Discovery of 7,9-Disulfatetrahydroberberine as Novel Lipid-Lowering Agents was written by Li, Dong-Dong;Yu, Pan;Wang, Zhen-Zhong;Xiao, Wei;Zhou, Xin-Hu;Zhao, Lin-Guo. And the article was included in ACS Omega in 2020.Electric Literature of C7H4ClF3O2S This article mentions the following:
Berberine (BBR), a well-known alkaloid, exhibits various pharmacol. activities, especially hypolipidemic activity, which has attracted much interest from medicinal chemists in the past decade. However, little progress was made on the structural modification of BBR for improving lipid-lowering activity, mainly due to its unclear biol. target and low safety. In this study, a new scaffold of 7,9-disulfatetrahydroberberine was discovered unexpectedly, provided with extremely low cytotoxicity. Hence, a novel series of highly safe 7,9-disulfatetrahydroberberines were designed, synthesized, and evaluated for their hypolipidemic activities. In order to investigate the significance of the 9-position substituent, another new series of 7-sulfatetrahydroberberines were designed and synthesized. Lipid-lowering experiments showed that among these compounds, 5f exhibited the best lipid-lowering activity based on two cell models, 3T3-L1 cells and HepG2 cells. Compared with the blank control, the inhibition rate of compound 5f against total cholesterol was over 60%, the inhibition rate against triglyceride was over 70%, the inhibition rate against low-d. lipoprotein cholesterol was approx. 75%, and the inhibition rate against high-d. lipoprotein cholesterol was close to 50%, which were far superior to the pos. control BBR. This result also verified the feasibility of the development of BBR as a lipid-lowering drug via disubstituted modification at the 7- and 9-position. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)benzene-1-sulfonyl chloride (cas: 777-44-6Electric Literature of C7H4ClF3O2S).
3-(Trifluoromethyl)benzene-1-sulfonyl chloride (cas: 777-44-6) belongs to organic chlorides. Organochlorines stimulate the central nervous system and cause convulsions, tremor, nausea, and mental confusion. Examples are dichlorodiphenyltrichloroethane (DDT), chlordane, lindane, endosulfan, and dieldrin. Aliphatic organochlorides are often alkylating agents as chlorine can act as a leaving group, which can result in cellular damage.Electric Literature of C7H4ClF3O2S
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics