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Bozilovic, Jelena’s team published research in Nucleosides, Nucleotides & Nucleic Acids in 2007 | CAS: 113162-36-0

Methyl 4-fluoro-1H-indole-2-carboxylate(cas: 113162-36-0) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).COA of Formula: C10H8FNO2

COA of Formula: C10H8FNO2On September 30, 2007 ,《Synthesis of Fluorinated Indoles as RNA Analogues》 was published in Nucleosides, Nucleotides & Nucleic Acids. The article was written by Bozilovic, Jelena; Engels, Joachim W.. The article contains the following contents:

Nucleoside analogs, e.g. I, are chem. means to investigate hydrogen bonds, base stacking, and solvation as the three predominant forces that are responsible for the stability of secondary structure of nucleic acids. To obtain deeper insight into the contributions of these interactions to RNA stability apart from the ones exerted by the predominant nucleosides we decided to synthesize some novel nucleic acid analogs where the nucleobases are replaced by fluoroindoles. Fluorinated indoles can be compared to fluorinated benzimidazoles to determine the role of nitrogen in five membered ring system. The synthesis of fluoroindole ribonucleosides is described here. In the experiment, the researchers used Methyl 4-fluoro-1H-indole-2-carboxylate(cas: 113162-36-0COA of Formula: C10H8FNO2)

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

Zhang, Shanshan’s team published research in World Journal of Microbiology & Biotechnology in 2020 | CAS: 120-72-9

1H-Indole(cas: 120-72-9) belongs to indole. 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.SDS of cas: 120-72-9

《Indole contributes to tetracycline resistance via the outer membrane protein OmpN in Vibrio splendidus》 was written by Zhang, Shanshan; Shao, Yina; Zhao, Xuelin; Li, Chenghua; Guo, Ming; Lv, Zhimeng; Zhang, Weiwei. SDS of cas: 120-72-9This research focused onVibrio indole tetracycline resistance outer membrane protein OmpN; Indole; Outer membrane protein; Tetracycline resistance; Vibrio splendidus. The article conveys some information:

As an interspecies and interkingdom signaling mol., indole has recently received attention for its diverse effects on the physiol. of both bacteria and hosts. In this study, indole increased the tetracycline resistance of Vibrio splendidus. The minimal inhibitory concentration of tetracycline was 10μg/mL, and the OD600 of V. splendidus decreased by 94.5% in the presence of 20μg/mL tetracycline; however, the OD600 of V. splendidus with a mixture of 20μg/mL tetracycline and 125μM indole was 10- or 4.5-fold higher than that with only 20μg/mL tetracycline at different time points. The percentage of cells resistant to tetracycline was 600-fold higher in culture with an OD600 of approx. 2.0 than that in culture with an OD600 of 0.5, which also meant that level of indole was correlated to tetracycline resistance of V. splendidus. Furthermore, one differentially expressed protein, which was identified as outer membrane porin OmpN using SDS-PAGE combined with MALDI-TOF/TOF MS, was upregulated. Consequently, expression of the ompN gene in the presence of either tetracycline or indole and simultaneously in the presence of indole and tetracycline was upregulated by 1.8-, 2.54-, and 6.01-fold, resp., compared to the control samples. The combined results demonstrated that indole enhanced the tetracycline resistance of V. splendidus, and this resistance was probably due to upregulation of the outer membrane porin OmpN. The experimental process involved the reaction of 1H-Indole(cas: 120-72-9SDS of cas: 120-72-9)

Surur, Abdrrahman Shemsu’s team published research in Drug Design, Development and Therapy in 2020 | CAS: 120-72-9

《Indole: the after next scaffold of antiplasmodial agents?》 was written by Surur, Abdrrahman Shemsu; Huluka, Solomon Assefa; Mitku, Melese Legesse; Asres, Kaleab. Category: indole-building-block And the article was included in Drug Design, Development and Therapy in 2020. The article conveys some information:

Malaria remains a global public health problem due to the uphill fight against the causative Plasmodium parasites that are relentless in developing resistance. Indole-based antiplasmodial compounds are endowed with multiple modes of action, of which inhibition of hemozoin formation is the major mechanism of action reported for compounds such as cryptolepine, flinderoles, and isosungucine. Indole-based compounds exert their potent activity against chloroquine-resistant Plasmodium strains by inhibiting hemozoin formation in a mode of action different from that of chloroquine or through a novel mechanism of action. For example, dysregulating the sodium and osmotic homeostasis of Plasmodium through inhibition of PfATP4 is the novel mechanism of cipargamin. The potential of developing multi-targeted compounds through mol. hybridization ensures the existence of indole-based compounds in the antimalarial pipeline. In the experiment, the researchers used many compounds, for example, 1H-Indole(cas: 120-72-9Category: indole-building-block)

You, Yong’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2019 | CAS: 399-52-0

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Fluorine-containing aromatics have been incorporated into crop-protection chemicals (herbicides, insecticides, fungicides). Liquid crystals, positron emission tomography, and imaging systems represent new areas where fluoroaromatics and fluoroheterocyclics have gained attention.Category: indole-building-block

The author of 《Enantioselective synthesis of isoquinoline-1,3(2H,4H)-dione derivatives via a chiral phosphoric acid catalyzed aza-Friedel-Crafts reaction》 were You, Yong; Lu, Wen-Ya; Xie, Ke-Xin; Zhao, Jian-Qiang; Wang, Zhen-Hua; Yuan, Wei-Cheng. And the article was published in Chemical Communications (Cambridge, United Kingdom) in 2019. Category: indole-building-block The author mentioned the following in the article:

A highly enantioselective aza-Friedel-Crafts reaction of structurally new ketimines with indoles and pyrrole was developed by using a chiral phosphoric acid as the catalyst. This protocol enabled the first enantioselective synthesis of isoquinoline-1,3(2H,4H)-dione derivatives in good to excellent yields (up to 99% yield) and excellent enantioselectivities (up to >99% ee). In addition to this study using 5-Fluoro-1H-indole, there are many other studies that have used 5-Fluoro-1H-indole(cas: 399-52-0Category: indole-building-block) was used in this study.

Slifirski, Grzegorz’s team published research in European Journal of Medicinal Chemistry in 2019 | CAS: 399-52-0

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).HPLC of Formula: 399-52-0

HPLC of Formula: 399-52-0In 2019 ,《Synthesis of novel pyrido[1,2-c]pyrimidine derivatives with rigidized tryptamine moiety as potential SSRI and 5-HT1A receptor ligands》 appeared in European Journal of Medicinal Chemistry. The author of the article were Slifirski, Grzegorz; Krol, Marek; Kleps, Jerzy; Ulenberg, Szymon; Belka, Mariusz; Baczek, Tomasz; Siwek, Agata; Stachowicz, Katarzyna; Szewczyk, Bernadeta; Nowak, Gabriel; Bojarski, Andrzej; Koziol, Anna E.; Turlo, Jadwiga; Herold, Franciszek. The article conveys some information:

In this study new derivatives of 4-aryl-pyrido[1,2-c]pyrimidine I (R1 = H, Cl, Me, F, OMe; R2 = H, Cl, F, OMe, Me, etc.; R3 = H, F, OMe) having conformationally restricted tryptamine moiety were prepared In vitro studies (RBA) have shown that a few compounds exhibit high affinity to mol. targets 5-HT1A receptor and SERT protein. In general, compounds with an unsubstituted or a para-substituted benzene ring on the pyrido[1,2-c]pyrimidine residue in the terminal part were characterized by higher binding ability, which can be justified by the greater flexibility of the structure. For I [R1 = R2 = R3 = H (II)], I [R1 = H; R2 = F; R3 = H (III)], I (R1 = H; R2 = OMe; R3 = H) and I [R1 = H; R2 = OMe; R3 = OMe (IV)], further in vitro, in vivo and metabolic stability tests were performed. The in vitro studies in the extended receptor profile (D2, 5-HT2A, 5-HT6 and 5-HT7) indicated their selectivity toward the 5-HT1A receptor and SERT protein. The in vivo studies (8-OH-DPAT-induced hypothermia in mice, FST) revealed that II has the properties of presynaptic agonist of the 5-HT1A receptor, and III demonstrated the properties of a presynaptic antagonist of the 5-HT1A receptor. Metabolic stability studies, in turn, showed that few compounds having an unsubstituted indole residue, were more resistant to biotransformation reactions of the first pass phase than was IV containing a 5-methoxy-substituted indole residue. After reading the article, we found that the author used 5-Fluoro-1H-indole(cas: 399-52-0HPLC of Formula: 399-52-0)

Cascioferro, Stella’s team published research in European Journal of Medicinal Chemistry in 2020 | CAS: 399-52-0

《Imidazo[2,1-b] [1,3,4]thiadiazoles with antiproliferative activity against primary and gemcitabine-resistant pancreatic cancer cells》 was published in European Journal of Medicinal Chemistry in 2020. These research results belong to Cascioferro, Stella; Li Petri, Giovanna; Parrino, Barbara; Carbone, Daniela; Funel, Niccola; Bergonzini, Cecilia; Mantini, Giulia; Dekker, Henk; Geerke, Daan; Peters, Godefridus J.; Cirrincione, Girolamo; Giovannetti, Elisa; Diana, Patrizia. Safety of 5-Fluoro-1H-indole The article mentions the following:

A new series of eighteen HBr salts or free bases of imidazo[2,1-b][1,3,4]thiadiazoles I [R = H, MeO, Cl, F, Br; R1 = H, Me; R2 = Ph, 3-thienyl, 4-fluorophenyl, etc.; R3 = H, CHO] were efficiently synthesized and screened for antiproliferative activity against the National Cancer Institute (NCI-60) cell lines panel. Two out of eighteen derivatives, HBr salt of compounds I [R = R1 = R3 = H, R2 = 3-thienyl; R = F, R1 = Me, R2 = 3-thienyl, R3 = H] showed remarkably cytotoxic activity with the half maximal inhibitory concentration values (IC50) ranging from 0.23 to 11.4μM, and 0.29-12.2μM, resp. However, two addnl. compounds, I [R = R3 = H, R1 = Me, R2 = 3-thienyl, HBr salt; R = F, R1 = R3 = H, R2 = 3-thienyl] displayed remarkable in-vitro antiproliferative activity against pancreatic ductal adenocarcinoma (PDAC) cell lines, including immortalized (SUIT-2, Capan-1, Panc-1), primary (PDAC-3) and gemcitabine-resistant (Panc-1R), eliciting IC50 values ranging from micromolar to sub-micromolar level, associated with significant reduction of cell-migration and spheroid shrinkage. These remarkable results were explained by modulation of key regulators of epithelial-to-mesenchymal transition (EMT), including E-cadherin and vimentin, and inhibition of metalloproteinase-2/-9. High-throughput arrays revealed a significant inhibition of the phosphorylation of 45 tyrosine kinases substrates, whose visualization on Cytoscape highlighted PTK2/FAK as an important hub. Inhibition of phosphorylation of PTK2/FAK was validated as one of the possible mechanisms of action, using a specific ELISA. In conclusion, novel imidazothiadiazoles show potent antiproliferative activity, mediated by modulation of EMT and PTK2/FAK. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0Safety of 5-Fluoro-1H-indole)

Shin, Subin’s team published research in Chemical Engineering Journal (Amsterdam, Netherlands) in 2019 | CAS: 120-72-9

The author of 《Metal-organic framework with various functional groups: Remarkable adsorbent for removal of both neutral indole and basic quinoline from liquid fuel》 were Shin, Subin; Sarker, Mithun; Lee, Hong-In; Jhung, Sung Hwa. And the article was published in Chemical Engineering Journal (Amsterdam, Netherlands) in 2019. Safety of 1H-Indole The author mentioned the following in the article:

Removal of nitrogen-containing compounds from fuel is very important for effective utilization of fuel. In this study, a stable metal-organic framework (MOF, here, MIL-125) and its amino form (MIL-125-NH2) were prepared, and the latter one was further modified to get MIL-125 with various functional groups or MIL-125-NH-C(O)-C(O)-OH. The obtained MIL-125s were applied in the adsorption of both neutral indole (IND) and basic quinoline (QUI) from model fuel in order to estimate the possible applications of the MOFs in adsorptive denitrogenation. MIL-125-NH-C(O)-C(O)-OH, MIL-125-VFG (VFG means various functional groups), showed remarkable performances in the adsorptions. Or, MIL-125-VFG showed the highest adsorption capacity for IND, compared with any adsorbent reported so far. The MOF also showed the second highest uptake of QUI, after the protonated polyaniline(5%)@MIL-101. The remarkable performances of MIL-125-VFG could be interpreted with ample active sites for H-bonding, or the adsorption could be explained via H-bonding (IND: H-donor; QUI: H-acceptor). Moreover, the MOF can be easily recycled by ethanol washing. Therefore, MOFs with ample active sites for H-bonding (or with various functional groups) can be suggested as a promising adsorbent for purification of liquid fuel or adsorptive denitrogenation. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Safety of 1H-Indole)

Vyhlidalova, Barbora’s team published research in International Journal of Molecular Sciences in 2020 | CAS: 120-72-9

《Gut microbial catabolites of tryptophan are ligands and agonists of the aryl hydrocarbon receptor: a detailed characterization》 was written by Vyhlidalova, Barbora; Krasulova, Kristyna; Pecinkova, Petra; Marcalikova, Adela; Vrzal, Radim; Zemankova, Lenka; Vanco, Jan; Travnicek, Zdenek; Vondracek, Jan; Karasova, Martina; Mani, Sridhar; Dvorak, Zdenek. Recommanded Product: 1H-IndoleThis research focused ontryptophan aryl hydrocarbon receptor signaling colorectal hepatocyte adenocarcinoma; aryl hydrocarbon receptor; indoles; microbiome; tryptophan. The article conveys some information:

We examined the effects of gut microbial catabolites of tryptophan on the aryl hydrocarbon receptor (AhR). Using a reporter gene assay, we show that all studied catabolites are low-potency agonists of human AhR. The efficacy of catabolites differed substantially, comprising agonists with no or low (i3-propionate, i3-acetate, i3-lactate, i3-aldehyde), medium (i3-ethanol, i3-acrylate, skatole, tryptamine), and high (indole, i3-acetamide, i3-pyruvate) efficacies. We displayed ligand-selective antagonist activities by i3-pyruvate, i3-aldehyde, indole, skatole, and tryptamine. Ligand binding assay identified low affinity (skatole, i3-pyruvate, and i3-acetamide) and very low affinity (i3-acrylate, i3-ethanol, indole) ligands of the murine AhR. Indole, skatole, tryptamine, i3-pyruvate, i3-acrylate, and i3-acetamide induced CYP1A1 mRNA in intestinal LS180 and HT-29 cells, but not in the AhR-knockout HT-29 variant. We observed a similar CYP1A1 induction pattern in primary human hepatocytes. The most AhR-active catabolites (indole, skatole, tryptamine, i3-pyruvate, i3-acrylate, i3-acetamide) elicited nuclear translocation of the AhR, followed by a formation of AhR-ARNT heterodimer and enhanced binding of the AhR to the CYP1A1 gene promoter. Collectively, we comprehensively characterized the interactions of gut microbial tryptophan catabolites with the AhR, which may expand the current understanding of their potential roles in intestinal health and disease. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Recommanded Product: 1H-Indole)

Zhang, Jitan’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2019 | CAS: 399-52-0

In 2019,Chemical Communications (Cambridge, United Kingdom) included an article by Zhang, Jitan; Wu, Manyi; Fan, Jian; Xu, Qiaoqiao; Xie, Meihua. Electric Literature of C8H6FN. The article was titled 《Selective C-H acylation of indoles with α-oxocarboxylic acids at the C4 position by palladium catalysis》. The information in the text is summarized as follows:

The first Pd-catalyzed direct C-H acylation of indoles at the C4 position with α-oxocarboxylic acids using a ketone directing group was described. This reaction exhibited high regioselectivity with the tolerance of a wide scope of functional groups to afford diverse acylated indoles I [R = Me, Ph, Bn, Ts; R1 = H, Me, Ph; R2 = H, Me, Et, t-Bu, Ph; R3 = Ph, 4-MeC6H4, 2-thienyl, etc.; R4 = H, 5-F, 6-Br, etc.] in moderate to good yields. The control experiments evidenced the generation of acyl radicals via K2S2O8 promoted decarboxylation of α-oxocarboxylic acids and the involvement of a PdII/PdIV catalytic cycle. Importantly, the synthetically useful selectivity observed might be applied to prepare indole derivatives with anti-tumor activity as tubulin inhibitors. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0Electric Literature of C8H6FN)

Scott, Samantha A.’s team published research in Proceedings of the National Academy of Sciences of the United States of America in 2020 | CAS: 120-72-9

《Microbial tryptophan metabolites regulate gut barrier function via the aryl hydrocarbon receptor》 was written by Scott, Samantha A.; Fu, Jingjing; Chang, Pamela V.. Formula: C8H7NThis research focused ontryptophan metabolite gut barrier aryl hydrocarbon receptor disease human; Crohn disease ulcerative colitis inflammatory bowel disease cytokine; colitis; gut microbiome; inflammatory bowel disease; intestinal epithelium. The article conveys some information:

Inflammatory bowel diseases (IBDs), including Crohn’s disease and ulcerative colitis, are associated with dysbiosis of the gut microbiome. Emerging evidence suggests that small-mol. metabolites derived from bacterial breakdown of a variety of dietary nutrients confer a wide array of host benefits, including amelioration of inflammation in IBDs. Yet, in many cases, the mol. pathways targeted by these mols. remain unknown. Here, we describe roles for three metabolites-indole-3-ethanol, indole-3-pyruvate, and indole-3-aldehyde-which are derived from gut bacterial metabolism of the essential amino acid tryptophan, in regulating intestinal barrier function. We determined that these metabolites protect against increased gut permeability associated with a mouse model of colitis by maintaining the integrity of the apical junctional complex and its associated actin regulatory proteins, including myosin IIA and ezrin, and that these effects are dependent on the aryl hydrocarbon receptor. Our studies provide a deeper understanding of how gut microbial metabolites affect host defense mechanisms and identify candidate pathways for prophylactic and therapeutic treatments for IBDs. In the experiment, the researchers used many compounds, for example, 1H-Indole(cas: 120-72-9Formula: C8H7N)