Month: October 2022

Georgieva, Miglena K.; Duarte, Filipe J. S.; Santos, A. Gil published an article in 2016, the title of the article was Directed electrostatic activation in enantioselective organocatalytic cyclopropanation reactions: a computational study.COA of Formula: C9H9NO2 And the article contains the following content:

Cyclopropane rings are versatile building blocks in organic chem. Their synthesis, by the reaction of sulfur ylides with α,β-unsaturated carbonyl compounds, has recently aroused renewed interest after the discovery of efficient catalysis by using (S)-indoline-2-carboxylic acid. In order to rationalize the behavior of this catalyst, MacMillan proposed a directed electrostatic activation (DEA) mechanism, in which the neg. carboxylate group interacts with the pos. thionium moiety, thus reducing the activation energy and increasing the reaction rate. More recently, Mayr refuted some of MacMillan conclusions, but accepted the DEA mechanism as a justification for the exptl. high reaction rates. In contrast, our results indicate that the selectivity obtained in the process seems to result from several strong hydrogen bond interactions between the two reacting species, while no strong evidence for a DEA mechanism was found. We also concluded that the hydrogen bonds don’t improve the reaction rate by lowering the activation energy of the rate-determining step, but can do it by promoting efficient reaction trajectories due to long-range complexation of the reagents. Finally, our results confirm that the cyclopropanation reaction occurs by a two-step mechanism, and that the overall enantioselectivity depends on the relative energies of the two steps, averaged by the relative populations of the iminium intermediates that are initially formed in the reaction. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).COA of Formula: C9H9NO2

The Article related to enantioselective cyclopropanation catalyst mechanism kinetics activation energy, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.COA of Formula: C9H9NO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On January 24, 2011, Roca-Lopez, David; Merino, Pedro; Sayago, Francisco J.; Cativiela, Carlos; Herrera, Raquel P. published an article.Electric Literature of 79815-20-6 The title of the article was Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octahydroindole-2-carboxylic acid, a new fused proline. And the article contained the following:

The authors present their results on the organocatalytic enantioselective Michael addition reaction of acetone to different nitroolefines using (2R,3aS,7aS)-octahydroindole-2-carboxylic acid [(R,S,S)-Oic] as a new and suitable catalyst. Computational calculations support the results obtained with (R,S,S)-Oic vs. its diastereomeric form (S,S,S)-Oic. The final products are obtained in good yields and moderate enantioselectivities (up to 58% ee). The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Electric Literature of 79815-20-6

The Article related to acetone nitroolefin michael addition, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Ketones and Derivatives, Including Quinones and Sulfur Analogs and other aspects.Electric Literature of 79815-20-6

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On November 20, 2002, Sun, Guobin; Pei, Weiwei; Wu, Yongqing; Huo, Jun; Ye, Weiping published an article.Reference of H-Idc-OH The title of the article was Enantioselective borane reduction of prochiral ketones catalyzed by (S)-(indolin-2-yl)methanol or (S)-indoline-2-carboxylic acid. And the article contained the following:

An enantioselective borane reduction of prochiral ketones directly catalyzed by (S)-(indolin-2-yl) methanol or (S)-indoline-2-carboxylic acid was examined and the resultant chiral secondary alcs. with 82% ∼ 87% enantiomeric excess were obtained. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Reference of H-Idc-OH

The Article related to enantioselective borane reduction prochiral ketone catalyzed indolinylmethanol indolinecarboxylic, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Ketones and Derivatives, Including Quinones and Sulfur Analogs and other aspects.Reference of H-Idc-OH

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On September 20, 2016, Fabry, David C.; Rueping, Magnus published an article.Electric Literature of 65417-22-3 The title of the article was Merging Visible Light Photoredox Catalysis with Metal Catalyzed C-H Activations: On the Role of Oxygen and Superoxide Ions as Oxidants. And the article contained the following:

Visible light photoredox catalysis as a new alternative to conventionally applied regeneration/oxidation procedures was examined This account summarizes these recent advances in this expanding area and will highlight the new concept of merging distinct redox catalytic processes for C-H functionalizations through the application of visible light photoredox catalysis. Photoredox catalysis can be considered as catalytic electron-donating or -accepting processes, making use of visible-light absorbing homogeneous and heterogeneous metal-based catalysts, as well as organic dye sensitizers or polymers. As a consequence, photoredox catalysis is, in principle, an ideal tool for the recycling of any given metal catalyst via a coupled electron transfer (ET) process. Here we describe our first successful endeavors to address the above challenges by combining visible light photoredox catalysis with different ruthenium, rhodium, or palladium catalyzed C-H activations. Since only small amounts of the oxidant are generated and are immediately consumed in these transformations, side reactions of substrates or products can be avoided. Thus, usually oxidant-sensible substrates can be used, which makes these methods highly suitable for complex mol. structure syntheses. Moreover, mechanistic studies shed light on new reaction pathways, intermediates, and in situ generated species. The successful development of our dual catalysis concept, consisting of combined visible light photoredox catalysis and metal catalyzed C-H functionalization, provides many new opportunities for further explorations in the field of C-H functionalization. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Electric Literature of 65417-22-3

The Article related to metal visible photocatalysis photoredox catalyst photocyclization olefination, Radiation Chemistry, Photochemistry, and Photographic and Other Reprographic Processes: Radiation Chemistry and Photochemistry and other aspects.Electric Literature of 65417-22-3

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On October 28, 2010, Kawano, Tomoaki; Yonetoku, Yasuhiro; Hanazawa, Takeshi; Nigawara, Takahiro; Fukudome, Hiroki; Moritani, Hiroshi published a patent.Category: indole-building-block The title of the patent was Preparation of diacylethylenediamine compounds as DGAT1 inhibitors. And the patent contained the following:

Title compounds I [A = (un)substituted aryl, (un)substituted cycloalkyl, (un)substituted heteroaryl, etc.; ring B1 = phenylene, pyridinediyl, naphthalenediyl, etc. (herein phenylene, pyridinediyl and naphthalenediyl are optionally substituted with hydroxy, alkyl, halo, etc.); W = -O-, bond, -NH-, etc.; ring B2 = cyclohexanediyl, cyclopentanediyl or bridged ring (herein cyclohexanediyl, cyclopentanediyl and bridged ring are optionally substituted with alkyl); Y = bond, alkylene or -O-alkylene; Z = -CO2H [or biol. equivalent group thereof], carbamoyl (optionally substituted with Ph or benzyl), -OH, etc.] or salts thereof were prepared For example, reaction of Et trans-4-hydroxycyclohexanecarboxylate with benzyl 4-hydroxybenzoate in the presence of 1,1′-(azodicarbonyl)dipiperidine followed by debenzylation, EDCI-mediated amidation with tert-Bu (2-aminoethyl)carbamate, treatment with HCl, carbamoylation with trans-2-phenylcyclopropyl isocyanate, and hydrolysis afforded compound II [R = trans-2-phenylcyclopropylamino; X = H]. In diacylglycerol acyltransferase 1 (DGAT1) inhibition assays, compound II [R = 5-fluorobenzothien-2-yl; X = F] showed IC50 of 0.1 nM. Compounds I are claimed useful for the treatment of obesity. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Category: indole-building-block

The Article related to diacylethylenediamine preparation dgat1 inhibitor, obesity treatment diacylethylenediamine dgat1 inhibition, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Amides, Amidines, Imidic Esters, Hydrazides, and Hydrazonic Esters and other aspects.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On June 18, 2021, Pollastrini, Matteo; Lipparini, Filippo; Pasquinelli, Luca; Balzano, Federica; Barretta, Gloria Uccello; Pescitelli, Gennaro; Angelici, Gaetano published an article.Category: indole-building-block The title of the article was A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives. And the article contained the following:

A thorough exptl. and computational study on the conformational properties of (S)-indoline-2-carboxylic acid derivatives has been conducted. Me (S)-1-acetylindoline-2-carboxylate, both a mimetic of proline and phenylalanine, shows a remarkable tendency toward the cis amide isomer when dissolved in polar solvents. This behavior is opposite to the general preference of proline for the trans isomer, making indoline-2-carboxylic acid a good candidate for the design of different secondary structures and new materials. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Category: indole-building-block

The Article related to proline mimetic indolinecarboxylic acid derivative amide conformation solvent effect, Physical Organic Chemistry: Resonance Spectra (Electron Spin, Nuclear Magnetic and Fourier Transform Nuclear Magnetic, Quadrupole, etc.) and other aspects.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On August 14, 2014, Dai, Xing; Liu, Hong; Palani, Anandan; He, Shuwen; Brockunier, Linda L.; Nargund, Ravi; Marcantonio, Karen; Zorn, Nicolas; Xiao, Dong; Peng, Xuanjia; Li, Peng; Guo, Tao published a patent.Recommanded Product: 4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole The title of the patent was Preparation of tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis C. And the patent contained the following:

The invention relates to compounds of formula I that are useful as hepatitis C virus (HCV) NS5B polymerase inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5B polymerase activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system. Compounds of formula I wherein A is C3-6 cycloalkyl and aromatic ring system; ring B is benzofuran, pyridinofuran pyrazolopyridine, etc.; E is absent and CR5R9; F is (CH)0-2 and (CH2)0-2; Z is N and CRa; Z1, Z2 and Z3 are independently CH and H, wherein 1 or 2 of Z1 – Z2 are N; R2 is H, C1-6 alkyl, and C1-6 alkoxy; R3 is H and C1-6 alkyl; R4 is C1-6 alkyl and C1-6 alkoxy; R5 is H, C1-6 alkyl, OH, halo, etc.; R9 is H; R5R9 taken together to form C3-6 cycloalkyl; R6 is H, OH, C1-6 alkyl, C1-6 haloalkyl, etc.; R7 is H and C1-6 alkyl; R6R7 taken together to form oxo; R8 is H, halo and OH and derivatives; R10 is H and C1-6 alkyl; Ra is H, halo and CN; dashed bond is single and double bond; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by a multistep procedure (procedure given). The invention compounds were evaluated for their anti-HCV activity. From the assay, it was determined that compound II exhibited IC50 values in the range of 3.784 nM to 4.674 nM. The experimental process involved the reaction of 4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole(cas: 1256359-96-2).Recommanded Product: 4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

The Article related to tetracyclic heterocycle preparation antiviral treatment hepatitis c, Heterocyclic Compounds (More Than One Hetero Atom): Fused-Ring Systems With Two Or More Hetero Atoms, No More Than One Hetero Atom Per Ring and other aspects.Recommanded Product: 4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On August 14, 2014, Dai, Xing; Liu, Hong; Palani, Anandan; He, Shuwen; Brockunier, Linda L.; Nargund, Ravi; Marcantonio, Karen; Zorn, Nicolas; Xiao, Dong; Peng, Xuanjia; Li, Peng; Guo, Tao published a patent.Related Products of 1256359-96-2 The title of the patent was Preparation of tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis C. And the patent contained the following:

The invention relates to compounds of formula I that are useful as hepatitis C virus (HCV) NS5B polymerase inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5B polymerase activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system. Compounds of formula I wherein A is C3-6 cycloalkyl and aromatic ring system; ring B is benzofuran, pyridinofuran pyrazolopyridine, etc.; E is absent and CR5R9; F is (CH)0-2 and (CH2)0-2; Z is N and CRa; Z1, Z2 and Z3 are independently CH and H, wherein 1 or 2 of Z1 – Z2 are N; R2 is H, C1-6 alkyl, and C1-6 alkoxy; R3 is H and C1-6 alkyl; R4 is C1-6 alkyl and C1-6 alkoxy; R5 is H, C1-6 alkyl, OH, halo, etc.; R9 is H; R5R9 taken together to form C3-6 cycloalkyl; R6 is H, OH, C1-6 alkyl, C1-6 haloalkyl, etc.; R7 is H and C1-6 alkyl; R6R7 taken together to form oxo; R8 is H, halo and OH and derivatives; R10 is H and C1-6 alkyl; Ra is H, halo and CN; dashed bond is single and double bond; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by a multistep procedure (procedure given). The invention compounds were evaluated for their anti-HCV activity. From the assay, it was determined that compound II exhibited IC50 values in the range of 3.784 nM to 4.674 nM. The experimental process involved the reaction of 4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole(cas: 1256359-96-2).Related Products of 1256359-96-2

The Article related to tetracyclic heterocycle preparation antiviral treatment hepatitis c, Heterocyclic Compounds (More Than One Hetero Atom): Fused-Ring Systems With Two Or More Hetero Atoms, No More Than One Hetero Atom Per Ring and other aspects.Related Products of 1256359-96-2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On June 30, 2008, Brochu, Jean-Louis; Prakesch, Michael; Enright, Gary D.; Leek, Donald M.; Arya, Prabhat published an article.Quality Control of H-Idc-OH The title of the article was Reagent-Based, Modular, Tandem Michael Approach for Obtaining Different Indoline Alkaloid-Inspired Polycyclic Architectures. And the article contained the following:

A modular, reagent-based approach to obtain different indoline alkaloid-inspired, tetracyclic architectures is developed. When TBSOTf was used as a Lewis acid, a tandem Michael-based approach resulted in formation of a diastereomeric mixture of tetracyclic derivatives I with two addnl. six-membered rings from functionalized indoline II. By simply changing the Lewis acid to TMSOTf, II was converted into a different tetracyclic compound III having addnl. functionalized 5- and 7-membered rings with complete stereocontrol. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Quality Control of H-Idc-OH

The Article related to indoline amidoacyl unsaturated preparation tandem intramol michael addition cyclization, Heterocyclic Compounds (More Than One Hetero Atom): Fused-Ring Systems With Two Or More Hetero Atoms, No More Than One Hetero Atom Per Ring and other aspects.Quality Control of H-Idc-OH

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On May 19, 2017, Zhang, Kaifan; Xu, Xiaoying; Zheng, Jiuan; Yao, Hequan; Huang, Yue; Lin, Aijun published an article.HPLC of Formula: 883526-76-9 The title of the article was [3 + 3] Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones. And the article contained the following:

A novel [3 + 3] cycloaddition between in situ formed azaoxyallyl cations and 2-alkenylindoles has been developed. This concise method allows the efficient construction of a series of tetrahydro-β-carbolinones in good yields under mild conditions. Gram-scale experiments and further derivatization of tetrahydro-β-carbolinones highlighted the potential utility of our method. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).HPLC of Formula: 883526-76-9

The Article related to tetrahydrocarbolinone preparation cycloaddition alkenylindole in situ formed azaoxyallyl cation, Heterocyclic Compounds (More Than One Hetero Atom): Fused-Ring Systems With Two Or More Hetero Atoms, No More Than One Hetero Atom Per Ring and other aspects.HPLC of Formula: 883526-76-9

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles