Indole Building Blocks

Recommanded Product: 5-Bromo-7-fluoro-1H-indoleOn May 12, 2022 ,《Identification of 2-Pyridinylindole-Based Dual Antagonists of Toll-like Receptors 7 and 8 (TLR7/8)》 appeared in ACS Medicinal Chemistry Letters. The author of the article were Sreekantha, Ratna Kumar; Mussari, Christopher P.; Dodd, Dharmpal S.; Pasunoori, Laxman; Hegde, Subramanya; Posy, Shana L.; Critton, David; Ruepp, Stefan; Subramanian, Murali; Salter-Cid, Luisa M.; Tagore, Debarati Mazumder; Sarodaya, Sanket; Dudhgaonkar, Shailesh; Poss, Michael A.; Schieven, Gary L.; Carter, Percy H.; Macor, John E.; Dyckman, Alaric J.. The article conveys some information:

The toll-like receptors (TLRs) play key roles in activation of the innate immune system. Aberrant activation of TLR7 and TLR8 pathways can occur in the context of autoimmune disorders due to the elevated presence and recognition of self-RNA as activating ligands. Control of this unintended activation via inhibition of TLR7/8 signaling holds promise for the treatment of diseases such as psoriasis, arthritis, and lupus. Optimization of a 2-pyridinylindole series of compounds led to the identification of potent dual inhibitors of TLR7 and TLR8, which demonstrated good selectivity against TLR9 and other family members. The in vitro characterization and in vivo evaluation in rodent pharmacokinetic/pharmacodynamic and efficacy studies of BMS-905 is detailed, along with structural information obtained through X-ray cocrystallog. studies. In the part of experimental materials, we found many familiar compounds, such as 5-Bromo-7-fluoro-1H-indole(cas: 883500-73-0Recommanded Product: 5-Bromo-7-fluoro-1H-indole)

5-Bromo-7-fluoro-1H-indole(cas: 883500-73-0) 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).Recommanded Product: 5-Bromo-7-fluoro-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

COA of Formula: C22H25NO9SOn November 13, 2013 ,《’Naked’ and Hydrated Conformers of the Conserved Core Pentasaccharide of N-linked Glycoproteins and Its Building Blocks》 appeared in Journal of the American Chemical Society. The author of the article were Barry, Conor S.; Cocinero, Emilio J.; Carcabal, Pierre; Gamblin, David P.; Stanca-Kaposta, E. Cristina; Remmert, Sarah M.; Fernandez-Alonso, Maria C.; Rudic, Svemir; Simons, John P.; Davis, Benjamin G.. The article conveys some information:

N-glycosylation of eukaryotic proteins is widespread and vital to survival. The pentasaccharide unit -Man3GlcNAc2- lies at the protein-junction core of all oligosaccharides attached to asparagine side chains during this process. Although its absolute conservation implies an indispensable role, associated perhaps with its structure, its unbiased conformation and the potential modulating role of solvation are unknown; both have now been explored through a combination of synthesis, laser spectroscopy, and computation. The proximal -GlcNAc-GlcNAc- unit acts as a rigid rod, while the central, and unusual, -Man-β-1,4-GlcNAc- linkage is more flexible and is modulated by the distal Man-α-1,3- and Man-α-1,6- branching units. Solvation stiffens the rod but leaves the distal residues flexible, through a β-Man pivot, ensuring anchored projection from the protein shell while allowing flexible interaction of the distal portion of N-glycosylation with bulk water and biomol. assemblies. In the part of experimental materials, we found many familiar compounds, such as Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2COA of Formula: C22H25NO9S)

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.COA of Formula: C22H25NO9SThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

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

《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)

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.Safety of 5-Fluoro-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

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)

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

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

Diem, Stefanie; Gutsche, Birgit; Herderich, Markus published their research in Journal of Agricultural and Food Chemistry on December 31 ,2001. The article was titled 《Degradation of Tetrahydro-β-carbolines in the Presence of Nitrite: HPLC-MS Analysis of the Reaction Products》.Reference of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid The article contains the following contents:

Motivated by the identification of numerous novel tetrahydro-β-carboline-carboxylic acids in food samples, the authors studied the reactions of tetrahydro-β-carbolines in the presence of nitrosating agents. The anticipated formation of nitroso derivatives from unsubstituted tetrahydro-β-carbolines, and from tetrahydro-β-carboline-3-carboxylic acids was indicated by HPLC-MS/MS anal. and validated by the characteristic product ion spectra of the resp. nitroso compounds In addition, oxidative decarboxylation resulted in formation of the corresponding dihydro-β-carbolines, and in the generation of the β-carbolines harman or norharman. Subsequently, the authors studied the reactivity of tetrahydro-β-carboline-1-carboxylic acids derived from the Pictet-Spengler condensation of indole amines with α-oxo acids. Again, in the presence of nitrosating agents the rapid disappearance of the starting material was obvious, but no nitroso derivatives could be observed Instead, further HPLC-MS/MS studies demonstrated that dihydro-β-carbolines were the major products of tetrahydro-β-carboline-1-carboxylic acids. Finally, the authors demonstrated that freshly isolated nitroso-precursors spontaneously decomposed to yield harman alkaloids. Thus, nitroso-tetrahydro-β-carbolines can represent intermediates involved in the generation of β-carbolines; the authors established a novel pathway for the formation of harman alkaloids from nutritional tetrahydro-β-carbolines. The experimental part of the paper was very detailed, including the reaction process of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid(cas: 59132-30-8Reference of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid)

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid(cas: 59132-30-8) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Reference of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acidThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

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

Meyer, Elisabeth M.; Le Bude, Anthony V.; Ranney, Thomas G. published their research in Journal of Environmental Horticulture on December 31 ,2009. The article was titled 《Vegetative propagation of Gordonieae trees by stem cuttings》.Name: Potassium 4-(1H-indol-3-yl)butanoate The article contains the following contents:

The Theaceae tribe Gordonieae contains trees with desirable ornamental characteristics and adaptability to a broad range of environmental conditions. To develop an effective protocol for vegetative propagation of five taxa in the tribe, terminal softwood, semi-hardwood, and hardwood cuttings were collected from these trees and treated with either 0, 2500, 5000, 7500, or 10000 ppm of the potassium salt of indolebutyric acid (K-IBA). The concentration of K-IBA only affected rooting percentage of hardwood cuttings of Franklinia alatamaha, Gordonia lasianthus, and Schima remotiserrata and had varying effects on root number and length of longest root amongst the taxa and cutting types. Franklinia alatamaha and G. lasianthus were rooted at high percentages (> 50%) from hardwood, semihardwood, and softwood cuttings, and S. khasiana rooted at high percentages (72%) from softwood cuttings. Despite poor rooting from all types of stem cuttings (< 23%), Schima remotiserrata and S. wallichii exhibited the highest rooting percentages from hardwood cuttings. Rooting percentage, root number, and length of longest root differed greatly in response to K-IBA concentration amongst the five taxa observed and the cutting types within each taxa. In the part of experimental materials, we found many familiar compounds, such as Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Name: Potassium 4-(1H-indol-3-yl)butanoate)

Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3) is auxin-family plant hormone, and is thought to be a precursor of indole-3-acetic acid (IAA) the most abundant and the basic auxin natively occurring and functioning in plants. IAA generates the majority of auxin effects in intact plants, and is the most potent native auxin.Name: Potassium 4-(1H-indol-3-yl)butanoate

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

Schlosser, Manfred; Ginanneschi, Assunta; Leroux, Frederic published an article in European Journal of Organic Chemistry. The title of the article was 《In search of simplicity and flexibility: a rational access to twelve fluoroindolecarboxylic acids》.Recommanded Product: 5-Bromo-7-fluoro-1H-indole The author mentioned the following in the article:

All twelve indolecarboxylic acids carrying both a fluorine substituent and a carboxy group at the benzo ring have been prepared either directly from the corresponding fluoroindoles or from the chlorinated derivatives by hydrogen/metal permutation (“”metalation””), or from the bromo- or iodofluoroindoles by halogen/metal permutation, the organometallic intermediate being each time trapped with carbon dioxide. In most, though not all cases, the nitrogen atom in the five-membered ring had to be protected by a trialkylsilyl group. Some of the bromo- or iodofluoroindoles were successfully subjected to a basicity gradient-driven selective migration of the heavy halogen. An unexpected finding on the way to the target compounds were the rigorously site-selective metalation of the 5-fluoro-N-(trialkylsilyl)indole (exclusive deprotonation of the 4-position). The fluoroindoles, although previously known, were accessed more conveniently from suitably substituted nitrobenzenes using the Bartoli or the Leimgruber-Batcho method. A new and very attractive indole synthesis was elaborated consisting of the ortho-lithiation of an N-acyl-protected aniline followed by ortho-formylation, Wittig chloromethylenation and base-catalyzed cyclization accompanied by dehydrochlorination. These five consecutive steps can be contracted to a convenient one-pot protocol. The results came from multiple reactions, including the reaction of 5-Bromo-7-fluoro-1H-indole(cas: 883500-73-0Recommanded Product: 5-Bromo-7-fluoro-1H-indole)

5-Bromo-7-fluoro-1H-indole(cas: 883500-73-0) 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).Recommanded Product: 5-Bromo-7-fluoro-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

Romney, David K.; Murciano-Calles, Javier; Wehrmuller, Jori E.; Arnold, Frances H. published their research in Journal of the American Chemical Society on August 9 ,2017. The article was titled 《Unlocking Reactivity of TrpB: A General Biocatalytic Platform for Synthesis of Tryptophan Analogues》.Recommanded Product: 5-Bromo-7-fluoro-1H-indole The article contains the following contents:

Derivatives of the amino acid tryptophan (Trp) serve as precursors for the chem. and biol. synthesis of complex mols. with a wide range of biol. properties. Trp analogs are also valuable as building blocks for medicinal chem. and as tools for chem. biol. While the enantioselective synthesis of Trp analogs is often lengthy and requires the use of protecting groups, enzymes have the potential to synthesize such products in fewer steps and with the pristine chemo- and stereoselectivity that is a hallmark of biocatalysis. The enzyme TrpB is especially attractive because it can form Trp analogs directly from serine (Ser) and the corresponding indole analog. However, many potentially useful substrates, including bulky or electron-deficient indoles, are poorly accepted. We have applied directed evolution to TrpB from Pyrococcus furiosus and Thermotoga maritima to generate a suite of catalysts for the synthesis of previously intractable Trp analogs. For the most challenging substrates, such as nitroindoles, the key to improving activity lay in the mutation of a universally conserved and mechanistically important residue, E104. The new catalysts express at high levels (>200 mg/L of E. coli culture) and can be purified by heat treatment; they can operate up to 75 °C (where solubility is enhanced) and can synthesize enantiopure tryptophan analogs substituted at the 4-, 5-, 6-, and 7-positions, using Ser and readily available indole analogs as starting materials. Spectroscopic anal. shows that many of the activating mutations suppress the decomposition of the active electrophilic intermediate, an amino-acrylate, which aids in unlocking the synthetic potential of TrpB.5-Bromo-7-fluoro-1H-indole(cas: 883500-73-0Recommanded Product: 5-Bromo-7-fluoro-1H-indole) was used in this study.

5-Bromo-7-fluoro-1H-indole(cas: 883500-73-0) 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).Recommanded Product: 5-Bromo-7-fluoro-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

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.

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

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

《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)

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.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