1776-08-5Relevant articles and documents
1-Aryl-3-(dimethylamino)propenones: Strong proton acceptors for hydrogen bonds
Pleier, Anna-Katharina,Herdtweck, Eberhardt,Mason, Sax A.,Thiel, Werner R.
, p. 499 - 506 (2003)
Because of the electron-donating effects of their terminal dimethylamino groups, the carbonyl units of 1-aryl-3-(dimethylamino)prop-2-en-1-ones are excellent proton acceptors. Intra- and intermolecular hydrogen bonds formed by these species were investigated by structural techniques (X-ray and neutron diffraction), spectroscopy, and density functional calculations. Co-crystallization of a derivative bearing three (dimethylamino)prop-2-en-1-one units attached at one center in the presence of different proton donors produced one- and two-dimensional H-bridged polymers. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Cascade reactions leading to the mechanism of action of vinaxanthone and xanthofulvin, natural products that drive nerve repair
Eliasen, Anders M.,Chin, Matthew R.,Axelrod, Abram J.,Abagyan, Ruben,Siegel, Dionicio
, p. 3238 - 3245 (2018)
The natural products vinaxanthone and xanthofulvin promote regeneration in animal models of spinal cord injury and corneal transplant. However, inhibition of the initially described biological target of these compounds, semaphorin 3A, does not fully account for the recovery demonstrated in vivo following administration of the natural products. Through chemical synthesis substantial quantities of both natural products have been accessed with early reaction development paving the way for synthesizing both compounds. The success of a model system, first disclosed herein, translated to the syntheses of both natural products. Following from this we also report for the first time the discovery of a new target of the natural products, the succinate receptor 1 (SUCNR1). Both natural products function as positive allosteric modulators of SUCNR1. As the first known allosteric modulators of SUCNR1, the compounds represent powerful new tools to understand the pharmacology of SUCNR1 and its control of growth and cellular defense.
X-ray diffraction and VT-NMR studies of (E)-3-(piperidinyl)-1-(2′-hydroxyphenyl)-prop-2-en-1-one
Choi, Seunghyun,Kim, Yunhye,Park, Bernie Byeonghoon,Park, Suzie,Park, Jonghyun,Ok, Kiwon,Koo, Jaehyung,Jung, Yong Woo,Jeon, Young Ho,Lee, Eun Hee,Lee, Ken S.,Byun, Youngjoo
, p. 600 - 605 (2014)
A series of 1-aryl-3-(cyclicamino)-prop-2-en-1-one analogs was synthesized from commercial acetophenones in 2 or 3 steps. Compound 6, (E)-3-(piperidinyl)-1-(2′-hydroxyphenyl)-prop-2-en-1-one, exhibited the unique shape and intensity of the Csp2
Mechanistic study of copper-catalyzed C-H Hydroxylation/C-S coupling by ESI-HR MS and DFT calculations
Xu, Runsheng,Cai, Rongrong,Zhou, Sixian,Zhou, Zhuoda,Li, Beibei,Xu, Dihui
, (2017)
The reaction mechanism of Cu-catalyzed C-H hydroxylation/C-S coupling was studied using electrospray ionization high resolution mass spectrometry (ESI-HR MS) and density functional theory calculations (DFT). Notably, a series of CuI and CuIII complexes were observed as key intermediates and identified using ESI-HR MS. Furthermore, a catalyst cycle involving proton abstraction/oxidative addition/reductive elimination was proposed. This study is important and valuable with respect to C-H functionalization.
Synthesis of 3,4,5-Trisubstituted Isoxazoles via the ANRORC Rearrangement
Balakrishna, C.,Bandaru, Sravan K.,Behera, Manoranjan,Chatterjee, Anindita,Kandula, Venu,Saunders, Graham C.,Yennam, Satyanarayana
, p. 6440 - 6446 (2020)
A facile and versatile procedure for the synthesis of new functionalized derivatives of 3-benzyl-5-(2-hydroxyphenyl) isoxazole-4-carbaldehyde oxime has been described. The key step in the synthesis involves the ANRORC reaction of in-situ generated 3-(phen
A catalyst-free approach to 3-thiocyanato-4H-chromen-4-ones
Zhang, Xiao-Zhuan,Ge, Dao-Liang,Chen, Shan-Yong,Yu, Xiao-Qi
, p. 66320 - 66323 (2016)
A facile and efficient approach to 3-thiocyanato-4H-chromen-4-ones was realized at room temperature. In the presence of KSCN and K2S2O8, various enaminones underwent thiocyanation and cyclization, affording 3-thiocyanatochromenones in good yields. In addition, one-pot synthesis of 3-thiocyanatochromenones from 2-hydroxylacetophenones was also developed.
Chiral FLP-catalyzed asymmetric hydrogenation of 3-fluorinated chromones
Dai, Yun,Du, Haifeng,Feng, Xiangqing,Meng, Wei
supporting information, p. 1558 - 1560 (2022/02/11)
The asymmetric hydrogenation of fluorinated olefins is an efficient pathway towards the synthesis of chiral fluorine-containing compounds. This paper described metal-free asymmetric hydrogenation of 3-fluorinated chromones with the use of readily availabl
CuI/Cu(OSO2CF3)2 catalysed convenient approach to dichromenopyridines and triazole-thiazole appended chromone derivatives
Yerrabelly, Jayaprakash Rao,Porala, Subbanarasimhulu,Kasireddy, Venkateshwar Reddy,Ghojala, Venkat Reddy,Rebelli, Pradeep
, p. 3781 - 3790 (2021/11/01)
A variety of new pentacyclic dichromenopyridines have been synthesized from 2-amino chromone and O-propargyloxy salicilaldehydes through intramolecular Povarov reaction using CuI/Cu(OSO2CF3)2 as a Lewis acid catalyst. The
Visible Light-Promoted Selenylation/Cyclization of Enaminones toward the Formation of 3-Selanyl-4H-Chromen-4-Ones
Liu, Hao-Yang,Zhang, Jia-Rong,Huang, Guo-Bao,Zhou, Yi-Huan,Chen, Yan-Yan,Xu, Yan-Li
supporting information, p. 1656 - 1661 (2021/02/12)
A simple and efficient visible-light-promoted selenylation/cyclization of enaminones have been realized for the practical synthesis of 3-selanyl-4H-chromen-4-ones. This reaction is performed in the mild conditions, no transition metal catalyst or photocatalysts and no additional oxidants are required. In addition, the 3-selanyl-4H-chromen-4-ones could be easily converted to selanyl-functionalized pyrimidines by reacting with benzamidine substrates. (Figure presented.).
Structure-Based Discovery of Pyrimidine Aminobenzene Derivatives as Potent Oral Reversal Agents against P-gp- And BCRP-Mediated Multidrug Resistance
Qiu, Qianqian,Zou, Feng,Li, Huilan,Shi, Wei,Zhou, Daoguang,Zhang, Ping,Li, Teng,Yin, Ziyu,Cai, Zilong,Jiang, Yuxuan,Huang, Wenlong,Qian, Hai
, p. 6179 - 6197 (2021/06/01)
Overexpression of ATP binding cassette (ABC) transporters, including P-glycoprotein (P-gp) and breast cancer resistance protein (BCRP), is an important factor leading to multidrug resistance (MDR) in cancer treatments. Three subclasses of dual inhibitors of P-gp and BCRP were designed based on the active moieties of BCRP inhibitors, tyrosine kinase inhibitors, and P-gp inhibitors, of which compound 21 possessed low cytotoxicity, high reversal potency, and good lipid distribution coefficient. 21 also increased the accumulation of Adriamycin (ADM) and Mitoxantrone (MX), blocked Rh123 efflux, and made no change in the protein expression of P-gp and BCRP. Importantly, coadministration of 21 can significantly improve the oral bioavailability of paclitaxel (PTX). It was also demonstrated that 21 significantly inhibited the growth of K562/A02 xenograft tumors by increasing the sensitivity of ADM in vivo. In summary, 21 has the potential to overcome MDR caused by P-gp and BCRP and to improve the oral bioavailability of PTX.
