172.2264 | - Indole Building Blocks

Dinesha, H. E. et al. published their research in Asian Journal of Chemistry in 2019 | CAS: 16502-01-5

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5) 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.Application of 16502-01-5

A novel method for synthesis of tetrahydro-2H-oxazolo[2,3-a]isoquinolines was written by Dinesha, H. E.;Sandhya, N. C.;Mantelingu, K.. And the article was included in Asian Journal of Chemistry in 2019.Application of 16502-01-5 This article mentions the following:

An efficient and direct method for the synthesis of tetrahydro-2H-oxazolo[2,3-a]isoquinolines I [R = H, 6-OMe; R¹ = H, Me, Ph; R² = H, 4-Me, 2-Br, etc.] was reported. This novel method involved T3P mediated in situ oxidation of benzyl alcs. to aldehyde followed by acetic acid mediated [3 + 2] cycloaddition reaction to afford tetrahydro-2H-oxazolo[2,3-a]isoquinolines I in one-pot operation with good to excellent yields. Heterocyclic alcs. also underwent the reaction with tetrahydroquinolines at room temperature In the experiment, the researchers used many compounds, for example, 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5Application of 16502-01-5).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zheng, Jianbin et al. published their research in Journal of Medicinal Chemistry in 2019 | CAS: 16502-01-5

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5) 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.Computed Properties of C11H12N2

Conversion of Quinazoline Modulators from Inhibitors to Activators of 尾-Glucocerebrosidase was written by Zheng, Jianbin;Jeon, Sohee;Jiang, Weilan;Burbulla, Lena F.;Ysselstein, Daniel;Oevel, Kristine;Krainc, Dimitri;Silverman, Richard B.. And the article was included in Journal of Medicinal Chemistry in 2019.Computed Properties of C11H12N2 This article mentions the following:

Gaucher’s disease is a lysosomal disease caused by mutations in the 尾-glucocerebrosidase gene (GBA1 and GCase) that have been also linked to increased risk of Parkinson’s disease (PD) and Diffuse Lewy body dementia. Prior studies have suggested that mutant GCase protein undergoes misfolding and degradation, and therefore, stabilization of the mutant protein represents an important therapeutic strategy in synucleinopathies. In this work, we present a structure-activity relationship (SAR) study of quinazoline compounds that serve as inhibitors of GCase. Unexpectedly, we found that N-methylation of these inhibitors transformed them into GCase activators. A systematic SAR study further revealed that replacement of the key oxygen atom in the linker of the quinazoline derivative also contributed to the activity switch. PD patient-derived fibroblasts and dopaminergic midbrain neurons were treated with a selected compound (9q) that partially stabilized GCase and improved its activity. These results highlight a novel strategy for therapeutic development of noninhibitory GCase modulators in PD and related synucleinopathies. In the experiment, the researchers used many compounds, for example, 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5Computed Properties of C11H12N2).

Darby, John F. et al. published their research in Scientific Reports in 2020 | CAS: 16502-01-5

Solution structure of the Hop TPR2A domain and investigation of target druggability by NMR, biochemical and in silico approaches was written by Darby, John F.;Vidler, Lewis R.;Simpson, Peter J.;Al-Lazikani, Bissan;Matthews, Stephen J.;Sharp, Swee Y.;Pearl, Laurence H.;Hoelder, Swen;Workman, Paul. And the article was included in Scientific Reports in 2020.Quality Control of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole This article mentions the following:

Heat shock protein 90 (Hsp90) is a mol. chaperone that plays an important role in tumor biol. by promoting the stabilization and activity of oncogenic’ client’ proteins. Inhibition of Hsp90 by small-mol. drugs, acting via its ATP hydrolysis site, has shown promise as a molecularly targeted cancer therapy. Owing to the importance of Hop and other tetratricopeptide repeat (TPR)-containing cochaperones in regulating Hsp90 activity, the Hsp90-TPR domain interface is an alternative site for inhibitors, which could result in effects distinct from ATP site binders. The TPR binding site of Hsp90 cochaperones includes a shallow, pos. charged groove that poses a significant challenge for druggability. Herein, we report the apo, solution-state structure of Hop TPR2A which enables this target for NMR-based screening approaches. We have designed prototype TPR ligands that mimic key native ‘carboxylate clamp’ interactions between Hsp90 and its TPR cochaperones and show that they block binding between Hop TPR2A and the Hsp90 C-terminal MEEVD peptide. We confirm direct TPR-binding of these ligands by mapping 1H-15N HSQC chem. shift perturbations to our new NMR structure. Our work provides a novel structure, a thorough assessment of druggability and robust screening approaches that may offer a potential route, albeit difficult, to address the chem. challenging nature of the Hop TPR2A target, with relevance to other TPR domain interactors. In the experiment, the researchers used many compounds, for example, 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5Quality Control of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole).

Sguazzin, Matthew A. et al. published their research in Organic Letters in 2021 | CAS: 16502-01-5

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5) 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). Application In Synthesis of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole

Hexafluoroisopropyl Sulfamate: A Useful Reagent for the Synthesis of Sulfamates and Sulfamides was written by Sguazzin, Matthew A.;Johnson, Jarrod W.;Magolan, Jakob. And the article was included in Organic Letters in 2021.Application In Synthesis of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole This article mentions the following:

Sulfamates and sulfamides were most often synthesized from alcs. and amines with sulfamoyl chloride, which was an unstable reagent. Hexafluoroisopropyl sulfamate (HFIPS) as a bench-stable solid that reacts readily with a wide variety of alcs., amines, phenols, and anilines under mild reaction conditions was identified. The sole byproduct of the reaction was hexafluoroisopropanol (HFIP) and reaction products was often isolated in high purity after an aqueous workup (optional) and removal of solvents by evaporation In the experiment, the researchers used many compounds, for example, 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5Application In Synthesis of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole).

Zhao, Si-Yu et al. published their research in Molecules in 2017 | CAS: 16502-01-5

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5) 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.SDS of cas: 16502-01-5

Chemotaxonomic classification applied to the identification of two closely-related Citrus TCMs using UPLC-Q-TOF-MS-based metabolomics was written by Zhao, Si-Yu;Liu, Zhen-Li;Shu, Yi-Song;Wang, Meng-Lei;He, Dan;Song, Zhi-Qian;Zeng, Hong-Lian;Ning, Zhang-Chi;Lu, Cheng;Lu, Ai-Ping;Liu, Yuan-Yan. And the article was included in Molecules in 2017.SDS of cas: 16502-01-5 This article mentions the following:

This manuscript elaborates on the establishment of a chemotaxonomic classification strategy for closely-related Citrus fruits in Traditional Chinese Medicines (TCMs). UPLC-Q-TOF-MS-based metabolomics was applied to depict the variable chemotaxonomic markers and elucidate the metabolic mechanism of Citrus TCMs from different species and at different ripening stages. Metabolomics can capture a comprehensive anal. of small mol. metabolites and can provide a powerful approach to establish metabolic profiling, creating a bridge between genotype and phenotype. To further investigate the different metabolites in four closely-related Citrus TCMs, non-targeted metabolite profiling anal. was employed as an efficient technique to profile the primary and secondary metabolites. The results presented in this manuscript indicate that primary metabolites enable the discrimination of species, whereas secondary metabolites are associated with species and the ripening process. In addition, anal. of the biosynthetic pathway highlighted that the syntheses of flavone and flavone glycosides are deeply affected in Citrus ripening stages. Ultimately, this work might provide a feasible strategy for the authentication of Citrus fruits from different species and ripening stages and facilitate a better understanding of their different medicinal uses. In the experiment, the researchers used many compounds, for example, 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5SDS of cas: 16502-01-5).

Zheng, Jianbin et al. published their research in Journal of Medicinal Chemistry in 2019 | CAS: 16502-01-5

Conversion of Quinazoline Modulators from Inhibitors to Activators of β-Glucocerebrosidase was written by Zheng, Jianbin;Jeon, Sohee;Jiang, Weilan;Burbulla, Lena F.;Ysselstein, Daniel;Oevel, Kristine;Krainc, Dimitri;Silverman, Richard B.. And the article was included in Journal of Medicinal Chemistry in 2019.Computed Properties of C11H12N2 This article mentions the following:

Gaucher’s disease is a lysosomal disease caused by mutations in the β-glucocerebrosidase gene (GBA1 and GCase) that have been also linked to increased risk of Parkinson’s disease (PD) and Diffuse Lewy body dementia. Prior studies have suggested that mutant GCase protein undergoes misfolding and degradation, and therefore, stabilization of the mutant protein represents an important therapeutic strategy in synucleinopathies. In this work, we present a structure-activity relationship (SAR) study of quinazoline compounds that serve as inhibitors of GCase. Unexpectedly, we found that N-methylation of these inhibitors transformed them into GCase activators. A systematic SAR study further revealed that replacement of the key oxygen atom in the linker of the quinazoline derivative also contributed to the activity switch. PD patient-derived fibroblasts and dopaminergic midbrain neurons were treated with a selected compound (9q) that partially stabilized GCase and improved its activity. These results highlight a novel strategy for therapeutic development of noninhibitory GCase modulators in PD and related synucleinopathies. In the experiment, the researchers used many compounds, for example, 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5Computed Properties of C11H12N2).

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