Month: November 2022

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

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

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

Hickman, Zachary L. published the artcileA concise synthesis of 3-hydroxyindole-2-carboxylates by a modified Baeyer-Villiger oxidation, Category: indole-building-block, the publication is Tetrahedron Letters (2000), 41(43), 8217-8220, database is CAplus.

Indole-2-carboxylates are converted in good yields to 3-hydroxyindole-2-carboxylates by use of a Vilsmeier-Haack/Baeyer-Villiger reaction sequence. A systematic examination of the various indole substituents revealed this route to be general in scope.

Tetrahedron Letters published new progress about 100123-25-9. 100123-25-9 belongs to indole-building-block, auxiliary class Indole,Bromide,Ester,Aldehyde, name is Ethyl 5-bromo-3-formyl-1H-indole-2-carboxylate, and the molecular formula is C12H10BrNO3, 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

Ma, Jiajia published the artcileDirect Dearomatization of Pyridines via an Energy-Transfer-Catalyzed Intramolecular [4+2] Cycloaddition, Quality Control of 167015-84-1, the publication is Chem (2019), 5(11), 2854-2864, database is CAplus.

A catalytic, dearomative cycloaddition reaction with pyridines, e.g., I using photoinduced energy transfer catalysis has been reported, thereby advancing dearomatization methodol. and increasing the topol. of pyridine dearomatization products, e.g., II. This unprecedented method features high yields, broad substrate scope, excellent functional group tolerance, and facile scalability. Furthermore, a recyclable and sustainable polymer immobilized photocatalyst was employed. Computational and exptl. investigations support a mechanism in which a cinnamyl moiety is promoted to its corresponding excited triplet state through visible-light-mediated energy transfer catalysis, followed by a regioselective and dearomative [4+2] cycloaddition to pyridines. This work demonstrates the contribution of visible light catalysis toward enabling thermally challenging organic transformations.

Chem 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, Quality Control of 167015-84-1.

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

Bilsland, Alan E. published the artcileMathematical model of a telomerase transcriptional regulatory network developed by cell-based screening: analysis of inhibitor effects and telomerase expression mechanisms, Name: SU6656, the publication is PLoS Computational Biology (2014), 10(2), e1003448/1-e1003448/19, 19 pp., database is CAplus and MEDLINE.

Cancer cells depend on transcription of telomerase reverse transcriptase (TERT). Many transcription factors affect TERT, though regulation occurs in context of a broader network. Network effects on telomerase regulation have not been investigated, though deeper understanding of TERT transcription requires a systems view. However, control over individual interactions in complex networks is not easily achievable. Math. modeling provides an attractive approach for anal. of complex systems and some models may prove useful in systems pharmacol. approaches to drug discovery. In this report, we used transfection screening to test interactions among 14 TERT regulatory transcription factors and their resp. promoters in ovarian cancer cells. The results were used to generate a network model of TERT transcription and to implement a dynamic Boolean model whose steady states were analyzed. Modelled effects of signal transduction inhibitors successfully predicted TERT repression by Src-family inhibitor SU6656 and lack of repression by ERK inhibitor FR180204, results confirmed by RT-QPCR anal. of endogenous TERT expression in treated cells. Modelled effects of GSK3 inhibitor 6-bromoindirubin-3′-oxime (BIO) predicted unstable TERT repression dependent on noise and expression of JUN, corresponding with observations from a previous study. MYC expression is critical in TERT activation in the model, consistent with its well known function in endogenous TERT regulation. Loss of MYC caused complete TERT suppression in our model, substantially rescued only by co-suppression of AR. Interestingly expression was easily rescued under modelled Ets-factor gain of function, as occurs in TERT promoter mutation. RNAi targeting AR, JUN, MXD1, SP3, or TP53, showed that AR suppression does rescue endogenous TERT expression following MYC knockdown in these cells and SP3 or TP53 siRNA also cause partial recovery. The model therefore successfully predicted several aspects of TERT regulation including previously unknown mechanisms. An extrapolation suggests that a dominant stimulatory system may program TERT for transcriptional stability.

PLoS Computational Biology 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, Name: SU6656.

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

Muscella, A. published the artcileRole of epidermal growth factor receptor signaling in a Pt(II)-resistant human breast cancer cell line, Recommanded Product: SU6656, the publication is Biochemical Pharmacology (Amsterdam, Netherlands) (2021), 114702, database is CAplus and MEDLINE.

Platinum complexes are currently used for breast cancer therapy, but, as with other drug classes, a series of intrinsic and acquired resistance mechanisms hinder their efficacy. To better understand the mechanisms underlying platinum complexes resistance in breast cancer, we generated a [Pt(O,O’-acac)(γ-acac)(DMS)]-resistant MCF-7, denoted as [Pt(acac)2]R. [Pt(O,O’-acac)(γ-acac)(DMS)] was chosen as previous works showed that it has distinct mechanisms of action from cisplatin, especially with regard to cellular targets. [Pt(acac)2]R cells are characterized by increased proliferation rates and aggressiveness with higher PKC-δ, BCL-2, MMP-9 and EGFR protein expressions and also by increased expression of various genes covering cell cycle regulation, invasion, survival, and hormone receptors. These [Pt(acac)2]R cells also displayed high levels of activated signaling kinases Src, AKT and ERK/2. [Pt(acac)2]R cells incubated with [Pt(O,O’-acac)(γ-acac)(DMS)], showed a relevant EGFR activation due to PKC-δ and Src phosphorylation that provoked proliferation and survival through MERK1/2/ERK1/2 and PI3K/Akt pathways. In addition, EGFR shuttled from the plasma membrane to the nucleus maybe acting as co-transcriptional factor. The data suggest that growth and survival of resistant cells rely upon a remarkable increase in EGFR level which, in collaboration with an enhanced role of PKC-δ and Src kinases support [Pt(acac)2]R cell. It could therefore be assumed that combination treatments targeting both EGFR and PKC-δ/Src can improve therapy for breast cancer patients.

Biochemical Pharmacology (Amsterdam, Netherlands) 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, Recommanded Product: SU6656.

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

Kim, Se Hun published the artcileSynthesis of scalaridine A, COA of Formula: C20H28BNO5, the publication is Tetrahedron Letters (2015), 56(43), 5914-5915, database is CAplus.

A synthesis of the pyridine-linked bisindole alkaloid scalaridine A is described. An iridium catalyzed, directed C-H borylation of N-Boc-5-methoxyindole gave the corresponding 3-borylindole, which underwent a one-pot, double Suzuki-Miyaura cross-coupling reaction with 3,5-dibromopyridine to install the entire heteroaromatic framework of the natural product. Removal of the protecting groups gave a synthetic sample of scalaridine A, which was spectroscopically identical to that described in the isolation report.

Tetrahedron Letters published new progress about 1256359-99-5. 1256359-99-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Amide,Ether,Boronic Acids,Boronate Esters, name is tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate, and the molecular formula is C20H28BNO5, COA of Formula: C20H28BNO5.

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

Kim, Se Hun published the artcileSynthesis of Alocasin A, Product Details of C20H28BNO5, the publication is Journal of Natural Products (2015), 78(12), 3080-3082, database is CAplus and MEDLINE.

Herein is reported a synthesis of alocasin A (I), an alkaloid component of Alocasia macrorrhiza, a herbaceous plant used in folk medicine throughout southern Asia. A double Suzuki-Miyaura cross-coupling reaction between a 3-borylindole and 2,5-dibromopyrazine was used to assemble the heteroaromatic framework of the natural product. Removal of the protecting groups gave a synthetic sample of I, the spectroscopic data of which matched those in the isolation report of this compound

Journal of Natural Products published new progress about 1256359-99-5. 1256359-99-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Amide,Ether,Boronic Acids,Boronate Esters, name is tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate, and the molecular formula is C20H28BNO5, Product Details of C20H28BNO5.

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