Indole Building Blocks

《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)

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.SDS of cas: 120-72-9

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: 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)

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

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

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)

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.

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

《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)

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.COA of Formula: C8H6FN

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

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)

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.

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 copper(II)-catalyzed and oxidant-promoted regioselective C-2 difluoromethylation of indoles and pyrroles》 was published in Chemical Communications (Cambridge, United Kingdom) in 2020. These research results belong to Zhang, Dong; Fang, Zheng; Cai, Jinlin; Liu, Chengkou; He, Wei; Duan, Jindian; Qin, Ning; Yang, Zhao; Guo, Kai. Reference of 5-Fluoro-1H-indole The article mentions the following:

A novel and efficient approach for the highly selective C-2 difluoromethylation of indole derivatives was developed by using sodium difluoromethylsulfinate (HCF2SO2Na) as the source of difluoromethyl groups and a Cu(II) complex as the catalyst. Various substrates were well tolerated in this transformation and the desired products, such as I [R = H, 3-Me, 4-Me, etc.] were obtained in moderate to good yields. Moreover, the late-stage C-2 difluoromethylation of bioactive mols. containing an indole ring was achieved in good yields. Generally, this reaction features excellent functional group compatibility, broad substrate scope and excellent C-2 selectivity. In the experiment, the researchers used 5-Fluoro-1H-indole(cas: 399-52-0Reference 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.Reference 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

Liu, Xiaoyu; He, Kun; Gao, Na; Jiang, Peiyun; Lin, Jun; Jin, Yi published their research in Chemical Communications (Cambridge, United Kingdom) in 2021. The article was titled 《A radical-mediated multicomponent cascade reaction for the synthesis of azide-biindole derivatives》.Formula: C8H6FN The article contains the following contents:

A radical-mediated, one-pot, multicomponent cascade reaction was developed for the synthesis of azide-biindole derivatives Mechanistic studies demonstrated that the nitrogen-centered free radical were formed by the reaction of heterocyclic N-H with CuII and PIFA and initiated the cascade reaction with indole to obtain the biindole intermediate. The obtained biindole intermediate then reacted with sodium azide in the presence of CuII catalyst and PIFA which then resulted in final products. This methodol. was useful for constructing other azido heterocycles. In the part of experimental materials, we found many familiar compounds, such as 5-Fluoro-1H-indole(cas: 399-52-0Formula: C8H6FN)

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.Formula: C8H6FN

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

Pillaiyar, Thanigaimalai; Sedaghati, Masoud; Mahardhika, Andhika B.; Wendt, Lukas L.; Mueller, Christa E. published their research in Beilstein Journal of Organic Chemistry in 2021. The article was titled 《Iodine-catalyzed electrophilic substitution of indoles: synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center》.Related Products of 399-52-0 The article contains the following contents:

A novel, versatile approach for the synthesis of unsym. 3,3′-diindolylmethanes (DIMs) with a quaternary carbon center has been developed via iodine-catalyzed coupling of trifluoromethyl(indolyl)phenylmethanols with indoles. In contrast to previously reported methods, the new procedure is characterized by chemoselectivity, mild conditions, high yields, and scalability to obtain gram amounts for biol. studies. Selected compounds were found to display affinity for cannabinoid receptors, which are promising drug targets for the treatment of inflammatory and neurodegenerative diseases. The results came from multiple reactions, including the reaction of 5-Fluoro-1H-indole(cas: 399-52-0Related Products of 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.Related Products of 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

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)

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.Computed Properties of C12H12KNO2

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

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)

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.HPLC of Formula: 60096-23-3

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