Tag: M.W=200-250

Gannon, Walter F. published the artcileFischer indole cyclization of several ortho-substituted phenylhydrazones, Related Products of indole-building-block, the publication is Journal of Organic Chemistry (1969), 34(10), 3002-6, database is CAplus.

Fischer indole cyclization of Et pyruvate o-methoxyphenylhydrazone in ethanolic HCl gave 2-carbethoxy-6-chloroindole (I) as the main product. Minor products included 2-carbethoxy-3-chloroindole, the expected 2-carbethoxy-7-methoxyindole and several indolic dimers. Similarly, Et pyruvate o-benzyloxyphenylhydrazone gave I. Cyclization of cyclohexanone o-methoxyphenylhydrazone in dilute H2SO4 yielded 8-methoxy-1,2,3,-4-tetrahydrocarbazole (II) as the major product. The only isolated by-product, previously reported to be 12-methoxy-1,2,3,4-tetrahydroisocarbazole, had a dimeric structure. When the reaction was run in ethanolic HCl, the dimer hydrochloride became the main product and II is formed in lower yield. The structure of the dimers and the reaction mechanism are discussed.

Journal of Organic Chemistry 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

Walsh, Martin J. published the artcile2-Oxo-N-aryl-1,2,3,4-tetrahydroquinoline-6-sulfonamides as activators of the tumor cell specific M2 isoform of pyruvate kinase, Application In Synthesis of 166883-20-1, the publication is Bioorganic & Medicinal Chemistry Letters (2011), 21(21), 6322-6327, database is CAplus and MEDLINE.

Compared to normal differentiated cells, cancer cells have altered metabolic regulation to support biosynthesis and the expression of the M2 isoenzyme of pyruvate kinase (PKM2) plays an important role in this anabolic metabolism While the M1 isoform is a highly active enzyme, the alternatively spliced M2 variant is considerably less active and expressed in tumors. While the exact mechanism by which decreased pyruvate kinase activity contributes to anabolic metabolism remains unclear, it is hypothesized that activation of PKM2 to levels seen with PKM1 may promote a metabolic program that is not conducive to cell proliferation. Here we report the third chemotype in a series of PKM2 activators based on the 2-oxo-N-aryl-1,2,3,4-tetrahydroquinoline-6-sulfonamide scaffold. The synthesis, structure activity relationships, selectivity and notable physiochem. properties are described.

Bioorganic & Medicinal Chemistry Letters published new progress about 166883-20-1. 166883-20-1 belongs to indole-building-block, auxiliary class Indoline,Chloride,Sulfonyl chlorides,Amide, name is 1-Methyl-2-oxoindoline-5-sulfonyl chloride, and the molecular formula is C4H6O3, Application In Synthesis of 166883-20-1.

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

Piers, E. published the artcileThe decarboxylation of ring-substituted indole-2(and 3)carboxylic acids, Safety of 6-Nitro-1H-indole-3-carboxylic acid, the publication is Canadian Journal of Chemistry (1962), 559-61, database is CAplus.

A mixture of the indole-2-carboxylic acid (0.01 mole) and its Cu salt (0.0004 mole) in 10 ml. synthetic quinoline was heated until CO₂ began to evolve and was kept at this temperature until gas evolution ceased (1.5-5 hrs.). The cooled solution was taken up in Et₂O, washed with N HCl, H₂O, Na₂CO₃, H₂O, and dried (Na₂SO₄). Removal of the Et₂O gave a solid, which was chromatographed on Al₂O₃ with CH₂Cl₂ as eluant. Thus, 6-Br 2-CO₂H analog, decarboxylated at 210-15° in 4 hrs., yield 63%, 7-Br 2-CO₂H analog, yield 74%, 4-PhCH₂S 2-CO₂H analog, yield 61%, 7-PhCH₂S 2-CO₂H analog, yield 80%, and 6-NO₂ 3-CO₂H analog, yield 85%, were prepared The Cu salt was prepared by heating a stirred mixture of the acid (0.01 mole), Na₂CO₃ (0.005 mole), and H₂O (100 ml.) until the acid dissolved. Upon addition of CuSO₄.5H₂O (0.005 mole) in 50 ml. H₂O, the blue cupric salt of the indole-2-carboxylic acid precipitated The solid was washed thoroughly with H₂O, air dried, then dried over CaCl₂ in vacuo.

Canadian Journal of 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, Safety of 6-Nitro-1H-indole-3-carboxylic acid.

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

Kerns, Jeffrey K. published the artcile3,5-Disubstituted-indole-7-carboxamides as IKKβ Inhibitors: Optimization of Oral Activity via the C3 Substituent, Formula: C9H6BrNO2, the publication is ACS Medicinal Chemistry Letters (2018), 9(12), 1164-1169, database is CAplus and MEDLINE.

IκB kinase β (IKKβ or IKK2) is a key regulator of nuclear factor kappa B (NF-κB) and has received attention as a therapeutic target. Herein the authors report on the optimization of a series of 3,5-disubstituted-indole-7-carboxamides for oral activity. In doing so, the authors focused attention on potency, ligand efficiency (LE), and physicochem. properties and have identified compounds I and II as having robust in vivo activity.

ACS Medicinal Chemistry Letters published new progress about 860624-90-4. 860624-90-4 belongs to indole-building-block, auxiliary class Indole,Bromide,Carboxylic acid,Indole, name is 5-Bromo-1H-indole-7-carboxylic acid, and the molecular formula is C9H6BrNO2, Formula: C9H6BrNO2.

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

Ji, Hong published the artcilePalladium-catalyzed borylation of aryl (pseudo)halides and its applications in biaryl synthesis, Category: indole-building-block, the publication is Chemistry Central Journal (2018), 136, database is CAplus and MEDLINE.

A facile and efficient palladium-catalyzed borylation of aryl (pseudo)halides at room temperature has been developed. Arylboronic esters were expeditiously assembled in good yields and with a broad substrate scope and good functional group compatibility. This approach has been successfully applied to the one-pot two-step borylation/ Suzuki-Miyaura cross-coupling reaction, providing a concise access to biaryl compounds from readily available aryl halides. Furthermore, a parallel synthesis of biaryl analogs is accomplished at room temperature using the strategy, which enhances the practical usefulness of this method.

Chemistry Central Journal 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, 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

Tani, Masanobu published the artcileNew strategy for indole synthesis from ethyl pyrrole-2-carboxylate (synthetic studies on indoles and related compounds. XXXIX), COA of Formula: C12H13NO3, the publication is Chemical & Pharmaceutical Bulletin (1996), 44(1), 55-61, database is CAplus.

As a synthetic application of the previously reported C₄-acylation of Et pyrrole-2-carboxylate, a new strategy for indole synthesis was developed. Et pyrrole-2-carboxylate was allowed to react with succinic anhydride or 3-methoxycarbonylpropionyl chloride to give, in good yield, a C₄-succinyl derivative, which was converted into Et 7-oxo-4,5,6,7-tetrahydroindole-2-carboxylate (I) as a key intermediate for indole synthesis. Starting from I, several indoles functionalized on the benzene moiety were synthesized.

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 C9H10O4, COA of 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

Alcaraz, Marie-Lyne published the artcileEfficient Syntheses of AZD4407 via Thioether Formation by Nucleophilic Attack of Organometallic Species on Sulphur, Formula: C9H8ClNO3S, the publication is Organic Process Research & Development (2005), 9(5), 555-569, database is CAplus.

The development of two efficient strategies for the synthesis of AZD4407 (I) is reported, both of which are considered suitable for large-scale manufacture In the first approach, 3-bromothiophene is coupled with (2S)-2-methyltetrahydropyran-4-one using Grignard chem. Following hydroxyl protection and lithiation at thiophene C-2, reaction with a protected 5-mercapto-1-methyl-1,3-dihydro-indol-2-one derivative bearing a leaving group on sulfur provides AZD4407 after acid-catalyzed deprotection and epimerization. The second approach starts from 2,4-dibromothiophene, which undergoes a selective Grignard exchange reaction at C-2 followed by reaction with similar protected mercapto-oxindole derivatives Reprotection of the oxindole ring, followed by a second Grignard exchange, and reaction with (2S)-2-methyltetrahydropyran-4-one provides AZD4407 after acid-catalyzed deprotection and epimerization.

Organic Process Research & Development published new progress about 166883-20-1. 166883-20-1 belongs to indole-building-block, auxiliary class Indoline,Chloride,Sulfonyl chlorides,Amide, name is 1-Methyl-2-oxoindoline-5-sulfonyl chloride, and the molecular formula is C9H8ClNO3S, Formula: C9H8ClNO3S.

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

Miller, David D. published the artcile3,5-Disubstituted-indole-7-carboxamides: The discovery of a novel series of potent, selective inhibitors of IKK-β, COA of Formula: C9H6BrNO2, the publication is Bioorganic & Medicinal Chemistry Letters (2011), 21(8), 2255-2258, database is CAplus and MEDLINE.

The discovery and hit-to-lead exploration of a novel series of selective IKK-β kinase inhibitors is described. The initial lead fragment 3 (I) was identified by pharmacophore-directed virtual screening. Homol. model-driven SAR exploration of the template led to potent inhibitors, such as 12 (II), which demonstrate efficacy in cellular assays and possess encouraging developability profiles.

Bioorganic & Medicinal Chemistry Letters published new progress about 860624-90-4. 860624-90-4 belongs to indole-building-block, auxiliary class Indole,Bromide,Carboxylic acid,Indole, name is 5-Bromo-1H-indole-7-carboxylic acid, and the molecular formula is C9H6BrNO2, COA of Formula: C9H6BrNO2.

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

Romagnoli, Romeo published the artcileDiscovery of 8-methoxypyrazino[1,2-a]indole as a new potent antiproliferative agent against human leukemia K562 cells. a structure-activity relationship study, Name: Ethyl 7-methoxy-1H-indole-2-carboxylate, the publication is Letters in Drug Design & Discovery (2009), 6(4), 298-303, database is CAplus and MEDLINE.

Identification of novel and selective anticancer agents remains an important and challenging goal in pharmacol. research. The indole nucleus, frequently encountered as a mol. fragment in natural products and pharmaceutically active compounds, was employed as the initial building block for the synthesis of a series of pyrazino[1,2-a]indoles 1a-k, variably substituted at the 6, 7, 8 and 9-positions. Compound 1e (I), bearing the methoxy group at the 8-position of the pyrazino[1,2-a]indole nucleus was identified as a novel potent antiproliferative agent against the human chronic myelogenous leukemia K562 cell line, but it was much less active against several other cancer cell lines. Comparison of positional isomers indicated that moving the methoxy group from the 8- to the 7- or 6-position, to furnish compounds 1f and 1g, resp., yielded inactive compounds The anal. of structure-activity relationships observed in the series of investigated compounds may represent the basis for the design of more active mols.

Letters in Drug Design & Discovery 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, Name: Ethyl 7-methoxy-1H-indole-2-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

Favalli, Nicholas published the artcileScreening of Three Transition Metal-Mediated Reactions Compatible with DNA-Encoded Chemical Libraries, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Helvetica Chimica Acta (2019), 102(4), n/a, database is CAplus and MEDLINE.

The construction of DNA-encoded chem. libraries (DECLs) crucially relies on the availability of chem. reactions, which are DNA-compatible and which exhibit high conversion rates for a large number of diverse substrates. In this work, we present our optimization and validation procedures for three copper and palladium-catalyzed reactions (Suzuki cross-coupling, Sonogashira cross-coupling, and copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC)), which have been successfully used by our group for the construction of large encoded libraries.

Helvetica Chimica Acta 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, Application of 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