33288-26-5Relevant academic research and scientific papers
Novel positive allosteric modulators of A2B adenosine receptor acting as bone mineralisation promoters
Barresi, Elisabetta,Giacomelli, Chiara,Marchetti, Laura,Baglini, Emma,Salerno, Silvia,Greco, Giovanni,Da Settimo, Federico,Martini, Claudia,Trincavelli, Maria Letizia,Taliani, Sabrina
, p. 286 - 294 (2020/12/22)
Small-molecules acting as positive allosteric modulators (PAMs) of the A2B adenosine receptor (A2B AR) could potentially represent a novel therapeutic strategy for pathological conditions characterised by altered bone homeostasis, including osteoporosis. We investigated a library of compounds (4-13) exhibiting different degrees of chemical similarity with three indole derivatives (1-3), which have been recently identified by us as PAMs of the A2B AR able to promote mesenchymal stem cell differentiation and bone formation. Evaluation of mineralisation activity of 4-13 in the presence and in the absence of the agonist BAY60-6583 allowed the identification of lead compounds with therapeutic potential as anti-osteoporosis agents. Further biological characterisation of one of the most performing compounds, the benzofurane derivative 9, confirmed that such a molecule behaves as PAM of the A2B AR.
A Regioselective Approach to Synthesize Indolyl Diketone Derivatives via Magnetic Polymeric Copper-Catalyst
Jarahiyan, Atefeh,Moghaddam, Firouz Matloubi,Pourjavadi, Ali
, (2021/06/21)
Abstract: In the present paper, an efficient Cu-catalyzed regioselective acylation of indoles with phenylglyoxals was developed which is the first example of indolyl diketones synthesis by a heterogeneous catalyst. The magnetic polyacrylonitrile was synth
Synthesis method of double-carbonyl indole compounds
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Paragraph 0111-0114, (2018/12/13)
The invention discloses a synthesis method of double-carbonyl indole compounds. The synthesis method comprises the following steps of performing oxidization coupling reaction on acetaldehyde derivatives I and indole derivatives II to obtain the double-car
Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles
Kumar, Yogesh,Jaiswal, Yogesh,Kumar, Amit
, p. 494 - 505 (2018/02/09)
An efficient one-pot two-step procedure for the synthesis of unsymmetrical (hetero)aryl 1,2-diketones has been developed. The reaction proceeds through a palladium-catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper-catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant. This represents the first example of the direct synthesis of unsymmetrical diaryl 1,2-diketones from arylacetonitriles. This method utilizes inexpensive, stable, nontoxic, and readily available starting materials, is highly effective in the presence of both electron-rich and electron-poor nitriles and aryltrifluoroborates, and tolerates a wide variety of functional groups. The synthetic utility of this transformation was shown by increasing the scale of the reaction and by carrying out the one-pot protocol for the preparation of quinoxaline and benzimidazole derivatives. A plausible reaction mechanism has also been proposed.
Synthesis of 3-acylated indoles through iron-catalyzed oxidative coupling of indoles with α-amino carbonyl compounds
Yi, Niannian,Li, Jinxia,Zhang, Hao,Wang, Ruijia,Jiang, Jun,Deng, Wei,Zeng, Zebing,Xiang, Jiannan
supporting information, p. 2062 - 2069 (2017/10/13)
A novel iron-catalyzed oxidative coupling of indoles with α-amino carbonyl compounds has been developed. The transformation provides an attractive approach to the synthesis of 3-acylindoles, with the advantages of easily available starting materials and high functional group tolerance. Furthermore, control experiments imply that a radical process maybe involved in this reaction.
Copper-catalyzed synthesis of indolyl diketones: Via C-H oxidation/diacylation of indoles with arylglyoxal hydrates
Wang, Cuiping,Zhang, Zhiqiang,Liu, Kui,Yan, Jingbo,Zhang, Tiexin,Lu, Gonghao,Meng, Qingtao,Chi, Haijun,Duan, Chunying
supporting information, p. 6185 - 6193 (2017/08/02)
An expedient protocol for Cu-catalyzed C-H oxidation/diacylation of indoles with arylglyoxal hydrates to construct indolyl diketones is developed. This methodology exhibits the synthetic utility of the synthesis of an indole-alkaloid 1,2-di(1H-indol-3-yl)ethane-1,2-dione and offers a straightforward means to produce different indolyl nitrogen-containing heterocycles such as indolyl quinoxaline, indolyl hydantoin and indolyl imidazole in high yields. Preliminary mechanistic studies indicate that two proposed pathways are involved in this process.
The dicarbonylation of indoles: Via Friedel-Crafts reaction with dicarbonyl nitrile generated in situ and retro-cyanohydrination
Yan, Jianwei,He, Guangjie,Yan, Fulin,Zhang, Jixia,Zhang, Guisheng
, p. 44029 - 44033 (2016/06/09)
A novel one-pot tandem reaction of indole and β-carbonyl nitrile to generate dicarbonyl indoles has been developed. This tandem process involves α-oxonation of the β-carbonyl nitrile to afford α,β-dicarbonyl nitrile, Friedel-Crafts reaction with indoles and subsequent retro-cyanohydrination of cyano tertiary alcohol form dicarbonyl indoles.
3-dicarbonyl substitution indole compound and preparation method thereof
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Paragraph 0015; 0016, (2016/10/09)
The invention discloses a 3-dicarbonyl substitution indole compound and a preparation method thereof, and belongs to the technical field of synthesis of indole derivatives. According to the technical scheme, the 3-dicarbonyl substitution indole compound i
Aminocatalytic cross-coupling approach via iminium ions to different C-C bonds
Mupparapu, Nagaraju,Battini, Narsaiah,Battula, Satyanarayana,Khan, Shahnawaz,Vishwakarma, Ram A.,Ahmed, Qazi Naveed
supporting information, p. 2954 - 2960 (2015/02/05)
Given the attractive ability of iminium ions to functionalize molecules directly at ostensibly unreactive positions, the reactivity of iminium ions, in which an α CH2 group is replaced by C=O was explored. Background studies on the ability of such iminium cations to promote reactions via an iminium-catalyzed or iminium-equivalent pathway are apparently unavailable. Previously, tandem cross-coupling reactions were reported, in which an iminium ion undergoes nucleophilic 1,2-addition to give a putative three-component intermediate that abstracts a proton in situ and undergoes self-deamination followed by unprecedented DMSO/ aerobic oxidation to generate a-ketoamides. However, later it was observed that iminium ions can generate valuable α-ketoamides through simple aerobic oxidation. In all reactions, iminium ions were generated in situ by reaction of 2-oxoaldehydes with secondary amines.
Palladium-catalyzed synthesis of 3-acylated indoles involving oxidative cross-coupling of indoles with α-amino carbonyl compounds
Tang, Ri-Yuan,Guo, Xiao-Kang,Xiang, Jian-Nan,Li, Jin-Heng
, p. 11163 - 11171 (2013/12/04)
A new and selective C-N bond oxidative cleavage method to 3-acylated indoles by Pd-catalyzed oxidative cross coupling of indoles with α-amino carbonyl compounds has been developed; moreover, one-pot synthesis of 3-acylated indoles from 2-ethynylanilines and α-amino carbonyl compounds has also been established. Importantly, the products 3-acylated indoles can be used to construct polyheterocyclic compound, which can be employed as efficient probes for Hg2+ and Fe3+.
