplus and MEDLINE.

Indole-2-¹⁴C has been synthesized from formate-¹⁴C and ο-toluidine via N-for-myltoluidine-¹⁴C. When fed to rats, the ¹⁴C of indole-¹⁴C (dose 70-80 mg./kg. body weight) is fairly rapidly excreted, and in 2 days an average of 81% appears in the urine, 11% in the feces and 2.4% as CO₂ in the expired air. Radioactivity is excreted in the urine as indoxyl sulfate (50% of the dose), indoxyl glucuronide (11%), oxindole (1.4%), isatin (5-8%), 5-hydroxyoxindole (I) conjugates (3.1%), N-formylanthranilic acid (II) (0.5%), and unchanged indole (0.07%). The feces contain indoxyl sulfate (0.4% of the dose) and indole (0.2%), but the major metabolites have not been identified. Fed to rats with biliary cannulas, an average of 5.6% of a dose of indole-¹⁴C (20-60 mg./kg. body weight) is excreted in the bile in 2 days. Radioactivity is present as indoxyl sulfate (0.8% of dose) and I conjugates (0.6%). Rats further metabolize indoxyl into II and anthranilic acid, and oxindole into I. With rat liver microsomes plus supernatant under aerobic conditions, indole gives indoxyl, oxindole, possibly isatin, II, and anthranilic acid, but under anaerobic conditions gives only oxindole. Similarly, under aerobic conditions, oxindole gives I, anthranilic acid, and ο-aminophenylacetic acid. Indole is metabolized by 2 pathways, 1 via indoxyl to isatin, II, and anthranilic acid, and the other via oxindole to I and possibly to ο-aminophenylacetic and anthranilic acids. The following new compounds are described: 4-hydroxy-2-nitrophenylacetic acid, 3-, 4-, and 5-benzyloxy-2-nitrophenylacetic acid, 5-and 7-hydroxy-oxindoles, and 5-aminoacridine indoxyl sulfate.

Biochemical Journal 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, HPLC of Formula: 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

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

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

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

Douat-Casassus, Celine published the artcileSynthetic anticancer vaccine candidates: rational design of antigenic peptide mimetics that activate tumor-specific T-cells, Synthetic Route of 167015-84-1, the publication is Journal of Medicinal Chemistry (2007), 50(7), 1598-1609, database is CAplus and MEDLINE.

A rational design approach was followed to develop peptidomimetic analogs of a cytotoxic T-cell epitope capable of stimulating T-cell responses as strong as or stronger (heteroclytic) than those of parental antigenic peptides. The work described herein focused on structural alterations of the central amino acids of the melanoma tumor-associated antigenic peptide Melan-A/MART-1_26-35 using nonpeptidic units. A screening was first realized in silico to select altered peptides potentially capable of fitting at the interface between the major histocompatibilty complex (MHC) class-I HLA-A2 mol. and T-cell receptors (TCRs). Two compounds appeared to be high-affinity ligands to the HLA-A2 mol. and stimulated several Melan-A/MART-1 specific T-cell clones. Most remarkably, one of them even managed to amplify the response of one clone. Together, these results indicate that central TCR-contact residues of antigenic peptides can be replaced by nonpeptidic motifs without loss of binding affinity to MHC class-I mols. and T-cell triggering capacity.

Journal of Medicinal Chemistry published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Synthetic Route of 167015-84-1.

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

Yang, Qing-Qing published the artcileVisible-Light-Induced Direct Photocatalytic Carboxylation of Indoles with CBr₄/MeOH, Recommanded Product: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Chemistry – A European Journal (2015), 21(50), 18052-18056, database is CAplus and MEDLINE.

Photocatalysis enables the cascade reactions of indoles and CBr₄ in MeOH through a C(sp²)-H functionalization/methanolysis sequence. The title reaction provides an efficient access to indole-2- and 3-carboxylates in a single operation (no preinstallation of protecting or directing groups was required) with good yields under mild reaction conditions.

Chemistry – A European Journal published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C40H35N7O8, Recommanded Product: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

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