October 2022 - Page 63 of 72 - Indole Building Blocks

Wang, Lei’s team published research in Journal of Medicinal Chemistry in 2020-01-23 | 399-76-8

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

Wang, Lei; Fang, Kun; Cheng, Junfei; Li, Yu; Huang, Yahui; Chen, Shuqiang; Dong, Guoqiang; Wu, Shanchao; Sheng, Chunquan published the artcile< Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer>, Application In Synthesis of 399-76-8, the main research area is colon cancer antitumor agents SAR topoisomerase tubulin scaffold apoptosis.

Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.

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

Xing, Siyang’s team published research in Organic Chemistry Frontiers in 2020 | 4771-48-6

Organic Chemistry Frontiers published new progress about C-H bond activation. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Product Details of C10H9NO.

Xing, Siyang; Guo, Junsuo; Wang, Yuhan; Wang, Chenyu; Wang, Kui; Zhu, Bolin published the artcile< General and efficient synthesis of 1,2-dihydropyrrolo[3,4-b]indol-3-ones via a formal [3 + 2] cycloaddition initiated by C-H activation>, Product Details of C10H9NO, the main research area is dihydropyrroloindolone preparation; isocyanate indole cycloaddition rhodium catalyst.

A [Cp*RhCl2]2-catalyzed formal [3 + 2] cycloaddition between isocyanates and indoles with electron-deficient alkenes at the C3-position of the indole moiety and directing groups at the N1-position of the indole moiety was described. Undergoing sequential coupling reaction initiated by C-H activation and aza-Michael addition, a series of 1,2-dihydropyrrolo[3,4-b]indol-3-ones I [R = Et, n-Bu, Bn, etc.; R1 = CO2Et, CO2Me, etc.; R2 = H, F, Cl, etc.; R3 = H, F, Br, etc.; R4 = H, Me, F, etc.; R5 = H, Me] was successfully afforded in moderate to good yields by the formation of one C-C bond and one C-N bond. Interestingly, the pyridyl group at the N1-position of the indole moiety not only played a role as the directing group, but also catalyzed further intramol. Michael addition as a base.

Organic Chemistry Frontiers published new progress about C-H bond activation. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Product Details of C10H9NO.

Yu, Hui-juan’s team published research in Analytical Chemistry (Washington, DC, United States) in 2020-02-18 | 399-76-8

Analytical Chemistry (Washington, DC, United States) published new progress about Confocal laser scanning microscopy. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Formula: C9H6FNO2.

Yu, Hui-juan; Zhao, Wei; Xie, Mengting; Li, Xiaoqing; Sun, Ming; He, Jun; Wang, Lu; Yu, Lin published the artcile< Real-Time Monitoring of Self-Aggregation of β-Amyloid by a Fluorescent Probe Based on Ruthenium Complex>, Formula: C9H6FNO2, the main research area is self aggregation beta amyloid ruthenium complex fluorescent imaging.

Self-accumulation of amyloid-β protein (Aβ) into insoluble fibrils is the major hallmark of Alzheimer’s disease. Real-time monitoring of fibril growth is essential for clarifying the mechanism underlying aggregation and discovering therapeutic targets. A variety of approaches including NMR, electron microscopy (EM), at. force microscopy (AFM), and total internal reflection fluorescence microscopy (TIRFM) have been explored to monitor the fibril growth or reveal morphol. of Aβ aggregates. However, none of the methods allow real-time observation under physiol. conditions while without any perturbations. Here, the authors present a fluorescent probe [Ru(phen)2(fipc)]2+ (Ru-fipc) (phen = 1,10-phenanthroline, fipc = 5-fluoro-N-(1,10-phenanthrolin-5-yl)-1H-indole-2-carboxamide) that can bind to all the Aβ forms, i.e., monomers, oligomers, and fibrils, while not perturbing aggregation. Using this probe in combination with laser confocal microscopy, the entire aggregation process could be clearly and exactly imaged at the single fibril level. The reliability of Ru-fipc was confirmed based on colocalization with thioflavin T (ThT). Importantly, Ru-fipc can be used to monitor the very early nucleation and oligomerization process, which is thought to be a critical step in the development of neurotoxicity while it cannot be visualized with ThT. To the knowledge, this is the first fluorescent probe developed for real-time monitoring of Aβ aggregation, especially for the very early assembly stage, in solution with minimal perturbation. This method is suitable for in vitro and in vivo studies. The authors believe this would provide a valuable complementary tool for the study of pathogenesis and discovery of therapeutic targets of neurodegenerative diseases.

Harada, Hiroshi’s team published research in Bioorganic & Medicinal Chemistry Letters in 2003-04-07 | 4771-48-6

Bioorganic & Medicinal Chemistry Letters published new progress about Aryl aldehydes, heteroaryl Role: RCT (Reactant), RACT (Reactant or Reagent). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Name: 4-Methyl-1H-indole-3-carbaldehyde.

Harada, Hiroshi; Hirokawa, Yoshimi; Suzuki, Kenji; Hiyama, Yoichi; Oue, Mayumi; Kawashima, Hitoshi; Yoshida, Naoyuki; Furutani, Yasuji; Kato, Shiro published the artcile< Novel and potent human and rat β3-adrenergic receptor agonists containing substituted 3-indolylalkylamines>, Name: 4-Methyl-1H-indole-3-carbaldehyde, the main research area is indolylalkylamine preparation adrenergic agonist.

A novel series of 2-(3-indolyl)alkylamino-1-(3-chlorophenyl)ethanols was prepared and evaluated for in vitro ability to stimulate cAMP production in Chinese hamster ovary cells expressing cloned human β3-adrenergic receptor (AR). The optically active I was found to be the most potent and selective human β3-AR agonist in this series with an EC50 value of 0.062 nM. In addition, the selectivity of I for human β3-AR was 210-fold and 103-fold that for human β2-AR and β1-AR, resp. Furthermore, I showed potent agonistic activity at rat β3-AR.

Kredel, Julia’s team published research in ACS Applied Polymer Materials in 2020-07-10 | 950846-89-6

ACS Applied Polymer Materials published new progress about Cellulose pulp. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Formula: C30H36N4O2.

Kredel, Julia; Gallei, Markus published the artcile< Ozone-Degradable Fluoropolymers on Textile Surfaces for Water and Oil Repellency>, Formula: C30H36N4O2, the main research area is ozone degradable fluoropolymer textile surfaces water oil repellency.

Resistant and functional coatings on surfaces have been of growing interest recently. Functional textiles featuring water- and oil-repellent properties can be achieved by convenient coating of textiles with highly fluorinated polymers. Recently, concerns about (per)fluorinated mols. have been reported due to the high persistence and accumulation capabilities in nature, driving the textile market to develop alternatives and novel strategies. Within this study an ozone-degradable fluorinated polymer for water and oil repellency on various textiles is reported. The monomer 2-((1,1,2-trifluoro-2-(perfluoropropoxy)ethyl)thio)ethyl acrylate is capable of side-chain degradation upon ozone treatment due to the presence of chem. cleavable moieties. The degradable fluorine-containing polymer is accessible via radical polymerization in emulsion polymerization and can be directly applied onto various textiles, e.g., polyamide, polyester, Nomex, or cotton, by using a foulard. To investigate the homogeneous coating performance on the resp. textiles, a model polymer featuring a fluorescent monomer as part of the polymer chain is prepared, enabling the investigation of the polymer distribution via confocal microscopy. Finally, the effect of the fluorine moieties and the molar mass of the polymers is investigated, and the ozone-induced degradation is elucidated. The herein-described fluorinated polymers are envisaged to be a promising and nonpersistent platform for the preparation of omniphobic textile coating.

ACS Applied Polymer Materials published new progress about Cellulose pulp. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Formula: C30H36N4O2.

Wang, Zhao-Yang’s team published research in Organic Chemistry Frontiers in 2021 | 4771-48-6

Organic Chemistry Frontiers published new progress about Aryl iodides Role: PRP (Properties), 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, COA of Formula: C10H9NO.

Wang, Zhao-Yang; Guo, Rui-Li; Zhang, Xing-Long; Wang, Meng-Yue; Chen, Gang-Ni; Wang, Yong-Qiang published the artcile< Regioselective C5-H direct iodination of indoles>, COA of Formula: C10H9NO, the main research area is iodo indole regioselective preparation; aryl iodide iodosuccinimide iodination.

An efficient regioselective C5-H direct iodination of indoles I [R = H, 6-Cl, 4-Me, etc.; R1 = C(O)H, CN, C(O)OMe, C(O)OEt] was developed for the first time. Due to the versatility of aryl iodides, the method offered a general and practical access to the C5 functionalization of indoles. The approach featured mild reaction conditions, good tolerance of functional groups and more crucially, no metal involved in the reaction, thereby benefitting the late-stage decoration of medicinal mols. A mechanistic study showed that the current iodination reaction proceeded via a radical pathway.

Guan, Dongliang’s team published research in Journal of Medicinal Chemistry in 2021-12-23 | 4771-48-6

Journal of Medicinal Chemistry published new progress about Amidrazones Role: PAC (Pharmacological Activity), PKT (Pharmacokinetics), PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Safety of 4-Methyl-1H-indole-3-carbaldehyde.

Guan, Dongliang; Rahman, Toufiqur Md; Gay, Elaine A.; Vasukuttan, Vineetha; Mathews, Kelly M.; Decker, Ann M.; Williams, Alexander H.; Zhan, Chang-Guo; Jin, Chunyang published the artcile< Indole-Containing Amidinohydrazones as Nonpeptide, Dual RXFP3/4 Agonists: Synthesis, Structure-Activity Relationship, and Molecular Modeling Studies>, Safety of 4-Methyl-1H-indole-3-carbaldehyde, the main research area is indole amidinohydrazone preparation SAR mol modeling RXFP3 RXFP4 agonist.

Herein, the first structure-activity relationship studies of a series of novel nonpeptide amidinohydrazone-based agonists I [R1 = H, 4-Me, 7-F, etc.; R2 = H, Me; R3 = ; 4-ClC6H4, 3,4-di-ClC6H3, 2-thienyl, etc.; R4 = H, Me; n = 0,1,2,3], which were characterized by RXFP3 functional and radioligand binding assays was reported. Several potent and efficacious RXFP3 agonists compound I [R1 = 5-CN-7-Me, R2 = H, R3 = 4-CO2MeC6H4, R4 = H, n = 2] were identified with EC50 values <10 nM. These compounds also had high potency at RXFP4 but no agonist activity at RXFP1, demonstrating > 100-fold selectivity for RXFP3/4 over RXFP1. In vitro ADME and pharmacokinetic assessments revealed that the amidinohydrazone derivatives might have limited brain permeability.

Fang, Fang’s team published research in Advanced Synthesis & Catalysis in 2022-07-05 | 93247-78-0

Advanced Synthesis & Catalysis published new progress about Aromatization. 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Recommanded Product: Methyl 1H-indole-7-carboxylate.

Fang, Fang; Zheng, Haolin; Li, Weipeng; Mao, Guojiang; Chen, Shanping; Deng, Guo-Jun published the artcile< Metal- and Solvent-Free Synthesis of Maleimide Fused Carbazoles from (Indol-3-yl)cyclohexanones and Maleimides>, Recommanded Product: Methyl 1H-indole-7-carboxylate, the main research area is indolyl cyclohexanone maleimide trimethylsulfoxonium iodide catalyst cyclization; maleimide fused carbazole preparation.

A metal- and solvent-free strategy for the preparation of maleimide-fused carbazoles had been developed. This protocol started from 2-(indol-3-yl)cyclohexanones and maleimides, provided various maleimide-fused carbazoles in 45-90% yields. The present approach was catalyzed by trimethylsulfoxonium iodide and involved a cascade of oxidation, [4+2] annulation, and dehydrogenative aromatization. Moreover, these maleimide-fused carbazole products could be further transformed into other polycyclic aromatic hydrocarbons.

Avula, Sreenivas’s team published research in Journal of Enzyme Inhibition and Medicinal Chemistry in 2022 | 399-76-8

Journal of Enzyme Inhibition and Medicinal Chemistry published new progress about Antitumor agents. 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Category: indole-building-block.

Avula, Sreenivas; Peng, Xudan; Lang, Xingfen; Tortorella, Micky; Josselin, Beatrice; Bach, Stephane; Bourg, Stephane; Bonnet, Pascal; Buron, Frederic; Ruchaud, Sandrine; Routier, Sylvain; Neagoie, Cleopatra published the artcile< Design and biological evaluation of substituted 5,7-dihydro-6H-indolo[2,3-c]quinolin-6-one as novel selective Haspin inhibitors>, Category: indole-building-block, the main research area is dihydroindoloquinolinone preparation; protein kinase haspin inhibition SAR antitumor cytotoxicity mol docking; Haspin kinase; Indoloquinoline; cell viability; docking.

A library of substituted indolo[2,3-c]quinolone-6-ones was developed as simplified Lamellarin isosters. Synthesis was achieved from indole after a four-step pathway sequence involving iodination, a Suzuki-Miyaura cross-coupling reaction and a reduction/lactamization sequence. The inhibitory activity of the 20 novel derivatives was assessed on Haspin kinase. Two of them possessed an IC50 of 1 and 2 nM with selectivity towards a panel of 10 other kinases including the parent kinases DYRK1A and CLK1. The most selective compound exerted addnl. a very interesting cell effect on the osteosarcoma U-2 OS cell line.

Vincent, Michel’s team published research in Drug Design and Discovery in 1992 | 145513-91-3

Drug Design and Discovery published new progress about Chirality. 145513-91-3 belongs to class indole-building-block, and the molecular formula is C9H15NO2, Related Products of 145513-91-3.

Vincent, Michel; Marchand, Bernard; Remond, Georges; Jaguelin-Guinamant, Sylvie; Damien, Gerard; Portevin, Bernard; Baumal, Jean Yves; Volland, Jean Paul; Bouchet, Jean Paul published the artcile< Synthesis and ACE inhibitory activity of the stereoisomers of perindopril (S 9490) and perindoprilate (S 9780)>, Related Products of 145513-91-3, the main research area is ACE inhibitor stereoisomer perindopril perindoprilate preparation; angiotensin converting enzyme perindopril perindoprilate stereoisomer.

Preindopril, a powerful ACE (angiotensin converting enzyme) inhibitor contains 5 chiral carbons, and thus there is the possibility of 25 = 32 stereoisomers for the general structure I. These 32 stereoisomers were prepared by crosscoupling the 8 stereoisomers of benzyl perhydroindole-2-carboxylate with the 4 stereoisomers of 2-(1-carbethoxybutylamino)propionic acid, and hydrogenating the resulting benzyl esters. Each stereoisomer of perindopril furnished by saponification of the corresponding diacid stereoisomer (II) of perindoprilate which is the active form of perindopril. For each of the 32 stereoisomers of II, the in vitro ACE inhibitory potency was determined Four of them, including perindoprilate, had activities in the nanomolar range, and 4 more were ca. 10-fold less active. The 4 acid esters of I corresponding resp. to the 4 most active diacids II, in vitro were studied (1 mg/kg via the oral route) for their in vivo activity in dogs. The oral absorption of the active acid esters I and their activation to the active diacid II depended only on the chiralities of the 2 ring junction carbons of the perhydroindole ring.

Drug Design and Discovery published new progress about Chirality. 145513-91-3 belongs to class indole-building-block, and the molecular formula is C9H15NO2, Related Products of 145513-91-3.