20/02/2023 - Page 14 of 14 - Indole Building Blocks

Henkel, Michael et al. published their research in Synthesis in 2020 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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.SDS of cas: 4769-96-4

Annulation of Indoles with 1,n-Dibromoalkanes by a Pd(II)-Catalyzed and Norbornene-Mediated Reaction Cascade was written by Henkel, Michael;Bach, Thorsten. And the article was included in Synthesis in 2020.SDS of cas: 4769-96-4 This article mentions the following:

By employing 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane as biselectrophiles, the annulation of indoles I (R = H, 5-Br, 4-CN, 5-t-BuO₂C, etc.) was probed in the presence of PdCl₂(CH₃CN)₂ as a catalyst and norbornene as a transpositional ligand. Ring formation to a five-membered ring was observed at positions C2 and N, while annulation of a six-membered ring occurred at positions C2 and C3. The latter cascade process was successfully applied to the direct synthesis of 1,2,3,4-tetrahydrocarbazoles II from indoles I (11 examples, 31-68% yields). Seven-membered-ring annulation was feasible by an initial coupling at position C2 followed by alkylation at C3. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4SDS of cas: 4769-96-4).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Grassl, Simon et al. published their research in Chemistry – A European Journal in 2019 | CAS: 14204-27-4

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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 14204-27-4

Copper-Catalyzed Electrophilic Thiolation of Organozinc Halides by Using N-Thiophthalimides Leading to Polyfunctional Thioethers was written by Grassl, Simon;Hamze, Clemence;Koller, Thaddaeus J.;Knochel, Paul. And the article was included in Chemistry – A European Journal in 2019.Reference of 14204-27-4 This article mentions the following:

(Hetero)aryl, benzylic, and alkyl zinc halides were thiolated with N-thiophthalimides at 25 闂佺娅ｉ悡?within 1 h in the presence of 5-10 % Cu(OAc)₂闁荤姾娅ｉ弸?sub>2O to furnish the corresponding polyfunctionalized thioethers in good yields. This electrophilic thiolation was extended to the introduction of trifluoromethylthio (SCF₃), thiocyanate (SCN), and selenophenyl (SePh) groups. The utility of this method was shown in a seven-step synthesis of a potent cathepsin D inhibitor in 34% overall yield. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Reference of 14204-27-4).

Ravi, Ch. et al. published their research in Nucleosides, Nucleotides & Nucleic Acids in 2019 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application of 827-01-0

Synthesis, spectral studies, DNA binding, photocleavage, antimicrobial and anticancer activities of isoindol Ru(II) polypyridyl complexes was written by Ravi, Ch.;Vuradi, Ravi Kumar;Avudoddi, Srishailam;Yata, Praveen Kumar;Putta, Venkat Reddy;Srinivas, G.;Merugu, Ramchander;Satyanarayana, S.. And the article was included in Nucleosides, Nucleotides & Nucleic Acids in 2019.Application of 827-01-0 This article mentions the following:

Three new Ru(II) polypyridyl complexes [Ru(phen)₂CIIP]²⁺ (1) {CIIP = 2-(5-Chloro-3aH-Isoindol-3-yl)-1H-Imidazo[4,5-f][1,10]phenanthroline} (phen = 1,10-phenanthroline), [Ru(bpy)₂CIIP]²⁺ (2) (bpy = 2,2′-bipyridine) and [Ru(dmb)₂CIIP]²⁺ (3) (dmb = 4,4′-dimethyl-2,2′-bipyridine) were synthesized and characterized by different spectral methods. The DNA-binding behavior of these complexes was studied by absorption, emission spectroscopic titration and viscosity measurements, indicating that these three complexes bind to CT-DNA in an intercalative mode, but binding affinities of these complexes were different. The DNA-binding constants K_b of 1–3 were calculated in the order of 10⁶. All three complexes cleave pBR322 DNA in photoactivated cleavage studies and exhibit good antimicrobial activity. Anticancer activity of these Ru(II) complexes was evaluated in MCF7 cells. Cytotoxicity by MTT assay showed growth inhibition in a dose dependent manner. Cell cycle anal. by flow cytometry data showed an increase in Sub G1 population. Annexin V FITC/PI staining confirms that these complexes cause cell death by the induction of apoptosis. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application of 827-01-0).

Simon, Sibu et al. published their research in New Phytologist in 2013 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid

Defining the selectivity of processes along the auxin response chain: a study using auxin analogues was written by Simon, Sibu;Kubes, Martin;Baster, Pawel;Robert, Stephanie;Dobrev, Petre Ivanov;Friml, Jiri;Petrasek, Jan;Zazimalova, Eva. And the article was included in New Phytologist in 2013.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

The mode of action of auxin is based on its non-uniform distribution within tissues and organs. Despite the wide use of several auxin analogs in research and agriculture, little is known about the specificity of different auxin-related transport and signalling processes towards these compounds Using seedlings of Arabidopsis thaliana and suspension-cultured cells of Nicotiana tabacum (BY-2), the physiol. activity of several auxin analogs was investigated, together with their capacity to induce auxin-dependent gene expression, to inhibit endocytosis and to be transported across the plasma membrane. This study shows that the specificity criteria for different auxin-related processes vary widely. Notably, the special behavior of some synthetic auxin analogs suggests that they might be useful tools in investigations of the mol. mechanism of auxin action. Thus, due to their differential stimulatory effects on DR5 expression, indole-3-propionic (IPA) and 2,4,5-trichlorophenoxy acetic (2,4,5-T) acids can serve in studies of TRANSPORT INHIBITOR RESPONSE 1/AUXIN SIGNALLING F-BOX (TIR1/AFB)-mediated auxin signalling, and 5-fluoroindole-3-acetic acid (5-F-IAA) can help to discriminate between transcriptional and non-transcriptional pathways of auxin signalling. The results demonstrate that the major determinants for the auxin-like physiol. potential of a particular compound are very complex and involve its chem. and metabolic stability, its ability to distribute in tissues in a polar manner and its activity towards auxin signalling machinery. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid).

Azumaya, Isao et al. published their research in Journal of the American Chemical Society in 1991 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. 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 C14H11NO

Twisted intramolecular charge-transfer fluorescence of aromatic amides: conformation of the amide bonds in excited states was written by Azumaya, Isao;Kagechika, Hiroyuki;Fujiwara, Yoshihisa;Itoh, Michiya;Yamaguchi, Kentaro;Shudo, Koichi. And the article was included in Journal of the American Chemical Society in 1991.Electric Literature of C14H11NO This article mentions the following:

The mechanism of the dual fluorescence of benzanilide (I) and N-methylbenzanilide (II) in methylcyclohexane was investigated. The emission at longer wavelength is composed of one component for I (婵?sub>max 477 nm) and of one major component (96%, 婵?sub>max 518 nm) for II. Various substitutions on the aromatic rings permit the study of the F₂ fluorescence wavelength and intensity on twisting about the Ar-CO, the Ar-N, and the amide bond (N-CO) itself. Though the ground-state structures of I and II are very different from each other, the structures of the emitting species of both compounds are considered to be similar. Studies on conformationally restricted derivatives showed that the amide bond must be rotated for the emission of longer wavelength. Quant. data indicate that the F₂ emissions are generated from excited twisted intramol. charge-transfer (TICT) species with twisted amide bonds. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Electric Literature of C14H11NO).

Shim, Sang Chul et al. published their research in Bulletin of the Korean Chemical Society in 1995 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. 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). Quality Control of 2-Phenylisoindolin-1-one

Synthesis of N-substituted isoindolin-1-ones via palladium-catalyzed carbonylative heterocyclization of o-bromobenzyl bromide with carbon monoxide and primary amines was written by Shim, Sang Chul;Jiang, Li Hong;Lee, Dong Yub;Cho, Chan Sik. And the article was included in Bulletin of the Korean Chemical Society in 1995.Quality Control of 2-Phenylisoindolin-1-one This article mentions the following:

A convenient method for the synthesis of N-substituted isoindolin-1-ones is disclosed in palladium(0)-catalyzed heterocyclization of o-bromobenzyl bromide with carbon monoxide (CO) and primary amines in DMF at 100 闂佺娅ｉ悡? In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Quality Control of 2-Phenylisoindolin-1-one).

Ditta, Jonathan L. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2013 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) 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.Recommanded Product: 5-Bromo-3-cyanoindole

Conformationally restricted homotryptamines. Part 6: Indole-5-cycloalkyl methylamines as selective serotonin reuptake inhibitors was written by Ditta, Jonathan L.;Denhart, Derek J.;Deskus, Jeffrey A.;Epperson, James R.;Meng, Zhaoxing;Gao, Qi;Mattson, Gail K.;LaPaglia, Mellissa A.;Taber, Matthew T.;Molski, Thaddeus F.;Lodge, Nicholas J.;Mattson, Ronald J.;Macor, John E.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Recommanded Product: 5-Bromo-3-cyanoindole This article mentions the following:

Racemic 5-(trans-2-aminomethylcyclopropyl)indoles, 5-(trans-2-aminomethylcyclopentyl) indoles, and 5-(cis-2-aminomethylcyclopentyl)indoles were synthesized and evaluated as selective serotonin reuptake inhibitors. These analogs followed SAR trends similar to those previously reported for 3-cycloalkyl substituted indoles. The most potent analogs exhibited single digit nanomolar inhibition at the human serotonin transporter but were 10-fold less active than the previously reported compounds In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Recommanded Product: 5-Bromo-3-cyanoindole).