Indole Building Blocks

Van Bragt, J.’s team published research in Scientia Horticulturae (Amsterdam, Netherlands) in 1976 | 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.Reference of Potassium 4-(1H-indol-3-yl)butanoate

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)

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

Niggemann, Jutta’s team published research in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry in 1998 | 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.Related Products of 99409-32-2They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

Related Products of 99409-32-2On September 21, 1998 ,《Application of β-1,4-galactosyltransferase in the synthesis of complex branched-chain oligosaccharide mimics of fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14》 was published in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry. The article was written by Niggemann, Jutta; Kamerling, Johannis P.; Vliegenthart, Johannes F. G.. The article contains the following contents:

The chemoenzymic synthesis is described of β-D-Galp-(1→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpNAc-(1→O[CH2]3O→4)-β-D-Glcp-(1→OCH2CH:CH2) and β-D-Galp-(1→4)-β-D-GlcpNAc-(1→O[CH2]3O→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpNAc-(1→O[CH2]3O→4)-β-D-Glcp-(1→OCH2-CH:CH2), representing hexa- and octasaccharide mimics of fragments of the Streptococcus pneumoniae type 14 polysaccharide. In a chem. approach the intermediate linear oligosaccharide mimics I (R1 = CH2CH:CH2; R2 = Q; R3 = H) and I (R2 = Q1) were synthesized, wherein both terminal and non-terminal N-acetyl-β-D-glucosamine residues were not yet galactosylated. The alkyl-bridged derivatives were found to be good acceptor substrates for bovine milk β-1,4-galactosyltransferase. Reaction of the anomeric allyl functions with cysteamine under UV-irradiation gave the corresponding 3-(2-aminoethylthio)propyl glycosides I (R1 = (CH2)3S(CH2)2NH2; R3 = Q) (II) and II (R2 = Q1; R3 = Q) suitable for further coupling of the oligosaccharide mimics to protein carriers. After reading the article, we found that the author used Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Related Products of 99409-32-2)

Liu, Li’s team published research in ARKIVOC (Gainesville, FL, United States) in 2022 | 20870-77-3

ARKIVOC (Gainesville, FL, United States) published new progress about Dephosphorylation (reductive). 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Category: indole-building-block.

Liu, Li; Li, Yue; Wang, Feng; Ning, Rui; Kong, Dulin; Wu, Mingshu published the artcile< A new synthetic approach to oxindoles (1,3-dihydro-2H-indol-2-ones) by reductive dephosphorylation with hydroiodic acid of 3-(diethylphosphoryloxy)-oxindoles, derived from isatins (1H-Indole-2,3-diones)>, Category: indole-building-block, the main research area is diethylphosphoryloxy oxindole preparation reductive dephosphorylation; oxindole preparation.

A novel method for the synthesis of 3-unsubstituted oxindoles by the reductive dephosphorylation of 3-(diethylphosphoryloxy)oxindoles with hydroiodic acid was developed. This synthetic strategy involved a two-step procedure including a phospha-Brook rearrangement of isatins with di-Et phosphite and a reductive dephosphorylation of the phosphorylated oxindoles.

Marcin, Lawrence R’s team published research in Organic Letters in 2005-06-23 | 4771-48-6

Organic Letters published new progress about Cyclopropanation catalysts, stereoselective. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

Marcin, Lawrence R.; Denhart, Derek J.; Mattson, Ronald J. published the artcile< Catalytic Asymmetric Diazoacetate Cyclopropanation of 1-Tosyl-3-vinylindoles. A Route to Conformationally Restricted Homotryptamines>, Application In Synthesis of 4771-48-6, the main research area is homotryptamine preparation vinylindole diazoacetate asym cyclopropanation.

Substituted 1-tosyl-3-vinylindoles undergo catalytic asym. cyclopropanation with Et and tert-Bu diazoacetate to afford N-protected trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters in good yield and high enantiomeric excess (81-88% ee). The resulting cycloadducts are demonstrated to be useful intermediates for the synthesis of conformationally restricted, homotryptamine-like analogs such as BMS-505130 (I.maleate).

Kim, Jaehyun’s team published research in ACS Nano in 2022-05-24 | 950846-89-6

ACS Nano published new progress about Convective flow. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Safety of 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one.

Kim, Jaehyun; Jeon, Joa; Wang, Cong; Chang, Gyu Tae; Park, Jungyul published the artcile< Asymmetric Nanochannel Network-Based Bipolar Ionic Diode for Enhanced Heavy Metal Ion Detection>, Safety of 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, the main research area is asym nanochannel bipolar ionic diode heavy metal ion detection; Biosensor; Bipolar ionic diode; Geometrical optimization; Ion current rectification; Ionic junction.

A higher rectification degree in ionic diodes is required to achieve better performance in applications. Nonetheless, the active geometrical change that is critical for inducing elec. potential asymmetry is difficult to realize in typical ionic diodes because of the intrinsic limitation of the fabrication method. Here, we propose a nanochannel-network-based bipolar diode with a high rectification degree of ≈1600-the highest value realized until now, to the best of our knowledge. Such a high rectification is obtained based on the synergetic effect of the bipolar surface charge and the optimization of the microchannel through exptl. studies and multiphysics numerical simulations. It induces ion concentrations at the heterogeneous junction based on the accumulation effect under the forward potential bias. In particular, this proposed mol. concentration occurs in the ohmic region without vortex and instability that is inevitable at the conventional nano-electrokinetic concentration Combining this accumulation with the horizontally aligned configuration of the nanochannel network membrane (NCNM), a highly sensitive and quant. mercury ion (Hg2+) sensor based on a fluorescent signal is fabricated that allows direct measurement using a general fluorescent microscope. The detection limit of Hg2+ is 10 pM, which is ≈10 times lower than the best detection limit realized so far (≈100 pM) in fluorescent dye-based detection. This demonstrates the potential of asym. NCNM for high-performance ion transport in applications such as energy conversion, based on its design and material flexibility.

Lu, Lin’s team published research in Organic Letters in 2019-04-19 | 4771-48-6

Organic Letters published new progress about Crystal structure. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

Lu, Lin; Luo, Chenguang; Peng, Hui; Jiang, Huanfeng; Lei, Ming; Yin, Biaolin published the artcile< Access to Polycyclic Sulfonyl Indolines via Fe(II)-Catalyzed or UV-Driven Formal [2 + 2 + 1] Cyclization Reactions of N-((1H-indol-3-yl)methyl)propiolamides with NaHSO3>, Application In Synthesis of 4771-48-6, the main research area is sulfonyl indoline iron catalyst UV cyclization indolylmethylpropiolamide sodium sulfite.

A variety of structurally novel polycyclic sulfonyl indolines were synthesized via FeCl2-catalyzed or UV-driven intramol. formal [2 + 2 + 1] dearomatizing cyclization reactions of N-(1H-indol-3-yl)methylpropiolamides with NaHSO3 in an aqueous medium. The reactions involve the formation of one C-C bond and two C-S bonds in a single step.

Organic Letters published new progress about Crystal structure. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

Kim, Yong-Guy’s team published research in Microbiology Spectrum in 2022-02-28 | 93247-78-0

Microbiology Spectrum published new progress about Acne vulgaris. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Recommanded Product: Methyl 1H-indole-7-carboxylate.

Kim, Yong-Guy; Lee, Jin-Hyung; Park, Sunyoung; Lee, Jintae published the artcile< The anticancer agent 3,3'-diindolylmethane inhibits multispecies biofilm formation by acne-causing bacteria and Candida albicans>, Recommanded Product: Methyl 1H-indole-7-carboxylate, the main research area is diindolylmethane anticancer Candida albicans acne causing bacteria agent biofilm; 3,3′-diindolylmethane; Cutibacterium acnes; antibiofilm; indole-3-carbinol; multispecies biofilms.

The Gram-pos. anaerobic bacterium Cutibacterium acnes is a major inhabitant of human skin and has been implicated in acne vulgaris formation and in the formation of multispecies biofilms with other skin-inhabiting organisms like Staphylococcus aureus and Candida albicans. Indoles are widespread in nature (even in human skin) and function as important signaling mols. in diverse prokaryotes and eukaryotes. In the present study, we investigated the antibacterial and antibiofilm activities of 20 indoles against C. acnes. Of the indoles tested, indole-3-carbinol at 0.1 mM significantly inhibited biofilm formation by C. acnes without affecting planktonic cell growth, and the anticancer drug 3,3′-diindolylmethane (DIM) at 0.1 mM (32μg/mL) also significantly inhibited planktonic cell growth and biofilm formation by C. acnes, whereas the other indoles and indole itself were less effective. Also, DIM at 0.1 mM successfully inhibited multispecies biofilm formation by C. acnes, S. aureus, and C. albicans. Transcriptional analyses showed that DIM inhibited the expressions of several biofilm-related genes in C. acnes, and at 0.05 mM, DIM inhibited hyphal formation and cell aggregation by C. albicans. These results suggest that DIM and other indoles inhibit biofilm formation by C. acnes and have potential use for treating C. acnes associated diseases.

Zhang, Xiaoxiang’s team published research in Organic & Biomolecular Chemistry in 2021 | 93247-78-0

Organic & Biomolecular Chemistry published new progress about C-C bond formation. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Formula: C10H9NO2.

Zhang, Xiaoxiang; Zhang, Yingying; Gu, Xiaoting; Zhang, Zhuan; Wei, Wanxing; Liang, Taoyuan published the artcile< Synthesis of 3-halogenated 2,3'-biindoles by a copper-mediated 2,3-difunctionalization of indoles>, Formula: C10H9NO2, the main research area is halo biindole green regioselective preparation; indole difunctionalization catalyst copper.

A copper-mediated 2,3-difunctionalization of indoles to afford 3-halogenated 2,3′-biindoles I [R1 = 5-Me, 4-Cl, 5-Cl, etc.; R2 = Me, Et, Ph, etc.; X = Cl, Br] was described herein. The protocol uses readily available feedstocks and a naturally abundant copper catalyst system, which allowed the regioselective formation of C-C and C-X (X = Cl and Br) bonds in one single operation. Here the copper metal salt served not only as a catalyst but also as a reactant to provide the source of halogen. This operationally simple procedure avoided the utilization of environmentally unfriendly reagents and displays good functional group compatibility. Noteworthily, the introduction of halogen into mols. would offered great potential for further chem. transformations.

Organic & Biomolecular Chemistry published new progress about C-C bond formation. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Formula: C10H9NO2.

Somei, Masanori’s team published research in Chemical & Pharmaceutical Bulletin in 1987-03-25 | 4771-48-6

Chemical & Pharmaceutical Bulletin published new progress about Coupling reaction catalysts. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Computed Properties of 4771-48-6.

Somei, Masanori; Yamada, Fumio; Naka, Katsumi published the artcile< The chemistry of indoles. XL. Tin-thall reaction, a versatile method for cross-coupling tin compounds with thallium compounds>, Computed Properties of 4771-48-6, the main research area is alkylindolecarboxaldehyde; indolylthallium fluoroacetate coupling organotin; coupling indolylthallium fluoroacetate catalyst.

Indolylthallium compound I was treated with organotin compounds and Pd acetate catalyst to yield 4-substituted indoles II (R1 = alkyl, Ph, pyridyl).

Valdenaire, Anja’s team published research in Bioorganic & Medicinal Chemistry Letters in 2013-02-15 | 4771-48-6

Bioorganic & Medicinal Chemistry Letters published new progress about Biological ion transport, calcium. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application of C10H9NO.

Valdenaire, Anja; Pothier, Julien; Renneberg, Dorte; Riederer, Markus A.; Peter, Oliver; Leroy, Xavier; Gnerre, Carmela; Fretz, Heinz published the artcile< Evolution of novel tricyclic CRTh2 receptor antagonists from a (E)-2-cyano-3-(1H-indol-3-yl)acrylamide scaffold>, Application of C10H9NO, the main research area is CRTh2 receptor antagonist cyanoindolylacrylamide preparation structure activity.

(E)-2-(3-(3-((3-Bromophenyl)amino)-2-cyano-3-oxoprop-1-en-1-yl)-1H-indol-1-yl)acetic acid (1) was discovered in a HTS campaign for CRTh2 receptor antagonists. An SAR around this hit could be established and representatives with interesting activity profiles were obtained. Ring closing tactics to convert this hit series into a novel 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole based CRTh2 receptor antagonist series is presented.