Category: indole-building-block

Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols was written by Jia, Xue-Gong;Guo, Peng;Duan, Jicheng;Shu, Xing-Zhong. And the article was included in Chemical Science in 2018.Application In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

A general and practical strategy to address the reaction between reactive and unreactive electrophiles by a combination of nickel and Lewis acid catalysis is reported. This strategy is used for the coupling of aryl bromides R¹Br (R¹ = 4-MeO₂CC₆H₄, benzofuran-5-yl, indol-4-yl, etc.) with allylic alcs. R²CH:CHCR³R⁴OH (R² = H, Me, Ph, etc.; R³ = R⁴ = H, Me; R³ = Me, Et, Ph, R⁴ = H) to form linear allylarenes R¹CR³R⁴CH:CHR². The reaction tolerates a wide range of functional groups (e.g. silanes, boronates, anilines, esters, alcs., and various heterocycles) and works with various allylic alcs. Complementary to most current routes for the C3 allylation of an unprotected indole, this method provides access to C2 and C4-C7 allylated indoles. Preliminary mechanistic experiments revealed that the reaction might start with an aryl nickel intermediate, which then reacts with Lewis acid activated allylic alcs. in the presence of Mn. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Application In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate).

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Application In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate

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

Identification and Optimization of the First Highly Selective GLUT1 Inhibitor BAY-876 was written by Siebeneicher, Holger;Cleve, Arwed;Rehwinkel, Hartmut;Neuhaus, Roland;Heisler, Iring;Mueller, Thomas;Bauser, Marcus;Buchmann, Bernd. And the article was included in ChemMedChem in 2016.Product Details of 774-47-0 This article mentions the following:

Despite the long-known fact that the facilitative glucose transporter GLUT1 is one of the key players safeguarding the increase in glucose consumption of many tumor entities even under conditions of normal oxygen supply (known as the Warburg effect), only few endeavors have been undertaken to find a GLUT1-selective small-mol. inhibitor. Because other transporters of the GLUT1 family are involved in crucial processes, these transporters should not be addressed by such an inhibitor. A high-throughput screen against a library of âˆ? million compounds was performed to find a small mol. with this challenging potency and selectivity profile. The N-(1H-pyrazol-4-yl)quinoline-4-carboxamides were identified as an excellent starting point for further compound optimization. After extensive structure-activity relationship explorations, single-digit nanomolar inhibitors with a selectivity factor of >100 against GLUT2, GLUT3, and GLUT4 were obtained. The most promising compound, BAY-876 [N⁴-[1-(4-cyanobenzyl)-5-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]-7-fluoroquinoline-2,4-dicarboxamide], showed good metabolic stability in vitro and high oral bioavailability in vivo. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Product Details of 774-47-0).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Product Details of 774-47-0

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

Chiral Imidodiphosphoric Acid-Catalyzed Highly Diastereo- and Enantioselective Synthesis of Poly-Substituted 3,4-Dihydro-2H-pyrans: [4 + 2] Cycloadditions of β,γ-Unsaturated α-Ketoesters and 3-Vinylindoles was written by Guan, Xu-Kai;Liu, Guo-Feng;An, Dong;Zhang, Heng;Zhang, Suo-Qin. And the article was included in Organic Letters in 2019.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Imidodiphosphoric acids were employed to catalyze inverse-electron-demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters and 3-vinylindoles. A series of optically active 3,4-dihydro-2H-pyran derivatives with three contiguous stereogenic centers was synthesized in excellent yields (70-99%), diastereoselectivities (>20:1), and enantioselectivities (73-99%). The resulting indole containing 3,4-dihydro-2H-pyran could be converted to tetrahydropyran derivatives, which appear in several biol. active compounds by simple hydrogenation reduction In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Safety of 5-Chloroindole-3-carboxaldehyde

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

Coordination chemistry of palladium(II) and platinum(II) complexes with bioactive Schiff bases: Synthetic, spectral, and biocidal aspects was written by Sharma, K.;Biyala, M. K.;Swami, M.;Fahmi, N.;Singh, R. V.. And the article was included in Russian Journal of Coordination Chemistry in 2009.Application In Synthesis of 7-Nitroindoline-2,3-dione This article mentions the following:

The Schiff bases, 5-nitro-indol-2,3-dionehydrazinecarboxamide (HSCZ¹) and 7-nitro-indol-2,3-dionehydrazinecarboxamide (HSCZ²), were synthesized by the condensation of 5-nitro-indol-2,3-dione and 7-nitro-1H-indol-2,3-dione with semicarbazide hydrochloride, resp. The palladium(II) and platinum(II) complexes were prepared by mixing palladium chloride and platinum chloride in 1:2 molar ratios with monobasic bidentate Schiff bases. The ligands and complexes of palladium and platinum were characterized by elemental analyses, m.p. determinations, conductance measurements, mol. weight determinations, and IR, ¹H NMR, and UV spectral studies. The ligands coordinate to the metal atoms in a monobasic bidentate mode, coordinating through oxygen and nitrogen donor systems. Thus, a tetracoordinated environment around the metal atom is proposed. Both the ligands and their complexes were screened for their biol. activity on several pathogenic fungi and bacteria and possess appreciable fungicidal and bactericidal properties. Plant growth regulating activity of one of the ligands and its complexes also was recorded on gram plant, and results are discussed. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Application In Synthesis of 7-Nitroindoline-2,3-dione).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application In Synthesis of 7-Nitroindoline-2,3-dione

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

Aerobic Transition-Metal-Free Visible-Light Photoredox Indole C-3 Formylation Reaction was written by Li, Xiang;Gu, Xiangyong;Li, Yongjuan;Li, Pixu. And the article was included in ACS Catalysis in 2014.Application of 170489-16-4 This article mentions the following:

An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs mol. oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups. In the experiment, the researchers used many compounds, for example, 1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4Application of 170489-16-4).

1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Application of 170489-16-4

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

Electrophilicity and nucleophilicity of commonly used aldehydes was written by Pratihar, Sanjay. And the article was included in Organic & Biomolecular Chemistry in 2014.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO₄ oxidation and NaBH₄ reduction of aldehydes. A transition state anal. of the KMNO₄ promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with exptl. results. The validity of the exptl. method has been tested using the exptl. activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theor. vs. exptl. relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chem. reactivity of aldehydes in various reactions. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Quality Control of 5-Chloroindole-3-carboxaldehyde

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

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives was written by Yuan, Yu-Chao;Kamaraj, Raghu;Bruneau, Christian;Labasque, Thierry;Roisnel, Thierry;Gramage-Doria, Rafael. And the article was included in Organic Letters in 2017.Name: 2-Phenylisoindolin-1-one This article mentions the following:

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO₂ release with water being the source of protons. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 2-Phenylisoindolin-1-one

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

Bioorthogonally Applicable Fluorogenic Cyanine-Tetrazines for No-Wash Super-Resolution Imaging was written by Knorr, Gergely;Kozma, Eszter;Schaart, Judith M.;Nemeth, Krisztina;Torok, Gyorgy;Kele, Peter. And the article was included in Bioconjugate Chemistry in 2018.Category: indole-building-block This article mentions the following:

The synthesis, fluorogenic characterization, and labeling application of four tetrazine-quenched cyanine probes with emission maxima in the red-far red range is reported. Fluorescence of the cyanine-cores is quenched via through-bond-energy-transfer (TBET) exerted by a bioorthogonal tetrazine unit. Upon bioorthogonal labeling reaction with cyclooctyne tagged proteins, the quenching effect ceases, and thus the fluorescence reinstates, resulting in an increase in fluorescence intensity. As a rare example among indocyanines, one of the new probes was found suitable in STED-based super-resolution imaging. The applicability of this fluorogenic Tet-Cy3 probe was therefore further demonstrated in the bioorthogonal labeling of cytoskeletal protein, actin, with subsequent super-resolution microscopy (STED) imaging even under no-wash conditions. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Category: indole-building-block).

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.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

Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines was written by Denmark, Scott E.;Chi, Hyung Min. And the article was included in Journal of Organic Chemistry in 2017.Electric Literature of C14H9NO2S This article mentions the following:

A method for the catalytic, enantioselective, intramol. sulfenoamination of alkenes with aniline nucleophiles has been developed. The method employs a chiral, Lewis basic selenophosphoramide catalyst and a Bronsted acid co-catalyst to promote stereocontrolled C-N and C-S bond formation by activation of an achiral sulfenylating agent. Benzoannulated nitrogen-containing heterocycles such as indolines, tetrahydroquinolines, e.g., I, and tetrahydrobenzazepines were prepared with high to excellent enantioselectivities. The impact of tether length and electron d. of both the nucleophile and olefin on the reactivity, site selectivity, and enantioselectivity were investigated and interpreted in terms of substrate-dependent stereodetermining thiiranium ion formation or capture. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Electric Literature of C14H9NO2S).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C14H9NO2S

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

Specific stabilization of DNA triple helices by indolo[2,1-b]quinazolin-6,12-dione derivatives was written by Chen, Grace Shiahuy;Bhagwat, Bhalchandra V.;Liao, Pei-Yin;Chen, Hui-Ting;Lin, Shwu-Bin;Chern, Ji-Wang. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.SDS of cas: 774-47-0 This article mentions the following:

Aminopropylamino indolo[2,1-b]quinazolinediones I•HX (R = H, Me; R¹ = H, F; X = F₃CCO₂, Cl) are prepared; the stabilization of a DNA triplex relative to its duplex by the aminopropylaminoindoloquinazolinediones is determined by UV and CD spectra and the changes in melting temperature The presence of either a fluorine substituent on the indoloquinazolinedione ring or of a Me group on the amino nitrogen attached to the indoloquinazolinedione ring improves the ability of the aminopropyl indoloquinazolinediones to stabilize DNA triplexes. The min. energy conformations of I (R = H, Me; R¹ = F) are determined by DFT calculations; the orientation of the aminopropylamino side chain of I (R = Me; R¹ = F) underlies its ability to stabilize a DNA triplex. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0SDS of cas: 774-47-0).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 774-47-0

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