January 2023 - Page 6 of 26 - Indole Building Blocks

Luo, Zaoli et al. published their research in Chemistry – An Asian Journal in 2021 | 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. 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 C8H6N2O2

Luminescent Platinum(II) Complexes with Bidentate Diacetylide Ligands: Structures, Photophysical Properties and Application Studies was written by Luo, Zaoli;Liu, Yungen;Tong, Ka-Chung;Chang, Xiao-Yong;To, Wai-Pong;Che, Chi-Ming. And the article was included in Chemistry – An Asian Journal in 2021.Computed Properties of C8H6N2O2 This article mentions the following:

A series of platinum(II) m-terphenyl 2,2”-diacetylide complexes supported by diimines (2,2′-bipyridines, 1,10-phenanthroline, 2,2′-bipyrimidine) or bis-N-heterocyclic carbenes 3-RIm(CH₂)_nImR-3′ (R = Bu, Me; n = 1-3) ligands have been prepared The diacetylide ligands adopt a cis coordination mode featuring non-planar terphenyl moieties as revealed by X-ray crystallog. analyses. The electrochem., photophys. and photochem. properties of these platinum(II) complexes have been investigated. These platinum(II) diimine complexes show broad emission with peak maxima from 566 nm to 706 nm, with two of them having emission quantum yields >60% and lifetimes <2μs in solutions at room temperature, whereas the platinum(II) diacetylide complexes having bis-N-heterocyclic carbene instead of diimine ligand display photoluminescence with quantum yields of up to 28% in solutions and excited state lifetimes of up to 62μs at room temperature Application studies revealed that one of the complexes can catalyze photoinduced aerobic dehydrogenation of alcs. and alkenes, and a relatively non-toxic water-soluble Pt(II) complex displays anti-angiogenic activity. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Computed Properties of C8H6N2O2).

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

Shirakawa, Seiji et al. published their research in Chemical Science in 2013 | CAS: 14204-27-4

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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione

Efficient approach for the design of effective chiral quaternary phosphonium salts in asymmetric conjugate additions was written by Shirakawa, Seiji;Kasai, Atsuyuki;Tokuda, Takashi;Maruoka, Keiji. And the article was included in Chemical Science in 2013.Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

An efficient approach for the design of chiral quaternary phosphonium bromides as chiral phase-transfer catalysts was demonstrated. A catalyst library of phosphonium salts with various structures was readily constructed using com. available chiral phosphines as catalyst precursors, and an optimized catalyst was successfully applied to highly enantioselective conjugate additions under base-free phase-transfer conditions with low catalyst loading. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione).

Raut, Amol B. et al. published their research in Journal of Catalysis in 2020 | CAS: 5388-42-1

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

Reductive amination of levulinic acid to N-substituted pyrrolidones over RuCl₃ metal ion anchored in ionic liquid immobilized on graphene oxide was written by Raut, Amol B.;Shende, Vaishali S.;Sasaki, Takehiko;Bhanage, Bhalchandra M.. And the article was included in Journal of Catalysis in 2020.SDS of cas: 5388-42-1 This article mentions the following:

Reductive amination of biomass derived Levulinic acid (LA) for the synthesis of N-substituted pyrrolidones is one of the highly attractive routes for biomass valorization. The supported homogeneous metal precursor into the solid surface is an important context in the field of catalysis because these types of catalysts provide the heterogeneous nature and meet the needs of recyclability. Herein, we have reported a synthesis of catalyst with ruthenium ion supported on ionic liquid immobilized into graphene oxide (Ru@GOIL) and its application for reductive amination reaction. Synthesized catalyst is characterized using different anal. techniques such as FT-IR, x-ray diffraction, XPS, TGA, FEG-SEM, TEM and EXAFS anal. The prepared Ru@GOIL found to be highly effective for reductive amination of LA and under these optimized conditions various N-substituted pyrrolidones derivatives were synthesized in excellent yield (78-93%). Ru@GOIL catalyst demonstrated great catalytic performance for reductive amination reaction of LA giving good turnover frequency (TOF = 62 h^-1) value in comparison with other catalysts. The Ru@GOIL catalyst was recycled for six reaction runs with slight drop-in activity after 4^th cycle. Practical applicability of the developed catalyst was successfully demonstrated by direct transformation of biomass waste (rice husk and wheat straw) derived LA to N-substituted pyrrolidones. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).

Winstead, Angela J. et al. published their research in Molecules in 2013 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Recommanded Product: 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate

Synthesis of quaternary heterocyclic salts was written by Winstead, Angela J.;Nyambura, Grace;Matthews, Rachael;Toney, Deveine;Oyaghire, Stanley. And the article was included in Molecules in 2013.Recommanded Product: 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate This article mentions the following:

The microwave synthesis of twenty quaternary ammonium salts, trimethylbenz[e]indolium derivatives I (R = CH₃, CH₂CH₃, (CH₂)₂CH₃, etc.; X = I, Br), quinolinium derivatives II, trimethyl-5-sulfo-3H-indolium derivatives III is described. The syntheses feature comparable yields to conventional synthetic methods reported in the current literature with reduced reaction times and the absence of solvent or minimal solvent. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Recommanded Product: 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate).

Taha, Muhammad et al. published their research in International Journal of Biological Macromolecules in 2021 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Formula: C10H8FNO2

Synthesis of indole derivatives as diabetics II inhibitors and enzymatic kinetics study of α-glucosidase and α-amylase along with their in-silico study was written by Taha, Muhammad;Alrashedy, Ahlam Sayer;Almandil, Noor Barak;Iqbal, Naveed;Anouar, El Hassane;Nawaz, Muhammad;Uddin, Nizam;Chigurupati, Sridevi;Wadood, Abdul;Rahim, Fazal;Das, Suprava;Venugopal, Vijayan;Nawaz, Faisal;Khan, Khalid Mohammed. And the article was included in International Journal of Biological Macromolecules in 2021.Formula: C10H8FNO2 This article mentions the following:

In this study, we have investigated a series of indole-based compounds for their inhibitory study against pancreatic α-amylase and intestinal α-glucosidase activity. Inhibitors of carbohydrate degrading enzymes appear to have an essential role as antidiabetic drugs. All analogus exhibited good to moderate α-amylase (IC₅₀ = 3.80 to 47.50 μM), and α-glucosidase inhibitory interactions (IC₅₀ = 3.10-52.20 μM) in comparison with standard acarbose (IC₅₀ = 12.28 μM and 11.29 μM). The analogs 4, 11, 12, 15, 14 and 17 had good activity potential both for enzymes inhibitory interactions. Structure activity relationships were deliberated to propose the influence of substituents on the inhibitory potential of analogs. Docking studies revealed the interaction of more potential analogs and enzyme active site. Further, we studied their kinetic study of most active compounds showed that compounds 15, 14, 12, 17 and 11 are competitive for α-amylase and non- competitive for α-glucosidase. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Formula: C10H8FNO2).

Ullah, Hayat et al. published their research in Chemical Papers in 2022 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Reference of 150560-58-0

Synthesis, in vitro thymidine phosphorylase activity and molecular docking study of thiadiazole bearing isatin analogs was written by Ullah, Hayat;Liaqat, Anjum;Khan, Qudrat Ullah;Taha, Muhammad;Khan, Fahad;Rahim, Fazal;Uddin, Imad;Rehman, Zia Ur. And the article was included in Chemical Papers in 2022.Reference of 150560-58-0 This article mentions the following:

A series of seventeen analogs I (R = 2-nitrophenyl, 2,4-dichlorophenyl, 2-hydrophenyl, etc.; R¹ = H, i-Pr; R² = H, i-Pr, n-Bu, pentyl) were synthesized and characterized through different spectroscopic techniques such as ¹H, ¹³CNMR, HR-EI-MS and was evaluated for in vitro thymidine phosphorylase inhibition. All compounds showed excellent to good thymidine phosphorylase activity having IC₅₀ value ranging between 4.10 ± 0.20 and 54.60 ±1.40μM when compared with standard drug 7-deazaxanthine (IC₅₀ = 38.68 ± 1.12μM). Among the series, compounds I (R = 2-nitrophenyl, R¹ = R² = H) (IC₅₀ = 8.30 ± 0.30μM), I (R = 2,4-dichlorophenyl, R¹ = H, R² = n-Bu) (IC₅₀ = 6.30 ± 0.10μM), I (R = 2,4-dichlorophenyl, R¹ = H, R² = pentyl) (IC₅₀ = 8.40 ± 0.30μM) and I (R = 2-hydrophenyl, R¹ = i-Pr, R² = H) (IC₅₀ = 4.10 ± 0.20μM) were found more potent. Potent compounds were further subjected to mol. docking study to identify their interactions with the active site of amino acid. Structure activity relationship was done for all analogs mostly based on substitution pattern on Ph and isatin rings. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Reference of 150560-58-0).

Bansode, Ajay H. et al. published their research in Advanced Synthesis & Catalysis in 2021 | 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Synthetic Route of C14H11NO

Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones was written by Bansode, Ajay H.;Suryavanshi, Gurunath. And the article was included in Advanced Synthesis & Catalysis in 2021.Synthetic Route of C14H11NO This article mentions the following:

A visible light-rose bengal-TBHP mediated, controlled oxidation of N-substituted 1,2,3,4-tetrahydroisoquinolines I (R = Me, 4-bromophenyl, thiophen-3-yl, etc.; R¹ = H, Br; R² = H, I) is developed for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones II and isoquinolin-1(2H)-ones III. The present method feature’s a broad substrate scope and good functional group tolerances, and the products II and III are prepared in good to excellent yields. The developed methodol. further demonstrated in the synthesis of isoindolo[2,1-b] isoquinolin-5(7H)-one (topoisomerase-I inhibitor). In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Synthetic Route of C14H11NO).

Xing, Liuzhuang et al. published their research in Journal of Chemistry in 2018 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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: C8H6N2O2

MCM-41-accelerated PWA catalysis of Friedel-Crafts reaction of indoles and isatins was written by Xing, Liuzhuang;Hui, YongHai;Yang, Jinghui;Xing, Xuejian;Hou, Yadong;Wu, Yang;Fan, Kui;Wang, Wei. And the article was included in Journal of Chemistry in 2018.COA of Formula: C8H6N2O2 This article mentions the following:

Ordered mesoporous siliceous material has been identified as one of the key elements of the catalysis concept. Herein, an efficient Friedel-Crafts reaction of indoles with isatins catalyzed by PWA/MCM-41, to obtain di(indolyl)indolin-2-one derivatives I (R¹ = H, 2-Me, 5-F, etc.; R² = H, 5-Me, 7-F, etc.) with high yield is reported. Moreover, the catalysts were characterized by XRD and SEM/EDS, the EDS spectrum indicated that the catalyst used in this reaction also contains tungsten, and the proposed mechanism for the synthesis of 3,3-di(indolyl)indolin-2-ones was also discussed. Finally, the catalyst can be reused repeatedly for several times without obvious loss of activity. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4COA of Formula: C8H6N2O2).

Mondal, Manas et al. published their research in Tetrahedron Letters in 2019 | 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.SDS of cas: 14204-27-4

Benign synthesis of thiophosphates, thiophosphinates and selenophosphates in neat condition using N-chalcogenoimides as the source of electrophilic sulfur/selenium was written by Mondal, Manas;Saha, Amit. And the article was included in Tetrahedron Letters in 2019.SDS of cas: 14204-27-4 This article mentions the following:

A neat reaction protocol was developed for synthesis of thiophosphate, thiophosphinate and selenophosphate compounds N-chalcogenoimides were used for chalcogenylation of P(O)H moieties of various H-phosphonates under solvent, catalyst and base free condition at room temperature in aerial atm. Both S-aryl and S-alkyl phosphorothioate compounds were prepared by this method in good yields. Selenophosphates were also synthesized using N-(phenylseleno)phthalimide under solvent free condition. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4SDS of cas: 14204-27-4).

Kumari, Seema et al. published their research in Journal Chemtracks in 2019 | CAS: 4769-96-4

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

Bioproduction of ethanol by Saccharomyces cerevisiae-20 exposed to 6-nitroindole was written by Kumari, Seema;Sharma, B. B.. And the article was included in Journal Chemtracks in 2019.Safety of 6-Nitro-1H-indole This article mentions the following:

The efficacy of 6-nitroindole on bioprodn. of ethanol by Saccharomyces cerevisiae-20 has been assessed. It has been found that the mutagen under trial, i.e., 6-nitroindole at 7.0 x 10-5 M molar concentration enhances the bioprodn. of ethanol by Saccharomyces cerevisiae-20 to an extent of 12.517% higher in comparison to control fermentor flask, i.e, 6.95 mL/100 in 55 h of optimum incubation period, 20% (w/v) molasses solution 4.8 pH and 30°C temperature alongwith other nutritional ingredients required by the yeast. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Safety of 6-Nitro-1H-indole).