200-300 | - Indole Building Blocks

Hulpia, Fabian et al. published their research in ACS Infectious Diseases in 2020 | CAS: 1000340-39-5

3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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: 1000340-39-5

Structure-Activity Relationship Exploration of 3′-Deoxy-7-deazapurine Nucleoside Analogues as Anti-Trypanosoma brucei Agents was written by Hulpia, Fabian;Campagnaro, Gustavo D.;Alzahrani, Khalid J.;Alfayez, Ibrahim A.;Ungogo, Marzuq A.;Mabille, Dorien;Maes, Louis;de Koning, Harry P.;Caljon, Guy;Van Calenbergh, Serge. And the article was included in ACS Infectious Diseases in 2020.Recommanded Product: 1000340-39-5 This article mentions the following:

Human African trypanosomiasis is a neglected tropical disease caused by Trypanosoma brucei parasites. These protists are unable to produce the purine ring, making them vulnerable to the effects of purine nucleoside analogs. Starting from 3′-deoxytubercidin (5), a lead compound with activity against central-nervous-stage human African trypanosomiasis, we investigate the structure-activity relationships of the purine and ribofuranose rings. The purine ring tolerated only modifications at C7, while from the many alterations of the 3′-deoxyribofuranosyl moiety only the arabino analog 48 showed pronounced antitrypanosomal activity. Profiling of the most potent analogs against resistant T. brucei strains (resistant to pentamidine, diminazene, and isometamidium) showed reduced dependence on uptake mediated by the P2 aminopurine transporter relative to 5. The introduction of a 7-substituent confers up to 10-fold increased affinity for the P1 nucleoside transporter while generally retaining high affinity for P2. Four of the most promising analogs were found to be metabolically stable, earmarking them as suitable backup analogs for lead 5. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Recommanded Product: 1000340-39-5).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Wu, Yinrong et al. published their research in Organic Letters in 2021 | CAS: 89245-41-0

4-Bromoindole-3-acetic Acid (cas: 89245-41-0) 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.Application of 89245-41-0

Copper-Mediated Decarboxylative Coupling between Arylacetic Acids and 1,3-Dicarbonyl Compounds was written by Wu, Yinrong;Wen, Kangmei;Chen, Jiewen;Shi, Jie;Yao, Xingang;Tang, Xiaodong. And the article was included in Organic Letters in 2021.Application of 89245-41-0 This article mentions the following:

A copper-mediated decarboxylative coupling reaction between arylacetic acids and 1,3-dicarbonyl compounds was described for the synthesis of ((indolyl)methyl)-oxocycloalkyl-esters, e.g., I. Significantly, methanocycloocta[b]indoles II [R = COOEt, CONHEt, SO₂Ph, etc.; R¹ = H, 4-Cl, 5-Br, etc.] were also obtained by sequential intramol. dehydrocyclization process in some cases. This protocol featured a broad substrate scope, simple operations, and good yields. Moreover, the products exhibited potent antiproliferative activity against the human cancer cell lines by a MTT assay. In the experiment, the researchers used many compounds, for example, 4-Bromoindole-3-acetic Acid (cas: 89245-41-0Application of 89245-41-0).

Paintner, Franz F. et al. published their research in Synlett in 2002 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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). Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione

Synthetic studies toward tetrodecamycin: an efficient approach to the core structure of the antibiotic was written by Paintner, Franz F.;Allmendinger, Lars;Bauschke, Gerd;Polborn, Kurt. And the article was included in Synlett in 2002.Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

An efficient synthetic pathway to the core structure I of the polyketide antibiotic tetrodecamycin has been developed. Our approach features the acid-catalyzed cyclization of a tert-butyldimethylsilyl protected Me 婵?(缂?hydroxyacyl) tetronate, leading to the novel tricyclic ring skeleton exhibited by I. An insight into the mechanism of this key ring closure step has been gained. Furthermore an alternative pathway to this ring skeleton, based on a fluoride ion induced desilylation-cyclization sequence, has been disclosed. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione).

Hopanna, Mamatha et al. published their research in Environmental Science & Technology in 2020 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. 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.Electric Literature of C14H11NO

Photochemistry of the Organoselenium Compound Ebselen: Direct Photolysis and Reaction with Active Intermediates of Conventional Reactive Species Sensitizers and Quenchers was written by Hopanna, Mamatha;Kelly, Lisa;Blaney, Lee. And the article was included in Environmental Science & Technology in 2020.Electric Literature of C14H11NO This article mentions the following:

Ebselen (EBS), 2-phenyl-1,2-benzisoselenazol-3(2H)-one, is an organoselenium pharmaceutical with antioxidant and anti-inflammatory properties. Furthermore, EBS is an excellent scavenger of reactive oxygen species. This property complicates conventional protocols for sensitizing and quenching reactive species because of potential generation of active intermediates that quickly react with EBS. In this study, the photochem. reactivity of EBS was investigated in the presence of (1) ¹O₂ and ^{闂?/sup>OH sensitizers [rose Bengal (RB), perinaphthanone, and H₂O₂] and (2) reactive species scavenging and quenching agents (sorbic acid, isopropanol, sodium azide, and tert-butanol) that are commonly employed to study photodegradation mechanisms and kinetics. The carbon analog of EBS, namely, 2-phenyl-3H-isoindol-1-one, was included as a reference compound to confirm the impact of the selenium atom on EBS photochem. reactivity. EBS does not undergo acid dissociation, but pH-dependent kinetics were observed in RB-sensitized solutions, suggesting EBS reaction with active intermediates (³RB^2-*, O₂^闂?, and H₂O₂) that are not kinetically relevant for other compounds In addition, the observed rate constant of EBS increased in the presence of sorbic acid, isopropanol, and sodium azide. These findings suggest that conventional reactive species sensitizers, scavengers, and quenchers need to be carefully applied to highly reactive organoselenium compounds to account for reactions that are typically slow for other organic contaminants. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Electric Literature of C14H11NO).}

Guarino, Victor R. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2020 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.COA of Formula: C14H9NO2S

An amide-based sulfenamide prodrug of gamma secretase inhibitor BMS-708163 delivers parent drug from an oral conventional solid dosage form in male beagle dog was written by Guarino, Victor R.;Olson, Richard E.;Everlof, J. Gerry;Wang, Nenghui;McDonald, Ivar;Haskell, Roy;Clarke, Wendy;Lentz, Kimberley A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2020.COA of Formula: C14H9NO2S This article mentions the following:

The objective of this Letter is to report the first (to our knowledge) in vivo proof of concept for a sulfenamide prodrug to orally deliver a poorly soluble drug containing a weakly-acidic NH-acid from a conventional solid dosage formulation. This proof of concept was established using BMS-708163 (1), a gamma secretase inhibitor containing a weakly acidic primary amide NH-acid as the chem. handle for attaching a series of thiol-based promoieties via a sulfenamide linkage. Aqueous stabilities and solubilities are reported for a series of six sulfenamide prodrugs (2-7) of 1. The sulfenamide prodrug containing the cysteine Me ester promoiety (5) was chosen for a orally-dosed PK study in male beagle dog comparing a solubilized formulation of 1 against a solid dosage form of 5 in a cross-over fashion at an equivalent molar dose of 3 mg/kg. Prodrug 5 delivered essentially a superimposable PK profile of 1 compared to the solubilized formulation of 1, without any detectable exposure of 5 in systemic circulation. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4COA of Formula: C14H9NO2S).

Shershov, Valeriy E. et al. published their research in Dyes and Pigments in 2013 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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.Formula: C13H17NO3S

Near-infrared heptamethine cyanine dyes. Synthesis, spectroscopic characterization, thermal properties and photostability was written by Shershov, Valeriy E.;Spitsyn, Maksim A.;Kuznetsova, Viktoriya E.;Timofeev, Edward N.;Ivashkina, Olga A.;Abramov, Ivan S.;Nasedkina, Tatyana V.;Zasedatelev, Alexander S.;Chudinov, Alexander V.. And the article was included in Dyes and Pigments in 2013.Formula: C13H17NO3S This article mentions the following:

Near-IR heptamethine cyanine dyes were synthesized without substitution to the polyene chain but with various substituents on the indoleninium fragments. To develop indotricarbocyanine dyes with improved photochem. characteristics, we studied the relation between the structures of these compounds, their spectral properties, their photostability, and thermal stability. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Formula: C13H17NO3S).

Do Minh, T. et al. published their research in Journal of Organic Chemistry in 1977 | 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 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). Reference of 5388-42-1

Reactions of phthalaldehyde with ammonia and amines was written by Do Minh, T.;Johnson, A. L.;Jones, J. E.;Senise, P. P. Jr.. And the article was included in Journal of Organic Chemistry in 1977.Reference of 5388-42-1 This article mentions the following:

Reactions of phthaladehyde with NH₃ and amines are described. Major products from NH₃ were phthalimidine and 3-(2-cyanophenyl)isoquinoline. Primary amines RNH₂ (R = Me, Ph, etc.) reacted with 2 moles of aldehyde to produce N-substituted adducts I, II whose steric requirements lead to unusual NMR spectra. At elevated temperatures unidentified colored materials were formed. 1-Hydroxyisoindoles are proposed intermediates. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

Qin, Mingze et al. published their research in Journal of Medicinal Chemistry in 2021 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester

Discovery of 4-Arylindolines Containing a Thiazole Moiety as Potential Antitumor Agents Inhibiting the Programmed Cell Death-1/Programmed Cell Death-Ligand 1 Interaction was written by Qin, Mingze;Meng, Yangyang;Yang, Haoshen;Liu, Lei;Zhang, Haotian;Wang, Simeng;Liu, Chunyang;Wu, Xia;Wu, Di;Tian, Ye;Hou, Yunlei;Zhao, Yanfang;Liu, Yajing;Xu, Congjun;Wang, Lihui. And the article was included in Journal of Medicinal Chemistry in 2021.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester This article mentions the following:

Through specific structural modification of a 4-phenylindoline precursor, new 4-arylindolines containing a thiazole moiety were developed and found to be promising modulators of the programmed cell death-1 (PD-1)/programmed cell death-ligand 1 (PD-L1) axis. Compound A30(I) exhibited outstanding biochem. activity, with an IC₅₀ of 11.2 nM in a homogeneous time-resolved fluorescence assay. In the cell-based assay, A30 significantly promoted IFN-缂?secretion and rescued T-cell proliferation, which were inhibited by PD-1 activation. Furthermore, A30 showed favorable in vivo antitumor activity in a mouse 4T1 breast carcinoma model. Moreover, in mouse CT26 colon carcinoma models, A30 potently suppressed the growth of CT26/PD-L1 tumor but did not obviously affect the growth of CT26/vector tumor. The results of flow cytometry anal. indicated that A30 inhibited tumor growth by activating the immune microenvironment. We concluded that A30 is a new starting point for further development of PD-1/PD-L1 interaction inhibitors as antitumor agents. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester).

Denmark, Scott E. et al. published their research in Journal of the American Chemical Society in 2011 | 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Formula: C14H9NO2S

Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes was written by Denmark, Scott E.;Kornfilt, David J. P.;Vogler, Thomas. And the article was included in Journal of the American Chemical Society in 2011.Formula: C14H9NO2S This article mentions the following:

Catalytic asym. sulfenylation of double bonds has been achieved using a BINAM-based phosphoramide catalyst and an electrophilic sulfur source. Simple alkenes as well as styrenes afforded sulfenylated tetrahydrofurans and tetrahydropyrans, e.g., I, by closure with pendant hydroxyl or carboxyl groups. Intermol. thiofunctionalizations were also achieved with simple alcs. or carboxylic acids as the nucleophiles. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Formula: C14H9NO2S).

Li, Fahui et al. published their research in Angewandte Chemie, International Edition in 2015 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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. 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.SDS of cas: 146368-07-2

A Covalent Approach for Site-Specific RNA Labeling in Mammalian Cells was written by Li, Fahui;Dong, Jianshu;Hu, Xiaosong;Gong, Weimin;Li, Jiasong;Shen, Jing;Tian, Huifang;Wang, Jiangyun. And the article was included in Angewandte Chemie, International Edition in 2015.SDS of cas: 146368-07-2 This article mentions the following:

Advances in RNA research and RNA nanotechnol. depend on the ability to manipulate and probe RNA with high precision through chem. approaches, both in vitro and in mammalian cells. However, covalent RNA labeling methods with scope and versatility comparable to those of current protein labeling strategies are underdeveloped. A method is reported for the site- and sequence-specific covalent labeling of RNAs in mammalian cells by using tRNA^Ile2-agmatidine synthetase (Tias) and click chem. The crystal structure of Tias in complex with an azide-bearing agmatine analog was solved to unravel the structural basis for Tias/substrate recognition. The unique RNA sequence specificity and plastic Tias/substrate recognition enable the site-specific transfer of azide/alkyne groups to an RNA mol. of interest in vitro and in mammalian cells. Subsequent click chem. reactions facilitate the versatile labeling, functionalization, and visualization of target RNA. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2SDS of cas: 146368-07-2).