04/01/2023 - Page 9 of 11 - Indole Building Blocks

Roth, H. J. et al. published their research in Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft in 1972 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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.Quality Control of 5-Bromo-2,3-dimethyl-1H-indole

Synthesis of indole and carbazole derivatives by condensation of α-hydroxyketones and aromatic amines was written by Roth, H. J.;Lepke, P.. And the article was included in Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft in 1972.Quality Control of 5-Bromo-2,3-dimethyl-1H-indole This article mentions the following:

Thirty title compounds [I; R = R1 = Me or Ph or RR1 = (CH2)4; R2 = H, 5-OH, 6-OH, 5-HO2C, 6-HO2C, 5-EtO2C, 5-MeO, 6-MeS, 5-Me, 7-Me, 4,7-Me2, 6,5-BrMe, 5-Cl, 5-Br, or 6-Cl or the naphthyl analogs] were prepared in 21-92% yield by condensation of R2C6H4NH2 and RCH(OH)COR1. The products were determined by NMR. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Quality Control of 5-Bromo-2,3-dimethyl-1H-indole).

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

Sagong, Hye Yeon et al. published their research in Medicinal Chemistry Research in 2022 | CAS: 210345-56-5

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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.SDS of cas: 210345-56-5

Antibacterial activity of MreB inhibitors against gram (-) bacteria was written by Sagong, Hye Yeon;Rosado-Lugo, Jesus D.;Bryan, Eric J.;Ferrer-Gonzalez, Edgar;Wang, Yiling;Cao, Yanlu;Parhi, Ajit K.;Pilch, Daniel S.;LaVoie, Edmond J.. And the article was included in Medicinal Chemistry Research in 2022.SDS of cas: 210345-56-5 This article mentions the following:

MreB is a cytoskeleton protein present in rod-shaped bacteria that is both essential for bacterial cell division and highly conserved. Because most Gram (-) bacteria require MreB for cell division, chromosome segregation, cell wall morphogenesis, and cell polarity, it is an attractive target for antibacterial drug discovery. As MreB modulation is not associated with the activity of antibiotics in clin. use, acquired resistance to MreB inhibitors is also unlikely. Compounds, such as A22and CBR-4830, are known to disrupt MreB function by inhibition of ATPase activity. However, the toxicity of these compounds has hindered efforts to assess the in vivo efficacy of these MreB inhibitors. The present study further examines the structure-activity of analogs related to CBR-4830 as it relates to relative antibiotic activity and improved drug properties. These data reveal that certain analogs have enhanced antibiotic activity. In addition, we evaluated several representative analogs (9, 10, 14, 26, and 31) for their abilities to target purified E. coli MreB (EcMreB) and inhibit its ATPase activity. Except for 14, all these analogs were more potent than CBR-4830 as inhibitors of the ATPase activity of EcMreB with corresponding IC₅₀ values ranging from 6 ± 2 to 29 ± 9 μM. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5SDS of cas: 210345-56-5).

Lipp, Alexander et al. published their research in Advanced Synthesis & Catalysis in 2021 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Name: 2-(Phenylthio)isoindoline-1,3-dione

Catalyst-Free Decarbonylative Trifluoromethylthiolation Enabled by Electron Donor-Acceptor Complex Photoactivation was written by Lipp, Alexander;Badir, Shorouk O.;Dykstra, Ryan;Gutierrez, Osvaldo;Molander, Gary A.. And the article was included in Advanced Synthesis & Catalysis in 2021.Name: 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

A catalyst- and additive-free decarbonylative trifluoromethylthiolation of aldehyde feedstocks has been developed. This operationally simple, scalable, and open-to-air transformation is driven by the selective photoexcitation of electron donor-acceptor (EDA) complexes, stemming from the association of 1,4-dihydropyridines (donor) with N-(trifluoromethylthio)phthalimide (acceptor), to trigger intermol. single-electron transfer events under ambient- and visible light-promoted conditions. Extension to other electron acceptors enables the synthesis of thiocyanates and thioesters, as well as the difunctionalization of [1.1.1]propellane. The mechanistic intricacies of this photochem. paradigm are elucidated through a combination of exptl. efforts and high-level quantum mech. calculations [dispersion-corrected (U)DFT, DLPNO-CCSD(T), and TD-DFT]. This comprehensive study highlights the necessity for EDA complexation for efficient alkyl radical generation. Computation of subsequent ground state pathways reveals that S_H2 addition of the alkyl radical to the intermediate radical EDA complex is extremely exergonic and results in a charge transfer event from the dihydropyridine donor to the N-(trifluoromethylthio)phthalimide acceptor of the EDA complex. Exptl. and computational results further suggest that product formation also occurs via S_H2 reaction of alkyl radicals with 1,2-bis(trifluoromethyl)disulfane, generated in-situ through combination of thiyl radicals. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Name: 2-(Phenylthio)isoindoline-1,3-dione).

Huang, Xu-Lun et al. published their research in Organic Letters in 2020 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Electric Literature of C9H6BrNO2

Photoredox-Catalyzed Intermolecular Hydroalkylative Dearomatization of Electron-Deficient Indole Derivatives was written by Huang, Xu-Lun;Cheng, Yuan-Zheng;Zhang, Xiao;You, Shu-Li. And the article was included in Organic Letters in 2020.Electric Literature of C9H6BrNO2 This article mentions the following:

Dearomatization of indole derivatives offers a straightforward approach to access diverse indolines. To date, the corresponding dearomative transformations involving electron-deficient indoles are limited. Herein, we report a one-electron strategy for dearomatization of electron-deficient indoles via a photoredox-catalyzed hydroalkylation employing com. available glycine derivatives as the hydrofunctionalization reagents. Followed by DBU-mediated lactamization, structurally appealing lactam-fused indolines are obtained in good to excellent yields with exclusive selectivity. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Electric Literature of C9H6BrNO2).

Cleghorn, Laura A. T. et al. published their research in Journal of Medicinal Chemistry in 2015 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Synthetic Route of C10H8FNO2

Discovery of Indoline-2-carboxamide Derivatives as a New Class of Brain-Penetrant Inhibitors of Trypanosoma brucei was written by Cleghorn, Laura A. T.;Albrecht, Sebastien;Stojanovski, Laste;Simeons, Frederick R. J.;Norval, Suzanne;Kime, Robert;Collie, Iain T.;De Rycker, Manu;Campbell, Lorna;Hallyburton, Irene;Frearson, Julie A.;Wyatt, Paul G.;Read, Kevin D.;Gilbert, Ian H.. And the article was included in Journal of Medicinal Chemistry in 2015.Synthetic Route of C10H8FNO2 This article mentions the following:

There is an urgent need for new, brain penetrant small mols. that target the central nervous system second stage of human African trypanosomiasis (HAT). We report that a series of novel indoline-2-carboxamides have been identified as inhibitors of Trypanosoma brucei from screening of a focused protease library against Trypanosoma brucei brucei in culture. We describe the optimization and characterization of this series. Potent antiproliferative activity was observed The series demonstrated excellent pharmacokinetic properties, full cures in a stage 1 mouse model of HAT, and a partial cure in a stage 2 mouse model of HAT. Lack of tolerability prevented delivery of a fully curative regimen in the stage 2 mouse model and thus further progress of this series. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Synthetic Route of C10H8FNO2).

Saravanan, Perumal et al. published their research in Organic Letters in 2014 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Synthetic Route of C14H9NO2S

Palladium Catalyzed Aryl(alkyl)thiolation of Unactivated Arenes was written by Saravanan, Perumal;Anbarasan, Pazhamalai. And the article was included in Organic Letters in 2014.Synthetic Route of C14H9NO2S This article mentions the following:

A general palladium-catalyzed aryl(alkyl)thiolation of various substituted unactivated arenes is accomplished for the synthesis of diverse unsym. diaryl(alkyl) sulfides in good yield employing electrophilic sulfur reagents derived from succinimide. E.g., in presence of Pd(OAc)₂ in TFA, arylthiolation of mesitylene with 1-(phenylthio)pyrrolidine-2,5-dione (I) gave 95% sulfide II. The developed strategy was coupled with intramol. arylation of a C-H bond to afford dibenzothiphene derivatives, an important moiety in material science as organic semiconductors. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Synthetic Route of C14H9NO2S).

Rahim, Abdul et al. published their research in Medicinal Chemistry Research in 2019 | 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. 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). HPLC of Formula: 827-01-0

Synthesis and biological evaluation of phenyl-amino-pyrimidine and indole/oxindole conjugates as potential BCR-ABL inhibitors was written by Rahim, Abdul;Syed, Riyaz;Poornachandra, Y.;Malik, M. Shaheer;Reddy, Ch. Venkata Ramana;Alvala, Mallika;Boppana, Kiran;Sridhar, B.;Amanchy, Ramars;Kamal, Ahmed. And the article was included in Medicinal Chemistry Research in 2019.HPLC of Formula: 827-01-0 This article mentions the following:

Indole/isatin conjugated phenyl-amino-pyrimidine derivatives have been synthesized, characterized and evaluated in vitro for their potential as BCR-ABL inhibitors. Among the series, all derivatives (7a-7o) were found to be more cytotoxic than standard Imatinib against K-562 cell line. Compound 7l(I) was the most active in the series with almost two folds more potency than imitanib (IC₅₀ 0.65 μM). In vitro enzymic studies with recombinant ABL kinase enzyme exhibited promising inhibition in the range of 30-71 μM for most of these novel conjugates. In addition, modeling and other computational studies have been carried out to draw insight into the BCR-ABL protein interactions with the target mols. and drug like properties of the conjugates, resp. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0HPLC of Formula: 827-01-0).

Green, Keith D. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2019 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 4769-96-4

Investigating the promiscuity of the chloramphenicol nitroreductase from Haemophilus influenzae towards the reduction of 4-nitrobenzene derivatives was written by Green, Keith D.;Fosso, Marina Y.;Mayhoub, Abdelrahman S.;Garneau-Tsodikova, Sylvie. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Recommanded Product: 4769-96-4 This article mentions the following:

Chloramphenicol nitroreductase (CNR), a drug-modifying enzyme from Haemophilus influenzae, has been shown to be responsible for the conversion of the nitro group into an amine in the antibiotic chloramphenicol (CAM). Since CAM structurally bears a 4-nitrobenzene moiety, we explored the substrate promiscuity of CNR by investigating its nitroredn. of 4-nitrobenzyl derivatives We tested twenty compounds containing a nitrobenzene core, two nitropyridines, one compound with a vinylogous nitro group, and two aliphatic nitro compounds In addition, we also synthesized twenty-eight 4-nitrobenzyl derivatives with ether, ester, and thioether substituents and assessed the relative activity of CNR in their presence. We found several of these compounds to be modified by CNR, with the enzyme activity ranging from 1 to 150% when compared to CAM. This data provides insights into two areas: (i) chemoenzymic reduction of select compounds to avoid harsh chems. and heavy metals routinely used in reductions of nitro groups and (ii) functional groups that would aid CAM in overcoming the activity of this enzyme. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 4769-96-4).

Hou, Jing et al. published their research in Angewandte Chemie, International Edition in 2018 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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

Visible-Light-Mediated Metal-Free Difunctionalization of Alkenes with CO₂ and Silanes or C(sp³)-H Alkanes was written by Hou, Jing;Ee, Aloysius;Cao, Hui;Ong, Han-Wee;Xu, Jin-Hui;Wu, Jie. And the article was included in Angewandte Chemie, International Edition in 2018.Electric Literature of C14H9NO2S This article mentions the following:

Catalytic alkene difunctionalization via Si-H and C-H activations represents an ideal atom- and step-economic pathway for quick assembly of mol. complexity. We herein developed a visible-light-promoted metal-free difunctionalization of alkenes using abundant CO₂ and readily available Si-H and C(sp³)-H bonds as feedstocks. Through the merger of photoredox and hydrogen-atom-transfer catalysis, a variety of value-added compounds, such as β-silacarboxylic acids and acids bearing a γ-heteroatom (e.g., N, O, S) could be directly accessed from simple alkenes in a redox-neutral fashion. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Electric Literature of C14H9NO2S).

Carrasco, Fernando et al. published their research in Journal of Chemistry in 2020 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Category: indole-building-block

Indole-3-carbaldehyde semicarbazone derivatives: Synthesis, characterization, and antibacterial activities was written by Carrasco, Fernando;Hernandez, Wilfredo;Chupayo, Oscar;Alvarez, Celedonio M.;Oramas-Royo, Sandra;Spodine, Evgenia;Tamariz-Angeles, Carmen;Olivera-Gonzales, Percy;Davalos, Juan Z.. And the article was included in Journal of Chemistry in 2020.Category: indole-building-block This article mentions the following:

Four indole-3-carbaldehyde semicarbazone derivatives, I (R = H, R¹ = Br, Cl, OMe; R = NO₂, R¹ = H) were synthesized and characterized by ESI-MS and spectroscopic (FT-IR, ¹H NMR, and ¹³C NMR) techniques. The two-dimensional NMR (in acetone-d₆) spectral data revealed that the mols. I (R = H, R¹ = Br, Cl) (II) in solution are in the cis E isomeric form. This evidence is supported by DFT calculations at the B3LYP/6-311++G(d,p) level of theory where it was shown that the corresponding most stable conformers of the synthesized compounds have a cis E geometrical configuration, in both the gas and liquid (acetone and DMSO) phases. The in vitro antibacterial activity of I was determined against Gram-pos. (Staphylococcus aureus and Bacillus subtilis) and Gram-neg. (Pseudomonas aeruginosa and Escherichia coli) bacteria. Among all the tested semicarbazones, II exhibited similar inhibitory activities against Staphylococcus aureus (MIC = 100 and 150μg/mL, resp.) and Bacillus subtilis (MIC = 100 and 150μg/mL, resp.). On the other hand, I (R = H, R¹ = OMe; R = NO₂, R¹ = H) were relatively less active against the tested bacterial strains compared with II and tetracycline. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Category: indole-building-block).