Indole Building Blocks

Palomba, Martina’s team published research in ARKIVOC (Gainesville, FL, United States) in 2019 | 399-76-8

ARKIVOC (Gainesville, FL, United States) published new progress about Amides Role: PAC (Pharmacological Activity), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), PREP (Preparation), USES (Uses). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Category: indole-building-block.

Palomba, Martina; Pompei, Sara; Roscini, Luca; Bagnoli, Luana published the artcile< Synthesis and biological evaluation of new indole and pyrrole carboxamides based on amino acids>, Category: indole-building-block, the main research area is indolecarboxamide preparation antifungal; pyrrolecarboxamide preparation antifungal.

A series of indole-carboxamides I [R = H, 5-MeO, 5-F, 7-NO2, 5,6-di-MeO; R1 = i-Pr, CH(Me)Et, Bn, etc.; R2 = Me, Et] and II was synthesized through coupling reactions. Several substitutions on the aromatic ring and on the amino acids were well tolerated, and corresponding indole-carboxamides I and II were obtained with good yields. The same procedure could be also extended to pyrrole-carboxamides III. The compounds I [R = 5-MeO, 5,6-di-MeO, 7-NO2; R1 = i-Pr; R2 = Et] and III [R1 = i-Pr, R2 = Et] were screened for their antimicrobial activity against ten different yeast strains and only compounds I [R = 7-NO2, R1 = i-Pr, R2 = Et] and III [R1 = i-Pr, R2 = Et] showed an antifungal activity. Further explorations were required to clarify a potential applicability in biol. fields.

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

Mallick, Debajani’s team published research in Dyes and Pigments in 2020-10-31 | 950846-89-6

Dyes and Pigments published new progress about Density functional theory. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Formula: C30H36N4O2.

Mallick, Debajani; Bag, Bamaprasad published the artcile< Altered metal ion selectivity in signalling with heterocyclic tripodal receptor appended rhodamine-B derivatives>, Formula: C30H36N4O2, the main research area is metal ion selectivity fluorescent sensor rhodamine B derivative.

The rhodamine derivatives (2-7) were shown to exhibit metal ion complexation induced photophys. ‘turn-on’ signalling responses, where the selectivity in signalling were driven by stereo-electronic environment of the receptor units that structurally differ as derivatization of different heterocyclic units. The chromogenic and fluorogenic spectral enhancements of two order higher in logarithmic scale were observed in these tripodal receptor incorporated amino-ethyl-rhodamine probes, where substitution of a 2-[2-[(thiophen-2-yl-methyl)-(2-pyridinylmethyl)-amino]-ethyl]- (as in 3) has shown selectivity for Hg(II) ion, a 2-[2-[(furan-2-yl-methyl)-(2-pyridinyl methyl)-amino]-ethyl]- (as in 5) for Al(III) ion and a 2-[2-[(phen-2-ylmethyl)-(2-pyridinylmethyl)-amino]-ethyl]- (as in 7) for Fe(III) ion resp. The higher order of association constants (log Ka > 9.0) of complexation, high sensitivity of detection(LOD < 2 nM) and higher rate of interaction between probe and metal ion (k ∼ 0.001 s-1) have showed potential of these probes in selective detection of corresponding metal ions. In general, the investigations on complexation induced photophys. signalling in these probes in terms of selectivity and sensitivity of detection, association constants of complex formation, reversibility in signalling, execution at different pH range, kinetics of spiro-ring opening and theor. structure elucidation have therefore put insights on their coordination mediated stereo-electronic environment to establish a rationality in structure-function correlation. Dyes and Pigments published new progress about Density functional theory. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Formula: C30H36N4O2.

Wang, Kun-Peng’s team published research in Journal of Luminescence in 2019-04-30 | 950846-89-6

Journal of Luminescence published new progress about Fluorescence. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Category: indole-building-block.

Wang, Kun-Peng; Zheng, Wen-Jun; Lei, Yang; Zhang, Si-Jie; Zhang, Qi; Chen, Shaojin; Hu, Zhi-Qiang published the artcile< A thiophene-rhodamine dyad as fluorescence probe for ferric ion and its application in living cells imaging>, Category: indole-building-block, the main research area is thiophene rhodamine dyad fluorescence probe ferric ion cell imaging.

A thiophene-rhodamine dyad (BYY) was easily synthesized as a fluorescence probe from 2-thiopheneacetic acid and N-(rhodamine-B)lactam-ethylenediamine. The probe showed high response speed and sensitivity toward Fe3+ in ethanol/water (2/3, volume/volume, pH = 7.2), and the limit of detection was as low as 10-7 M. From the Job’s plot, mass spectrum, 1H NMR spectra and the theor. calculation, the 1:2 complex ratio of Fe3+-probe was obtained and the response mechanism was determined Significantly, the reversible binding of BYY to Fe3+ was achieved through the strong Fe3+ affinity of Na4P2O7, and the probe showed well antijamming abilities in the presence of common metal ions. Moreover, the probe was cell-permeable and could sensitively response to Fe3+ in living cells with satisfying resolution

Journal of Luminescence published new progress about Fluorescence. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Category: indole-building-block.

Kaewtong, Chatthai’s team published research in Environmental Technology in 2022 | 950846-89-6

Environmental Technology published new progress about Absorption. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, SDS of cas: 950846-89-6.

Kaewtong, Chatthai; Wanich, Suchana; Wanno, Banchob; Tuntulani, Thawatchai; Pulpoka, Buncha published the artcile< An ultra-low detection limit gold(III) probe based on rhodamine-covalent hydrogel sensor>, SDS of cas: 950846-89-6, the main research area is gold probe rhodamine covalent hydrogel sensor; Agarose hydrogel; DFT; gold; rhodamine; sensor.

A highly sensitive and selective optical chemosensor (Arg-Rhoen) for determination of Au3+ was prepared by covalent immobilization of rhodamine ethylenediamine on agarose gel. Spectrophotometric studies of complex formation, chem. structures and purity of the hydrogel sensor were carried out using TGA, NMR, TEM, and IR. The complexation study results indicated that this probe can selectively detect Au3+ via a metal ion chelation-induced ring-opening reaction, and then caused a remarkable color change from colorless to pink and a strong fluorescence enhancement. Theor. DFT calculation results suggested that the hydrogel sensor formed stable complexes with Au3+ through a large number of cation-dipole interactions. Reusability has been established by repeatedly dipping and rinsing the hydrogel in aqueous Au3+ and EDTA in basic solutions We believe that this approach may provide an easily measurable and inherently sensitive method for Au3+ detection in environmental and biol. applications.

Environmental Technology published new progress about Absorption. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, SDS of cas: 950846-89-6.

Wang, Xin’s team published research in Organic Letters in 2021-08-06 | 4771-48-6

Organic Letters published new progress about Cyclization. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Category: indole-building-block.

Wang, Xin; Lou, Chenhao; Lv, Leiyang; Li, Zhiping published the artcile< Annulative π-Extension (APEX) of Indoles to Pyrido[1,2-a]indoles Using 4-Oxo Peroxides as C4 Units>, Category: indole-building-block, the main research area is pyridoindole preparation; indole annulative pi extension.

Annulative π-extension (APEX) of 3-substituted indoles to pyrido[1,2-a]indoles is developed by using 4-oxo peroxides as π-extending reagents, which are employed as versatile C4 building blocks. This transformation is initiated by Bronsted acid-mediated Hock rearrangement of the peroxyl group. Notably, the pyrido[1,2-a]indole products are obtained by elimination of the indole moiety from the corresponding dihydropyrido[1,2-a]indoles, which could be selectively formed at room temperature

Organic Letters published new progress about Cyclization. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Category: indole-building-block.

Sayago, Francisco J’s team published research in Tetrahedron in 2008-01-01 | 145513-91-3

Tetrahedron published new progress about Alkylation, stereoselective. 145513-91-3 belongs to class indole-building-block, and the molecular formula is C9H15NO2, SDS of cas: 145513-91-3.

Sayago, Francisco J.; Isabel Calaza, M.; Jimenez, Ana I.; Cativiela, Carlos published the artcile< Versatile methodology for the synthesis and α-functionalization of (2R,3aS,7aS)-octahydroindole-2-carboxylic acid>, SDS of cas: 145513-91-3, the main research area is indolecarboxylic octahydro alkylated asym synthesis; indolooxazolidinone preparation stereoselective alkylation.

An improved strategy for the effective synthesis of enantiomerically pure (2R,3aS,7aS)-octahydroindole-2-carboxylic acid, based on the formation of a trichloromethyloxazolidinone derivative, has been developed. Addnl., the completely diastereoselective α-alkylation of such oxazolidinone provides a very convenient and concise route to enantiopure α-tetrasubstituted derivatives of this stereoisomer of octahydroindole-2-carboxylic acid.

Tetrahedron published new progress about Alkylation, stereoselective. 145513-91-3 belongs to class indole-building-block, and the molecular formula is C9H15NO2, SDS of cas: 145513-91-3.

Cheng, Zhiyang’s team published research in Journal of Membrane Science in 2021-10-15 | 950846-89-6

Journal of Membrane Science published new progress about Electric conductivity. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Reference of 950846-89-6.

Cheng, Zhiyang; Qin, Qingwen; Jia, Hui; Li, Juan; Yan, Fanyong; Meng, Xia; Wang, Jie published the artcile< Scale evaluation and antiscalant testing based on fluorescent probe technology in RO process>, Reference of 950846-89-6, the main research area is aminotrimethylene phosphonic acid fluorescent probe reverse osmosis.

Inventing the technol. based on fluorescent probes to detect antiscalants in reverse osmosis (RO) concentrated water is of great significance for guiding the use of antiscalant and the control of scale. In this study, Amino trimethylene phosphonic acid (ATMP) was taken as the representative of the antiscalant, and a new fluorescent probe for ATMP detection was designed and synthesized. The new fluorescent probe showed high accuracy for ATMP detection (R2 > 0.94) and resistance to the interference of ions (change rate <3%). Further, the use of probe to detect the antiscalant in RO concentrate and realize the evaluation of the scaling phenomenon was carried out. The model of the relationship between the probe fluorescence intensity and the concentration of precipitated ions was established to analyze the scale evaluation mechanism of the probe. Meanwhile, Critical fluorescence intensity (CFI) was introduced for scale evaluation. The results showed that the new probe could accurately judge the formation of scale under the condition of different antiscalant concentrations, and 926 ± 20 a.u. was judged as CFI for scaling evaluation. Finally, results of the new probe detection in RO scale evaluation test were consistent with the membrane flux and SEM detection, indicating that the probe can accurately evaluate scale during the RO operation. This research can provide tech. support for the precise application of antiscalants and scale inhibition. Journal of Membrane Science published new progress about Electric conductivity. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Reference of 950846-89-6.

Xu, Chong-Hui’s team published research in Organic Chemistry Frontiers in 2022 | 93247-78-0

Organic Chemistry Frontiers published new progress about Aryl alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Formula: C10H9NO2.

Xu, Chong-Hui; Xiong, Zhi-Qiang; Li, Yang; Zhu, Yan-Ping; Li, Jin-Heng published the artcile< Copper-catalyzed oxidative phosphonoheteroarylation of alkenes with phosphonates and N-heteroarenes via P-H/C-H functionalization>, Formula: C10H9NO2, the main research area is heteroaryl alkylphosphonate preparation; alkene phosphonate heteroarene oxidative intermol phosphonoheteroarylation copper catalyst.

A copper-catalyzed oxidative intermol. phosphonoheteroarylation of alkenes R1C(R1)=CHR2 (R1 = 4-methoxyphenyl, 6-bromo-2H-1,3-benzodioxol-5-yl, 3-methylthiophen-2-yl, etc.; R2 = H, Me, Ph, 4-methylphenyl, 4-chlorophenyl; R3 = H, Me) with phosphonates ((R4)2)P(O)H [R4 = OMe, OEt, Oi-Pr, Ph, (2-methylpropyl)oxidanyl] and nucleophilic N-heteroarenes I (R5 = 5-OMe, 4-CHO, 7-COOMe ; R6 = H, Bn, Me, Ph; R7 = H, Me, COOMe) and 1-phenyl-1H-pyrrole involving P-H/C-H functionalization for the synthesis of highly valuable β-(N-heteroaryl)-alkylphosphonates II and III is disclosed. This method allows the incorporation of two functional groups, a phosphonate and a N-heteroarene, into the alkene in a single reaction step through oxidative formation of the P-centered radicals, addition across the C=C bond, single electron oxidation and C-H functionalization cascades.

Kilic-Kurt, Zuehal’s team published research in Archiv der Pharmazie (Weinheim, Germany) in 2020-08-31 | 399-76-8

Archiv der Pharmazie (Weinheim, Germany) published new progress about Annexin V Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

Kilic-Kurt, Zuehal; Acar, Cemre; Ergul, Mustafa; Bakar-Ates, Filiz; Altuntas, Tunca G. published the artcile< Novel indole hydrazide derivatives: Synthesis and their antiproliferative activities through inducing apoptosis and DNA damage>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is anticancer activity apoptosis cell cycle DNA damage Bax Bcl2; DNA damage; anticancer activity; apoptosis; cell cycle; synthesis.

A series of novel indole hydrazide derivatives was synthesized and evaluated for their anticancer activities. Compound 12(I) exhibited the highest antiproliferative activity against the MCF-7 cell line, with an IC50 value of 3.01μM. Treatment of MCF-7 cells with compound 12 led to cell cycle arrest at the G0/G1 phase and also displayed a significant annexin V binding pattern, indicating that compound 12 is effective in apoptotic cell death. The Western blot anal. showed that compound 12 increased the expression of proapoptotic Bax and decreased the levels of the antiapoptotic Bcl-2 protein. It was also observed that MCF-7 cells treated with compound 12 showed reduced levels of procaspase-3 and -9 proteins. Moreover, compound 12 treatment induced a significant DNA damage in MCF-7 cells by increasing H2AX and ATM phosphorylation.

Zhang, Mengyao’s team published research in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 2020-04-15 | 950846-89-6

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

Zhang, Mengyao; Shen, Chuanchuan; Jia, Ting; Qiu, Jianwen; Zhu, Hu; Gao, Yong published the artcile< One-step synthesis of rhodamine-based Fe3+ fluorescent probes via Mannich reaction and its application in living cell imaging>, Name: 2-(2-Aminoethyl)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, the main research area is iron ion bioimaging fluorescent probe Mannich reaction; Fe(3+); Fluorescence probe; Mannich reaction; Rhodamine.

Four rhodamine-based fluorescent probes M1-M4 were synthesized in one step using Mannich reaction. The Mannich reaction based approach has the advantages of simplicity, good yield and excellent at. economy. The structures were determined by 1H NMR, 13C NMR, IR and HRMS. The probe M3 as a representative compound was characterized by single-crystal X-ray analyses. The fluorescence and absorbance spectra research of the probes demonstrated that they could be used as Fe3+-selective fluorescent probes with good sensitivity, excellent linearity, and outstanding anti-interference in acetonitrile/Tris-HCl buffer solution (3:7, V/V; pH = 7.4). Moreover, confocal laser scanning microscopy experiments have proven that the probe M3 was successfully used for fluorescence imaging in MCF-7 cells.