February 2023 - Page 105 of 117 - Indole Building Blocks

Yilmaz, Ayse Didem et al. published their research in Journal of Enzyme Inhibition and Medicinal Chemistry in 2012 | CAS: 827-01-0

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.Product Details of 827-01-0

Synthesis and antioxidant activity evaluations of melatonin-based analogue indole-hydrazide/hydrazone derivatives was written by Yilmaz, Ayse Didem;Coban, Tulay;Suzen, Sibel. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2012.Product Details of 827-01-0 This article mentions the following:

Melatonin (MLT) is a hormone synthesized from the pineal gland. It is a direct scavenger of free radicals, which is related to its ability to defend cells from oxidative stress. Recently MLT-related compounds are under investigation to establish which ones exhibit the maximum activity with the lowest side effects. In this study, 5-chloroindole hydrazide/hydrazone derivatives were synthesized from 5-chloroindole-3-carboxaldehyde and phenylhydrazine derivatives All the compounds were characterized and in vitro antioxidant activity was investigated against MLT and BHT. Most of the compounds showed strong inhibitory effect on the superoxide radical scavenging assay at 1 mM concentration (79 to 95%). Almost all the tested compounds possessed strong scavenging activity against the DPPH radical scavenging activity with IC₅₀ values (2 to 60 μM). Lastly, compound (E)-I revealed stronger inhibitory activity against MLT in the LP inhibitory assay at 0.1mM concentration (51%) while the rest of the compounds showed moderate inhibition. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Product Details of 827-01-0).

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

Indrigo, Eugenio et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2016 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Product Details of 754214-56-7

Palladium-mediated in situ synthesis of an anticancer agent was written by Indrigo, Eugenio;Clavadetscher, Jessica;Chankeshwara, Sunay V.;Lilienkampf, Annamaria;Bradley, Mark. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2016.Product Details of 754214-56-7 This article mentions the following:

As a novel prodrug activation strategy Pd(0) nanoparticles, entrapped within a modular polymeric support, were used in cell culture, to synthesize the anticancer agent PP-121 from two non-toxic precursors, thereby inducing cell death in the first example of in situ mediated drug synthesis. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Product Details of 754214-56-7).

Mironov, Yu. V. et al. published their research in Russian Chemical Bulletin in 2010 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Computed Properties of C14H9NO2S

A study of the mechanism of the azidophenylselenylation of glycals was written by Mironov, Yu. V.;Grachev, A. A.;Lalov, A. V.;Sherman, A. A.;Egorov, M. P.;Nifantiev, N. E.. And the article was included in Russian Chemical Bulletin in 2010.Computed Properties of C14H9NO2S This article mentions the following:

Chem. and physicochem. studies of homogeneous azidophenylselenylation of glycols with diacetoxyiodobenzene, trimethylsilyl azide, and di-Ph diselenide in dichloromethane revealed that the most probable key reaction step is the formation of phenylselenyl azide, an azide radical donor. A method for azidophenylsulfenylation of glycals, e.g. I, with diacetoxyiodobenzene, di-Ph diselenide, and sodium azide to give the corresponding glycosides, e.g. II, was proposed. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Computed Properties of C14H9NO2S).

Wu, Yinrong et al. published their research in Organic Letters in 2021 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C10H8ClNO2

Copper-Mediated Decarboxylative Coupling between Arylacetic Acids and 1,3-Dicarbonyl Compounds was written by Wu, Yinrong;Wen, Kangmei;Chen, Jiewen;Shi, Jie;Yao, Xingang;Tang, Xiaodong. And the article was included in Organic Letters in 2021.Computed Properties of C10H8ClNO2 This article mentions the following:

A copper-mediated decarboxylative coupling reaction between arylacetic acids and 1,3-dicarbonyl compounds was described for the synthesis of ((indolyl)methyl)-oxocycloalkyl-esters, e.g., I. Significantly, methanocycloocta[b]indoles II [R = COOEt, CONHEt, SO₂Ph, etc.; R¹ = H, 4-Cl, 5-Br, etc.] were also obtained by sequential intramol. dehydrocyclization process in some cases. This protocol featured a broad substrate scope, simple operations, and good yields. Moreover, the products exhibited potent antiproliferative activity against the human cancer cell lines by a MTT assay. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Computed Properties of C10H8ClNO2).

Silveira, Claudio C. et al. published their research in Tetrahedron Letters in 2010 | CAS: 14204-27-4

The use of anhydrous CeCl₃ as a catalyst for the synthesis of 3-sulfenyl indoles was written by Silveira, Claudio C.;Mendes, Samuel R.;Wolf, Lucas;Martins, Guilherme M.. And the article was included in Tetrahedron Letters in 2010.Formula: C14H9NO2S This article mentions the following:

Anhydrous CeCl₃ was successfully used as a catalyst for the synthesis of several 3-sulfenyl indoles in good to excellent yields through the reaction of indoles with N-(alkylthio) and N-(arylthio)phthalimides in DMF. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Formula: C14H9NO2S).

Hay, Duncan A. et al. published their research in Journal of the American Chemical Society in 2014 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Related Products of 4583-55-5

Discovery and Optimization of Small-Molecule Ligands for the CBP/p300 Bromodomains was written by Hay, Duncan A.;Fedorov, Oleg;Martin, Sarah;Singleton, Dean C.;Tallant, Cynthia;Wells, Christopher;Picaud, Sarah;Philpott, Martin;Monteiro, Octovia P.;Rogers, Catherine M.;Conway, Stuart J.;Rooney, Timothy P. C.;Tumber, Anthony;Yapp, Clarence;Filippakopoulos, Panagis;Bunnage, Mark E.;Muller, Susanne;Knapp, Stefan;Schofield, Christopher J.;Brennan, Paul E.. And the article was included in Journal of the American Chemical Society in 2014.Related Products of 4583-55-5 This article mentions the following:

Small-mol. inhibitors that target bromodomains outside of the bromodomain and extra-terminal (BET) sub-family are lacking. Here, the authors describe highly potent and selective ligands for the bromodomain module of the human lysine acetyl transferase CBP/p300, developed from a series of 5-isoxazolyl-benzimidazoles. The starting point was a fragment hit, which was optimized into a more potent and selective lead using parallel synthesis employing Suzuki couplings, benzimidazole-forming reactions, and reductive aminations. The selectivity of the lead compound against other bromodomain family members was investigated using a thermal stability assay, which revealed some inhibition of the structurally related BET family members. To address the BET selectivity issue, x-ray crystal structures of the lead compound bound to the CREB binding protein (CBP) and the first bromodomain of BRD4 (BRD4(1)) were used to guide the design of more selective compounds The crystal structures obtained revealed two distinct binding modes. By varying the aryl substitution pattern and developing conformationally constrained analogs, selectivity for CBP over BRD4(1) was increased. The optimized compound is highly potent (K_d = 21 nM) and selective, displaying 40-fold selectivity over BRD4(1). Cellular activity was demonstrated using fluorescence recovery after photo-bleaching (FRAP) and a p53 reporter assay. The optimized compounds are cell-active and have nanomolar affinity for CBP/p300; therefore, they should be useful in studies investigating the biol. roles of CBP and p300 and to validate the CBP and p300 bromodomains as therapeutic targets. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Related Products of 4583-55-5).

Prager, Rolf H. et al. published their research in Journal of Heterocyclic Chemistry in 2000 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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). Product Details of 5388-42-1

Carbene and radical pathways in pyrolysis of benzisoxazolones and benzotriazoles was written by Prager, Rolf H.;Baradarani, Mehdi M.;Khalafy, Jabbar. And the article was included in Journal of Heterocyclic Chemistry in 2000.Product Details of 5388-42-1 This article mentions the following:

Conference proceedings containing review material. A comparative study of the flash vacuum pyrolysis of a number of N-alkyl- and N-acylbenzotriazoles and -benzisoxazolones has confirmed that carbene-derived pathways predominate at lower temperatures, and radical pathways at higher temperatures Two new general unimol. thermal reactions are also highlighted. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Product Details of 5388-42-1).

Aslan, Murat et al. published their research in Journal of Organic Chemistry in 2022 | CAS: 320734-35-8

7-Bromooxindole (cas: 320734-35-8) 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 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: C8H6BrNO

Functionalization at Nonperipheral Positions of Triazatruxene: Modular Construction of 1,6,11-Triarylated-Triazatruxenes for Potentially Organic Electronics and Optoelectronics was written by Aslan, Murat;Taskesenligil, Yunus;Pravadl, Selin;Saracoglu, Nurullah. And the article was included in Journal of Organic Chemistry in 2022.COA of Formula: C8H6BrNO This article mentions the following:

Functionalization from nonperipheral positions of triazatruxene is representing a challenge. Triarylation of the nonperipheral positions (1, 6, and 11) in triazatruxene scaffold has been achieved for the first time via two approaches. The transformations involve arylation/cyclotrimerization and cyclotrimerization/arylation sequences. POCl3-mediated direct cyclotrimerization of oxindoles containing electron-deficient substituents on the aryl group at the C7-position resulted in the formation of 2-chloroindoles, whereas oxindoles containing electron-donating substituents gave the triazatruxenes. Furthermore, desired triazatruxenes were achieved through cyclotrimerization of 7-bromooxindole followed by coupling with arylboronic acids. As a representative triazatruxene scaffold, the optoelectronic properties of I have also been studied via UV-visible (UV-vis) absorption spectra and fluorescence spectra of I thin films. Also, d. functional theory calculation was realized to get knowledge about frontier MOs. In the light of the information obtained, an organic light-emitting diode (OLED) device utilizing I as an emissive layer was applied to obtain white emission. In brief, this study provides the first examples of the synthesis of triazatruxenes bearing aryl substituents at the nonperipheral positions as candidate compounds for organic electronics, optoelectronics, and material chem. In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8COA of Formula: C8H6BrNO).

Ma, Bingqing et al. published their research in Journal of Fluorine Chemistry in 2015 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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.Name: 6-Nitro-1H-indole

BrOsted acid-catalyzed electrophilic trifluoromethylthiolation of indoles using thermally stable trifluoromethylthiolating reagent was written by Ma, Bingqing;Shao, Xinxin;Shen, Qilong. And the article was included in Journal of Fluorine Chemistry in 2015.Name: 6-Nitro-1H-indole This article mentions the following:

A BrOsted acid-catalyzed electrophilic trifluoromethylthiolation of indoles under mild conditions is described. The reaction was insensitive to moisture and oxygen, that should allow for easy handling. In addition, the reaction is compatible with a variety of functional groups. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).

Ma, Zhenhui et al. published their research in Nano Research in 2019 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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. 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). Electric Literature of C8H6N2O2

Magnetically recyclable Sm₂Co₁₇/Cu catalyst to chemoselectively reduce the 3-nitrostyrene into 3-vinylaniline under room temperature was written by Ma, Zhenhui;Liu, Hu;Yue, Ming. And the article was included in Nano Research in 2019.Electric Literature of C8H6N2O2 This article mentions the following:

Using non-noble metal catalysts to chemoselectively reduce the 3-nitrostyrene into 3-vinylaniline is extremely attractive due to the important applications of aromatic amines. However, the separation and recycle of catalytic particles to sustainably catalyze are still challenging on account of their small size. In this communication, we report a novel magnetically recyclable catalyst of Sm₂Co₁₇/Cu to chemoselectively reduce 3-nitrostyrene into 3-vinylaniline by activating ammonia borane (AB) to yield hydrogen. The Sm₂Co₁₇, composited of 180 nm Sm₂Co₁₇ nanomagnet and 10 nm Cu catalyst nanoparticles, shows a high conversion (98%) and a high selectivity (99%) for 3-nitrostyrene under ultrasonic concussion. More importantly, they are easily collected by self-separation method without any magnetic field. As a consequence, the excellent recyclable feature is acquired even underwent 10 cycles. Our approach provides a green strategy to synthesize magnetically recyclable catalysts. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Electric Literature of C8H6N2O2).