444926-52-7

Upstream product

• 106-47-8 4-chloro-aniline 
• 3696-23-9 N-(4-chlorophenyl)thiourea 
• 95-24-9 6-chloro-2-aminobenzothiazole 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 

Downstream Products

• 93532-56-0 N-(6-chlorobenzothiazol-2-yl)-4-aminobenzenesulfonamide 

Relevant academic research and scientific papers

Identification of: N -benzothiazolyl-2-benzenesulfonamides as novel ABCA1 expression upregulators

ATP binding cassette transporter A1 (ABCA1) is a critical transporter that mediates cellular cholesterol efflux from macrophages to apolipoprotein A-I (ApoA-I). Therefore, increasing the expression level of ABCA1 is anti-atherogenic and ABCA1 expression upregulators have become novel choices for atherosclerosis treatment. In this study, a series of N-benzothiazolyl-2-benzenesulfonamides, based on the structure of WY06 discovered in our laboratory, were designed and synthesized as novel ABCA1 expression upregulators. Based on an in vitro ABCA1 upregulatory cell model, ABCA1 upregulation of target compounds was evaluated. Compounds 6c, 6d, and 6i have good upregulated ABCA1 expression activities, with EC50 values of 0.97, 0.37, and 0.41 ΜM, respectively. A preliminary structure-activity relationship is summarized. Replacing the methoxy group on the benzothiazole moiety of WY06 with a fluorine or chlorine atom and exchanging the ester group with a cyano group resulted in more potent ABCA1 upregulating activity. Moreover, compound 6i increased ABCA1 mRNA and protein expression and significantly promoted cholesterol efflux in RAW264.7 cells. In conclusion, N-benzothiazolyl-2-benzenesulfonamides were identified as novel ABCA1 expression upregulators.

N-benzothiazole benzene sulfonamide derivative as well as preparation method and application thereof

The invention discloses an N-benzothiazole benzene sulfonamide derivative as well as a preparation method and application thereof. A family-B type-I scavenger receptor (SR-BI) plays a key role in thereverse cholesterol transport process of HDL, thereby reducing the cholesterol level in plasma, inhibiting the oxidation of LDL and reducing the blood vessel injury caused by the oxidized LDL. The invention provides a series of N-benzothiazole benzene sulfonamide derivatives capable of improving the SR-BI expression, a general formula of a chemical structure is as shown in formula (I), wherein R1independently represents-OCH3, -F, -H, -Cl or -NO2, and a substituent position of a substituent group R1 on a ring A is site 3, 4, 5 or 6; and the substituent group NHR2 is in di-, meta- or para- substitution on a ring B. The prior art does not disclose a chemical structure, a preparation method and pharmaceutical activity of the N-benzothiazole benzene sulfonamide derivatives.

Synthesis, in vitro and computational studies of protein tyrosine phosphatase 1B inhibition of a small library of 2-arylsulfonylaminobenzothiazoles with antihyperglycemic activity

The 2-arylsulfonylaminobenzothiazole derivatives 1-27 were prepared using a one step reaction. The in vitro inhibitory activity of the compounds against protein tyrosine phosphatase 1B (PTP-1B) was evaluated. Compounds 4 and 16 are rapid reversible (mixed-type) inhibitors of PTP-1B with IC50 values in the low micromolar range. The most active compounds (4 and 16) were docked into the crystal structure of PTP-1B. Docking results indicate potential hydrogen bond interactions between the nitro group in both compounds and the catalytic amino acid residues Arg 221 and Ser 216. Both compounds were evaluated for their in vivo antihyperglycemic activity in a type 2 diabetes mellitus rat model, showing significant lowering of plasma glucose concentration, during the 7 h post-intragastric administration.