05/01/2023 - Page 7 of 11 - Indole Building Blocks

Cox, Brian et al. published their research in ACS Medicinal Chemistry 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Computed Properties of C9H6BrNO2

Escaping from Flatland: Antimalarial Activity of sp³-Rich Bridged Pyrrolidine Derivatives was written by Cox, Brian;Duffy, James;Zdorichenko, Victor;Bellanger, Corentin;Hurcum, Jessica;Laleu, Benoit;Booker-Milburn, Kevin I.;Elliott, Luke D.;Robertson-Ralph, Michael;Swain, Christopher J.;Bishop, Stephen J.;Hallyburton, Irene;Anderson, Mark. And the article was included in ACS Medicinal Chemistry Letters in 2020.Computed Properties of C9H6BrNO2 This article mentions the following:

Synthetic photochem. to generate novel sp3-rich scaffolds and report the design, synthesis, and biol. testing of a diverse series of amides based on the 1-(amino-methyl)-2-benzyl-2-aza-bicyclo[2.1.1]hexane scaffold was utilized . Preliminary antimalarial screening of the library provided promising compounds with activity in the 1-5μM range with an enhanced hit rate. Further evaluation (solubility, drug metabolism and pharmacokinetics (DMPK), and toxicity) of a selected compound (9) suggested that this series represents an excellent opportunity for further optimization with the framework offering multiple opportunities for the addition of uniquely vectorally positioned extra functionality. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Computed Properties of C9H6BrNO2).

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

Zaryanova, Ekaterina V. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2017 | CAS: 112656-95-8

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

Oxindole-based intraocular pressure reducing agents was written by Zaryanova, Ekaterina V.;Lozinskaya, Nataly A.;Beznos, Olga V.;Volkova, Maria S.;Chesnokova, Nataly B.;Zefirov, Nikolay S.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.HPLC of Formula: 112656-95-8 This article mentions the following:

The study represents the new findings at the crossroads of chem. and medicine, particularly between medicinal and organic chem. and ophthalmol. In this work we describe how the chem. reactivity of indolinone scaffold may be used to create small mol. ligands with strong biol. response comparable with and larger than that of endogenous hormone. The synthesis of oxindole-based melatonin and 5-methoxycarbonylamino-N-acetyltryptamine (5-MCA-NAT) analogs was proposed and their ability to influence intraocular pressure (IOP) was studied in vivo. Time-dependent study revealed the prolonged effect (more than 6 h) of the lead-compound This effect in combination with high IOP reducing effect (41 ± 6%) in low concentrations of the active compound (0.1 wt%) and with high water solubility represents a great potential of low-cost oxindole derivatives as potent antiglaucoma agents. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8HPLC of Formula: 112656-95-8).

Pan, Han-Peng et al. published their research in Journal of Organic Chemistry in 2021 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Quality Control of 5-Bromo-2,3-dimethyl-1H-indole

Dearomatization of 2,3-Disubstituted Indoles via 1,8-Addition of Propargylic (Aza)-para-Quinone Methides was written by Pan, Han-Peng;Zhu, Zhi-Qiang;Qiu, Zong-Wang;Liu, Hong-Fu;Ma, Jiong-Dong;Li, Bao Qiong;Feng, Na;Ma, Ai-Jun;Peng, Jin-Bao;Zhang, Xiang-Zhi. And the article was included in Journal of Organic Chemistry in 2021.Quality Control of 5-Bromo-2,3-dimethyl-1H-indole This article mentions the following:

An efficient method for dearomatization of 2,3-disubstituted indoles to generate diverse indolimines with tetrasubstituted allenes is described. This work accomplishes dearomatization of 2,3-disubstituted indoles I [R¹ = H, F, MeO, MeO₂C, etc.; R² = R³ = Me; R²R³ = (CH₂)₄] through 1,8-addition of (aza)-para-quinone methides, generated in situ from propargylic alcs. II (R⁴ = OH, AcNH, t-BuCONH, TsNH, etc.; R⁵ = Me, n-Pr, Ph, 4-FC₆H₄, 4-ClC₆H₄; R⁶ = n-Bu, cyclopropyl, 1-cyclohexenyl, Ph, etc.). A series of synthetically useful indolenines containing quaternary carbon centers and tetrasubstituted allenes III can be accessed in good yields (up to 99%). Addnl., the separability of product isomers, diversified product transformations, and easy scale-up of the reaction demonstrate the potential application of this method. 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).

Bowman, W. Russell et al. published their research in Tetrahedron in 1994 | 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Recommanded Product: 14204-27-4

Generation of aminyl radicals using sulfenamides as synthetic precursors was written by Bowman, W. Russell;Clark, David N.;Marmon, Robert J.. And the article was included in Tetrahedron in 1994.Recommanded Product: 14204-27-4 This article mentions the following:

Sulfenamides R¹R²NSPh (R¹, R² = alkyl, cycloalkyl, bicycloalkyl, aryl et al.)are synthesized from reactions of R¹R²NH and N-(benzenesulfenyl)phthalimide or PhSCl. The sulfenamides undergo reaction with Bu₃SnH to yield aminyl radicals which can be cyclized onto suitable alkenes. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Recommanded Product: 14204-27-4).

Zhu, Peng-Long et al. published their research in ChemCatChem in 2015 | 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. 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 5-Chloroindole-3-carboxaldehyde

Gold- and Silver-Catalyzed Intramolecular Cyclizations of Indolylcyclopropenes for the Divergent Synthesis of Azepinoindoles and Spiroindoline Piperidines was written by Zhu, Peng-Long;Zhang, Zhen;Tang, Xiang-Ying;Marek, Ilan;Shi, Min. And the article was included in ChemCatChem in 2015.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Gold- and silver-catalyzed intramol. cycloisomerizations of nitrogen or carbon-tethered indolylcyclopropenes I [X = 4-BrC₆H₄SO₂N, 4-O₂NC₆H₄SO₂, 4-H₃CC₆H₄SO₂, C(CO₂CH₃)₂; Y = CH₂, CH₂CH₂; R¹ = H, 5-Me, 7-Me, etc.; R² = Et, Me, Bn] to furnish biol. and pharmaceutically valuable azepino[4,5-b]indoles II and spiro[indoline-3,4′-piperidine] derivatives III have been developed. Both reactions exhibit high chemoselectivity and stereospecificity through completely different reaction pathways. Based on mechanistic studies, it is well demonstrated that gold and silver catalysts act differently to promote the anti- and syn-addition and the steric effect of the catalysts play an important role to switch the addition mode, affording the catalyst-controlled-divergent synthesis. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

Katekar, GerardF. et al. published their research in Phytochemistry (Elsevier) in 1983 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid

Auxins. Part 3. Structure-activity differences between indoleacetic acid auxins on pea and wheat was written by Katekar, GerardF.;Geissler, Art E.. And the article was included in Phytochemistry (Elsevier) in 1983.Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

A series of halogenated indoleacetic acids were assessed for auxin activity on pea stem and wheat coleoptile sections. Activity differences between the 2 species were found. These are discussed in terms of differences in receptor models for pea and wheat, with the models differing in the areas covered by the 6- and 7-substituted compounds In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid).

Hong, Jiankai et al. published their research in New Journal of Chemistry in 2022 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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.Safety of 5,6-Difluoroindoline-2,3-dione

Copper(I)-catalyzed synthesis of natural alkaloid tryptanthrin and its derivatives was written by Hong, Jiankai;Zhang, Min;Shi, Liang;Liu, Peng;Guo, Yuchao;Zhao, Ting;Li, Qing X.;Yang, Liuqing. And the article was included in New Journal of Chemistry in 2022.Safety of 5,6-Difluoroindoline-2,3-dione This article mentions the following:

A mild method for the preparation of tryptanthrin and its derivatives by copper(I) catalysis with two identical isatins in the presence of KHCO₃ as a base was described. Furthermore, more complicated tryptanthrin derivatives were obtained in two steps with two different isatins in one pot. This work featured readily available starting materials, mild reaction conditions, simple operation, good functional group tolerance, high yields and selectivity. This transformation not only provided a new method to access tryptanthrin and its derivatives, but also enriched the chem. of isatins and copper catalysis. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Safety of 5,6-Difluoroindoline-2,3-dione).

Rodriguez, Jessica et al. published their research in ACS Catalysis in 2022 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 6-Nitro-1H-indole

Au(I)/Au(III) Catalytic Allylation Involving π-Allyl Au(III) Complexes was written by Rodriguez, Jessica;Vesseur, David;Tabey, Alexis;Mallet-Ladeira, Sonia;Miqueu, Karinne;Bourissou, Didier. And the article was included in ACS Catalysis in 2022.Recommanded Product: 6-Nitro-1H-indole This article mentions the following:

A (MeDalphos)AuCl complex was found to efficiently catalyze the cross-coupling of indoles and allyl acetates/alcs. The reaction tolerated many functional groups and selectively affords the branched C3-allylated products from both α- and γ-substituted allyl substrates. It took the advantage of the hemilabile character of the PN ligand. The C(sp²)-C(sp³) coupling operated via a Au(I)/Au(III) redox cycle and involves a dicationic π-allyl Au(III) complex as a key intermediate. In this case, the allyl moiety adopted an asym. σ + π-coordination mode, as substantiated by NMR spectroscopy and d. functional theory (DFT) calculations In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 6-Nitro-1H-indole).

Rani, B. Shoba et al. published their research in International Journal of Pharmacy and Biological Sciences in 2016 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Category: indole-building-block

Antioxidant activity profile of some new benzimidazole carbamates was written by Rani, B. Shoba;Priyanka, K. Blessi;Harikiran, L.;Sammaiah, G.. And the article was included in International Journal of Pharmacy and Biological Sciences in 2016.Category: indole-building-block This article mentions the following:

The present study involves the antioxidant study of 3-((5-((6-benzoyl)-1H-benzo[d]imidazol -2-yl) amino)-1, 3, 4-oxadiazol-2-yl imino) substituted indolin-2-ones by DPPH assay method. Among the compounds, compound without any substitution possessed good activity when compared with Ascorbic acid. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Category: indole-building-block).

Kumar, Vishal et al. published their research in Advanced Synthesis & Catalysis in 2012 | 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Reference of 5388-42-1

Cobalt(II) Phthalocyanine-Catalyzed Highly Chemoselective Reductive Amination of Carbonyl Compounds in a Green Solvent was written by Kumar, Vishal;Sharma, Upendra;Verma, Praveen K.;Kumar, Neeraj;Singh, Bikram. And the article was included in Advanced Synthesis & Catalysis in 2012.Reference of 5388-42-1 This article mentions the following:

Cobalt phthalocyanine has been employed for the highly chemoselective reductive amination of aldehydes and ketones in ethanol as a green solvent. A large range of functional groups such as nitro, acid, amide, ester, nitrile, halogen, lactone, methoxy, hydroxy, alkene, N-benzyl, O-benzyl and heterocyclic rings were well tolerated under the present reaction conditions. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).