1677-47-0 | - Page 2 of 2 - Indole Building Blocks

Polychronopoulos, Panagiotis’s team published research in Journal of Medicinal Chemistry in 2004-02-12 | CAS: 1677-47-0

Journal of Medicinal Chemistry published new progress about AM1 (molecular orbital method). 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, Application In Synthesis of 1677-47-0.

Polychronopoulos, Panagiotis published the artcileStructural Basis for the Synthesis of Indirubins as Potent and Selective Inhibitors of Glycogen Synthase Kinase-3 and Cyclin-Dependent Kinases, Application In Synthesis of 1677-47-0, the main research area is indirubin derivative preparation; glycogen synthase kinase inhibitor indirubin derivative; cyclin dependent kinase inhibitor indirubin derivative; mol modeling AM1 Monte Carlo indirubin derivative.

Pharmacol. inhibitors of glycogen synthase kinase-3 (GSK-3) and cyclin-dependent kinases have promising potential for applications against several neurodegenerative diseases such as Alzheimer’s disease. Indirubins, a family of bis-indoles isolated from various natural sources, are potent inhibitors of several kinases, including GSK-3. Using the co-crystal structures of various indirubins with GSK-3β, CDK2 and CDK5/p25, we have modeled the binding of indirubins within the ATP-binding pocket of these kinases. This modeling approach provided some insight into the mol. basis of indirubins’ action and selectivity and allowed us to forecast some improvements of this family of bis-indoles as kinase inhibitors. Predicted mols., including 6-substituted and 5,6-disubstituted indirubins, were synthesized and evaluated as CDK and GSK-3 inhibitors. Control, kinase-inactive indirubins were obtained by introduction of a Me substitution on N1.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Damgaard, Maria’s team published research in ACS Chemical Neuroscience in 2015-09-16 | CAS: 1677-47-0

ACS Chemical Neuroscience published new progress about Central nervous system agents. 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, COA of Formula: C8H3Cl2NO2.

Damgaard, Maria published the artcileIdentification of the First Highly Subtype-Selective Inhibitor of Human GABA Transporter GAT3, COA of Formula: C8H3Cl2NO2, the main research area is isatin derivative screening structure preparation GABA transporter GAT3 inhibitor; GABA uptake; hGAT3 selective; inhibitor; isatin; kinetics; noncompetitive.

Screening a library of small-mol. compounds using a cell line expressing human GABA transporter 3 (hGAT3) in a [3H]GABA uptake assay identified isatin derivatives as a new class of hGAT3 inhibitors. A subsequent structure-activity relationship (SAR) study led to the identification of hGAT3-selective inhibitors (i.e., compounds 20 and 34) that were superior to the reference hGAT3 inhibitor, (S)-SNAP-5114, in terms of potency (low micromolar IC50 values) and selectivity (>30-fold selective for hGAT3 over hGAT1/hGAT2/hBGT1). Further pharmacol. characterization of compound 20 (5-(thiophen-2-yl)indoline-2,3-dione) revealed a noncompetitive mode of inhibition at hGAT3. This suggests that this compound class, which has no structural resemblance to GABA, has a binding site different from the substrate, GABA. This was supported by a mol. modeling study that suggested a unique binding site that matched the observed selectivity, inhibition kinetics, and SAR of the compound series. These compounds are the most potent GAT3 inhibitors reported to date that provide selectivity for GAT3 over other GABA transporter subtypes.

Tangella, Yellaiah’s team published research in Organic Letters in 2018-06-15 | CAS: 1677-47-0

Organic Letters published new progress about Aryl aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, Application of 4,5-Dichloroisatin.

Tangella, Yellaiah published the artcileRegioselective Ring Expansion of Isatins with In Situ Generated α-Aryldiazomethanes: Direct Access to Viridicatin Alkaloids, Application of 4,5-Dichloroisatin, the main research area is isatin aldehyde aryldiazomethane regioselective ring expansion one pot green; hydroxy arylquinolinone preparation; viridicatin preparation; viridicatol preparation.

A novel efficient one-pot regioselective ring-expansion reaction of isatins with in situ generated α-aryl/heteroaryldiazomethanes for the construction of viridicatin alkaloids has been described under metal-free conditions. The utility of this protocol is further demonstrated in the synthesis of naturally occurring viridicatin, viridicatol, and substituted 3-O-Me viridicatin and their scale up.

James, C. S.’s team published research in Annals of Applied Biology in 1968 | CAS: 1677-47-0

Annals of Applied Biology published new progress about Hormones, plant Role: BIOL (Biological Study). 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, HPLC of Formula: 1677-47-0.

James, C. S. published the artcilePlant growth-regulating substances. XXVI. Isatic and anthranilic acids, HPLC of Formula: 1677-47-0, the main research area is isatic acid growth regulation; anthranilic acid growth regulation; growth regulation anthranilic acid.

The plant growth-regulating activities of isatic acid and 26 isatic acid derivatives, together with the 27 corresponding anthranilic acids, were assessed in the wheat cylinder, the pea segment, and pea curvature tests. Activity was sustained by substitution in the 4-and 5-positions of isatic acid as in Na 4-chloroisatate and Na 5-bromoisatate but decreased by substitution in the 3- and 6-positions as in Na 3-chloroisatate and Na 6-chloroisatate. In the anthranilic acid series, the parent acid was inactive but the introduction of a large grouping (Br or I) into the 5-position as in Na 5-iodoanthranilate conferred activity. The 3,6- and 5,6-dichloro and the 3,6-dibromo acids such as Na 3,6-dichloroisatate were also active; compounds substituted in the 4-position to the carboxyl group or disubstituted in the 3 and 5 positions as in Na 3,5-dichloroisatate, were, as expected, inactive. Wheat coleoptile and pea stem segments metabolized Na isatate and Na 5-chloroisatate to the corresponding Na anthranilate and Na 5-chloroanthranilate, together with an unidentified nonacidic metabolite in each case. The acids apparently possess activity per se since there was no evidence that the growth regulating activity of isatic acids was related to this breakdown. 19 references.

Bromidge, Steven M.’s team published research in Journal of Medicinal Chemistry in 1998-05-07 | CAS: 1677-47-0

Journal of Medicinal Chemistry published new progress about Anxiolytics. 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, Synthetic Route of 1677-47-0.

Bromidge, Steven M. published the artcileNovel and Selective 5-HT2C/2B Receptor Antagonists as Potential Anxiolytic Agents: Synthesis, Quantitative Structure-Activity Relationships, and Molecular Modeling of Substituted 1-(3-Pyridylcarbamoyl)indolines, Synthetic Route of 1677-47-0, the main research area is pyridylcarbamoylindoline preparation 5HT receptor antagonist anxiolytic.

The synthesis, biol. activity, and mol. modeling of a novel series of substituted 1-(3-pyridylcarbamoyl)indolines are reported. These compounds are isosteres of the previously published indole urea SB-206553 and illustrate the use of aromatic disubstitution as a replacement for fused five-membered rings in the context of 5-HT2C/2B receptor antagonists. By targeting a region of space previously identified as sterically allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor, a number of compounds which are the most potent and selective 5-HT2C/2B receptor antagonists yet reported, were identified. 1-(3-Pyridylcarbamoyl)-5-methylthio-6-trifluoromethylindoline was selected on the basis of its overall biol. profile for further evaluation as a novel, potential nonsedating anxiolytic agent. A CoMFA anal. of these compounds produced a model with good predictive value and in addition good qual. agreement with both a 5-HT2C receptor model and a proposed binding mode for this class of ligands within that model.

Lindsay-Scott, Peter J.’s team published research in Synlett in 2016-06-30 | CAS: 1677-47-0

Synlett published new progress about Anilines Role: RCT (Reactant), RACT (Reactant or Reagent). 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, Safety of 4,5-Dichloroisatin.

Lindsay-Scott, Peter J. published the artcileUtilizing Solubility Differences to Achieve Regiocontrol in the Synthesis of Substituted Quinoline-4-carboxylic Acids, Safety of 4,5-Dichloroisatin, the main research area is isonitrosoacetanilide Sandmeyer reaction; isatin preparation regioselective Pfitzinger reaction; quinoline carboxylic acid preparation regioselective.

A practical method for the regiocontrolled synthesis of substituted quinoline-4-carboxylic acids was described. Solubility differences between the product quinoline regioisomers enabled their facile separation, thus avoiding any challenging chromatog. purifications and allowing access to highly substituted quinoline compounds in three steps from com. available anilines.