Category: indole-building-block

Ishii, Hisashi published the artcileFischer indolization and its related compounds. XXIV. Fischer indolization of ethyl pyruvate 2-(2-methoxyphenyl)phenylhydrazone, COA of Formula: C12H13NO3, the publication is Chemical & Pharmaceutical Bulletin (1991), 39(3), 572-8, database is CAplus.

In order to clarify the mechanism of Fischer indolization of 2-methoxyphenylhydrazones, Fischer indolization of Et pyruvate 2-(2-methoxyphenyl)phenylhydrazone I was carried out with hydrochloric acid in ethanol and zinc chloride in acetic acid. The reactions proceeded smoothly to give N-arylindoles II (R = Ph, R¹ = R² = H; R¹ = Cl, R² = H; R¹ = H, R² = OMe; R = 2-MeOC₆H₄, R¹ = R² = H) and some chlorinated diphenylamine derivatives III (R³ = Cl, R⁴ = R⁵ = H; R³ = R⁵ = H, R⁴ = Cl; R³ = R⁴ = H, R⁵ = Cl, R³-R⁵ = H) as byproducts. Consideration of the indole products revealed that the Fischer indolization proceeded mainly at the unsubstituted Ph nucleus rather than at the 2-methoxyphenyl nucleus. This result is inconsistent with the previous result that Fischer indolization of diarylhydrazones proceeded at the electron-richer nucleus. The structures of the diphenylamines III were determined by chem. means and the mechanism of their formation is discussed.

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 C12H13NO3, 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

Gong, Liang published the artcileNi-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers, Safety of 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, the publication is Journal of the American Chemical Society (2019), 141(19), 7680-7686, database is CAplus and MEDLINE.

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Journal of the American Chemical Society published new progress about 1206163-56-5. 1206163-56-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, and the molecular formula is C21H24BNO2, Safety of 1-Benzyl-5-(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

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

Everett, Steven A. published the artcileControlling the rates of reductively-activated elimination from the (indol-3-yl)methyl position of indolequinones, Product Details of C18H16N2O6, the publication is Journal of the Chemical Society, Perkin Transactions 2 (2001), 843-860, database is CAplus.

A series of substituted 3-(4-nitrophenyloxy)methylindole-4,7-diones (Q) were synthesized. The effects of substitution patterns on the indole core on rates of elimination of 4-nitrophenol as a model for drug release following fragmentation of a phenolic ether linker were studied. After reduction to either the radical anion (Q√^–) or hydroquinone (QH₂) elimination of 4-nitrophenol occurred from the (indol-3-yl)methyl position. The half-lives of Q√^– radicals at [O₂] ≈ 5 mmol dm^-3, typical of tumor hypoxia, were t_1/2 ≈ 0.3-1.8 ms, the higher values associated with higher reduction potentials. Half-lives for the autoxidation of the QH₂ were markedly longer at the same oxygen concentration (t₁/2 ≈ 8-102 min) and longer still in the presence of 4 mmol dm^-3 superoxide dismutase (t_1/2 ≈ 8-19 h). Although the indolequinones were able to eliminate 4-nitrophenol with high efficiency only Q√^– radicals of the 3-carbonyl substituted derivatives did so with sufficiently short half-lives (t_1/2 41-2 ms) to compete with electron transfer to oxygen and therefore have the potential to target the leaving group to hypoxic tissue. The hydroquinones are not sufficiently oxygen sensitive to prevent the elimination of 4-nitrophenol (t_1/2 1.5-3.5 s) even at oxygen concentrations expected in normal tissue. By incorporating electron rich substituents at the indolyl carbonyl position it is possible to control the rate of reductive fragmentation. This may prove an important factor in the design of an indolequinone-based bioreductive drug delivery system.

Journal of the Chemical Society, Perkin Transactions 2 published new progress about 192820-78-3. 192820-78-3 belongs to indole-building-block, auxiliary class Fused/Partially Saturated Cycles,Dihydroindoles, name is 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, and the molecular formula is C18H16N2O6, Product Details of C18H16N2O6.

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

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, Recommanded Product: 5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, 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 1256358-91-4. 1256358-91-4 belongs to indole-building-block, auxiliary class Indole,Chloride,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C5H8N2O, Recommanded Product: 5-Chloro-2-(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

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

Lim, Yee Hwee published the artcileDirect Conversion of Indoles to 3,3-Difluoro-2-oxindoles via Electrophilic Fluorination, Name: 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, the publication is Organic Letters (2012), 14(22), 5676-5679, database is CAplus and MEDLINE.

3,3-Difluoro-2-oxindoles can be obtained directly from indoles in moderate yields via electrophilic fluorination using N-fluorobenzenesulfonimide as a mild fluorinating reagent. The presence of tert-Bu hydroperoxide during the reaction, together with addnl. heating after quenching the reaction with triethylamine, is beneficial to the formation of the desired product.

Organic Letters published new progress about 1206163-56-5. 1206163-56-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, and the molecular formula is C21H24BNO2, Name: 1-Benzyl-5-(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

Yoshida, Keiichiro published the artcilePlasmodium induced by SU6656, an Src family kinase inhibitor, is accompanied by a contractile ring defect, Quality Control of 330161-87-0, the publication is Cell Biochemistry and Function (2012), 30(1), 33-40, database is CAplus and MEDLINE.

We have shown that SU6656, a potent Src family kinase inhibitor, has the ability to induce multinucleation at a high frequency in diverse cells: rat skin fibroblasts, bone marrow adherent cells, 5F9A mesenchymal stem cell-like clones, 2C5 tracheal epithelial cells and MDCK epithelial cells from dog kidney. To gain insight into the mechanism of multinucleation, we observed the process by time-lapse and confocal microscopy. These multinuclei generally seem to exist independently in one cell without any connections with each other. By time-lapse microscopy, multinucleated cells were found to be formed through the mechanism of plasmodium: karyokinesis without cytokinesis. The observation of EGFP-actin transfected cells by time-lapse confocal laser scanning microscopy suggested that plasmodium occurred with deficient contractile ring formation. Although we examined the differentiation of these cells, the multinucleated cells could not be categorized into any type of cell in vivo known to exhibit multinuclei. Copyright © 2011 John Wiley & Sons, Ltd.

Cell Biochemistry and Function 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 C9H20Cl2Si, Quality Control of 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

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