14/10/2022 - Page 2 of 9 - Indole Building Blocks

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)

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’s team published research in European Journal of Organic Chemistry in 2006 | 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

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)

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.

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.

Surur, Abdrrahman Shemsu’s team published research in Drug Design, Development and Therapy 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.Category: indole-building-block

《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)

Zhang, Shanshan’s team published research in World Journal of Microbiology & Biotechnology in 2020 | 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)

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)

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)

Lu, Fo-Yun’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2020 | CAS: 399-52-0

《Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones》 was written by Lu, Fo-Yun; Chen, Yu-Jue; Chen, Yuan; Ding, Xuan; Guan, Zhi; He, Yan-Hong. COA of Formula: C8H6FN And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020. The article conveys some information:

A highly enantioselective and direct synthesis of C2-quaternary indolin-3-ones from 2-arylindoles by combining electrochem. and organocatalysis is described. Excellent enantioselectivities (up to 99% ee) and diastereoselectivities (>20 : 1) can be obtained through anodic oxidation in combination with asym. proline-catalyzed alkylation in an undivided cell under constant-current conditions. Thus, e.g., 2-phenylindole + cyclohexanone → I (67%, > 20:1 d.r., 98% ee) in presence of L-proline as chiral organic catalyst using DMF as solvent, TFE as cosolvent, TEMPO as mediator, benzoic acid as additive and tetrabutylammonium perchlorate as electrolyte in undivided cell with Pt anode and cathode. In the experiment, the researchers used 5-Fluoro-1H-indole(cas: 399-52-0COA of Formula: C8H6FN)

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)