Category: indole-building-block

Product class 13: indole and its derivatives was written by Joule, J. A.. And the article was included in Science of Synthesis in 2001.Reference of 16732-64-2 This article mentions the following:

A review of preparation of indoles and its derivatives Covered reactions include cyclization, ring transformation, aromatization and substituent modifications. Subclasses covered include 1H-indol-1-ols, 1,3-dihydro-2H-indol-2-ones, and 1,2-dihydro-3H-indol-3-ones. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Reference of 16732-64-2).

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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.Reference of 16732-64-2

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

Synthesis, computational, and spectroscopic analysis of tunable highly fluorescent BN-1,2-azaborine derivatives containing the N-BOH moiety was written by Saint-Louis, Carl Jacky;Shavnore, Renee N.;McClinton, Caleb D. C.;Wilson, Julie A.;Magill, Lacey L.;Brown, Breanna M.;Lamb, Robert W.;Webster, Charles Edwin;Schrock, Alan K.;Huggins, Michael T.. And the article was included in Organic & Biomolecular Chemistry in 2017.COA of Formula: C8H6N2O3 This article mentions the following:

Nine new polycyclic aromatic BN-1,2-azaborine analogs containing the N-BOH moiety were synthesized using a convenient two-step, one-pot procedure. Characterization of the prepared compounds show the luminescence wavelength and the quantum yields of the azaborines were tunable by controlling the power and location of the donor and acceptor substituents on the chromophore. UV-visible spectroscopy and d. functional theory (DFT) computations revealed that the addition of electron-donating moieties to the isoindolinone hemisphere raised the energy of the HOMO, resulting in the reduction of the HOMO-LUMO gap. The addition of an electron-accepting moiety to the isoindolinone hemisphere and an electron-donating group to the boronic acid hemisphere decreased the HOMO-LUMO gap considerably, leading to emission properties from partial intramol. charge transfer (ICT) states. The combined effect of an acceptor on the isoindolinone side and a donor on the boronic acid side (strong acceptor-π-donor) gave the most red-shifted absorption. The polycyclic aromatic BN-1,2-azaborines emitted strong fluorescence in solution and in the solid-state with the largest red-shifted emission at 640 nm and a Stokes shift of Δλ = 218 nm, or Δν = 8070 cm^-1. In the experiment, the researchers used many compounds, for example, 6-Nitroisoindolin-1-one (cas: 110568-64-4COA of Formula: C8H6N2O3).

6-Nitroisoindolin-1-one (cas: 110568-64-4) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.COA of Formula: C8H6N2O3

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

Palladium oxidative addition complex-enabled synthesis of amino-substituted indolyl-4(3H)-quinazolinones and their antitumor activity evaluation was written by Jiang, Zhi;Zhao, Dan-Dan;Hu, Yu-Tao;Rao, Yong;Guo, Shi-Yao;Xu, Yao-Hao;Li, Qingjiang;Huang, Zhi-Shu. And the article was included in Organic & Biomolecular Chemistry in 2022.Computed Properties of C9H6BrNO2 This article mentions the following:

A palladium-mediated amination of halogen-containing indolyl-4(3H)-quinazolinones such as I (R = Br) with a variety of primary and secondary amines, e.g., morpholine via the corresponding palladium oxidative addition complexes was reported. The protocol allows the facile synthesis of indolyl-4(3H)-quinazolinone derivatives with amino groups at all the positions of the benzene ring such as I (R = 4-morpholinyl) in moderate to good yields with mild reaction conditions and good functional group tolerance. Furthermore, the antitumor activity of these products was evaluated. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Computed Properties of C9H6BrNO2).

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Computed Properties of C9H6BrNO2

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

Rhodium-catalyzed oxidative coupling of N-acyl anilines with alkynes using an acylamino moiety as the traceless directing group was written by Geng, Kaijun;Fan, Zhoulong;Zhang, Ao. And the article was included in Organic Chemistry Frontiers in 2016.Recommanded Product: 2-Phenylisoindolin-1-one This article mentions the following:

A rhodium-catalyzed oxidative annulation of N-acyl anilines with alkynes was developed by using the acylamino group as a traceless directing group for the first time. Various N-acyl anilines and para- or meta-substituted diphenylacetylenes were well tolerated, and a series of 1,2,3,4-tetrasubstituted naphthalenes were readily synthesized in good to excellent yields. Meanwhile, this method also provided a new strategy for the N-dearylation of N-phenylamides. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Recommanded Product: 2-Phenylisoindolin-1-one).

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 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

Palladium-catalyzed α-arylation of indolin-3-ones was written by Chang, Yu-Hsuan;Peng, Wan-Ling;Chen, I-Chia;Hsu, Hsin-Yun;Wu, Yen-Ku. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)₂ and PAd₃ was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line. 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, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.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

Biology-Oriented Combined Solid- and Solution-Phase Synthesis of a Macroline-Like Compound Collection was written by Wilk, Wolfram;Noeren-Mueller, Andrea;Kaiser, Markus;Waldmann, Herbert. And the article was included in Chemistry – A European Journal in 2009.Formula: C9H6ClNO This article mentions the following:

Macrolines constitute a class of natural products that has more than 100 members and displays diverse biol. activities. These compounds feature a cycloocta[b]indole scaffold that represents an interesting target structure for biol.-oriented synthesis (BIOS). We have presented a solid-phase synthesis of isomerically pure cycloocta[b]indoles (e.g. I) by employing the Pictet-Spengler reaction and the Dieckmann cyclization as key steps. The scope of this reaction sequence was investigated in more detail by using various addnl. diversification procedures, such as Pd-catalyzed Sonogashira or Suzuki couplings on a solid phase, thus allowing, for example, the generation of 10-substituted cycloocta[b]indole derivatives Finally, solution-phase decoration of the cycloocta[b]indole skeleton by reduction and saponification was evaluated, thereby further extending the scope of the solid-phase synthesis. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Formula: C9H6ClNO).

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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Formula: C9H6ClNO

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

Discovery, Synthesis, and Characterization of an Orally Bioavailable, Brain Penetrant Inhibitor of Mixed Lineage Kinase 3 was written by Goodfellow, Val S.;Loweth, Colin J.;Ravula, Satheesh B.;Wiemann, Torsten;Nguyen, Thong;Xu, Yang;Todd, Daniel E.;Sheppard, David;Pollack, Scott;Polesskaya, Oksana;Marker, Daniel F.;Dewhurst, Stephen;Gelbard, Harris A.. And the article was included in Journal of Medicinal Chemistry in 2013.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester This article mentions the following:

Inhibition of mixed lineage kinase 3 (MLK3) is a potential strategy for treatment of Parkinson’s disease and HIV-1 associated neurocognitive disorders (HAND), requiring an inhibitor that can achieve significant brain concentration levels. We report here URMC-099 (1) an orally bioavailable (F = 41%), potent (IC₅₀ = 14 nM) MLK3 inhibitor with excellent brain exposure in mouse PK models and minimal interference with key human CYP450 enzymes or hERG channels. The compound inhibits LPS-induced TNFα release in microglial cells, HIV-1 Tat-induced release of cytokines in human monocytes and up-regulation of phospho-JNK in Tat-injected brains of mice. Compound 1 likely functions in HAND preclin. models by inhibiting multiple kinase pathways, including MLK3 and LRRK2 (IC₅₀ = 11 nM). We compare the kinase specificity and BBB penetration of 1 with CEP-1347 (2). Compound 1 is well tolerated, with excellent in vivo activity in HAND models, and is under investigation for further development. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester).

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester

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

Preparation of 2-[(2-cyanoethyl)thio]-1H-isoindole-1,3(2H)-dione and related sulfur-transfer agents was written by Klose, Jana;Reese, Colin B.;Song, Quanial. And the article was included in Tetrahedron in 1997.Formula: C14H9NO2S This article mentions the following:

The title compound (I, R = CH₂CH₂CN) and a morpholine analog (II) are both conveniently prepared in good yield from 2-cyanoethyl disulfide, which itself is readily prepared in one step from S-(2-cyanoethyl)isothiouronium chloride. In the same way, di-Me and di-Ph disulfides are converted to I (R = Me, Ph, resp.), also in good yields. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Formula: C14H9NO2S).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Formula: 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

Rapid synthesis of the indole-indolone scaffold via [3+2] annulation of arynes by methyl indole-2-carboxylates was written by Rogness, Donald C.;Larock, Richard C.. And the article was included in Tetrahedron Letters in 2009.Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

The reaction of Me indole-2-carboxylates, e.g., I, and arynes afforded a very efficient, high yielding synthesis of a novel indole-indolone ring system, e.g., II, which tolerated considerable functionality, was broad in scope, and proceeded under mild reaction conditions. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Quality Control of Methyl 5-fluoro-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

Visible-Light-Irradiated Cascade Reaction of Indole-Tethered Alkenes to Access Tetracyclic Tetrahydro-γ-carbolines was written by Mei, Haibo;Liu, Aiyao;He, Jingrui;Yu, Yingjie;Han, Jianlin. And the article was included in Organic Letters in 2022.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A series of indole-derived alkenes I (R = H, Cl, Br; R¹ = Me, OMe, F, etc.; R² = H, Me, F, etc.; R³ = R⁴ = H, Me; Ar = Ph, 4-methylphenyl, 4-bromophenyl, 4-methyoxphenyl) have been designed and applied in a photocatalytic cascade reaction with bromodifluoroacetate esters BrCF₂C(O)OR⁵ (R⁵ = Me, Bn, cyclopentyl, etc.), affording an unknown type of tetracyclic tetrahydro-γ-carboline derivative II in up to 90% yields. Mechanistic studies suggest that the reaction proceeds with tetrahydro-γ-carboline III (Ar = 4-methylphenyl, R⁵ = Et;) as a key intermediate. The reaction tolerates a diverse pool of substrates, which provides an efficient method for the construction of tetracyclic tetrahydro-γ-carboline II compounds 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. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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