Tag: 100-200

Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic π-Systems was written by Padwa, Albert;Hertzog, Donald L.;Nadler, William R.. And the article was included in Journal of Organic Chemistry in 1994.Name: 3-(1H-Indol-1-yl)propanoic acid This article mentions the following:

A series of furanyl-, thienyl-, and indolo-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomuenchnone dipoles. The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom. The scope and limitations of the intramol. 1,3-dipolar cycloaddition of the isomuenchnones across a tethered furan and thiophene ring were studied. The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities. The reaction is critically dependent on conformational factors in the transition state. In addition, the first examples of intramol. cycloaddition of isomuenchnones to indole dipolarophiles are reported. Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Name: 3-(1H-Indol-1-yl)propanoic acid).

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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Name: 3-(1H-Indol-1-yl)propanoic acid

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

Photocatalytic Dearomative Intermolecular [2 + 2] Cycloaddition of Heterocycles for Building Molecular Complexity was written by Oderinde, Martins S.;Ramirez, Antonio;Dhar, T. G. Murali;Cornelius, Lyndon A. M.;Jorge, Christine;Aulakh, Darpandeep;Sandhu, Bhupinder;Pawluczyk, Joseph;Sarjeant, Amy A.;Meanwell, Nicholas A.;Mathur, Arvind;Kempson, James. And the article was included in Journal of Organic Chemistry in 2021.Product Details of 167631-84-7 This article mentions the following:

Indole and indoline rings are important pharmacophoric scaffolds found in marketed drugs, agrochems., and biol. active mols. The [2 + 2] cycloaddition reaction is a versatile strategy for constructing architecturally interesting, sp³-rich cyclobutane-fused scaffolds with potential applications in drug discovery programs. A general platform for visible-light mediated intermol. [2 + 2] cycloaddition of indoles with alkenes has been realized. A substrate-based screening approach led to the discovery of tert-butyloxycarbonyl (Boc)-protected indole-2-carboxyesters as suitable motifs for the intermol. [2 + 2] cycloaddition reaction. Significantly, the reaction proceeds in good yield with a wide variety of both activated and unactivated alkenes, including those containing free amines and alcs., and the transformation exhibits excellent regio- and diastereoselectivity. Moreover, the scope of the indole substrate is very broad, extending to previously unexplored azaindole heterocycles that collectively afford fused cyclobutane containing scaffolds that offer unique properties with functional handles and vectors suitable for further derivatization. DFT computational studies provide insights into the mechanism of this [2 + 2] cycloaddition, which is initiated by a triplet-triplet energy transfer process. The photocatalytic reaction was successfully performed on a 100 g scale to provide the dihydroindole analog. 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).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Product Details of 167631-84-7

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

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).

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

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

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).

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

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

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).

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

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

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).

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

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

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).

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

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

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).

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

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

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).

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

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

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).

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

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