1006620-01-4

Upstream product

• 2789-92-6 3,5-dichloroantranilic acid 
• 4693-00-9 6,8-dichloro-2H-3,1-benzoxazine-2,4-dione 
• 75-31-0 isopropylamine 
• 30391-89-0 2-amino-N-isopropylbenzamide 

Downstream Products

• 1447721-16-5 C₂₀H₁₆BrCl₃N₆O₂S 

Relevant academic research and scientific papers

Design, Synthesis, and Mechanism of Antiviral Acylurea Derivatives Containing a Trifluoromethylpyridine Moiety

Novel acylurea derivatives 7a-7ab were designed and synthesized by linking the active substructures trifluoromethylpyridine and anthranilic diamide via an acylurea bridge. Most of the title compounds exhibited good activity against tobacco mosaic virus (TMV), particularly compound 7x (EC50 of 211.8 μg/mL), which showed much higher curative activity than ningnanmycin (EC50 of 389.8 μg/mL), and compound 7ab, which showed excellent inactivation activity (EC50 of 36.1 μg/mL), similar to ningnanmycin (EC50 of 23.2 μg/mL). The preliminary mechanism of these derivatives was investigated. Autodocking analysis revealed that compounds 7x and 7ab had good affinity for TMV coat protein (TMV CP), with low binding energies (-7.86 and -8.59 kcal/mol) comparable to ningnanmycin (-8.75 kcal/mol). Molecular dynamics simulation showed that compound 7x had a stable system structure with a better binding free energy (-32.94 kcal/mol) than ningnanmycin (-25.62 kcal/mol). Microscale thermophoresis showed that compound 7x bound more strongly to TMV CP (Kd of 19.8 ± 7.3 μM) than ningnanmycin (Kd of 21.2 ± 7.3 μM). Transmission electron microscopy and self-assembly experiments demonstrated that compounds 7x and 7ab significantly obstructed the self-assembly of TMV RNA and TMV CP. This new acylurea derivative has excellent antiviral activity by targeting TMV CP and inhibiting TMV self-assembly and can be considered a candidate for antiviral applications.

Method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide

The invention discloses a method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide. The method comprises the following steps: (1) preparation of mixed amide: adding isatoic anhydride to a reaction solvent with the reaction concentration, which is a ratio of the solvent volume to the weight of isatoic anhydride, of 5-10 times and the reaction temperature at 20-40 DEG C, adding isopropylaminedropwise, monitoring the reaction progress in the liquid phase, and performing a reaction of a next step directly without separation after completion of the monitored reaction; and (2), preparation of2-amino-3,5-dichloro-N-isopropylbenzamide: adding dichlorohydantoin slowly to the reaction solution of the step (1), controlling the reaction temperature at 20-40 DEG C, monitoring the reaction progress in the liquid phase, performing vacuum concentration on the reaction system after completion of the reaction, performing suction filtration, washing the solid with a little hot water, and performing beating with methanol so as to obtain a white compound. According to the method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide, a novel chlorination method is adopted so as to obtain 2-amino-3,5-dichloro-N-isopropylbenzamide efficiently, and the preparation method has simple post-treatment and a high total yield.