February 2023 - Page 117 of 117 - Indole Building Blocks

Yenireddy, Veera Reddy et al. published their research in Chemical Data Collections in 2022 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Electric Literature of C9H5BrN2

Synthesis, characterization, biological evaluation and molecular docking of novel amide derivatives of indole-1,2,4-oxadiazole clubbed thiazoles was written by Yenireddy, Veera Reddy;Vejendla, Anuradha. And the article was included in Chemical Data Collections in 2022.Electric Literature of C9H5BrN2 This article mentions the following:

In the present study, a series of some novel amide derivatives of indole-1,2,4-oxadiazole clubbed thiazoles I (Ar = 4-MeC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, etc.) were designed and prepared Antiproliferative activity of these compounds against four human cancer cell lines such as SiHa (cervix), A549 (lung), MCF-7 (breast) and Colo-205 (colon) evaluated by using MTT assay and compared with therapeutic agent etoposide. Among them, compounds I (Ar = 3,4,5-triMeOC₆H₂, 3,5-diMeOC₆H₃, 4-MeOC₆H₄, 2-thiazolyl, 4-pyridyl) demonstrated very potent activity. Mol. modeling studies were performed on the binding site of Human Protein tyrosine kinase 6 (PTK6) to correlate the outcome of in vitro cytotoxic assays and therefore rationalize the binding interactions. In silico ADME and toxicity experiment were shown that all synthesized compounds have good oral bioavailability and free from toxicity. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Electric Literature 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

Buchman, Edwin R. et al. published their research in Journal of the American Chemical Society in 1947 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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.HPLC of Formula: 112656-95-8

8-Nitrocinchoninic acids and related substances was written by Buchman, Edwin R.;McCloskey, Chester M.;Seneker, J. Albert. And the article was included in Journal of the American Chemical Society in 1947.HPLC of Formula: 112656-95-8 This article mentions the following:

Tech. lepidine (650 g.), nitrated at 0-3°, gives 372 g. (48.2%) 8-nitrolepidine (I), m. 126-6.5° absorption maximum at 283, 314 mμ, and 112 g. (13.3%) of an isomer, light yellow, m. 127.5-9°, absorption maximum at 222, 278, and 316 mμ. Details are given of the oxidation of 200 g. I through the aldehyde to 160 g. crude 8-nitrocinchoninic acid (absorption maximum at 224, 293-6 mμ); Et ester (II) m. 84-5° absorption maximum at 226, 304 mμ (44% based on I). Catalytic reduction of II in EtOH over Pt oxide gives 91% Et 8-aminocinchoninate (III), red-orange, m. 77.5-8° absorption maximum at 267, 330, 400-1 mμ; free acid, dark red, m. 280-1° (rapid heating), absorption maximum at 262, 380 mμ (not reproducible); HCl salt, sparingly soluble in cold H₂O. III and BzCl in C₅H₅N give 96% of the Bz derivative, m. 194-4.5° absorption maximum at 255, 334, and 348 mμ. α-Isonitroso-o-nitroacetanilide (preparation in 47.8% yield from o-O₂NC₆H₄NH₂, given) and concentrated H₂SO₄ give 68% 7-nitroisatin (IV). PhAc (18 ml.), 15.6 g. IV, and 80 ml. concentrated NH₄OH, heated 8 hrs. at 130° give 87% 2-phenyl-8-nitrocinchoninamide (V), m. 274.5-5°, absorption maximum at 266-7, 340-3 mμ. V (0.5 g.) in 2 ml. concentrated H₂SO₄, heated 3 hrs. at 145° and the solution refluxed 4 hrs. with 20 ml. EtOH, gives 31% Et 2-phenyl-8-nitrocinchoninate (VI), m. 143-3.5° absorption maximum at 268, 347 mμ; VI was also prepared in 34.2% yield by the Doebner reaction (using o-O₂NC₆H₄NH₂, BzH, AcCO₂H, and concentrated H₂SO₄); the effect of varying the quantities of H₂SO₄ and AcCO₂H on the yield was studied. Reduction of VI in MeOH over Pt oxide gives 88% Et 2-phenyl-8-aminocinchoninate, m. 69-9.5° absorption maximum at 231-2, 297, 343-8, and 400-20 mμ. The 8-HO analog, yellow, m. 71-1.5° absorption maximum at 283-5, 347-8 mμ. 2,4-O₂N-(MeO)C₆H₃NH₂ (21 g.), 13.25 g. BzH, and 12.5 ml. AcOH, treated with 7 ml. concentrated H₂SO₄ and, after 5 min., with 11 g. AcCO₂H, and heated on the steam bath 30 min., give 23% Et 2-phenyl-6-methoxy-8-nitrocinchoninate, pale yellow, m. 160-5°, absorption maximum at 264-6, 372-3 mμ; the 8-NH₂ analog, red, m. 120-20.5°, absorption maximum at 299-302, 410-12 mμ, 96% yield. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8HPLC of Formula: 112656-95-8).

Li, Chang-Feng et al. published their research in Organic Letters in 2007 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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 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 167631-84-7

Enantioselective Organocatalytic Intramolecular Ring-Closing Friedel-Crafts-Type Alkylation of Indoles was written by Li, Chang-Feng;Liu, Hiu;Liao, Jie;Cao, Yi-Ju;Liu, Xiao-Peng;Xiao, Wen-Jing. And the article was included in Organic Letters in 2007.Product Details of 167631-84-7 This article mentions the following:

An enantioselective organocatalytic intramol. ring-closing Friedel-Crafts-type alkylation of indolyl α,β-unsaturated aldehydes has been developed. This powerful new strategy allows enantioselective access to THPIs (tetrahydropyrano[3,4-b]indoles), e.g., I, and THBCs (tetrahydro-β-carbolines), e.g., II, in a straightforward and atom-economical manner. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Product Details of 167631-84-7).

Kovtunenko, V. A. et al. published their research in Ukrainskii Khimicheskii Zhurnal (Russian Edition) in 1983 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of 2-Phenylisoindolin-1-one

Condensation of o-(bromomethyl)benzoic acid with amines was written by Kovtunenko, V. A.;Tyltin, A. K.;Dobrenko, T. T.;Babichev, F. S.. And the article was included in Ukrainskii Khimicheskii Zhurnal (Russian Edition) in 1983.Quality Control of 2-Phenylisoindolin-1-one This article mentions the following:

Isoindolinones I [R = Me, (un)substituted Ph, PhCH₂, H, 1-C₁₀H₇] were prepared in 43-80% yields by cyclocondensation of o-(XCH₂)C₆H₄CO₂R¹ (R¹ = H, Me, X = Br, Cl) with RNH₂. Heating I (R = Me, Ph, 4-MeOC₆H₄, 4-MeC₆H₄) in the presence of P₄S₁₀ gave 48-55% II. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Quality Control of 2-Phenylisoindolin-1-one).

Yan, Xue et al. published their research in Monatshefte fuer Chemie in 2020 | CAS: 4769-96-4

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

Synthesis and assessment of bisindoles as a new class of antibacterial agents was written by Yan, Xue;Tang, Ying-De;He, Fei;Yu, Shu-Juan;Liu, Xigong;Bao, Jie;Zhang, Hua. And the article was included in Monatshefte fuer Chemie in 2020.Application of 4769-96-4 This article mentions the following:

Antimicrobial screening of an inhouse library containing both natural products and synthetic compounds identified a bisindole mol. as a selective antibacterial hit. Further evaluation and structural modification afforded a series of dimeric indole derivatives, most of which showed moderate to good antibacterial activity against two Gram-pos. strains Staphylococcus aureus and Bacillus subtilis. Chiral HPLC was employed to sep. these racemates and the bioactive differences between the enantiomeric pairs were also assessed and discussed. Three dihalogenaged analogs also showed mild growth inhibition against a drug-resistant S. aureus strain. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Application of 4769-96-4).

Wu, Wenliang et al. published their research in Journal of the American Chemical Society in 2011 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Electric Literature of C9H6ClNO

Mild and Selective Ru-Catalyzed Formylation and Fe-Catalyzed Acylation of Free (N-H) Indoles Using Anilines as the Carbonyl Source was written by Wu, Wenliang;Su, Weiping. And the article was included in Journal of the American Chemical Society in 2011.Electric Literature of C9H6ClNO This article mentions the following:

Indoles undergo regioselective formylation and acylation reactions with N-methylaniline or N-benzylanilines in the presence of either ruthenium(III) or iron(II) chlorides using tert-Bu hydroperoxide as the oxidant to give 3-formyl or 3-benzoylindoles in 34-86% yields. The processes are operationally simple and compatible with a variety of functional groups. Reaction of indole with N-(¹³C-methyl)aniline yields 3-(¹³C-formyl)indole in 70% yield, unambiguously establishing that the carbonyl carbon in the formylation products originates from the Me group of N-Me aniline. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Electric Literature of C9H6ClNO).

Gutierrez-Tarrino, Silvia et al. published their research in Green Chemistry in 2021 | 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C14H11NO

Cobalt nanoclusters coated with N-doped carbon for chemoselective nitroarene hydrogenation and tandem reactions in water was written by Gutierrez-Tarrino, Silvia;Rojas-Buzo, Sergio;Lopes, Christian W.;Agostini, Giovanni;Calvino, Jose. J.;Corma, Avelino;Ona-Burgos, Pascual. And the article was included in Green Chemistry in 2021.Formula: C14H11NO This article mentions the following:

The development of active and selective non-noble metal-based catalysts for the chemoselective reduction of nitro compounds in aquo media under mild conditions is an attractive research area. Herein, the synthesis of subnanometric and stable cobalt nanoclusters, covered by N-doped carbon layers as core-shell (Co@NC-800), for the chemoselective reduction of nitroarenes is reported. The Co@NC-800 catalyst was prepared by the pyrolysis of the Co(tpy)₂ complex impregnated on Vulcan carbon. In fact, the use of a mol. complex based on six N-Co bonds drives the formation of a well-defined and distributed cobalt core-shell nanocluster covered by N-doped carbon layers. In order to elucidate its nature, it has been fully characterized by using several advanced techniques. In addition, this as-prepared catalyst showed high activity, chemoselectivity and stability toward the reduction of nitro compounds with H₂ and under mild reaction conditions; water was used as a green solvent, improving the previous results based on cobalt catalysts. Moreover, the Co@NC-800 catalyst is also active and selective for the one-pot synthesis of secondary aryl amines and isoindolinones through the reductive amination of nitroarenes. Finally, based on diffraction and spectroscopic studies, metallic cobalt nanoclusters with surface CoN_x patches have been proposed as the active phase in the Co@NC-800 material. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Formula: C14H11NO).

Zhigulin, A. G. et al. published their research in Zhurnal Fizicheskoi Khimii in 1976 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Formula: C10H10BrN

Mechanism of ionization of indole derivatives in aqueous solutions of strong acids was written by Zhigulin, A. G.;Librovich, N. B.;Yudin, L. G.;Kost, A. N.;Vinnik, M. I.. And the article was included in Zhurnal Fizicheskoi Khimii in 1976.Formula: C10H10BrN This article mentions the following:

The equilibrium constants of protonation and ion-pair formation for 1,2- and 2,3-dimethylindoles substituted by MeO, NO2, and Br groups were determined in aqueous H2SO4, HClO4, and HCl. The acidity of the medium and the activity of the acid affected the equilibrium In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Formula: C10H10BrN).