21388-77-2Relevant articles and documents
Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia
Liu, Caiping,Han, Jingxuan,Marcelina, Olivia,Nugrahaningrum, Dyah Ari,Huang, Song,Zou, Meijuan,Wang, Guixue,Miyagishi, Makoto,He, Yun,Wu, Shourong,Kasim, Vivi
supporting information, p. 135 - 162 (2022/01/14)
Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.
Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis
Guo, Peng,Wang, Ke,Jin, Wen-Jie,Xie, Hao,Qi, Liangliang,Liu, Xue-Yuan,Shu, Xing-Zhong
, p. 513 - 523 (2021/01/12)
Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.
Preparation method of diarylmethane structure compound
-
Paragraph 0137-0141, (2020/08/26)
The invention discloses a preparation method of a diarylmethane structure compound. The preparation method disclosed by the invention is as shown in a formula I, and a target compound is prepared through reaction of benzyl alcohol and an aryl electrophilic reagent by utilizing a cheap metal nickel catalyst, taking 1, 1 '-bis (diphenylphosphine) ferrocene and 1, 10-phenanthroline as ligands, takingdimethyl oxalate as an additive and taking manganese powder as a reducing agent. The method has the advantages of easily available raw materials, mild reaction conditions, wide reaction substrate, good compatibility of reaction functional groups, unique chemical selectivity and the like. The method not only can be used for preparing the simple diarylmethane compound, but also can be suitable formodifying bioactive molecules with similar structures of raw materials.
The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling
Hayashi, Ryutaro,Shimizu, Akihiro,Yoshida, Jun-Ichi
, p. 8400 - 8403 (2016/07/27)
Electrochemical oxidation of toluene derivatives in the presence of a sulfilimine gave benzylaminosulfonium ions as stabilized benzyl cation pools, which reacted with subsequently added aromatic nucleophiles to give the corresponding cross-coupling produc
Proton-exchanged montmorillonite-mediated reactions of methoxybenzyl esters and ethers
Chen, Dongyin,Xu, Chang,Deng, Jie,Jiang, Chunhuan,Wen, Xiaoan,Kong, Lingyi,Zhang, Ji,Sun, Hongbin
, p. 1975 - 1983 (2014/03/21)
Proton-exchanged montmorillonite (H-mont) was found to be an eco-friendly and cost-effective catalyst for the generation of O-methylated quinone methides (QM) from the corresponding p or o-methoxybenzyl esters and ethers. Nucleophilic trapping of the O-methylated QM with arenes, alcohols, 1,3-dicarbonyl compounds, silyl enol ethers, and allylsilanes has been carried out, respectively, leading to eco-friendly benzylation reactions. Using this protocol, H-mont-mediated deprotection of PMB-protected esters and ethers have been realized for the first time. This work would pave the way for further exploration in O-alkylated QM that are of chemical and biological significance.
Br?nsted acid-catalyzed synthesis of diarylmethanes under non-genotoxic conditions
Mendoza, Oscar,Rossey, Guy,Ghosez, Léon
experimental part, p. 2235 - 2239 (2011/05/05)
Triflic acid and triflimide were found to efficiently catalyze the formation of a wide diversity of diarylmethanes from the non-genotoxic benzylic acetates and electron-rich arenes or heteroarenes. The reaction worked best with acetates capable of generating a stabilized benzylic cationic species. In most cases, the reactions were conveniently run in the absence of solvent under mild conditions.
Extremely efficient cross-coupling of benzylic halides with aryltitanium tris(isopropoxide) catalyzed by low loadings of a simple palladium(II) acctate/Tris(p-tolyl)phosphine system
Chen, Chi-Ren,Zhou, Shuangliu,Biradar, Deepak Baburao,Gau, Han-Mou
experimental part, p. 1718 - 1727 (2010/09/18)
Highly efficient coupling reactions of benzylic bromides or chlorides with aryltitanium tris(isopropoxide) [ArTi(O-i-Pr)3] catalyzed by a simple palladium(II) Acctate/tris(p-tolyl)phosphine [Pd(OAc)2/ P(p-tolyl)3] system are reported. The coupling reactions proceed in general at room temperature employing low catalyst loadings of 0.02 to 0.2 mol%, affording coupling products in excellent yields of up to 99%. For benzylic bromides bearing strong electronwithdrawing cyano (CN) or trifluoromethyl (CF 3) substituents, the reactions require a higher catalyst loading of 1 mol%, or the reactions are carried out at 60°C. The catalytic system also tolerates (1-bromoethyl)benzene bearing β-hydrogen atoms while using a catalyst loading of 1 mol% to afford the coupling product in a 70% yield.
TiCl4-activated selective nucleophilic substitutions of tert-butyl alcohol and benzyl alcohols with π-donating substituents
Tsai, Chen-Yu,Sung, Robert,Zhuang, Bo-Ren,Sung, Kuangsen
experimental part, p. 6869 - 6872 (2010/09/18)
TiCl4-activated selective nucleophilic substitution reactions of tert-butyl alcohol and benzyl alcohols with π-donating substituents in the presence of primary and secondary alcohols can be carried out with various oxygen, nitrogen and carbon nucleophiles in good yields.
Effect of substituents on diarylmethanes for antitubercular activity
Panda, Gautam,Parai, Maloy Kumar,Das, Sajal Kumar,Shagufta,Sinha, Manish,Chaturvedi, Vinita,Srivastava, Anil K.,Manju,Gaikwad, Anil N.,Sinha, Sudhir
, p. 410 - 419 (2008/02/02)
Aminoalkyl derivatives of diarylmethanes were prepared using Grignard, Friedel-Crafts arylation and aminohydrochloride chain formation reactions. These series of compounds were evaluated against Mycobacterium tuberculosis H37Rv and s
Disproportionation reaction of diarylmethylisopropyl ethers: a versatile access to diarylmethanes from diarylcarbinols speeded up by the use of microwave irradiation
L'Hermite, Nathalie,Giraud, Anne,Provot, Olivier,Peyrat, Jean-Fran?ois,Alami, Mouad,Brion, Jean-Daniel
, p. 11994 - 12002 (2007/10/03)
An efficient synthesis of diarylmethanes under classical thermal conditions and under microwave heating is described from diarylcarbinols via a new disproportionation reaction. The key step involves a selective hydride transfer of isopropyl ether intermed
