January 2023 - Page 8 of 26 - Indole Building Blocks

Pang, Yuan-Ping et al. published their research in Journal of the American Chemical Society in 1999 | CAS: 6639-06-1

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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 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). Computed Properties of C11H11NO2

Computational and Experimental Studies of (2,2)-Bis(indol-1-yl-methyl)acetate Suggest the Importance of the Hydrophobic Effect in Aromatic Stacking Interactions was written by Pang, Yuan-Ping;Miller, Jennifer L.;Kollman, Peter A.. And the article was included in Journal of the American Chemical Society in 1999.Computed Properties of C11H11NO2 This article mentions the following:

To understand the driving forces of aromatic stacking interactions in water, we have performed conformational searches, mol. dynamics simulations, potential of mean force (PMF) and free energy perturbation (FEP) calculations, syntheses, and NMR studies on sodium (2,2)-bis(indol-1-yl-methyl)acetate (1), sodium 3-indol-1-yl-2-methyl-propionate (2), and sodium 3-indol-1-yl-propionate (3). The conformational searches on 1 revealed that the isobutyric acid linker of 1 allows the mol. to adopt the tilted T-shaped stacked, off-center stacked, face-to-face stacked, and non-stacked conformations in a vacuum. The PMF and FEP calculations suggested that the most thermodynamically stable conformers in water are the tilted T-shaped stacked and non-stacked conformers. Independent NMR spectroscopic studies of 1-3 revealed that both the tilted T-shaped stacked and non-stacked conformers are populated in D₂O and in d₆-DMSO, and they are in a rapid equilibrium Furthermore, the NMR studies found (i) a larger population of the tilted T-shaped stacked conformation of 1 at 22 ° in D₂O than in d₆-DMSO and (ii) more different populated stacked conformations of 1 at 60° in D₂O than in d₆-DMSO. One would expect larger populations of the stacked conformations in d₆-DMSO, whose dielec. constant is smaller than that of water, if the electrostatic interaction were the only driving force of the aromatic stacking interactions. The results, therefore, suggest that the hydrophobic effect plays an important role in the stacking interaction of 1 in water. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Computed Properties of C11H11NO2).

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

Cai, Lu et al. published their research in Organic Letters in 2019 | CAS: 85696-95-3

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) 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.Reference of 85696-95-3

Chiral Phosphoric-Acid-Catalyzed Regioselective and Enantioselective C7-Friedel-Crafts Alkylation of 4-Aminoindoles with Trifluoromethyl Ketones was written by Cai, Lu;Zhao, Yunlong;Huang, Tongkun;Meng, Shanshui;Jia, Xian;Chan, Albert S. C.;Zhao, Junling. And the article was included in Organic Letters in 2019.Reference of 85696-95-3 This article mentions the following:

A highly regioselective and enantioselective C7-Friedel-Crafts alkylation of 4-aminoindoles with trifluoromethyl ketones promoted by a spirocyclic phosphoric acid was developed. This strategy was applicable to various substituted trifluoromethyl ketones and 4-aminoindole derivatives, affording the corresponding C7-functionalized indole derivatives, bearing a pharmaceutically interesting trifluoromethylated tertiary alc. scaffold, in 21%-98% yields with up to >99% enantiomeric excess (ee). In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Reference of 85696-95-3).

Shen, Mengqi et al. published their research in Journal of the American Chemical Society in 2018 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: 6-Nitro-1H-indole

Room-Temperature Chemoselective Reduction of 3-Nitrostyrene to 3-Vinylaniline by Ammonia Borane over Cu Nanoparticles was written by Shen, Mengqi;Liu, Hu;Yu, Chao;Yin, Zhouyang;Muzzio, Michelle;Li, Junrui;Xi, Zheng;Yu, Yongsheng;Sun, Shouheng. And the article was included in Journal of the American Chemical Society in 2018.Recommanded Product: 6-Nitro-1H-indole This article mentions the following:

We report a new strategy of controlling catalytic activity and selectivity of Cu nanoparticles (NPs) for the ammonia borane-initiated hydrogenation reaction. Cu NPs are active and selective for chemoselective reduction of nitrostyrene to vinylaniline under ambient conditions. Their activity, selectivity, and more importantly, stability are greatly enhanced by their anchoring on WO_2.72 nanorods, providing a room-temperature full conversion of nitrostyrene selectively to vinylaniline (>99% yield). Compared with all other catalysts developed thus far, our new Cu/WO_2.72 catalyst shows much enhanced hydrogenation selectivity and stability without the use of pressured hydrogen. The synthetic approach demonstrated here can be extended to prepare various M/WO_2.72 catalysts (M = Fe, Co, Ni), with M being stabilized for many chem. reactions. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 6-Nitro-1H-indole).

Sammaiah, G. et al. published their research in International Journal of Chemical Sciences in 2008 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Safety of 7-Nitroindoline-2,3-dione

Anticancer and antioxidant activities of 2-aminobenzoic acid (2-oxo-1,2-dihydro-indol-3-ylidene) hydrazides was written by Sammaiah, G.;Narsaiah, N.;Krishnaveni, J.;Dayakar, G.;Sarangapani, M.. And the article was included in International Journal of Chemical Sciences in 2008.Safety of 7-Nitroindoline-2,3-dione This article mentions the following:

In this communication, the anticancer and antioxidant activities of some new 2-aminobenzoic acid (2-oxo-1,2-dihydro-indol-3-ylidene) hydrazides are presented. The new compounds were prepared by the condensation of indole-2,3-diones with 2-aminobenzoic acid hydrazide. All the compounds were evaluated for anticancer activity (against HeLa cell lines, IMR-32 cell lines) and antioxidant activity. Some of the compounds exhibited moderate anticancer activity against the cell lines employed and promising antioxidant activity. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Safety of 7-Nitroindoline-2,3-dione).

Murugesan, Kathiravan et al. published their research in Green Chemistry in 2018 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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: 5-Bromo-3-cyanoindole

Stable and reusable nanoscale Fe₂O₃-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides was written by Murugesan, Kathiravan;Senthamarai, Thirusangumurugan;Sohail, Manzar;Sharif, Muhammad;Kalevaru, Narayana V.;Jagadeesh, Rajenahally V.. And the article was included in Green Chemistry in 2018.Recommanded Product: 5-Bromo-3-cyanoindole This article mentions the following:

The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized mols. is of fundamental interest because nitrogen-containing motifs are found in a large number of life science mols., natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O₂ or air was reported. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesize functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Addnl., applying this iron-based protocol, primary amides have also been prepared in a water medium. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Recommanded Product: 5-Bromo-3-cyanoindole).

Cui, Yi et al. published their research in New Journal of Chemistry in 2008 | CAS: 85696-95-3

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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). Formula: C9H10N2

The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogen storage was written by Cui, Yi;Kwok, Samantha;Bucholtz, Andrew;Davis, Boyd;Whitney, Ralph A.;Jessop, Philip G.. And the article was included in New Journal of Chemistry in 2008.Formula: C9H10N2 This article mentions the following:

Substituted piperidines and octahydroindoles are compared in terms of their usability as reversible organic hydrogen storage liquids for hydrogen-powered fuel cells. Theor. Gaussian calculations indicate which structural features probably lower the enthalpy of dehydrogenation. Exptl. results show that attaching electron donating or conjugated substituents to the piperidine ring greatly increases the rate of catalytic dehydrogenation, with the greatest rates being observed with 4-aminopiperidine and piperidine-4-carboxamide. Undesired side reactions were observed with some compounds such as alkyl transfer reactions during the dehydrogenation of 4-dimethylaminopiperidine, C-O and C-N cleavage reactions during hydrogenation and/or subsequent dehydrogenation of 4-alkoxy- and 4-aminoindoles, and disproportionation during the hydrogenation of 4-aminopyridine. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Formula: C9H10N2).

Zhao, Yin et al. published their research in Synlett in 2022 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde

Visible-Light-Promoted Indole C-3 Formylation Using Eosin Y as a Photoredox Catalyst was written by Zhao, Yin;Li, Hongfang;Yin, Shan;Wu, Yandan;Ni, Guanghui. And the article was included in Synlett in 2022.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A visible-light-mediated C-3 formylation of indole catalyzed by eosin Y has been developed using tetramethylethylenediamine as a carbon source and air as an oxidant. This protocol shows high tolerance to a large quantity of functional groups under mild conditions and provides 3-formylated indoles with good yields. This method is a highly attractive alternative to the approach of traditional formylation. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application In Synthesis of 5-Chloroindole-3-carboxaldehyde).

Xu, Dekang et al. published their research in Organic Letters in 2019 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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

Manipulation of Water for Diversified Functionalization of Tetrahydro-β-carbolines (THβCs) with Indoles was written by Xu, Dekang;Ye, Fu;Ye, Jinxiang;Gao, Yu;Chen, Haijun. And the article was included in Organic Letters in 2019.Computed Properties of C8H6N2O2 This article mentions the following:

Water plays a crucial role in organic synthesis. However, diversified functionalization manipulated by water is still rare and remains unexplored. Herein, we report the first water-manipulated protocol to achieve the diversified functionalization of tetrahydro-β-carbolines (THβCs) in an open flask at room temperature that exhibit a broad functional-group tolerance. More water leads to monoarylation, while less water leads to diarylation. Further one-step transformation afforded oxidized bis(indolyl)methanes, eudistomin U, and the related derivatives in satisfactory yields. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Computed Properties of C8H6N2O2).

Pan, Xuling et al. published their research in Frontiers in Chemistry (Lausanne, Switzerland) in 2022 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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.Quality Control of 5-Chloroindole-3-carboxaldehyde

2-alkylation of 3-alkyindoles with unactivated alkenes was written by Pan, Xuling;Liu, Qian;Nong, Yingling. And the article was included in Frontiers in Chemistry (Lausanne, Switzerland) in 2022.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

An acid-catalyzed 2-alkylation of indole mols. is developed. Only catalytic amount of the com. available, inexpensive and traceless hydriodic acid is used as the sole reaction promoter. 2,3-Disubstituted indole mols. bearing congested tertiary carbon centers are afforded as the final products in moderate to excellent yields. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

Cai, Yunfei et al. published their research in Organic Letters in 2012 | 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. 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). SDS of cas: 14204-27-4

Catalytic Asymmetric Sulfenylation of Unprotected 3-Substituted Oxindoles was written by Cai, Yunfei;Li, Jun;Chen, Weiliang;Xie, Mingsheng;Liu, Xiaohua;Lin, Lili;Feng, Xiaoming. And the article was included in Organic Letters in 2012.SDS of cas: 14204-27-4 This article mentions the following:

Catalytic asym. sulfenylation of unprotected 3-substituted oxindoles I (R¹ = Ph, R² = H, 5-Me, 6-Br, 7-F, etc.; R¹ = Me, Et, i-Bu, H₂C:CHCH₂, MeCO₂CH₂, 2-MeC₆H₄, 4-MeOC₆H₄CH₂, 2-naphthylmethyl, etc., R² = H) has been developed via cooperative catalysis of a chiral N,N’-dioxide-Sc(OTf)₃ complex and a Bronsted base. Utilizing readily available N-(phenylthio)phthalimide as the sulfur source, a wide range of optically active 3-phenylthiooxindoles II were obtained in excellent yields with excellent enantioselectivities under mild reaction conditions. 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).