Indole Building Blocks

Forster, Michael’s team published research in International Journal of Molecular Sciences in 2020 | 101083-92-5

International Journal of Molecular Sciences published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 101083-92-5 belongs to class indole-building-block, and the molecular formula is C7H5N3O2, Application In Synthesis of 101083-92-5.

Forster, Michael; Liang, Xiaojun Julia; Schroeder, Martin; Gerstenecker, Stefan; Chaikuad, Apirat; Knapp, Stefan; Laufer, Stefan; Gehringer, Matthias published the artcile< Discovery of a novel class of covalent dual inhibitors targeting the protein kinases BMX and BTK>, Application In Synthesis of 101083-92-5, the main research area is phenyl pyrrolopyridine prepare kinase inhibitor mol docking SAR; Bruton’s tyrosine kinase; Janus kinase 3; bone marrow tyrosine kinase on chromosome X; chemical probes; covalent inhibitors; tyrosine kinases.

Here a novel class of dual BMX/BTK inhibitors, which were designed from irreversible inhibitors of Janus kinase (JAK) 3 targeting a cysteine located within the solvent-exposed front region of the ATP binding pocket was presented. Structure-guided design exploiting the differences in the gatekeeper residues enabled the achievement of high selectivity over JAK3 and certain other kinases harboring a sterically demanding residue at this position. The most active compounds inhibited BMX and BTK with apparent IC50 values in the single digit nanomolar range or below showing moderate selectivity within the TEC family and potent cellular target engagement. These compounds represent an important first step towards selective chem. probes for the protein kinase BMX.

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

Pedrazzani, Riccardo’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2022 | 93247-78-0

Chemical Communications (Cambridge, United Kingdom) published new progress about Carboxylation. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Electric Literature of 93247-78-0.

Pedrazzani, Riccardo; Pinosa, Emanuele; Bertuzzi, Giulio; Monari, Magda; Lauzon, Samuel; Ollevier, Thierry; Bandini, Marco published the artcile< Convenient synthesis of tricyclic N(1)-C(2)-fused oxazino-indolones via [Au(I)] catalyzed hydrocarboxylation of allenes>, Electric Literature of 93247-78-0, the main research area is oxazinoindolone preparation; allenyl indole carboxylic acid hydrocarboxylation gold catalyst.

A new [Au(I)] catalyzed intramol. hydrocarboxylation of allenes was presented as a valuable synthetic route to oxazino[4,3-a]indolones I [R = H, Me, c-hexyl; R1 = H, 8-Me, 8-F, etc.]. The use of 3,5-(CF3)2-C6H3-ImPyAuSbF6 as the optimal catalyst (5 mol%) was necessary to guarantee (i) wide tolerance of functional groups, (ii) mild reaction conditions (r.t., 16 h), and (iii) high yields (up to 90%). Preliminary attempts toward an enantioselective version (81 : 19 er) were also documented by means of a new family of chiral C1-sym. ImPyAuCl complexes.

Kong, Lingkai’s team published research in Journal of Organic Chemistry in 2022-06-17 | 399-76-8

Journal of Organic Chemistry published new progress about Antitumor agents. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Reference of 399-76-8.

Kong, Lingkai; Tian, Wenyue; Liu, Zhiyan; Xu, Ting; Wen, Haoyue; Chen, Zihan; Gao, Jin; Bai, Li-Ping published the artcile< TfOH-Catalyzed Cascade C-H/N-H Chemo-/Regioselective Annulation of Indole-2-carboxamides with Benzoquinones for the Construction of Anticancer Tetracyclic Indolo[2,3-c]quinolinones>, Reference of 399-76-8, the main research area is indoloquinolinone preparation antitumor human; indole carboxamide benzoquinone cyclization trifluoromethanesulfonic acid.

An efficient TfOH-catalyzed cascade C-H/N-H annulation of indole-2-carboxamides with benzoquinones has been developed for the synthesis of tetracyclic indolo[2,3-c]quinolinones. This reaction exhibits excellent chemo-/regioselectivity, achieving functionalization of the C-3 of indole and N-H of the amide moiety to form the new C-C and C-N bonds. Various expected products were synthesized from readily available starting materials in good to high yields with a wide substrate scope and good functional group tolerance. Among all synthetic products, I showed the most potent cytotoxicity toward the 4T1 cancer cell line with an IC50 value of 0.62 +/- 0.05μM. In vivo study demonstrated that I remarkably suppressed 4T1 xenograft tumor growth without body weight loss.

Journal of Organic Chemistry published new progress about Antitumor agents. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Reference of 399-76-8.

Pu, Xingwen’s team published research in Organic Letters in 2019-02-15 | 93247-78-0

Organic Letters published new progress about C-H bond activation. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Synthetic Route of 93247-78-0.

Pu, Xingwen; Zhang, Mangang; Lan, Jingbo; Chen, Shuyou; Liu, Zheng; Liang, Wenbo; Yang, Yudong; Zhang, Min; You, Jingsong published the artcile< Tandem Rh(III)-Catalyzed C-H Heteroarylation of Indolyl Ketones and Cu(II)-Promoted Intramolecular Cyclization: One-Pot Access to Blue-Emitting Phenanthrone-Type Polyheterocycles>, Synthetic Route of 93247-78-0, the main research area is indolyl ketone rhodium copper catalyst tandem heteroarylation cyclization; phenanthrone type polyheterocycle one pot preparation blue emission.

Disclosed herein is a highly efficient one-pot synthetic strategy to phenanthrone-type polyheterocycles via tandem rhodium(III)-catalyzed ortho-C-H heteroarylation of indolyl ketones and copper(II)-promoted intramol. cyclization. This protocol enables a library of blue-emitting fluorophores with high quantum yields and narrow full widths at half-maximum to be rapidly built from readily available substrates, among of which 6,6,7,9,12-pentamethyl-6,12-dihydro-5H-benzofuro[2,3-a]carbazol-5-one exhibits pure blue emission with Commission Internationale de I’Eclairage coordinates of (0.15, 0.09) and a high quantum yield of 85% in CH2Cl2 solution

Organic Letters published new progress about C-H bond activation. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Synthetic Route of 93247-78-0.

Pipattanawarothai, Athit’s team published research in Dyes and Pigments in 2020-02-29 | 950846-89-6

Dyes and Pigments published new progress about Colorimetry. 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.

Pipattanawarothai, Athit; Trakulsujaritchok, Thanida published the artcile< Hybrid polymeric chemosensor bearing rhodamine derivative prepared by sol-gel technique for selective detection of Fe3+ ion>, Recommanded Product: 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, the main research area is hybrid polymeric chemosensor rhodamine B derivative functionalized; ferric ion detection colorimetry.

To develop a reusable and selective colorimetric chemosensor for visual detection of ferric ion, a new rhodamine-based chelator (RB-UTES) was prepared The structural constitution and sensing property of RB-UTES were examined The chelator was sensitive and selective for recognition of ferric ion and could be covalently attached to poly(vinyl alc.) through siloxane linkage formed by the sol-gel reaction. The physicochem. properties and sensing behavior of the functional chemosensor films were studied. By simply soaking in aqueous media, the free-standing sensor film exhibited high selectivity and sensitivity to ferric ion and permitted the convenient detection by naked eye with prominent development of pink color throughout the film. The sensor film could return to its original color by washing with 0.1M ethylenediamine allowing repeated cycles of detection. The combination of its anal. performance, simplicity of operation as well as reusability made this functional sensor promising for the use in aqueous solutions and real samples.

Fang, Fang’s team published research in Journal of Organic Chemistry in 2022-05-06 | 93247-78-0

Journal of Organic Chemistry published new progress about [4+2] Cycloaddition reaction (regioselective). 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Application In Synthesis of 93247-78-0.

Fang, Fang; Zheng, Haolin; Mao, Guojiang; Chen, Shanping; Deng, Guo-Jun published the artcile< Metal- and Solvent-Free Synthesis of Tetrahydrobenzo[c]carbazolones through NaI-Catalyzed Formal [4+2] Annulation>, Application In Synthesis of 93247-78-0, the main research area is indolyl cyclohexanone unsaturated compound sodium iodide catalyst regioselective cycloaddition; tetrahydrobenzocarbazolone preparation.

A novel strategy for the preparation of functional carbazoles through NaI-catalyzed formal [4+2] annulation of 2-(indol-3-yl)cyclohexanones and alkynes/alkenes was developed. The present approach started from easily available raw materials and provided a variety of tetrahydrobenzo[c]carbazolones in satisfactory yields under metal- and solvent-free conditions. The products could be further transformed into structurally valuable carbazole-based conjugated derivatives

Ellervik, Ulf’s team published research in Carbohydrate Research in 1996 | 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.Safety of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranosideThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

Ellervik, Ulf; Magnusson, Goeran published an article on January 11 ,1996. The article was titled 《Glycosylation with N-Troc-protected glycosyl donors》, and you may find the article in Carbohydrate Research.Safety of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside The information in the text is summarized as follows:

N-troc-protected (Troc = 2,2,2-trichloroethoxycarbonyl) glucosamine and galactosamine glycosyl donors, e.g. I (R1,R2 = H, OAc), (1-O-acetyl sugar, bromo sugar, and thioglycoside) were compared with the corresponding N-Phth-protected derivatives II (R1,R2 = H, OAc)in glycosylations of 2-(trimethylsilyl)ethanol, 2-bromoethanol, Me 3-mercaptopropionate, N-Fmoc-protected serine, and 2-(trimethylsilyl)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside. The N-Troc-protected donors gave pure β-glycosides in somewhat higher yields than the N-Phth-protected counterparts. The N-Troc protecting group can be removed by reduction with zinc, which allows selective N-deprotection in oligosaccharides containing both N-Troc and N-Phth groups. The results came from multiple reactions, including the reaction of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Safety of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside)

Veeneman, G. H.’s team published research in Tetrahedron Letters in 1990 | 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.Category: indole-building-blockThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

The author of 《Iodonium ion-promoted reactions at the anomeric center. II. An efficient thioglycoside-mediated approach toward the formation of 1,2-trans-linked glycosides and glycosidic esters》 were Veeneman, G. H.; Van Leeuwen, S. H.; Van Boom, J. H.. And the article was published in Tetrahedron Letters in 1990. Category: indole-building-block The author mentioned the following in the article:

N-Iodosuccinimide (I) in the presence of an organic acid was effective for the activation of fully acylated thioglycosides leading to 1,2-trans linked esters. For example, tetrabenzoylthiogalactopyranoside II (R = EtS) was treated with I and MeOCH2CO2H in Et2O-ClCH2CH2Cl to give 98% II (R = MeOCH2CO2). On the other hand, I together with a catalytic amount of trifluoromethanesulfonic acid was very convenient for the rapid, high-yielding and stereoselective (1,2-trans) glycosidation of esterified thioglycosides with glycosyl acceptors, e.g., III, to give title compds, e.g., IV.Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Category: indole-building-block) was used in this study.

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.Category: indole-building-blockThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

Nguyen, Ngoc-Khanh’s team published research in Molecular Catalysis in 2021 | 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.Computed Properties of C8H6FN

Nguyen, Ngoc-Khanh; Nam, Duong Ha; Phuc, Ban Van; Nguyen, Van Ha; Trinh, Quang Thang; Hung, Tran Quang; Dang, Tuan Thanh published their research in Molecular Catalysis in 2021. The article was titled 《Efficient copper-catalyzed synthesis of C3-alkylated indoles from indoles and alcohols》.Computed Properties of C8H6FN The article contains the following contents:

A highly efficient copper(II) catalyst system for alkylation of indoles with alcs. via hydrogen borrowing method has been developed to afford C3-alkylated indoles I (R1 = H, 5-OMe, 7-Me, etc.; R2 = n-pentyl, Ph, 3-FC6H4, etc.) in good to excellent yields. Cu(OAc)2 in the combination with dppm ligand has been found to be the most suitable catalyst system for this alkylation reaction. After reading the article, we found that the author used 5-Fluoro-1H-indole(cas: 399-52-0Computed Properties of C8H6FN)

Agostini, Federica’s team published research in ACS Central Science in 2021 | CAS: 399-52-0

Agostini, Federica; Sinn, Ludwig; Petras, Daniel; Schipp, Christian J.; Kubyshkin, Vladimir; Berger, Allison Ann; Dorrestein, Pieter C.; Rappsilber, Juri; Budisa, Nediljko; Koksch, Beate published an article in 2021. The article was titled 《Multiomics Analysis Provides Insight into the Laboratory Evolution of Escherichia coli toward the Metabolic Usage of Fluorinated Indoles》, and you may find the article in ACS Central Science.Formula: C8H6FN The information in the text is summarized as follows:

Organofluorine compounds are known to be toxic to a broad variety of living beings in different habitats, and chem. fluorination has been historically exploited by mankind for the development of therapeutic drugs or agricultural pesticides. However, several studies so far demonstrated that, under appropriate conditions, living systems (in particular bacteria) can tolerate the presence of fluorinated mols. (e.g., amino acids analogs) within their metabolism and even repurpose them as alternative building blocks for the synthesis of cellular macromols. such as proteins. Understanding the mol. mechanism behind these phenomena would greatly advance approaches to the biotechnol. synthesis of recombinant proteins and peptide drugs. However, information about the metabolic effects of long-term exposure of living cells to fluorinated amino acids remains scarce. Hereby, the authors report the long-term propagation of Escherichia coli (E. coli) in an artificially fluorinated habitat that yielded two strains naturally adapted to live on fluorinated amino acids. In particular, the authors applied selective pressure to force a tryptophan (Trp)-auxotrophic strain to use either 4- or 5-fluoroindole as essential precursors for the in situ synthesis of Trp analogs, followed by their incorporation in the cellular proteome. Full adaptation to both fluorinated Trp analogs requires a low number of genetic mutations but is accompanied by large rearrangements in regulatory networks, membrane integrity, and quality control of protein folding. These findings highlight the cellular mechanisms behind the adaptation to unnatural amino acids and provide the mol. foundation for bioengineering of novel microbial strains for synthetic biol. and biotechnol. The authors eliminated the metabolic ability of E. coli to produce the canonical amino acid tryptophan and introduced synthesis of two fluorinated analogs in vivo using 4- and 5-fluoroindole as precursors. After reading the article, we found that the author used 5-Fluoro-1H-indole(cas: 399-52-0Formula: C8H6FN)