13/10/2022 - Page 3 of 6 - Indole Building Blocks

Schlegel, Marcel’s team published research in Journal of Organic Chemistry in 2019-05-03 | 399-76-8

Journal of Organic Chemistry published new progress about [4+2] Cycloaddition reaction. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Quality Control of 399-76-8.

Schlegel, Marcel; Schneider, Christoph published the artcile< Iron(III)-Catalyzed (4 + 2)-Cycloannulation of 2-Hydroxy Ketoxime Ethers with Indol-2-ylamides: Synthesis of Indole-Fused 2-Piperidinones>, Quality Control of 399-76-8, the main research area is indole fused piperidinone diastereoselective preparation; hydroxy ketoxime ether indolecarboxamide cycloaddition iron catalyst.

A highly regio- and diastereoselective (4 + 2)-cycloannulation process of indanone-derived 2-hydroxy ketoxime ethers with 1,4-bisnucleophilic indol-2-ylamides has been developed. In the presence of 5 mol % FeCl3, densely functionalized 2-piperidinones containing two new σ-bonds and two vicinal quaternary stereogenic centers were formed under mild reaction conditions in a one-pot operation. Moreover, most of the products directly precipitated out of the solution and were isolated by simple filtration without purification by column chromatog.

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

Xie, Xiu-Ying’s team published research in Synthesis in 2021-08-31 | 93247-78-0

Synthesis published new progress about Aliphatic esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Reference of 93247-78-0.

Xie, Xiu-Ying; Jiang, Wei-Tao; Xiao, Bin published the artcile< Alkyl Carbagermatrane Enabled Synthesis of Seven-Membered Carbocycle-Fused Aromatics through Catellani Strategy>, Reference of 93247-78-0, the main research area is bromoalkyl carbagermatrane preparation iodoarene palladium phosphine regioselective Catellani cyclization; carbocycle fused arene preparation.

Synthesis of seven-membered carbocycle-fused aromatics was realized by Catellani reaction using terminally brominated alkyl carbagermatranes through intermol. cyclization manner. Various functional groups were well tolerated and this transformation was also expanded to the synthesis of carbocycles of other size. The utility of the above method was demonstrated by modification of natural product derivatives and synthesis of bioactive mols.

Zhang, Cheng’s team published research in iScience in 2019-11-22 | 93247-78-0

iScience published new progress about Alkynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Product Details of C10H9NO2.

Zhang, Cheng; Hong, Kemiao; Dong, Shanliang; Pei, Chao; Zhang, Xiaolu; He, Ciwang; Hu, Wenhao; Xu, Xinfang published the artcile< Gold(I)-Catalyzed Aromatization: Expeditious Synthesis of Polyfunctionalized Naphthalenes>, Product Details of C10H9NO2, the main research area is polyfunctionalized naphthalene preparation; alkynyl diazoacetate endo dig carbocyclization gold catalyst; Catalysis; Organic Reaction; Organic Synthesis.

A gold-catalyzed 6-endo-dig carbocyclization of alkyne with the pendent diazo group is reported. It provides an expeditious approach for the synthesis of multi-functionalized naphthalene derivatives under mild conditions. Mechanistic studies suggest that a vinyl gold carbene is generated as the key intermediate in this cascade transformation that smoothly delivers naphthalene products through an unprecedented stepwise aromatization or an intermol. aromatic substitution process. The unique endocyclic vinyl species is inaccessible with other precursors; thus, novel carbene cascade transformations could be envisioned with the current catalytic model. Functional groups, such as alkenyl, hydroxyl, amino, and carboxyl groups, remain untouched under these conditions. In addition, the utility of these generated 2-carboxyl naphthalenes is illustrated by the synthesis of chiral 1,2′-binaphthalene ligands and π-conjugated polycyclic hydrocarbons (CPHs).

Gao, Xuebo’s team published research in Journal of Organic Chemistry in 2022-06-17 | 4771-48-6

Journal of Organic Chemistry published new progress about Carboxylic esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Reference of 4771-48-6.

Gao, Xuebo; Chang, Rong; Rao, Junxin; Hao, Danyang; Zhang, Zhuxia; Zhou, Cong-Ying; Guo, Zhen published the artcile< Halogen-Bonding-Promoted C-H Malonylation of Indoles under Visible-Light Irradiation>, Reference of 4771-48-6, the main research area is indole diethyl bromomalonate photochem malonylation green chem; diethyl indolyl propanedioate preparation.

A halogen-bonding-based electron donor-acceptor (EDA) complex-promoted photoreaction for the synthesis of C2-malonylated indoles was reported. The protocol provided access to a broad range of functionalized indoles in good yields through the coupling reaction of indoles with di-Et bromomalonate under visible-light irradiation without the need for any transition-metal catalyst or photocatalyst.

Xu, Xiang’s team published research in European Polymer Journal in 2022-05-15 | 93247-78-0

European Polymer Journal published new progress about Blue light. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Application of C10H9NO2.

Xu, Xiang; Shen, Yi; Shu, Yue; Guan, Yong; Wei, Dafu published the artcile< Synthesis and application of poly methyl indole-4-carboxylate with blue light blocking properties>, Application of C10H9NO2, the main research area is polyindole oxidative polymerization optical blue light blocking property DFT.

Blue light hazards have garnered increasing attention owing to the popularity of displays. Although melanin on the retina acts as a blue light barrier, overexposure to blue light increases the risk of visual damage. A class of Me indole-n-carboxylate oligomers (O-MInC, n = 3, 4, 5, 6, and 7) was synthesized through solid-phase oxidative polymerization Based on the exptl. characterizations, including time-of-flight mass spectrometry, IR spectroscopy, and d. functional theory calculations of the average local ionization energy, the authors proposed a mechanism for the oxidative polymerization of Me indole-4-carboxylate (MI4C). Me indole-4-carboxylate oligomer (O-MI4C) is composed of cyclic oligomers containing large conjugated structures that are generated by the repetition of electron deprivation, radical coupling, and dehydrogenation reactions. O-MI4C exhibits the best blue light absorption among its allotropes substituted at different positions with a cut-off absorption wavelength of 530 nm. Finally, O-MI4C was added to polymethyl methacrylate (PMMA) and Columbia resin 39 (CR-39) flakes through in situ polymerization to investigate the behavior of blue light blocking. The PMMA/O-MI4C (0.01 wt%) and CR-39/O-MI4C (0.02 wt%) can block 25% and 35% of blue light; however, they have no significant effect on green and orange lights.

European Polymer Journal published new progress about Blue light. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Application of C10H9NO2.

Hu, Jiwen’s team published research in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 2020-11-05 | 950846-89-6

Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy published new progress about Colorimetric sensors. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Recommanded Product: 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one.

Hu, Jiwen; Yu, Xili; Zhang, Xin; Jing, Changcheng; Liu, Tingting; Hu, Xiaochun; Lu, Senlin; Uvdal, Kajsa; Gao, Hong-Wen; Hu, Zhangjun published the artcile< Rapid detection of mercury (II) ions and water content by a new rhodamine B-based fluorescent chemosensor>, Recommanded Product: 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, the main research area is detection mercury ion water content fluorescent chemosensor; Fluorescence; Mercury; Rhodamine B; Water content.

A rhodamine B-based sensor (RS, I) was designed and synthesized by a combination of the spirolacton rhodamine B (fluorophore) and multidentate chelates (ionophore) with high affinity towards Hg2+. In the presence of Hg2+, the resulting red-orange fluorescence (under UV light) and naked eye red color of RS are supposed to be used for quant. and qual. measurement of Hg2+. Further fluorescent titration and anal. demonstrate that RS can selectively detect Hg2+ within 1 s with a low limit of detection (LOD) of 16 nM in acetonitrile media, meanwhile, the association constant (Ka) was calculated to be 0.32 x 105 M-1. More importantly, the resultant complex (RSHg) of RS and Hg2+ has also been successfully applied to detect limited water content in acetonitrile solution

Velezheva, Valeriya’s team published research in Bioorganic & Medicinal Chemistry Letters in 2016 | CAS: 380448-07-7

5-Chloro-3-formyl-1H-indole-2-carboxylic acid(cas: 380448-07-7) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Synthetic Route of C10H6ClNO3

Velezheva, Valeriya; Brennan, Patrick; Ivanov, Pavel; Kornienko, Albert; Lyubimov, Sergey; Kazarian, Konstantin; Nikonenko, Boris; Majorov, Konstantin; Apt, Alexander published an article on February 1 ,2016. The article was titled 《Synthesis and antituberculosis activity of indole-pyridine derived hydrazides, hydrazide-hydrazones, and thiosemicarbazones》, and you may find the article in Bioorganic & Medicinal Chemistry Letters.Synthetic Route of C10H6ClNO3 The information in the text is summarized as follows:

We describe the design, synthesis, and in vitro antimycobacterial activity of a series of novel simple hybrid hydrazides and hydrazide-hydrazones combining indole and pyridine nuclei. The compounds are derivatives of 1-acetylindoxyl or substituted indole-3-carboxaldehydes tethered via a hydrazine group by simple C-N or double C:N bonds with 3- and 4-pyridines, 1-oxide 3- and 4-pyridine carbohydrazides. The most active of the 15 compounds showed MICs values against an INH-sensitive strain of Mycobacterium tuberculosis H37Rv equal to that of INH (0.05-2 μg/mL). Five compounds demonstrated appreciable activity against the INH-resistant M. tuberculosis CN-40 clin. isolate (MICs: 2-5 μg/mL), providing justification for further in vivo studies. The results came from multiple reactions, including the reaction of 5-Chloro-3-formyl-1H-indole-2-carboxylic acid(cas: 380448-07-7Synthetic Route of C10H6ClNO3)

Zhang, Jitan’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.Electric Literature of C8H6FN

In 2019,Chemical Communications (Cambridge, United Kingdom) included an article by Zhang, Jitan; Wu, Manyi; Fan, Jian; Xu, Qiaoqiao; Xie, Meihua. Electric Literature of C8H6FN. The article was titled 《Selective C-H acylation of indoles with α-oxocarboxylic acids at the C4 position by palladium catalysis》. The information in the text is summarized as follows:

The first Pd-catalyzed direct C-H acylation of indoles at the C4 position with α-oxocarboxylic acids using a ketone directing group was described. This reaction exhibited high regioselectivity with the tolerance of a wide scope of functional groups to afford diverse acylated indoles I [R = Me, Ph, Bn, Ts; R1 = H, Me, Ph; R2 = H, Me, Et, t-Bu, Ph; R3 = Ph, 4-MeC6H4, 2-thienyl, etc.; R4 = H, 5-F, 6-Br, etc.] in moderate to good yields. The control experiments evidenced the generation of acyl radicals via K2S2O8 promoted decarboxylation of α-oxocarboxylic acids and the involvement of a PdII/PdIV catalytic cycle. Importantly, the synthetically useful selectivity observed might be applied to prepare indole derivatives with anti-tumor activity as tubulin inhibitors. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0Electric Literature of C8H6FN)

Vyhlidalova, Barbora’s team published research in International Journal of Molecular Sciences 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.Recommanded Product: 1H-Indole

《Gut microbial catabolites of tryptophan are ligands and agonists of the aryl hydrocarbon receptor: a detailed characterization》 was written by Vyhlidalova, Barbora; Krasulova, Kristyna; Pecinkova, Petra; Marcalikova, Adela; Vrzal, Radim; Zemankova, Lenka; Vanco, Jan; Travnicek, Zdenek; Vondracek, Jan; Karasova, Martina; Mani, Sridhar; Dvorak, Zdenek. Recommanded Product: 1H-IndoleThis research focused ontryptophan aryl hydrocarbon receptor signaling colorectal hepatocyte adenocarcinoma; aryl hydrocarbon receptor; indoles; microbiome; tryptophan. The article conveys some information:

We examined the effects of gut microbial catabolites of tryptophan on the aryl hydrocarbon receptor (AhR). Using a reporter gene assay, we show that all studied catabolites are low-potency agonists of human AhR. The efficacy of catabolites differed substantially, comprising agonists with no or low (i3-propionate, i3-acetate, i3-lactate, i3-aldehyde), medium (i3-ethanol, i3-acrylate, skatole, tryptamine), and high (indole, i3-acetamide, i3-pyruvate) efficacies. We displayed ligand-selective antagonist activities by i3-pyruvate, i3-aldehyde, indole, skatole, and tryptamine. Ligand binding assay identified low affinity (skatole, i3-pyruvate, and i3-acetamide) and very low affinity (i3-acrylate, i3-ethanol, indole) ligands of the murine AhR. Indole, skatole, tryptamine, i3-pyruvate, i3-acrylate, and i3-acetamide induced CYP1A1 mRNA in intestinal LS180 and HT-29 cells, but not in the AhR-knockout HT-29 variant. We observed a similar CYP1A1 induction pattern in primary human hepatocytes. The most AhR-active catabolites (indole, skatole, tryptamine, i3-pyruvate, i3-acrylate, i3-acetamide) elicited nuclear translocation of the AhR, followed by a formation of AhR-ARNT heterodimer and enhanced binding of the AhR to the CYP1A1 gene promoter. Collectively, we comprehensively characterized the interactions of gut microbial tryptophan catabolites with the AhR, which may expand the current understanding of their potential roles in intestinal health and disease. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Recommanded Product: 1H-Indole)

Vesely, Jan’s team published research in Collection of Czechoslovak Chemical Communications in 2003 | 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.Electric Literature of C22H25NO9SThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

Vesely, Jan; Ledvina, Miroslav; Jindrich, Jindrich; Saman, David; Trnka, Tomas published an article in Collection of Czechoslovak Chemical Communications. The title of the article was 《Improved synthesis of 1,2-trans-acetates and 1,2-trans ethyl 1-thioglycosides derived from 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-hexopyranosides》.Electric Literature of C22H25NO9S The author mentioned the following in the article:

Effective one-pot synthesis of 1,2-trans-acetates derived from N-phthaloyl-protected D-glucosamine, D-galactosamine and D-mannosamine, resp., is presented. Anomerization of the corresponding 1,2-cis-acetates and direct conversion of all of them to 1,2-trans Et 1-thioglycosides are also described and discussed. In the experiment, the researchers used many compounds, for example, Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Electric Literature of C22H25NO9S)