October 2022 - Page 46 of 72 - Indole Building Blocks

Dai, Chunxiao’s team published research in Environmental Science and Pollution Research in 2022 | 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.Safety of 1H-Indole

In 2022,Dai, Chunxiao; Ma, Fang; Ma, Qiao; Yang, Jing; Li, Yan; Yang, Bingyu; Qu, Yuanyuan published an article in Environmental Science and Pollution Research. The title of the article was 《Investigation of indole biodegradation by Cupriavidus sp. strain IDO with emphases on downstream biotransformation and indigo production》.Safety of 1H-Indole The author mentioned the following in the article:

Indole, as a typical N-heterocyclic aromatic pollutant, poses risks to living things; however, indole-biotransformation mechanisms remain under-discussed, especially those related to its downstream biotransformation. Here, we systematically investigated the characteristics of indole degradation by strain Cupriavidus sp. IDO. We found that Cupriavidus sp. IDO could utilize 25 to 150 mg/L indole within 40 h and identified three intermediates (2-oxindole, indigo, and isatin). Addnl., integrated genomics and proteomics anal. of the indole biotransformation mechanism in strain IDO revealed 317 proteins showing significant changes (262 upregulated and 55 downregulated) in the presence of indole. Among these, three clusters containing indole oxidoreductase, CoA-thioester ligase, and gentisate 1,2-oxidoreductase were identified as potentially responsible for upstream and downstream indole metabolism Moreover, HPLC-MS and -omics anal. offered insight into the indole-degradation pathway in strain IDO. Furthermore, the indole oxidoreductase IndAB, which initiates indole degradation, was heterologously expressed in Escherichia coli BL21(DE3). Optimization by the response surface methodol. resulted in a maximal production of 135.0 mg/L indigo by the recombination strains in tryptophan medium. This work enriches our understanding of the indole-biodegradation process and provides new insights into multiple indole-degradation pathways in natural environments. The experimental part of the paper was very detailed, including the reaction process of 1H-Indole(cas: 120-72-9Safety of 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

O’Mahony, Cian’s team published research in International Journal of Molecular Sciences in 2022 | CAS: 120-72-9

Reference of 1H-IndoleIn 2022 ,《Diet-Microbiota Interplay: An Emerging Player in Macrophage Plasticity and Intestinal Health》 appeared in International Journal of Molecular Sciences. The author of the article were O’Mahony, Cian; Amamou, Asma; Ghosh, Subrata. The article conveys some information:

A review. Inflammatory bowel diseases (IBD) are chronic disorders of the gastrointestinal tract with an increasing prevalence worldwide. Targeted therapies for IBD are limited by several factors, including the therapeutic ceiling and the high incidence of non-responders or loss-of-response. In order to improve therapeutic efficacy, there is critical need to decipher disease pathogenesis, currently not well understood. Macrophages, innate immune cells that exhibit high plasticity, perpetuate inflammatory signalling in IBD through excessive release of inflammatory mediators. In recent years, pioneering research has revealed the importance of the interplay between macrophages and gut microbiota in maintaining intestinal homeostasis. Particular attention is focusing on microbiota-derived metabolites, believed to possess immunomodulatory properties capable of manipulating macrophage plasticity. Microbiota-derived short-chain fatty acids (SCFAs) and indole compounds, along with dietary sourced omega-3 (ω-3) polyunsaturated fatty acids (PUFA), exert anti-inflammatory effects, attributable to interactions with macrophages. Before we can effectively incorporate these metabolites into IBD therapies, a deeper understanding of microbiota-macrophage interactions at a mol. level is necessary. Therefore, the aim of this review is firstly to detail current knowledge regarding how diet and microbiota-derived metabolites modify macrophage plasticity. Later, we discuss the concept of therapeutic strategies directed at microbiota-macrophage interactions, which could be highly valuable for IBD therapies in the future. After reading the article, we found that the author used 1H-Indole(cas: 120-72-9Reference of 1H-Indole)

Kaur, Kamalpreet’s team published research in Anti-Cancer Agents in Medicinal Chemistry in 2020 | CAS: 120-72-9

Recommanded Product: 1H-IndoleIn 2020 ,《Recent Development in Indole Derivatives as Anticancer Agents for Breast Cancer》 appeared in Anti-Cancer Agents in Medicinal Chemistry. The author of the article were Kaur, Kamalpreet; Jaitak, Vikas. The article conveys some information:

A review. Background: Breast Cancer (BC) is the second most common cause of cancer related deaths in women. Due to severe side effects and multidrug resistance, current therapies like hormonal therapy, surgery, radiotherapy and chemotherapy become ineffective. Also, the existing drugs for BC treatment are associated with several drawbacks such as poor oral bioavailability, non-selectivity and poor pharmacodynamics properties. Therefore, there is an urgent need for the development of more effective and safer anti BC agents. Objective: This article explored in detail the possibilities of indole-based heterocyclic compounds as anticancer agents with breast cancer as their major target. Methods: Recent literature related to indole derivatives endowed with encouraging anti BC potential is reviewed. With special focus on BC, this review offers a detailed account of multiple mechanisms of action of various indole derivatives: aromatase inhibitor, tubulin inhibitor, microtubule inhibitor, targeting estrogen receptor, DNA-binding mechanism, induction of apoptosis, inhibition of PI3K/AkT/NFkB/mTOR, and HDAC inhibitors, by which these derivatives have shown promising anticancer potential. Results: Exhaustive literature survey indicated that indole derivatives are associated with properties of inducing apoptosis and disturbing tubulin assembly. Indoles are also associated with the inhibition of NFkB/mTOR/PI3K/AkT and regulation of estrogen-mediated activity. Furthermore, indole derivatives have been found to modulate critical targets such as topoisomerase and HDAC. These derivatives have shown significant activity against breast cancer cells. Conclusion: In BC, indole derivatives seem to be quite competent and act through various mechanisms that are well established in case of BC. This review has shown that indole derivatives can further be explored for the betterment of BC chemotherapy. A lot of potential is still hidden which demands to be discovered for upgrading BC chemotherapy. In addition to this study using 1H-Indole, there are many other studies that have used 1H-Indole(cas: 120-72-9Recommanded Product: 1H-Indole) was used in this study.

Sreekantha, Ratna Kumar’s team published research in ACS Medicinal Chemistry Letters in 2022 | CAS: 883500-73-0

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

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)

Barry, Conor S.’s team published research in Journal of the American Chemical Society in 2013 | CAS: 99409-32-2

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.

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)

Cascioferro, Stella’s team published research in European Journal of Medicinal Chemistry in 2020 | 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.Safety of 5-Fluoro-1H-indole

《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)

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)

Diem, Stefanie’s team published research in Journal of Agricultural and Food Chemistry in 2001 | CAS: 59132-30-8

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.

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)

Meyer, Elisabeth M.’s team published research in Journal of Environmental Horticulture in 2009 | CAS: 60096-23-3

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

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)

Schlosser, Manfred’s team published research in European Journal of Organic Chemistry in 2006 | CAS: 883500-73-0

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)