Day: November 24, 2022

White, James D. published the artcileTandem Intramolecular Photocycloaddition-Retro-Mannich Fragmentation as a Route to Spiro[pyrrolidine-3,3′-oxindoles]. Total Synthesis of (卤)-Coerulescine, (卤)-Horsfiline, (卤)-Elacomine, and (卤)-6-Deoxyelacomine, Safety of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Journal of Organic Chemistry (2010), 75(11), 3569-3577, database is CAplus and MEDLINE.

Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramol. [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-Mannich fission to produce a spiro[indoline-3,3′-pyrrolenine] with relative configuration defined by the orientation of substituents in the transient cyclobutane. The tandem intramol. photocycloaddition-retro-Mannich process, abbreviated as TIPCARM, leads to a spiropyrrolidine which is poised to undergo a second retro-Mannich fragmentation that expels the malonate unit and generates transiently an indolenine. The latter undergoes rearrangement to a 尾-carboline, which upon brominative oxidation undergoes further rearrangement to an oxindole. With tryptamine as starting material, the entire sequence leads to the alkaloid (卤)-coerulescine (I, R = H). Starting from 5-methoxytryptamine, a parallel series affords (卤)-horsfiline I (R = MeO). Modification of the malonylidene unit to include an iso-Bu substituent at C3 affords a photosubstrate which also undergoes the TIPCARM process. In this case, a 2′-isobutyl-substituted spiro[indoline-3,3′-pyrrolenine] results. This undergoes stereoselective hydride reduction to give a product with relative orientation at the spiro carbon and the new stereocenter bearing the iso-Bu appendage corresponding to that of the alkaloid elacomine. From tryptamine, the sequence paralleling that leading to coerulescine and horsfiline terminates at 6-deoxyelacomine, whereas 6-methoxytryptamine as starting material affords (卤)-elacomine (II) itself.

Journal of Organic 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 C7H16Cl2Si, Safety of 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

Wang, Ke published the artcileSynthesis and antitumor activity of bisindolylmaleimide and amino acid ester conjugates, Computed Properties of 149108-61-2, the publication is Journal of Asian Natural Products Research (2010), 12(1), 36-42, database is CAplus and MEDLINE.

A series of novel bisindolylmaleimide and natural amino acid ester conjugates were synthesized and evaluated for their inhibitory activity against six tumor cell lines. Some compounds displayed interesting cytotoxic profiles. The most active compound 8e showed inhibitory activity against several human cancer cell lines.

Journal of Asian Natural Products Research published new progress about 149108-61-2. 149108-61-2 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-tosyl-1H-Indol-3-yl)boronic acid, and the molecular formula is C21H24O8, Computed Properties of 149108-61-2.

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

Gu, Lijun published the artcileMicrowave-assisted synthesis of indole-2-carboxylic acid esters in ionic liquid, Computed Properties of 20538-12-9, the publication is Journal of the Brazilian Chemical Society (2011), 22(11), 2036-2039, database is CAplus.

An improved procedure for the synthesis of indole-2-carboxylic acid esters, e.g. Et 1-methoxy-1H-indole-2-carboxylate, in excellent yields has been achieved by the condensation of 2-halo aryl aldehydes or ketones and Et isocyanoacetate using ionic liquid under controlled microwave irradiation (100 W) at 50 掳C. This method offers a number of advantages in terms of methodol., high-product yield, short period of conversion, mild reaction conditions and easy workup.

Journal of the Brazilian Chemical Society 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, Computed Properties of 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

Huang, Shenlin published the artcileSynthesis and biological study of 2-amino-4-aryl-5-chloropyrimidine analogues as inhibitors of VEGFR-2 and cyclin dependent kinase 1 (CDK1), Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Bioorganic & Medicinal Chemistry Letters (2007), 17(8), 2179-2183, database is CAplus and MEDLINE.

The series of 2-amino-4-aryl-5-chloropyrimidines, e.g., I, was discovered to be potent for both VEGFR-2 and CDK1. Described here are the chem. for analog synthesis, SAR study, and its kinase selectivity profiling. The full rat PK data and in vivo efficacy study are also included.

Bioorganic & Medicinal Chemistry Letters published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Name: 6-(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

Tan, Yu Jia published the artcileAmide-Amine Replacement in Indole-2-carboxamides Yields Potent Mycobactericidal Agents with Improved Water Solubility, Recommanded Product: 5-Fluoro-1H-indole-2-carbaldehyde, the publication is ACS Medicinal Chemistry Letters (2021), 12(5), 704-712, database is CAplus and MEDLINE.

Indolecarboxamides are potent but poorly soluble mycobactericidal agents. Here, it was found that modifying the incipient scaffold by amide-amine substitution and replacing the indole ring with benzothiophene or benzoselenophene led to striking (10-20-fold) improvements in solubility Potent activity could be achieved without the carboxamide linker but not in the absence of the indole ring. The indolylmethylamine, N-cyclooctyl-6-trifluoromethylindol-2-ylmethylamine (MIC_90Mtb 0.13渭M, MBC_99.9Mtb 0.63渭M), exemplifies a promising member that is more soluble and equipotent to its carboxamide equivalent It is also an inhibitor of the mycolate transporter MmpL3, a property shared by the methylamines of benzothiophene and benzoselenophene.

ACS Medicinal Chemistry Letters 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 C10H10O2, Recommanded Product: 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

Danieli, Bruno published the artcileFormal enantioselective synthesis of tacamonine starting from asymmetrized 2-substituted propane-1,3-diols, COA of Formula: C15H20N2O2, the publication is Tetrahedron: Asymmetry (1999), 10(20), 4057-4064, database is CAplus.

2-Substituted propanediols monoacetates, derived from enzymic asymmetrization of the corresponding diols, have been obtained in high yields and enantiomeric excesses by using lipases and vinyl acetate as both solvent and acylating agent. These chiral building blocks have been transformed into the advanced intermediate I, useful for the enantioselective synthesis of tacamane alkaloids.

Tetrahedron: Asymmetry 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, COA of Formula: C15H20N2O2.

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

Sen, S. P. published the artcilePaper chromatography of plant-growth regulators and allied compounds, Formula: C8H6KNO4S, the publication is Physiologia Plantarum (1954), 98-108, database is CAplus.

The chromatog. behavior of a number of indole derivatives in several solvent systems is described, along with their detection by fluorescence in UV light and their color reactions with FeCl₃-HClO₄, p-dimethylaminobenzaldehyde, KNO₂-HNO₃, cinnamaldehyde-HCl, dichloroquinone chlorimide, and other reagents. The following compounds were tested: indole, 2-methylindole, 3-methylindole, 3-indolecarboxylic acid, 3-indoleacetic acid, 3-indolepropionic acid, 3-indolebutyric acid, 3-indolecarboxaldehyde, 3-indoleacetaldehyde, 3-indoleacetonitrile, 3-indolebutyronitrile, Et 3-indoleacetate, tryptophan, tryptamine, gramine, isatin, N-acetylisatin, dihydroxyindole, indican, indican glucoside, indoxylacetate, N-acetylindoxyl, indigotin, indigodisulfonate, indigotetrasulfonate, and indirubin. R_f values, as detected by spraying with bromocresol green, were also determined for a number of aromatic acids. These included 1-naphthaleneacetic acid; 2-naphthoxyacetic acid; phenylacetic acid; phenoxyacetic acid, and its 慰-chloro, p-chloro, 2,4-dichloro, and 3,4,5-trichloro derivatives; and benzoic acid and its following derivatives: 慰-bromo, m-bromo, p-bromo, 慰-chloro, m-chloro, p-chloro, 2,4-dichloro, 3,4-dichloro, 2,3,5-triiodo, m-hydroxy; p-hydroxy, 2,4-dihydroxy, 慰-amino, p-amino, 2,5-dinitro, 3,5-dinitro, 2-amino-5-chloro, and 2-chloro-5-nitro.

Physiologia Plantarum 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 C9H7NO3, 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

Bartscht, Tobias published the artcileThe Src family kinase inhibitors PP2 and PP1 effectively block TGF-beta1-induced cell migration and invasion in both established and primary carcinoma cells, Category: indole-building-block, the publication is Cancer Chemotherapy and Pharmacology (2012), 70(2), 221-230, database is CAplus and MEDLINE.

Purpose: We have previously demonstrated that in pancreatic ductal adenocarcinoma (PDAC)-derived cell lines, the common Src family kinase inhibitors PP2 and PP1 effectively inhibited morphol. alterations associated with TGF尾1-mediated epithelial-to-mesenchymal transition (EMT) by blocking the kinase activity of the TGF-尾 type I receptor ALK5 rather than Src (Ungefroren et al. in Curr Cancer Drug Targets 11:524, 2011). In this report, the ability of PP2 and PP1, the more specific Src inhibitor SU6656, and the ALK5 inhibitor SB431542 to functionally block TGF-尾1-dependent EMT and cell motility in established PDAC (Panc-1, Colo 357) and primary NSCLC (Tu459) cell lines were investigated. Methods: The effects of PP2, PP1, SU6656, and SB431542 on TGF-尾1-dependent cell scattering/EMT, cell migration/invasion, and expression of invasion-associated genes were measured by using the real-time cell anal. assay on the xCELLigence system and quant. real-time RT-PCR, resp. Results: In all three cell lines tested, PP1, PP2, and SB431542 effectively blocked TGF-尾1-induced cell scattering/EMT, migration, and invasion and in Colo 357 cells inhibited the induction of the invasion-associated MMP2 and MMP9 genes. In contrast, SU6656 only blocked TGF-尾1-induced invasion in Panc-1 and Tu459 but not Colo 357 cells. PP1, and to a greater extent PP2, also inhibited the high spontaneous migratory activity of Panc-1 cells expressing a kinase-active ALK5 mutant. Conclusions: These data provide evidence that PP2 and PP1 are powerful inhibitors of TGF-尾-induced cell migration and invasion in vitro and directly target ALK5. Both agents may be useful as dual TGF-尾/Src inhibitors in exptl. therapeutics to prevent metastatic spread in late-stage PDAC and NSCLC.

Cancer Chemotherapy and Pharmacology 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, 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

Chang, Ying-Hsin published the artcileEffects of cannabinoids on LPS-stimulated inflammatory mediator release from macrophages: involvement of eicosanoids, Product Details of C23H23ClN2O4, the publication is Journal of Cellular Biochemistry (2001), 81(4), 715-723, database is CAplus and MEDLINE.

螖⁹-Tetrahydrocannabinol (螖⁹-THC) is the major psychoactive component of marijuana and elicits pharmacol. actions via cannabinoid receptors. Anandamide (AEA) and 2-arachidonoyl-glycerol (2-AG) are endogenous ligands for cannabinoid receptors, which because of their structural similarities to arachidonic acid (AA), AEA, and 2-AG could serve as substrates for lipoxygenases and cyclooxygenases (COXs) that metabolize polyunsaturated fatty acids to potent bioactive mols. In this study, we have compared the effects of 螖⁹-THC, AEA, 2-AG, and another cannabinoid agonist, indomethacin morpholinylamide (IMMA), on lipopolysaccharide (LPS)-induced NO, IL-6, and PGE₂ release from J774 macrophages. 螖⁹-THC, IMMA, and AEA diminish LPS-induced NO and IL-6 production in a concentration-dependent manner. 2-AG inhibits the production of IL-6 but slightly increases iNOS-dependent NO production 螖⁹-THC and IMMA also inhibit LPS-induced PGE₂ production and COX-2 induction, while AEA and 2-AG have no effects. These discrepant results of 2-AG on iNOS and COX-2 induction might be due to its bioactive metabolites, AA and PGE₂, whose incubation cause the potentiation of both iNOS and COX-2 induction. On the contrary, the AEA metabolite, PGE₂-ethanolamide, influences neither the LPS-induced NO nor IL-6 production Taken together, direct cannabinoid receptor activation leads to anti-inflammatory action via inhibition of macrophage function. The endogenous cannabinoid, 2-AG, also serves as a substrate for COX-catalyzing PGE₂ production, which in turn modulates the action of CB2.

Journal of Cellular Biochemistry published new progress about 2854-32-2. 2854-32-2 belongs to indole-building-block, auxiliary class GPCR/G Protein,Cannabinoid Receptor, name is 2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-1-morpholinoethanone, and the molecular formula is C23H23ClN2O4, Product Details of C23H23ClN2O4.

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

Zhu, Weng-E. published the artcileAn Image-Based, High-Throughput Screening Assay for Molecules that Induce Excess DNA Replication in Human Cancer Cells, SDS of cas: 330161-87-0, the publication is Molecular Cancer Research (2011), 9(3), 294-310, database is CAplus and MEDLINE.

Previous studies have shown DNA re-replication can be induced in cells derived from human cancers under conditions in which it is not possible for cells derived from normal tissues. Because DNA re-replication induces cell death, this strategy could be applied to the discovery of potential anticancer therapeutics. Therefore, an imaging assay amenable to high-throughput screening was developed that measures DNA replication in excess of four genomic equivalent in the nuclei of intact cells and indexes cell proliferation. This assay was validated by screening a library of 1,280 bioactive mols. on both normal and tumor-derived cells where it proved more sensitive than current methods for detecting excess DNA replication. This screen identified known inducers of excess DNA replication, such as inhibitors of microtubule dynamics, and novel compounds that induced excess DNA replication in both normal and cancer cells. In addition, two compounds were identified that induced excess DNA replication selectively in cancer cells and one that induced endocycles selectively in cancer cells. Thus, this assay provides a new approach to the discovery of compounds useful for investigating the regulation of genome duplication and for the treatment of cancer.

Molecular Cancer Research 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 C11H15NO2, SDS of cas: 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