22720-75-8Relevant articles and documents
Inhibitors of tissue-nonspecific alkaline phosphatase: Design, synthesis, kinetics, biomineralization and cellular tests
Debray, Julien,Chang, Lei,Marquès, Stéphanie,Pellet-Rostaing, Stéphane,Le Duy, Do,Mebarek, Saida,Buchet, René,Magne, David,Popowycz, Florence,Lemaire, Marc
, p. 7981 - 7987 (2013)
Chronic kidney disease (CKD) is associated with numerous metabolic and endocrine disturbances, including abnormalities of calcium and phosphate metabolism and an inflammatory syndrome. The latter occurs early in the course of CKD and contributes to the development and progression of vascular calcification. A few therapeutic strategies are today contemplated to target vascular calcification in patients with CKD: vitamin K2, calcimimetics and phosphate binders. However, none has provided complete prevention of vascular calcification and there is an urgent need for alternate efficient treatments. Recent findings indicate that tissue-nonspecific alkaline phosphatase (TNAP) may represent a very promising drug target due to its participation in mineralization by vascular smooth muscle cells. We report the synthesis of four levamisole derivatives having better inhibition property on TNAP than levamisole. Their IC50, Ki and water solubility have been determined. We found that the four inhibitors bind to TNAP in an uncompetitive manner and are selective to TNAP. Indeed, they do not inhibit intestinal and placental alkaline phosphatases. Survival MTT tests on human MG-63 and Saos-2 osteoblast-like cells have been performed in the presence of inhibitors. All the inhibitors are not toxic at concentrations that block TNAP activity. Moreover, they are able to significantly reduce mineralization in MG63 and Saos-2 osteoblast-like cells, indicating that they are promising molecules to prevent vascular calcification.
Synthesis of substituted 2-mercaptobenzaldehydes and 2-substituted benzo[b]thiophenes
Gallagher, Timothy,Pardoe, David A.,Porter, Roderick A.
, p. 5415 - 5418 (2000)
Simple and rapid single-pot preparations of substituted 2- mercaptobenzaldehydes 5 and 2-substituted benzo[b]thiophenes 3 based on ortho-lithiation methodology are described. (C) 2000 Elsevier Science Ltd.
Investigation on the one-step preparation of 2-substituted benzo[B]thiophenes
Zhao, Qian,Qian, Chao,Chen, Xin-Zhi
, p. 873 - 878 (2013)
A convenient and efficient synthesis of 2-substituted benzo[b]thiophenes is described. This one-step reaction of alkylthiobenzaldehyde and activated electrophiles proceeded smoothly in toluene at 120 °C with magnesium oxide as a catalyst. The target 2-sub
Overcoming Electron-Withdrawing and Product-Inhibition Effects by Organocatalytic Aerobic Oxidation of Alkylpyridines and Related Alkylheteroarenes to Ketones
Wang, Hua,Liu, Jie,Qu, Jian-Ping,Kang, Yan-Biao
, p. 3942 - 3948 (2020/03/23)
An organocatalyzed aerobic benzylic C-H oxidation of alkyl and aryl heterocycles has been developed. This transition metal-free method is able to overcome the electron-withdrawing effect as well as product-inhibition effects in heterobenzylic radical oxidation. A variety of ketones bearing N-heterocyclic groups could be prepared under relatively mild conditions with moderate to high yields.
Iron–PNP-Pincer-Catalyzed Transfer Dehydrogenation of Secondary Alcohols
Budweg, Svenja,Wei, Zhihong,Jiao, Haijun,Junge, Kathrin,Beller, Matthias
, (2019/05/10)
The well-defined iron PNP pincer complex catalyst [Fe(H)(BH4)(CO)(HN{CH2CH2P(iPr)2}2] was used for the catalytic dehydrogenation of secondary alcohols to give the corresponding ketones. Using acetone as inexpensive hydrogen acceptor enables the oxidation with good to excellent yields. DFT computations indicate an outer-sphere mechanism and support the importance of an acceptor to achieve this transformation under milder conditions.
Thiyl radical promoted chemo- and regioselective oxidation of CC bonds using molecular oxygen: Via iron catalysis
Xiong, Baojian,Zeng, Xiaoqin,Geng, Shasha,Chen, Shuo,He, Yun,Feng, Zhang
supporting information, p. 4521 - 4527 (2018/10/17)
The first example of the thiyl radical promoted ligand-free iron-catalyzed oxidative cleavage of alkenes using molecular oxygen (1 atm) has been developed. The reaction proceeds under mild reaction conditions with high efficiency and high chemo- and regioselectivity. It features a broad substrate scope and excellent functional group compatibility, enabling facile access to valuable molecules for application in medicinal chemistry. Preliminary mechanistic studies reveal that a vital intermediate dioxetane might be involved in the reaction and a thiyl radical plays a synergistic role in facilitating the selective oxidation of the CC bond.
Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream
Liu, Guangchang,Xu, Bo
supporting information, p. 869 - 872 (2018/02/09)
We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.
Copper-catalyzed synthesis of 2-acylbenzo[: B] thiophenes from 3-(2-iodophenyl)-1-arylpropan-1-ones and potassium sulfide under aerobic conditions
Zheng, Zhilei,Chen, Liang,Qian, Cheng,Zhu, Xiaoming,Yang, Yuzhong,Liu, Jianbing,Yang, Yuan,Liang, Yun
, p. 8020 - 8024 (2018/11/23)
A method was developed for the synthesis of 2-acylbenzo[b]thiophenes via a copper-catalyzed sulfuration of 3-(2-iodophenyl)-1-arylpropan-1-ones with K2S under aerobic conditions. Mechanistically, this procedure was proved to involve the formati
Synthesis of 2-Acylbenzo[b]thiophenes via Cu-Catalyzed α-C-H Functionalization of 2-Halochalcones Using Xanthate
Sangeetha, Subramani,Sekar, Govindasamy
supporting information, p. 1670 - 1673 (2017/04/11)
An efficient protocol is described for the synthesis of 2-acylbenzo[b]thiophenes from easily accessible 2-iodochalcones through α-C-H functionalization using Cu(OAc)2 catalyst and xanthate as sulfur source. Less reactive 2-bromochalcones also yielded the corresponding 2-acylbenzothiophenes in good yield. The reaction proceeds via in situ incorporation of sulfur followed by copper-catalyzed cyclization to generate 2-acylbenzothiophenes without external acyl source. The synthetic importance is showcased by synthesis of 1-(5-hydroxybenzothiophene-2-yl)ethanone, which is a known pre-mRNA splicing modulator.
Copper(I)-Catalyzed Chemoselective Reduction of Benzofuran-2-yl Ketones to Alcohols with B2pin2 via a Domino-Borylation-Protodeboronation Strategy
Xuan, Qingqing,Kong, Weiguang,Song, Qiuling
, p. 7602 - 7607 (2017/07/26)
A novel copper(I)-catalyzed chemoselective reduction of the carbonyls of benzofuran-2-yl ketones over furan rings with B2pin2 has been developed. This reaction proceeded under mild conditions. High valuable secondary alcohol derivatives of benzofurans were obtained in good to excellent yields with a broad substrate scope. The mechanistic studies suggested that a domino-borylation-protodeboronation pathway was involved in this reaction.
