14/10/2022 - Page 7 of 9 - Indole Building Blocks

Morigi, Rita’s team published research in European Journal of Medicinal Chemistry in 2019-03-15 | 20870-77-3

European Journal of Medicinal Chemistry published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Related Products of 20870-77-3.

Morigi, Rita; Locatelli, Alessandra; Leoni, Alberto; Rambaldi, Mirella; Bortolozzi, Roberta; Mattiuzzo, Elena; Ronca, Roberto; Maccarinelli, Federica; Hamel, Ernest; Bai, Ruoli; Brancale, Andrea; Viola, Giampietro published the artcile< Synthesis, in-vitro and in-vivo biological evaluation of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones as new potent anticancer agents>, Related Products of 20870-77-3, the main research area is imidazothiazolylmethylene indolinone preparation antitumor activity SAR cytotoxicity apoptosis; 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones; Antiproliferative; Antitumor; Apoptosis; Synthesis.

A small library of 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones were synthesized and screened according to protocols available at the National Cancer Institute (NCI). Some derivatives were potent antiproliferative agents, showing GI50 values in the nanomolar range. Remarkably, when most active compounds against leukemia cells were tested in human peripheral blood lymphocytes from healthy donors, were 100-200 times less cytotoxic. Some compounds, selected by the Biol. Evaluation Committee of NCI, were examined to determine tubulin assembly inhibition. Furthermore, flow cytometric studies performed on HeLa, HT-29, and A549 cells, showed that compounds and caused a block in the G2/M phase. Interestingly, these derivatives induced apoptosis through the mitochondrial death pathway, causing in parallel significant activation of both caspase-3 and -9, PARP cleavage and down-regulation of the anti-apoptotic proteins Bcl-2 and Mcl-1. Finally, compound was also tested in-vivo in the murine BL6-B16 melanoma and E0771 breast cancer cells, causing in both cases a significant reduction in tumor volume

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

Cockerill, G Stuart’s team published research in Journal of Medicinal Chemistry in 2021-04-08 | 20870-77-3

Journal of Medicinal Chemistry published new progress about Antiviral agents. 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Reference of 20870-77-3.

Cockerill, G. Stuart; Angell, Richard M.; Bedernjak, Alexandre; Chuckowree, Irina; Fraser, Ian; Gascon-Simorte, Jose; Gilman, Morgan S. A.; Good, James A. D.; Harland, Rachel; Johnson, Sara M.; Ludes-Meyers, John H.; Littler, Edward; Lumley, James; Lunn, Graham; Mathews, Neil; McLellan, Jason S.; Paradowski, Michael; Peeples, Mark E.; Scott, Claire; Tait, Dereck; Taylor, Geraldine; Thom, Michelle; Thomas, Elaine; Villalonga Barber, Carol; Ward, Simon E.; Watterson, Daniel; Williams, Gareth; Young, Paul; Powell, Kenneth published the artcile< Discovery of Sisunatovir (RV521), an Inhibitor of Respiratory Syncytial Virus Fusion>, Reference of 20870-77-3, the main research area is Sisunatovir analog drug discovery synthesis RSV antiviral.

RV521 is an orally bioavailable inhibitor of respiratory syncytial virus (RSV) fusion that was identified after a lead optimization process based upon hits that originated from a phys. property directed hit profiling exercise at Reviral. This exercise encompassed collaborations with a number of contract organizations with collaborative medicinal chem. and virol. during the optimization phase in addition to those utilized as the compound proceeded through preclin. and clin. evaluation. RV521 exhibited a mean IC50 of 1.2 nM against a panel of RSV A and B laboratory strains and clin. isolates with antiviral efficacy in the Balb/C mouse model of RSV infection. Oral bioavailability in preclin. species ranged from 42 to >100% with evidence of highly efficient penetration into lung tissue. In healthy adult human volunteers exptl. infected with RSV, a potent antiviral effect was observed with a significant reduction in viral load and symptoms compared to placebo.

Journal of Medicinal Chemistry published new progress about Antiviral agents. 20870-77-3 belongs to class indole-building-block, and the molecular formula is C8H6ClNO, Reference of 20870-77-3.

Xie, Jia-Hao’s team published research in Angewandte Chemie, International Edition in 2021-10-04 | 93247-78-0

Angewandte Chemie, International Edition published new progress about Allylation catalysts, stereoselective. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Formula: C10H9NO2.

Xie, Jia-Hao; Zheng, Chao; You, Shu-Li published the artcile< Palladium-Catalyzed Dearomative Methoxyallylation of 3-Nitroindoles with Allyl Carbonates>, Formula: C10H9NO2, the main research area is nitroindole allyl carbonate palladium catalyst dearomative methoxyallylation; methoxy nitro propenyl indole carboxylate diastereoselective preparation; 3-nitroindole; allylic substitution; dearomatization; diastereoselectivity; palladium.

A Pd-catalyzed dearomative methoxyallylation of 3-nitroindoles with readily available allyl carbonates was reported. Good yields (up to 86%) and diastereoselectivity (up to >20:1 dr) were obtained for a wide range of substrates. The compatibility of gram-scale synthesis and the relatively low catalyst loading (down to 1 mol % of [Pd]) enhanced the practicality of this method. The kinetic experiments indicated that the rate-determining step of this reaction was the nucleophilic attack of the alkoxide anion.

Jakkampudi, Satish’s team published research in Chemistry – A European Journal in 2019 | 145513-91-3

Chemistry – A European Journal published new progress about Acetalization catalysts, stereoselective. 145513-91-3 belongs to class indole-building-block, and the molecular formula is C9H15NO2, HPLC of Formula: 145513-91-3.

Jakkampudi, Satish; Parella, Ramarao; Arman, Hadi D.; Zhao, John C.-G. published the artcile< Diastereodivergent Synthesis of Hexahydro-6H-benzo[c]chromen-6-one Derivatives Catalyzed by Modularly Designed Organocatalysts>, HPLC of Formula: 145513-91-3, the main research area is oxo heptenal hydroxy nitrostyrene organocatalyst Michael acetalization oxidation; nitro oxoethyl hexahydrobenzochromenone enantioselective diastereoselective preparation; chromanone; diastereodivergent catalysis; domino reaction; enantioselectivity; organocatalysis; self-assembly.

The diastereodivergent synthesis of hexahydro-6H-benzo[c]chromen-6-one derivatives with good to high diastereoselectivities (up to 98:2 d.r.) and enantioselectivities (up to >99 % ee) was achieved by using a domino Michael/Michael/hemiacetalization reaction between trans-2-hydroxy-β-nitrostyrenes and trans-7-oxo-5-heptenals followed by oxidation With use of appropriate modularly designed organocatalysts that were self-assembled in-situ from amino acid derivatives and cinchona alkaloid derivatives two different diastereomers of the desired hexahydro-6H-benzo[c]chromen-6-ones were obtained from the same substrates.

Hamstra, Anna’s team published research in Journal of Fluorescence in 2022-05-31 | 950846-89-6

Journal of Fluorescence published new progress about Excited singlet state. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Electric Literature of 950846-89-6.

Hamstra, Anna; Cai, Yajie; Reynolds, Zachary; Griffins, Cody S.; Rheingold, Arnold L.; Schaaf, Nicholas J.; Sinn, Ekkehard; Bates, Jefferson E.; Weerasinghe, Aruna J. published the artcile< Utilizing Experiment and Theory to Evaluate Rhodamine B ethylenediamine as a Fluorescent Sensor for G-type Nerve Agents>, Electric Literature of 950846-89-6, the main research area is rhodamine ethylenediamine diethyl chlorophosphate fluorescence excited state; Computational; Fluorescence; Nerve Agents; Rhodamine; Sensor.

Nerve gas mimic binding with Rhodamine B ethylenediamine (1) was studied in organic media. Binding of the nerve gas mimic, di-Et chlorophosphate (DCP), with the probe generated a non-fluorescent intermediate and a fluorescent product. Fluorescent and non-fluorescent products generated were identified using mass spectrometry and X-ray crystallog. Time-dependent d. functional theory calculations were also used to investigate the electronic structure of the fluorescent probe in the ground and lowest lying π → π* singlet excited state. Though good agreement between theory and experiment can be obtained for the intense peak in the exptl. spectrum using non-hybrid functionals, care must be taken when modeling these complexes due to the appearance of an n → π* transition that is too low in energy and appears to fall in the shoulders of the π → π* transitions.

Lu, Ming-Zhu’s team published research in Organic Letters in 2020-04-03 | 93247-78-0

Organic Letters published new progress about Aryl silanes 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, Quality Control of 93247-78-0.

Lu, Ming-Zhu; Ding, Xin; Shao, Changdong; Hu, Zhengsong; Luo, Haiqing; Zhi, Sanjun; Hu, Huayou; Kan, Yuhe; Loh, Teck-Peng published the artcile< Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp2)-H Bonds Enabled by Cobalt Catalysis>, Quality Control of 93247-78-0, the main research area is pyrimidyl indole arylsilane cobalt catalyst Hiyama cross coupling arylation; arylsilane pyrimidyl pyrrole cobalt catalyst Hiyama cross coupling arylation.

A chelation-assisted C-H arylation of various indoles with sterically and electronically diverse (hetero)arylsilanes enabled by cost-effective Cp*-free cobalt catalysis was reported. Key to the success of this strategy was the judicious choice of copper(II) fluoride as a bifunctional sliane activator and catalyst reoxidant. This methodol. features a broad substrate scope and good functional group compatibility. The synthetic versatility of this protocol was highlighted by the gram-scale synthesis and late-stage diversification of biol. active mols.

Adak, Arup Kumar’s team published research in New Journal of Chemistry in 2019 | 950846-89-6

New Journal of Chemistry published new progress about Complexation. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Electric Literature of 950846-89-6.

Adak, Arup Kumar; Purkait, Rakesh; Manna, Saikat Kumar; Ghosh, Bankim Chandra; Pathak, Sudipta; Sinha, Chittaranjan published the artcile< Fluorescence sensing and intracellular imaging of Pd2+ ions by a novel coumarinyl-rhodamine Schiff base>, Electric Literature of 950846-89-6, the main research area is coumarinyl rhodamine Schiff base fluorescence imaging Palladium ion.

Coumarinyl-rhodamine, HCR, served as an extremely selective sensor for Pd2+ ions in ethanol/H2O (8 : 2, volume/volume, HEPES buffer, pH 7.2) solution and the limit of detection (LOD) was 18.8 nM (3σ method). The free sensor, HCR, was weakly emissive and in the presence of Pd2+, the color changed from straw to pink with very strong emission at 598 nm in the presence of eighteen other cations. A plausible mechanism involved opening of the spirolactam ring of rhodamine on interaction with Pd2+, which was justified by structure optimization and transition energy calculations using the DFT technique. HCR underwent 1 : 1 complexation with Pd2+, which was confirmed via the Job’s plot, mass spectra and Benesi-Hildebrand plot (association constant Ka, 9.1 × 104 M-1). A sep. in vitro experiment showed that HCR could specifically sense Pd2+ in MCF7 (human breast adenocarcinoma) cell lines.

New Journal of Chemistry published new progress about Complexation. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Electric Literature of 950846-89-6.

Qian, Chenxiao’s team published research in Organic Chemistry Frontiers in 2022 | 4771-48-6

Organic Chemistry Frontiers published new progress about Alcohols, propargyl 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, Synthetic Route of 4771-48-6.

Qian, Chenxiao; Liu, Meiwen; Sun, Jianwei; Li, Pengfei published the artcile< Chiral phosphoric acid-catalyzed regio- and enantioselective reactions of functionalized propargylic alcohols>, Synthetic Route of 4771-48-6, the main research area is spiro isoindoline pyrroloindolone preparation regioselective enantioselective.

Here, the scope of propargylic alcs. and the power of CPA catalysis was expanded. With the established system, racemic 3-alkynyl-3-hydroxyisoindolinones reacted efficiently to form diverse spirocyclic heterocycles I [R1 = Ph, 4-BrC6H4, 2-thienyl, etc.; R2 = Me, Ph; R3 = H, 5-Me, 6-F, etc.] with high enantioselectivity. Regiodivergence was also observed with different indole nucleophiles. Importantly, the key covalently bonded CPA adduct was isolated, characterized and further confirmed to be chem. competent, and a possible covalent activation mode was proposed accordingly.

Song, Fan’s team published research in Tetrahedron Letters in 2019-05-16 | 950846-89-6

Tetrahedron Letters published new progress about Fluorescence. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Electric Literature of 950846-89-6.

Song, Fan; Shao, Xiaotao; Zhu, Jing; Bao, Xiaofeng; Du, Lei; Kan, Chun published the artcile< Reversible ""turn-off-on"" fluorescence response of Fe(III) towards Rhodamine B based probe in vivo and plant tissues>, Electric Literature of 950846-89-6, the main research area is fluorescence iron Rhodamine B probe plant tissue.

A Fe3+-specific probe (N-TC)(I) based on Rhodamine B was designed and synthesized. N-TC has a good spectral response to Fe3+ in the EtOH/H2O solution (1:1, volume/volume, HEPES, 0.5 mM, pH = 7.38) with low detection limits and high binding constants N-TC displays the reversible “”turn-off-on”” fluorescence response with 1:1 binding stoichiometry. It is further proven to be practical in sensitively monitoring trace Fe3+ in environmental water specimens. Biol. experiments demonstrated that N-TC can be resp. used as a probe for detection of Fe3+ in living cells, animals and plant tissues.

Tetrahedron Letters published new progress about Fluorescence. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Electric Literature of 950846-89-6.

Wang, Limei’s team published research in Food Packaging and Shelf Life in 2021-09-30 | 399-76-8

Food Packaging and Shelf Life published new progress about Agaricus bernardii. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Recommanded Product: 5-Fluoroindole-2-carboxylic acid.

Wang, Limei; Zhou, Yanfang; Wang, YangYang; Bu, Hongyu; Dong, Tungalag published the artcile< Changes in cell wall metabolism and flavor qualities of mushrooms (Agaricus bernardii) under EMAP treatments during storage>, Recommanded Product: 5-Fluoroindole-2-carboxylic acid, the main research area is Agaricus bernardii flavor cell wall metabolism EMAP storage.

To clarify the dynamic changes of cell wall metabolism and flavor components in Agaricus bernardii packed with the packaging materials during storage. The polyethylene (PE), poly (butylene adipate-co-terephthalate)/ poly (L-lactic acid) (ECFPLA) and PBAT/PLLA/ hydrophobic silica (ECFPLASiO2) with a different gas/water vapor permeability were used as equilibrium modified atm. packaging (EMAP) materials, and an appropriate gas concentration [O2 (0.01-0.03%), CO2 (4.58-6.62%)] was created inside the ECFPLASiO2 packaging, which led to Agaricus bernardii with higher level of cell wall components and lower level of cell wall degrading enzymes during the storage period. For the first time application of HS-SPME-GC-MS on an extract from fresh Agaricus bernardii. The results showed that volatile compounds of fresh Agaricus bernardii mainly consists of alcs., ketones and aldehydes, with 3-octanol, 3-octanone, 1-octene-3-alc. and phenylcarbinol being most abundant compounds During the storage time, the varieties and content of volatile compounds were changed in all treatments. Alcs., aldehydes, hydrocarbons and esters contents increased during the storage while ketones declined. Among all treatment groups, ECFPLASiO2 group showed higher most abundant compounds and organic acid content. The results suggest that ECFPLASiO2 film could be used to reduce the changes in cell walls and flavor components after harvest and extend the shelf life of Agaricus bernardii.