Day: February 22, 2023

Indole-3-acetic acid is synthesized by the endophyte Cyanodermella asteris via a tryptophan-dependent and -independent way and mediates the interaction with a non-host plant was written by Jahn, Linda;Hofmann, Uta;Ludwig-mueller, Jutta. And the article was included in International Journal of Molecular Sciences in 2021.Category: indole-building-block This article mentions the following:

The plant hormone indole-3-acetic acid (IAA) is one of the main signals playing a role in the communication between host and endophytes. Endophytes can synthesize IAA de novo to influence the IAA homeostasis in plants. Although much is known about IAA biosynthesis in microorganisms, there is still less known about the pathway by which IAA is synthesized in fungal endophytes. The aim of this study is to examine a possible IAA biosynthesis pathway in Cyanodermella asteris. In vitro cultures of C. asteris were incubated with the IAA precursors tryptophan (Trp) and indole, as well as possible intermediates, and they were addnl. treated with IAA biosynthesis inhibitors (2-mercaptobenzimidazole and yucasin DF) to elucidate possible IAA biosynthesis pathways. It was shown that (a) C. asteris synthesized IAA without adding precursors; (b) indole-3-acetonitrile (IAN), indole-3-acetamide (IAM), and indole-3-acetaldehyde (IAD) increased IAA biosynthesis; and (c) C. asteris synthesized IAA also by a Trp-independent pathway. Together with the genome information of C. asteris, the possible IAA biosynthesis pathways found can improve the understanding of IAA biosynthesis in fungal endophytes. The uptake of fungal IAA into Arabidopsis thaliana is necessary for the induction of lateral roots and other fungus-related growth phenotypes, since the application of the influx inhibitor 2-naphthoxyacetic acid (NOA) but not the efflux inhibitor N-1-naphtylphthalamic acid (NPA) were altering these parameters. In addition, the root phenotype of the mutation in an influx carrier, aux1, was partially rescued by C. asteris. In the experiment, the researchers used many compounds, for example, Indole-3-acetamide (cas: 879-37-8Category: indole-building-block).

Indole-3-acetamide (cas: 879-37-8) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Category: indole-building-block

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

Enantioselective Synthesis of Functionalized Arenes by Nickel-Catalyzed Site-Selective Hydroarylation of 1,3-Dienes with Aryl Boronates was written by Marcum, Justin S.;Taylor, Tiffany R.;Meek, Simon J.. And the article was included in Angewandte Chemie, International Edition in 2020.Category: indole-building-block This article mentions the following:

A catalytic method for the site-selective and enantioselective synthesis of functionalized arenes by the intermol. hydroarylation of terminal and internal 1,3-dienes with aryl pinacolato boronates is reported. The reactions are promoted by 5.0 mol % of a readily available monodentate phosphoramidite-Ni complex in ethanol, affording a variety of enantioenriched products in up to 96% yield and 99:1 er. Mechanistic studies indicate that Ni-allyl formation is irreversible and related to the nature of the arylboronate. In the experiment, the researchers used many compounds, for example, 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (cas: 837392-62-8Category: indole-building-block).

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (cas: 837392-62-8) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Category: indole-building-block

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

Effect of selection of QTc formula on eligibility of cancer patients for phase I clinical trials was written by Borad, Mitesh J.;Soman, Arundhati D.;Benjamin, Martin;Casa, Daniel;Tembe, Waibhav D.;Piper, Barbara F.;Ramanathan, Ramesh;Tibes, Raoul;Jameson, Gayle;Ansaldo, Karen;Hoff, Daniel D.. And the article was included in Investigational New Drugs in 2013.Computed Properties of C19H20N2O3 This article mentions the following:

A retrospective anal. of 130 patients was conducted in a Phase I oncol. clinic to assess the effect of QTc formula selection on clin. trial eligibility. QTc values were calculated from screening electrocardiograms using 7 formulas (Bazett, Fridericia, Framingham, Hodges, Mayeda, Van de Water and Wohlfart). QTc values>470 ms for females and>450 ms for males were used to define prolongation. Concomitant medication potential for QTc prolongation was determined using a public database (AzCert). Ineligibility rates ranged from 3.1 % to 17.7 % (Framingham: 3.1 %, Van de Water: 3.1 %, Hodges: 3.1 %, Wohlfart: 3.1 %, Fridericia: 3.9 %, Bazett: 10.8 % and Mayeda: 17.7 %). A consistent ineligibility rate was achieved by using formulas-specific thresholds. Fifty one percent of patients were taking concomitant medications with QTc prolongation potential. The proportion of concomitant medications with the potential to prolong QTc was 11.57 % (96 of 830). Uniform criteria and guidelines for selection of QTc formulas need to be developed. Formulas-specific QTc thresholds also need to be specified. In the experiment, the researchers used many compounds, for example, rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate (cas: 115956-12-2Computed Properties of C19H20N2O3).

rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate (cas: 115956-12-2) 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.Computed Properties of C19H20N2O3

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

Stereoselective Synthesis of Vinylcyclopropa[b]indolines via a Rh-Migration Strategy was written by Guo, Pan;Sun, Wangbin;Liu, Yu;Li, Yong-Xin;Loh, Teck-Peng;Jiang, Yaojia. And the article was included in Organic Letters in 2020.Computed Properties of C7H6N2 This article mentions the following:

A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[b]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes in situ. By employing a Rh-migration strategy, the products can be obtained with good to excellent E:Z ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities. In the experiment, the researchers used many compounds, for example, 1H-Pyrrolo[2,3-b]pyridine (cas: 271-63-6Computed Properties of C7H6N2).

1H-Pyrrolo[2,3-b]pyridine (cas: 271-63-6) 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. 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 C7H6N2

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

Synthesis and evaluation of the anti-proliferative activity of diaryl-3-pyrrolin-2-ones and fused analogs was written by Mowery, Patricia;Banales Mejia, Fernando;Franceschi, Courtney L.;Kean, Maeve H.;Kwansare, Deborah O.;Lafferty, Megan M.;Neerukonda, Namita D.;Rolph, Carly E.;Truax, Nathanyal J.;Pelkey, Erin T.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Formula: C11H11NO2 This article mentions the following:

Analogs containing a central 3-pyrrolin-2-one core with different methoxyphenyl and/or indole substituents, e.g. I, were prepared and tested for anti-proliferative activity in U-937 cells. The most efficacious analogs were non-rigid, (non-fused) contained methoxyaryl groups located at the 4-position, and contained either methoxyaryl or indole groups located at the 3-position. Both the number of methoxy groups contained in the substituents and the particular location of the indole rings with respect to the lactam carbonyl had significant affects on anti-proliferative activity. This work provides a framework to better understand structure-activity relationships for inducing anti-proliferative activity in diaryl heterocyclic scaffolds. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-indoleacetic acid (cas: 1912-48-7Formula: C11H11NO2).

1-Methyl-3-indoleacetic acid (cas: 1912-48-7) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Formula: 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

Acceptorless Dehydrogenation of N-Heterocycles and Secondary Alcohols by Ru(II)-NNC Complexes Bearing a Pyrazoyl-indolyl-pyridine Ligand was written by Wang, Qingfu;Chai, Huining;Yu, Zhengkun. And the article was included in Organometallics in 2018.Formula: C8H8FN This article mentions the following:

Ru(II) hydride complexes bearing a pyrazolyl-(2-indol-1-yl)-pyridine ligand were synthesized and structurally characterized by NMR anal. and x-ray single crystal crystallog. determinations These complexes efficiently catalyzed acceptorless dehydrogenation of N-heterocycles and secondary alcs., resp., exhibiting highly catalytic activity with a broad substrate scope. The present work established a strategy to construct highly active transition-metal complex catalysts, and provides an atom-economical and environmentally benign protocol for the synthesis of aromatic N-heterocyclic compounds and ketones. In the experiment, the researchers used many compounds, for example, 5-Fluoroindoline (cas: 2343-22-8Formula: C8H8FN).

5-Fluoroindoline (cas: 2343-22-8) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Formula: C8H8FN

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

ω-Phthalimidoalkyl Aryl Ureas as Potent and Selective Inhibitors of Cholesterol Esterase was written by Dato, Florian M.;Sheikh, Miriam;Uhl, Rocky Z.;Schueller, Alexandra W.;Steinkrueger, Michaela;Koch, Peter;Neudoerfl, Joerg-Martin;Guetschow, Michael;Goldfuss, Bernd;Pietsch, Markus. And the article was included in ChemMedChem in 2018.Product Details of 3130-75-4 This article mentions the following:

Cholesterol esterase (CEase), a serine hydrolase thought to be involved in atherogenesis and thus coronary heart disease, is considered as a target for inhibitor development. We investigated recombinant human and murine CEases with a new fluorometric assay in a structure-activity relationship study of a small library of ω-phthalimidoalkyl aryl ureas. The urea motif with an attached 3,5-bis(trifluoromethyl)phenyl group and the aromatic character of the ω-phthalimide residue were most important for inhibitory activity. In addition, an alkyl chain composed of three or four methylene groups, connecting the urea and phthalimide moieties, was found to be an optimal spacer for inhibitors. The so-optimized compounds 2 [1-(3,5-bis(trifluoromethyl)phenyl)-3-(3-(1,3-dioxoisoindolin-2-yl)propyl)urea] and 21 [1-(3,5-bis(trifluoromethyl)phenyl)-3-(4-(1,3-dioxoisoindolin-2-yl)butyl)urea] exhibited dissociation constants (K_i) of 1-19 μM on the two CEases and showed either a competitive (2 on the human enzyme and 21 on the murine enzyme) or a noncompetitive mode of inhibition. Two related human serine hydrolases – monoacylglycerol lipase (MAGL)and fatty acid amide hydrolase (FAAH) – were inhibited by ω-phthalimidoalkyl aryl ureas to a lesser extent. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4Product Details of 3130-75-4).

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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. 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 3130-75-4

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

In vitro treatment of mouse and human cells with endogenous ligands for activation of the aryl hydrocarbon receptor was written by Yamada, Taisho;Takaoka, Akinori. And the article was included in Bio-Protocol in 2017.Category: indole-building-block This article mentions the following:

Activation of the aryl hydrocarbon receptor (AHR) by endogenous ligands has been implicated in a variety of physiol. processes such as cell cycle regulation, cell differentiation and immune responses. It is reported that tryptophan metabolites, such as kynurenine (Kyn) and 6-formylindolo(3,2-b)carbazole (FICZ), are endogenous ligands for AHR (Stockinger et al., 2014). This protocol is designed for treatment with Kyn or FICZ in mouse embryonic fibroblasts (MEFs) or primary peripheral monocytes. In the experiment, the researchers used many compounds, for example, 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7Category: indole-building-block).

5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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). Category: indole-building-block

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

High Proportion of Chiral Crystallization of Achiral Indolyl Sulfonamides: Effect of Intermolecular Interactions was written by Kikkawa, Shoko;Maeno, Isae;Katagiri, Kosuke;Murayama, Yuta;Nozawa, Mariko;Hikawa, Hidemasa;Azumaya, Isao. And the article was included in Crystal Growth & Design in 2021.Product Details of 4769-97-5 This article mentions the following:

We investigated the effect of indole moieties on chiral crystallization In this regard, we assessed the influence of intermol. interactions and contacts on the assembly of these mols. A systematic anal. of 62 crystal structures of secondary aromatic sulfonamides bearing 4-, 5-, 6-, and 7-aminoindolyl groups revealed that the proportion of indolyl compounds showing chiral crystallization was apparently higher (21%, except for crypto-racemate) than that of nonindolyl sulfonamides (11%). Moreover, 33% (5 out of 15 crystals) and 44% (7 out of 16 crystals) of 4- and 7-indolyl sulfonamide derivatives preferred chiral crystallization, resp. This suggested a correlation between the type of contact and the chirality of the assembly of adjacent mols. Specifically, the proportion of achiral indolyl sulfonamides undergoing chiral crystallization was drastically increased by N(indole)H···O interactions, slightly increased by C(sp²)H···π interactions, and decreased owing to π···π interactions. These tendencies were also true for sulfonamides with different substituents, which suggested that the T-shape contact would be more favorable than π···π interactions for chiral crystallization In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5Product Details of 4769-97-5).

4-Nitroindole (cas: 4769-97-5) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Product Details of 4769-97-5

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

Design, synthesis and evaluation of new bioactive oxadiazole derivatives as anticancer agents targeting Bcl-2 was written by Hamdy, Rania;Elseginy, Samia A.;Ziedan, Noha I.;El-Sadek, Mohamed;Lashin, Elsaid;Jones, Arwyn T.;Westwell, Andrew D.. And the article was included in International Journal of Molecular Sciences in 2020.Application In Synthesis of 5-Methoxyindole-2-carboxylic acid This article mentions the following:

A series of 2-(1H-indol-3-yl)-5-substituted-1,3,4-oxadiazoles I [R = benzyl, 4-methylphenoxymethyl, 4-nitrophenyl, etc.] were designed, synthesized and tested in-vitro as potential pro-apoptotic Bcl-2 inhibitory anticancer agents based on previously reported compounds Synthesis of the target 1,3,4-oxadiazoles I were readily accomplished through a cyclization reaction of indole carboxylic acid hydrazide with substituted carboxylic acid derivatives RC(O)OH in the presence of phosphorus oxychloride. New compounds I showed a range of IC₅₀ values concentrated in the low micromolar range selectively in Bcl-2 pos. human cancer cell lines. The most potent candidate I [R = 4-trifluorophenyl] showed selective IC₅₀ values of 0.52-0.88μM against Bcl-2 expressing cell lines with no inhibitory effects in the Bcl-2 neg. cell line. Moreover, I [R = 4-trifluorophenyl] showed binding that was two-fold more potent than the pos. control gossypol in the Bcl-2 ELISA binding affinity assay. Mol. modeling studies helped to further rationalize anti-apoptotic Bcl-2 binding and identified compound I [R = 4-trifluorophenyl] as a candidate with drug-like properties for further investigation as a selective Bcl-2 inhibitory anticancer agent. In the experiment, the researchers used many compounds, for example, 5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1Application In Synthesis of 5-Methoxyindole-2-carboxylic acid).

5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1) 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.Application In Synthesis of 5-Methoxyindole-2-carboxylic 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