Category: 883500-73-0

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K. published their research in Journal of Medicinal Chemistry on December 10 ,2015. The article was titled 《Development of a Highly Potent D2/D3 Agonist and a Partial Agonist from Structure-Activity Relationship Study of N6-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine Analogues: Implication in the Treatment of Parkinson’s Disease》.Name: 5-Bromo-7-fluoro-1H-indole The article contains the following contents:

The structure-activity relationship studies with N6-(2-(4-(1H-indol-5-yl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine derivatives led to development of a lead compound I which exhibited very high affinity (Ki, D2 = 16.4 nM, D3 = 1.15 nM) and full agonist activity (EC50 (GTPγS); D2 = 3.23 and D3 = 1.41 nM) at both D2 and D3 receptors. A partial agonist mol. II (EC50 (GTPγS); D2 = 21.6 (Emax = 27%) and D3 = 10.9 nM) was also identified. In a Parkinson’s disease (PD) animal model, I was highly efficacious in reversing hypolocomotion in reserpinized rats with a long duration of action, indicating its potential as an anti-PD drug. Compound II was also able to elevate locomotor activity in the above PD animal model significantly, implying its potential application in PD therapy. Furthermore, I was shown to be neuroprotective in protecting neuronal PC12 from toxicity of 6-OHDA. This report, therefore, underpins the notion that a multifunctional drug like I might have the potential not only to ameliorate motor dysfunction in PD patients but also to modify disease progression by protecting DA neurons from progressive degeneration. In the experiment, the researchers used many compounds, for example, 5-Bromo-7-fluoro-1H-indole(cas: 883500-73-0Name: 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).Name: 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

Boville, Christina E.; Romney, David K.; Almhjell, Patrick J.; Sieben, Michaela; Arnold, Frances H. published an article in Journal of Organic Chemistry. The title of the article was 《Improved Synthesis of 4-Cyanotryptophan and Other Tryptophan Analogues in Aqueous Solvent Using Variants of TrpB from Thermotoga maritima》.Category: indole-building-block The author mentioned the following in the article:

The use of enzymes has become increasingly widespread in synthesis as chemists strive to reduce their reliance on organic solvents in favor of more environmentally benign aqueous media. With this in mind, we previously endeavored to engineer the tryptophan synthase β-subunit (TrpB) for production of noncanonical amino acids that had previously been synthesized through multi-step routes involving water-sensitive reagents. This enzymic platform proved effective for the synthesis of analogs of the amino acid tryptophan (Trp), which are frequently used in pharmaceutical synthesis as well as chem. biol. However, certain valuable compounds, such as the blue fluorescent amino acid 4-cyanotryptophan (4-CN-Trp), could only be made in low yield, even at elevated temperature (75 °C). Here, we describe the engineering of TrpB from Thermotoga maritima that improved synthesis of 4-CN-Trp from 24% to 78% yield. Remarkably, although the final enzyme maintains high thermostability (T50 = 93 °C), its temperature profile is shifted, such that high reactivity is observed at ∼37 °C (76% yield), creating the possibility for in vivo 4-CN-Trp production The improvements are not specific to 4-CN-Trp; a boost in activity at lower temperature is also demonstrated for other Trp analogs. In addition to this study using 5-Bromo-7-fluoro-1H-indole, there are many other studies that have used 5-Bromo-7-fluoro-1H-indole(cas: 883500-73-0Category: indole-building-block) 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).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

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

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

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