12/10/2022 - Page 5 of 8 - Indole Building Blocks

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.

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

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.

Sarkar, Souradip’s team published research in Organic Letters in 2022-07-01 | 23077-43-2

Organic Letters published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation) (isolamellarins). 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, HPLC of Formula: 23077-43-2.

Sarkar, Souradip; Samanta, Rajarshi published the artcile< Weakly Coordinating tert-Amide-Assisted Ru(II)-Catalyzed Synthesis of Azacoumestans via Migratory Insertion of Quinoid Carbene: Application in the Total Synthesis of Isolamellarins>, HPLC of Formula: 23077-43-2, the main research area is azacoumestan preparation; diazonaphthoquinone indole migratory insertion cyclization ruthenium catalyst.

A weakly coordinating tert-amide-directed straightforward method was developed for the synthesis of azacoumestans, e.g., I, using the corresponding azaheterocycle derivatives II (R1 = H, Me, Bn, etc., R2 = H, Me, R3 = Cl, F, R4 = MeO, Br, Ph, etc.) and diazonaphthoquinones III (R5 = OH, R6 = Br, COMe, Ph, etc.) under cheap Ru(II)-catalyzed conditions. The reaction proceeds via migratory insertion of quinoid carbene and subsequent Bronsted acid-mediated cyclization. The optimized C2-selective method offered a wide scope of important azaheterocycles. Bioactive natural products like isolamellarins A and B were synthesized via the developed protocol. Preliminary mechanistic studies highlighted the probable mechanistic pathway.

Zhang, Ming-Zhi’s team published research in Tetrahedron in 2021-01-22 | 4771-48-6

Tetrahedron published new progress about Disease, plant. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application of C10H9NO.

Zhang, Ming-Zhi; Mulholland, Nick; Seville, Anne; Hough, Gemma; Smith, Nicholas; Dong, Hong-Qiang; Zhang, Wei-Hua; Gu, Yu-Cheng published the artcile< First discovery of pimprinine derivatives and analogs as novel potential herbicidal, insecticidal and nematicidal agents>, Application of C10H9NO, the main research area is pimprinine derivative analog preparation herbicidal insecticidal nematicidal.

Pimprinine and streptochlorin are indole natural products produced by many species of organisms, and they are reported to possess a wide range of biol. activities, such as anticancer, antiviral, antifungal activity and so on. In this study, three series of pimprinine derivatives or analogs were efficiently synthesized under the optimized methods. Biol. assays conducted at Syngenta firstly indicated the pimprinine derivatives or analogs possessed potential herbicidal and insecticidal activity, and this is highlighted by several compounds that possessed significant biol. activity as well as broad spectrum. Meanwhile, compounds with benzothiophene-oxazole core showed effective nematicidal activity in primary screening. Compounds 5-(benzofuran-3-yl)oxazole and 5-(benzodioxol-5-yl)oxazole were identified as the most promising lead structures for further study.

Tetrahedron published new progress about Disease, plant. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application of C10H9NO.

Mumtaz, Yasir’s team published research in Asian Journal of Organic Chemistry in 2022-08-31 | 93247-78-0

Asian Journal of Organic Chemistry published new progress about Indoles 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, Category: indole-building-block.

Mumtaz, Yasir; Liu, Jie published the artcile< Iodine-catalyzed Regioselective Electrophilic (Fluoroalkyl) Sulfenylation of Indoles with (RSO2)2O via Deoxygenative Reduction>, Category: indole-building-block, the main research area is indole sulfonic anhydride iodine catalyst regioselective sulfenylation deoxygenative reduction; thioindole preparation.

A method for electrophilic C-H sulfenylation by deoxygenative reduction from less expensive and easily available sulfonic anhydrides was reported. This C-S bond-forming reaction allowed a general access to sulfenyl electrophiles, including important trifluoromethyl, perfluoroalkyl and aryl derivatives that are otherwise difficult to afford. Under metal-free conditions, the reaction yielded 3-arylthio (fluoroalkylthio) indoles in good to excellent yields. The catalytic technique tolerated a wide range of functional groups.

Wang, Xiaochun’s team published research in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 2020-03-15 | 950846-89-6

Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy published new progress about Biological imaging. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Related Products of 950846-89-6.

Wang, Xiaochun; Li, Tiechun published the artcile< A novel ""off-on"" rhodamine-based colorimetric and fluorescent chemosensor based on hydrolysis driven by aqueous medium for the detection of Fe3+>, Related Products of 950846-89-6, the main research area is rhodamine colorimetric fluorescent chemosensor hydrolysis iron; Chemosensor; Fe(3+); Fluorescence enhancement; Living cell imaging; Rhodamine B.

A novel “”off-on”” colorimetric and fluorescent chemosensor N2,N6-bis(2-(rhodamine B amido)ethyl)pyridine-2,6-dicarboxamide (RhBEP) (I) has been designed and synthesized, which can selectively detect the presence of Fe3+ with about 75-fold enhancement in fluorescence emission intensity at 585 nm over various environmentally relevant metal cations such as Hg2+, Cu2+, Cr3+, Li+, Na+, K+, Ag+, Zn2+, Mg2+, Ca2+, Ba2+, Fe2+, Cd2+, Ni2+, Mn2+, Al3+, Bi3+ and Au3+ in PBS reaction media. The remarkable color change from UV-Vis titration experiments indicates that RhBEP can be used as a colorimetric chemosensor for Fe3+. The ultrasensitive detection limit for Fe3+ in the fluorescence measurement is down to 2.0 × 10-8 mol·L-1. The recognition mechanism of RhBEP to Fe3+ was analyzed by Job’s plot and mass spectrometry anal. In addition, the data from fluorescent cell imaging experiments confirmed that the chemosensor RhBEP has a promising application for the detection of Fe3+ in biol. systems.

Ji, Xiaoqian’s team published research in Progress in Organic Coatings in 2019-06-30 | 950846-89-6

Progress in Organic Coatings published new progress about Color. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Electric Literature of 950846-89-6.

Ji, Xiaoqian; Zhang, Wan; Ge, Fangqing; Wang, Chaoxia; Yin, Yunjie; Chen, Kunlin published the artcile< Thermochromic behavior analysis of terminated polyurethane functionalized with rhodamine B derivative>, Electric Literature of 950846-89-6, the main research area is rhodamine B derivative terminated polyurethane print thermochromic cotton fabric; thermochromic property.

A novel “”off-on”” terminated polyurethane based on the rhodamine B modified dye RhEA was constructed with the polyethylene glycol (PEG) and 1,4-butanediol (BDO) as soft segment, isophorone diisocyanate (IPDI) as hard segment. The RhEA terminated polyurethane turned to red from colorless after 254 nm UV induction accompanying transformation of RhEA from a twisted spirolactam to a planarized ring-opened amide. The intensity of absorbance enhanced as UV induction time increased. And the color of the RhEA terminated polyurethane changed from red turned to light red (45 °C) and colorless (65 °C), reversibly. The RhEA terminated polyurethane showed good thermal stability. The thermochromic cotton fabric was obtained with RhEA terminated polyurethane via flat screen printing and it turned to red from white after 254 nm UV induction. The K/S values decreased nearly 65.8% at 45 °C compared to 40 °C suggesting the thermochromic cotton became light red and it turned to white completely at 65 °C. The lactam ring was still retained during the printing process and the thermochromic cotton fabric possessed thermochromic behavior after UV induction. They can be a promising candidate for developing a flexible sensor to monitor environmental changes.

Progress in Organic Coatings published new progress about Color. 950846-89-6 belongs to class indole-building-block, and the molecular formula is C30H36N4O2, Electric Literature of 950846-89-6.

Zhang, Yan’s team published research in Synthesis in 2019-04-30 | 399-76-8

Synthesis published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Name: 5-Fluoroindole-2-carboxylic acid.

Zhang, Yan; Hu, Zhe-Yao; Li, Xin-Chang; Guo, Xun-Xiang published the artcile< Copper-Catalyzed Decarboxylative N-Arylation of Indole-2-Carboxylic Acids>, Name: 5-Fluoroindole-2-carboxylic acid, the main research area is aryl indole preparation; indole carboxylic acid aryl halide copper catalyst decarboxylative arylation.

A novel decarboxylative N-arylation of indole-2-carboxylic acids with aryl halides was developed. The reaction proceeded efficiently in the presence of Cu2O as the catalyst to give the corresponding N-aryl indoles I [R1 = 4-Me, 5-F, 6-MeO, etc.; R2 = Ph, 3-FC6H4, 4-ClC6H4, etc.] in high yields. This synthetic method showed good functional group tolerance and offered an alternative route to construct N-aryl indoles.