- Three-Step One-Pot Process of 3-Methyl-5-Benzofuranol from Amine, Aldehydes, and p-Benzoquinone
-
3-Methyl-5-benzofuranol was prepared by a one-pot process from morpholine, propionaldehyde, and p-benzoquinone in 85-87% isolated yields. Avoiding the tedious multistep isolation and purification operations, this practical and efficient process dramatically enhanced the production efficiency as well as reduced the amount of chemical wastes of reaction. The scale-up results showed that the performance was maintained, suggesting potential large-scale applications. Furthermore, the synthesis strategy showed high efficiency for a wide range of aliphatic aldehydes and ketone derivatives.
- Liang, Chaoming,Sun, Maolin,Shen, Xinyuan,Shan, Chao,Wang, Weijuan,Cheng, Ruihua,Ye, Jinxing
-
p. 810 - 816
(2021/04/05)
-
- Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile
-
In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control β-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H … π interactions with Trp105 and Phe178 residues compared to the control β-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation.
- Bian, Jinlei,Li, Xiang,Wang, Nan,Wu, Xingsen,You, Qidong,Zhang, Xiaojin
-
-
- Dyeing composition for keratinous fibers, containing oxidation dye precursors and hydroxybenzofurane used as couplers, and dyeing process using these compositions
-
The invention relates to the use, as coupler in a dyeing composition, of a hydroxybenzofuran of formula (I): STR1 in which R1 and R2, which are identical or different, represent a hydrogen atom or a C1 -C6 alkyl radical. When they denote an alkyl radical, R1 and R2 can occupy any position on the benzofuran ring except the positions 2 and 3 at the same time. The OH group may occupy one of the positions 4, 5, 6 or 7, in combination with one or more para type or ortho type oxidation dye precursors or mixtures thereof, for dyeing keratinous fibers and in particular human hair. The dyeing composition according to the invention makes it possible to confer on the keratinous fibers a color which is fast to light, washes, adverse weather conditions and perspiration.
- -
-
-