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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)

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

Blythe, Eugene K.’s team published research in Journal of Environmental Horticulture in 2004 | 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

Blythe, Eugene K.; Sibley, Jeff L.; Tilt, Ken M.; Ruter, John M. published an article in Journal of Environmental Horticulture. The title of the article was 《Auxin application to stem cuttings of selected woody landscape plants by incorporation into a stabilized organic rooting substrate》.Name: Potassium 4-(1H-indol-3-yl)butanoate The author mentioned the following in the article:

Stem cuttings of Buxus sinica var. insularis “”Wintergreen””, Elaeagnus × ebbingei, Ficus benjamina, Gardenia augusta “”Radicans””, Ilex glabra “”Nigra””, Ilex vomitoria “”Nana””, Juniperus conferta “”Blue Pacific””, Ternstroemia gymnanthera, and Trachelospermum asiaticum were inserted into a stabilized organic rooting substrate (plugs comprised of peat and a polymer binder) that had been soaked in water, aqueous solutions of K-IBA (15 to 75 ppm), or K-IBA + K-NAA (15 ppm + 7.5 ppm to 60 ppm + 30 ppm). Rooting and initial shoot growth responses were compared with cuttings receiving a basal quick-dip in K-IBA (1000 ppm) or K-IBA + K-NAA (1000 ppm + 500 ppm). Rooting percentage, number of roots per rooted cutting, and total root length per rooted cutting for cuttings rooted in auxin-treated plugs were similar to or greater than cuttings receiving a basal quick-dip; lesser results were obtained in a few cases with K-IBA + K-NAA. Percent of rooted cuttings with new shoots and shoot length per rooted cutting for cuttings rooted in plugs treated with K-IBA were mostly similar to cuttings receiving a basal quick-dip in K-IBA, while cuttings rooted in plugs treated with K-IBA + K-NAA exhibited similar or lesser results compared to cuttings receiving a basal quick-dip in K-IBA + K-NAA. In the experimental materials used by the author, we found Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Name: Potassium 4-(1H-indol-3-yl)butanoate)

Van Bragt, J.’s team published research in Scientia Horticulturae (Amsterdam, Netherlands) in 1976 | CAS: 60096-23-3

The author of 《Rooting of shoot cuttings of ornamental shrubs after immersion in auxin-containing solutions》 were Van Bragt, J.; Van Gelder, H.; Pierik, R. L. M.. And the article was published in Scientia Horticulturae (Amsterdam, Netherlands) in 1976. Reference of Potassium 4-(1H-indol-3-yl)butanoate The author mentioned the following in the article:

Shoot cuttings of Berberis hybrido-gagne painii, B. ottawensis, Cotoneaster salicifolia, Lavandula angustifolia Prunus laurocerasus, Pyracantha, and Viburnum plicatum were immersed in a solution of the auxins, IAA K salt (I K salt) [2338-19-4] and IBA K salt [60096-23-3], in water. In general, this treatment gave better rooting than the commonly used method of dipping the basal part of the cutting in a powder mixture containing auxin. After reading the article, we found that the author used Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Reference of Potassium 4-(1H-indol-3-yl)butanoate)

Lambert, Christopher R.’s team published research in Journal of Environmental Horticulture in 2012 | CAS: 60096-23-3

Lambert, Christopher R.; Blazich, Frank A.; LeBude, Anthony V. published an article in Journal of Environmental Horticulture. The title of the article was 《Propagation of Ilex vomitoria ‘Dare County’ by stem cuttings》.HPLC of Formula: 60096-23-3 The author mentioned the following in the article:

Semi-hardwood or hardwood stem cuttings of Ilex vomitoria Soluble ex Ait. ‘Dare County’ [‘Dare County’ yaupon holly (syn. ‘Virginia Dare’ yaupon holly)] were treated with solutions of the potassium (K) salt (K-salt) of indolebutyric acid (K-IBA) at 0 to 8000 mg·liter-1 (ppm). Nontreated semi-hardwood cuttings rooted at 78% whereas, regardless of auxin treatment, hardwood cuttings taken on two dates rooted at ≤ 15%. Treatment of cuttings with K-IBA was generally ineffective and resulted in a linear decrease (P ≤ 0.05) in percent rooting of semi-hardwood cuttings. The results came from multiple reactions, including the reaction of Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3HPLC of Formula: 60096-23-3)

Karam, N. S.’s team published research in Journal of Horticultural Science & Biotechnology in 2004 | CAS: 60096-23-3

Computed Properties of C12H12KNO2On September 30, 2004 ,《Rooting of Cercis siliquastrum cuttings influenced by cutting position on the branch and indole-butyric acid》 was published in Journal of Horticultural Science & Biotechnology. The article was written by Karam, N. S.; Gebre, G. H.. The article contains the following contents:

The effects of cutting position within the source shoot and concentration of 1H-indole-3-butyric acid (IBA) or its potassium salt (K-IBA) on rooting in Cercis siliquastrum were assessed. Stem cuttings were taken from terminal or basal portions of the shoots in early spring, early summer, or winter and treated with 0, 24, 48, 72 or 96 mM IBA in 50% ethanol or K-IBA in water. Terminal cuttings were also treated with a com. rooting powder containing 0.1, 0.3 or 0.8% IBA. Rooting was unsuccessful except when cuttings were taken in the summer. Percent rooting was not significantly affected by concentration of IBA, but terminal cuttings exhibited higher rooting (43%) than basal ones (13%). Length and dry mass of roots produced per rooted cutting were significantly increased with increasing concentration of IBA. Basal cuttings performed poorly irresp. of K-IBA concentration, whereas terminal cuttings treated with the higher concentrations (72 and 96 mM) exhibited greater rooting than those treated with the lower concentrations (0-48 mM). The highest rooting percentage (80%) was obtained at 72 mM K-IBA, but the shape of the response curve suggests that the optimum concentration is probably slightly above 96 mM, the highest concentration tested. The quantity of roots produced per rooted cutting was not affected by cutting position or K-IBA concentration Treating terminal cuttings with 0.3 or 0.8% IBA powder resulted in 60% or 73% rooting, resp. The slope of the response curve suggests that the optimum might be above 0.8%, the highest concentration tested. The quantity of roots was not affected by IBA powder concentration The results came from multiple reactions, including the reaction of Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Computed Properties of C12H12KNO2)

Varnes, Jeffrey G.’s team published research in Bioorganic & Medicinal Chemistry Letters in 2007 | CAS: 219552-64-4

tert-Butyl 6-nitro-1H-indole-1-carboxylate(cas: 219552-64-4) 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.Synthetic Route of C13H14N2O4They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

Varnes, Jeffrey G.; Wacker, Dean A.; Jacobson, Irina C.; Quan, Mimi L.; Ellis, Christopher D.; Rossi, Karen A.; He, Ming Y.; Luettgen, Joseph M.; Knabb, Robert M.; Bai, Steven; He, Kan; Lam, Patrick Y. S.; Wexler, Ruth R. published their research in Bioorganic & Medicinal Chemistry Letters on December 1 ,2007. The article was titled 《Design, structure-activity relationship, and pharmacokinetic profile of pyrazole-based indoline factor Xa inhibitors》.Synthetic Route of C13H14N2O4 The article contains the following contents:

Aminobenzoisoxazolylpyrazolecarboxamides of arylamines and fused arylamines such as I are prepared as factor Xa inhibitors and razaxaban analogs; the inhibition of factor Xa by the title compounds, their selectivities for factor Xa over thrombin and trypsin, and the pharmacokinetic profiles of selected compounds (including I) in dogs are determined Carboxamides derived from fused or secondary arylamines are used rather than those derived from primary arylamines to inhibit the formation of aniline metabolites derived from amide hydrolysis. Indoline-derived aminobenzoisoxazolylpyrazolecarboxamides provide the most selective and active factor Xa inhibitors of the compounds tested, with subnanomolar factor Xa binding Kis, modest to high selectivities vs. other serine proteases, and good in vitro clotting activity in some cases. E.g, I inhibits human factor Xa with a Ki value of 2.7 nM while inhibiting human thrombin and trypsin with Ki values of >21 μM and >2.5 μM, resp.; when tested in vivo, however, I has lower anticoagulant activity than razaxaban. In the experiment, the researchers used many compounds, for example, tert-Butyl 6-nitro-1H-indole-1-carboxylate(cas: 219552-64-4Synthetic Route of C13H14N2O4)

Valin, Nathan’s team published research in Mutation Research, Genetic Toxicology Testing in 1985 | 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.Application In Synthesis 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.

Valin, Nathan; Haybron, David; Groves, Linda; Mower, H. F. published their research in Mutation Research, Genetic Toxicology Testing on December 31 ,1985. The article was titled 《The nitrosation of alcohol-induced metabolites produces mutagenic substances》.Application In Synthesis of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid The article contains the following contents:

The results of mutagen testing of reaction mixtures of nitrite and representative structures of tetrahydro-β-carbolines, tetrahydroisoquinolines, and tryptophols using Salmonella typimimium strains TA100, TA98, and TA97A are presented. All reaction mixtures were pos. for mutagenicity for ≥1 strains except for the nitrosation mixtures of tetrahydroisoquinoline and 1-methyl-1-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline-HCl [101372-78-5]. The highest mutagenic activity was observed with strain TA98 with the exception of the reaction mixture of 5-hydroxytryptophol [154-02-9] which was more active with TA100. The results came from multiple reactions, including the reaction of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid(cas: 59132-30-8Application In Synthesis of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid)

Romney, David K.’s team published research in Journal of the American Chemical Society in 2017 | CAS: 883500-73-0

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.

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)

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

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)