Tag: M.W=150-200

Masters, Kye-Simeon published the artcileortho-Bromo(propa-1,2-dien-1-yl)arenes: Substrates for domino reactions, Formula: C11H11NO2, the publication is Journal of Organic Chemistry (2011), 76(21), 9060-9067, database is CAplus and MEDLINE.

O-Bromo(propa-1,2-dien-1-yl)arenes exhibit novel and orthogonal reactivity under Pd catalysis in the presence of secondary amines to form enamines (concerted Pd insertion, intramol. carbopalladation, and terminative Buchwald-Hartwig coupling) and of amides to form indoles (addition, Buchwald-Hartwig cyclization, and loss of the acetyl group). The substrates for these reactions can be accessed in a reliable and highly selective two-step process from 2-bromoaryl bromides.

Journal of Organic Chemistry published new progress about 57663-18-0. 57663-18-0 belongs to indole-building-block, auxiliary class Indole,Ester, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Formula: C11H11NO2.

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

Wu, Shuhong published the artcileAnalogues and Derivatives of Oncrasin-1, a Novel Inhibitor of the C-Terminal Domain of RNA Polymerase II and Their Antitumor Activities, Product Details of C9H6FNO, the publication is Journal of Medicinal Chemistry (2011), 54(8), 2668-2679, database is CAplus and MEDLINE.

To optimize the antitumor activity of oncrasin-1, a small mol. RNA polymerase II inhibitor, we evaluated 69 oncrasin-1 analogs for their cytotoxic activity against normal human epithelial cells and K-Ras mutant tumor cells. About 40 of those compounds were as potent as or more potent than oncrasin-1 in tumor cells and had a minimal cytotoxic effect on normal cells. Structure-activity relation anal. revealed that most of the active compounds contained either a hydroxymethyl group or an aldehyde group as a substitute at the 3-position of the indole. Both electron-donating and electron-withdrawing groups in the benzene ring were well tolerated. The hydroxymethyl compounds ranged from equipotent with to 100 times as potent as the corresponding aldehyde compounds We tested three active analogs’ effect on RNA polymerase phosphorylation and found that they all inhibited phosphorylation of the C-terminal domain of RNA polymerase II, suggesting that the active compounds might act through the same mechanisms as oncrasin-1.

Journal of Medicinal Chemistry 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 C7H7BrN2O2, Product Details of C9H6FNO.

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, Liang published the artcileAsymmetric organocatalytic N-alkylation of indole-2-carbaldehydes with α,β-unsaturated aldehydes: one-pot synthesis of chiral pyrrolo[1,2-a]indole-2-carbaldehydes, Recommanded Product: 5-Fluoro-1H-indole-2-carbaldehyde, the publication is Chemistry – A European Journal (2010), 16(2), 440-444, S440/1-S440/53, database is CAplus and MEDLINE.

Diphenylprolinol trimethylsilyl ether-catalyzed asym. aza-Michael addition/aldol addition of indole-2-carboxaldehyde with unsaturated aldehydes is described. A series of chiral pyrrolo[1,2-a]indole-2-carbaldehydes were obtained in good yields with excellent stereoselectivities.

Chemistry – A European Journal 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 C9H6FNO, 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

Hong, Liang published the artcileAsymmetric organocatalytic N-alkylation of indole-2-carbaldehydes with α,β-unsaturated aldehydes: one-pot synthesis of chiral pyrrolo[1,2-a]indole-2-carbaldehydes, Recommanded Product: 5-Fluoro-1H-indole-2-carbaldehyde, the publication is Chemistry – A European Journal (2010), 16(2), 440-444, S440/1-S440/53, database is CAplus and MEDLINE.

Diphenylprolinol trimethylsilyl ether-catalyzed asym. aza-Michael addition/aldol addition of indole-2-carboxaldehyde with unsaturated aldehydes is described. A series of chiral pyrrolo[1,2-a]indole-2-carbaldehydes were obtained in good yields with excellent stereoselectivities.

Chemistry – A European Journal 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 C9H6FNO, 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

Liu, Yonggui published the artcileCarbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones, Category: indole-building-block, the publication is Angewandte Chemie, International Edition (2020), 59(1), 442-448, database is CAplus and MEDLINE.

The aromatic nitrogen atoms of heteroarylaldehydes were activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products I [R¹ = H, 8′-Br, 7′-Cl, etc.; R² = H, 4-Br, 5-Cl, etc.; R³ = Me, Bn, Trt], II [R¹ = H, 8-Br, 7-F, etc.; R² = H, 3-Me, 4-Cl, etc.; R³ = Me, Et, Ph, Bn, CHPh₂] and III [R¹ = H, 6;t-Bu, 7’Cl, etc.; R² = H, 4-Cl, 5-Me, etc.] were afforded in good to excellent yields and optical purities. Reaction involved the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibited excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichems. for plant protection.

Angewandte Chemie, International Edition 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 C9H6FNO, 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

Lamotte, Yann published the artcileSynthesis and biological activities of novel indole derivatives as potent and selective PPARγ modulators, Quality Control of 57663-18-0, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(4), 1399-1404, database is CAplus and MEDLINE.

Starting from the structure of Telmisartan, a new series of potent and selective PPARγ modulators was identified. The synthesis, in vitro and in vivo evaluation of the most potent compounds were reported and the X-ray structure of compound I bound to the PPARγ ligand binding domain was described.

Bioorganic & Medicinal Chemistry Letters published new progress about 57663-18-0. 57663-18-0 belongs to indole-building-block, auxiliary class Indole,Ester, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Quality Control of 57663-18-0.

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

O’Reilly, Matthew C. published the artcileFurther evaluation of novel structural modifications to scaffolds that engender PLD isoform selective inhibition, Recommanded Product: 5-Fluoro-1H-indole-2-carbaldehyde, the publication is Bioorganic & Medicinal Chemistry Letters (2014), 24(24), 5553-5557, database is CAplus and MEDLINE.

This Letter describes the on-going SAR efforts based on two scaffolds, a PLD1-biased piperidinyl benzimidazolone and a PLD2-biased piperidinyl triazaspirone, with the goal of enhancing PLD inhibitory potency and isoform selectivity. Here, we found that addition of an α-Me moiety within the PLD2-biased piperidinyl triazaspirone scaffold abolished PLD2 preference, while the incorporation of substituents onto the piperidine moiety of the PLD1-biased piperidinyl benzimidazolone, or replacement with a bioisosteric [3.3.0] core, generally retained PLD1 preference, but at diminished significance. The SAR uncovered within these two allosteric PLD inhibitor series further highlights the inherent challenges of developing isoform selective PLD inhibitors.

Bioorganic & 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 C9H6FNO, 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

Soderberg, Bjorn C. G. published the artcileIntramolecular cyclization reactions of unsaturated amino Fischer chromium carbenes forming indoles and quinolines, Product Details of C11H11NO2, the publication is Tetrahedron (2003), 59(44), 8775-8791, database is CAplus.

A thermally induced intramol. annulation reaction of N-(2-alkenylphenyl)amino substituted Fischer chromium carbenes has been extensively examined The carbene complexes were prepared in moderate to good yields by reaction of 2-aminostyrenes with intermediately formed acyloxy substituted carbenes. Upon heating, the thermally labile carbenes decomposed producing indoles and quinolines as the major products. The product distribution was found to be highly dependent on the substitution pattern and electronic properties of the starting material, and on the solvent used. The reaction of pentacarbonyl[1-[[2-ethenyl-3-(methoxycarbonyl)phenyl]amino]ethylidene]chromium gave 2-methyl-1H-indole-4-carboxylic acid Me ester. The reaction of pentacarbonyl[1-[[2-(1-methylethenyl)phenyl]amino]ethylidene]chromium gave 2,4-dimethylquinoline and 1,2,3,4-tetrahydro-2,4-dimethylquinoline.

Tetrahedron published new progress about 57663-18-0. 57663-18-0 belongs to indole-building-block, auxiliary class Indole,Ester, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C3H5BN2O2, Product Details of C11H11NO2.

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

McDonald, Brian G. published the artcileConversion of (2-chlorallyl)amines into heterocyclic compounds. I. 2-Methylindoles, 1,5,6,7-tetrahydro-3-methylindol-4-ones, and related heterocycles, Related Products of indole-building-block, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1975), 1446-50, database is CAplus.

The allylanilines I [R = H, Me, (CH2)2CO2Me, R1 = H; R = H, R1 = 2-Ph, 2-CO2Me, 3-Me, 4-Cl, 4-Me, 4-CO2Me], prepared by condensation of R1C6H4NHR with CH2:CClCH2R2 (R2 = Cl, I), gave 5-75% II on heating with polyphosphoric acid at 100° or BF3-MeOH at 150°. This method was used for the preparation of other heterocyclic compounds e.g. condensation of 4,7-dichloroquinoline with R3NHCH2CCl:CH2 (R3 = Ph, Et) and cyclization of the product formed gave 30-42% pyrroloquinolines III.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 57663-18-0. 57663-18-0 belongs to indole-building-block, auxiliary class Indole,Ester, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, 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

McDonald, Brian G. published the artcileConversion of (2-chlorallyl)amines into heterocyclic compounds. I. 2-Methylindoles, 1,5,6,7-tetrahydro-3-methylindol-4-ones, and related heterocycles, Related Products of indole-building-block, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1975), 1446-50, database is CAplus.

The allylanilines I [R = H, Me, (CH2)2CO2Me, R1 = H; R = H, R1 = 2-Ph, 2-CO2Me, 3-Me, 4-Cl, 4-Me, 4-CO2Me], prepared by condensation of R1C6H4NHR with CH2:CClCH2R2 (R2 = Cl, I), gave 5-75% II on heating with polyphosphoric acid at 100° or BF3-MeOH at 150°. This method was used for the preparation of other heterocyclic compounds e.g. condensation of 4,7-dichloroquinoline with R3NHCH2CCl:CH2 (R3 = Ph, Et) and cyclization of the product formed gave 30-42% pyrroloquinolines III.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 57663-18-0. 57663-18-0 belongs to indole-building-block, auxiliary class Indole,Ester, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, 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