Category: indole-building-block

Flame-resisting wool with halo-organic compounds. Part I: Water-soluble or emulsifiable bromine derivatives incorporating one or more reactive centers was written by Thorsen, W. J.. And the article was included in Textile Research Journal in 1976.Reference of 24407-32-7 This article mentions the following:

The flame retardancy of aromatic compounds having Br incorporated with SO3H groups and other reactive sites increased as the acidic nature of the mol. increased. 2,4,6-Tribromometanilic acid [58585-89-0] and tetrabromophthalic acid [13810-83-8], although not washfast, were the most promising; the former was capable of fireproofing wool which had been made shrink-resistant by ozone. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Reference of 24407-32-7).

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 24407-32-7

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

Fluorogenic Labeling of 5-Formylpyrimidine Nucleotides in DNA and RNA was written by Samanta, Biswajit;Seikowski, Jan;Hoebartner, Claudia. And the article was included in Angewandte Chemie, International Edition in 2016.Application In Synthesis of 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate This article mentions the following:

5-Formylcytosine (5fC) and 5-formyluracil (5fU) are natural nucleobase modifications that were generated by oxidative modification of 5-methylcytosine and thymine (or 5-methyluracil). Herein, the authors describe chemoselective labeling of 5-formylpyrimidine nucleotides in DNA and RNA by fluorogenic aldol-type condensation reactions with 2,3,3-trimethylindole derivatives Mild and specific reaction conditions were developed for 5fU and 5fC to produce hemicyanine-like chromophores with distinct photophys. properties. Residue-specific detection was established by fluorescence readout as well as primer-extension assays. The reactions were optimized on DNA oligonucleotides and were equally suitable for the modification of 5fU- and 5fC-modified RNA. This direct labeling approach of 5-formylpyrimidines is expected to help in elucidating the occurrence, enzymic transformations, and functional roles of these epigenetic/epitranscriptomic nucleobase modifications in DNA and RNA. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Application In Synthesis of 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate).

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Application In Synthesis of 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate

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

Highly convenient and large scale synthesis of 5-chloroindole and its 3-substituted analogues was written by Keetha, Laxminarayana;Palle, Sadanandam;Ramanatham, Vinodkumar;Khagga, Mukkanti;Chinnapillai, Rajendiran. And the article was included in Journal of the Korean Chemical Society in 2011.Synthetic Route of C9H5BrN2 This article mentions the following:

A large scale and com. feasible synthesis of 5-chloroindole and its 3-substituted analogs was described via a halogen-halogen exchange reaction from 5-bromoindole and its derivatives using cuprous chloride and dipolar aprotic solvent N-methyl-2-pyrrolidone in one-pot with good yields. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Synthetic Route of C9H5BrN2).

5-Bromo-3-cyanoindole (cas: 90271-86-6) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Synthetic Route of C9H5BrN2

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

Effect of heterocyclic ring system on formation of dimeric quinolones under catalyst-free conditions: a green approach was written by Madhu, Bandi;Raja sekar, B.;Venkata Ramana Reddy, C. H.;Dubey, P. K.. And the article was included in Research on Chemical Intermediates in 2017.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

The intermediate-dependent green and efficient synthesis of dimeric quinolones I (R¹ = Me, Et; R² = H, Me, OMe, Cl, Br, NO₂) and II (R³ = Me, Et; R⁴ = Ph, 3-ClC₆H₄, 3,4-(OMe)₂, etc.) was described. Compounds I were prepared by either the Knoevenagel condensation of 4-hydroxy-quinolin-2(1H)-ones with indole-3-carboxaldehydes in water followed by Michael-type addition of the (3-indolylmethylene)quinoline diones under catalyst-free conditions with another equivalent of indole-3-carboxaldehyde or via a one-pot reaction using two equivalent of the aldehyde. Compounds II were prepared by the tandem one-pot Knoevenagel condensation followed by Michael-type addition of 4-hydroxy-quinolin-2(1H)-ones with aromatic aldehydes in water. This reaction was found to be environmentally friendly, has easy-workup and shorter reaction times giving good yields of the product without the need for its isolation using column chromatog. 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, 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.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

Boron-Catalyzed Arylthiooxygenation of N-Allylamides: Synthesis of (Arylsulfanyl)oxazolines was written by Yu, Jipan;Tian, Hua;Gao, Chang;Yang, Haijun;Jiang, Yuyang;Fu, Hua. And the article was included in Synlett in 2015.COA of Formula: C14H9NO2S This article mentions the following:

Oxazoles and aryl sulfides are chem. entities that are found in many natural products and biol. and pharmaceutically active mols. It is therefore highly desirable to develop an efficient and practical approach to the synthesis of arylthio-substituted oxazolines. The authors developed a simple and efficient method for boron-catalyzed sequential arylsulfanylation and oxygenation of N-allylamides. The protocol uses readily available 1-(arylthio)pyrrolidine-2,5-diones as the arylsulfanylation reagents and inexpensive boron trifluoride etherate as the catalyst; no ligands or additives are required, and it is not necessary to purge the reaction vessel of air. The method therefore provides an efficient and practical strategy for the synthesis of arylthio-substituted heterocycles. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4COA of Formula: C14H9NO2S).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.COA of 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

Auxins II: the effect of chlorinated indolylacetic acids on pea stems was written by Katekar, Gerard F.;Geissler, Art E.. And the article was included in Phytochemistry (Elsevier) in 1982.Electric Literature of C10H8ClNO2 This article mentions the following:

Assessment of a series of chlorinated IAA derivatives for auxin activity on pea stem sections gave results suggesting that the activities shown are reasonably consistent with a receptor site theory of structure-activity previously proposed by G. F. Katekar (1979). In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Electric Literature of C10H8ClNO2).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Electric Literature of C10H8ClNO2

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

Microwave-induced one pot synthesis of fluorinated spiro [indole-pyrimidines] was written by Sachdeva, Harshita. And the article was included in Indian Journal of Heterocyclic Chemistry in 2009.Quality Control of 7-Nitroindoline-2,3-dione This article mentions the following:

A series of fluorinated spiro[indole-pyrimidines] were synthesized in 75-85% yields by rapid and highly efficient one-pot microwave-induced technique involving condensation of 3-aroylmethylene-2H-indol-ones with fluorinated phenylthioureas using ethanol as energy transfer medium. Aroylmethylene-indolones was synthesized in situ by the reaction of substituted indole-2,3-diones and fluorinated acetophenones. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Quality Control of 7-Nitroindoline-2,3-dione).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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.Quality Control 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

The response of stomata to ring-substituted indolylacetic acids was written by Thomson, A.;Cox, R. C.;Mansfield, T. A.. And the article was included in New Phytologist in 1988.Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

Indol-3-ylacetic acids with substituents in the aromatic ring (Cl, Cl₂, Me) have been synthesized and their effect on stomata on isolated Commelina communis epidermis tested. Unlike IAA which induces stomatal opening, all the substituted acids caused closure. The perception mechanism in the guard cells may therefore involve receptors with high specificity for IAA. The ability of guard cells to discriminate IAA from closely related mols. may be higher than in other cellular systems. There was no synergism between the IAA derivatives and ABA. Also, the percentage stomatal closure induced by CO₂ was more or less constant regardless of the concentration of substituted IAAs. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid

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

Copper-Mediated Cyclization of o-Hydroxyaryl Enaminones with 3-Indoleacetic Acids toward the Synthesis of 3-Indolmethyl-Chromones was written by Wen, Kangmei;Li, Yinyan;Gao, Qiwen;Chen, Jiewen;Yang, Jie;Tang, Xiaodong. And the article was included in Journal of Organic Chemistry in 2022.Synthetic Route of C10H8ClNO2 This article mentions the following:

A copper-mediated tandem decarboxylative coupling/annulation protocol of o-hydroxyaryl enaminones with 3-indoleacetic acids. A series of 3-indolmethyl-chromones were afforded in up to 97% yield. A one-pot method for 3-indolmethyl-chromones from o-hydroxy acetophenones, N, N-dimethylformamide di-Me acetal, and 3-indoleacetic acids was also developed. Derivatization of the products was conducted to provide various indolmethyl-substituted pyrimidines. Moreover, a biol. evaluation revealed that some compounds had anti-influenza viral activities. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Synthetic Route of C10H8ClNO2).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Synthetic Route of C10H8ClNO2

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

α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands was written by Ann, Jihyae;Czikora, Agnes;Saini, Amandeep S.;Zhou, Xiaoling;Mitchell, Gary A.;Lewin, Nancy E.;Peach, Megan L.;Blumberg, Peter M.;Lee, Jeewoo. And the article was included in Journal of Medicinal Chemistry in 2018.Name: 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Diacylglycerol-lactones have proven to be a powerful template for the design of potent ligands targeting C1 domains, the recognition motif for the cellular second messenger diacylglycerol. A major objective has been to better understand the structure activity relations distinguishing the seven families of signaling proteins that contain such domains, of which the protein kinase C (PKC) and RasGRP families are of particular interest. Here, we synthesize a series of aryl/alkyl substituted diacylglycerol-lactones and probe their relative selectivities for RasGRP3 vs. PKC. Compound I showed 72.6-fold selectivity relative to PKC alpha and 45.1-fold selectivity relative to PKC epsilon for in vitro binding activity. Likewise, in intact cells compound I induced Ras activation, a downstream response to RasGRP stimulation, with 8-29 fold selectivity relative to PKC delta S299 phosphorylation, a measure of PKC delta stimulation. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Name: 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Name: 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