Synthesis and Biological Evaluation of 4-Chloro-3,5-dinitrobenzotrifluoride Analogues as Antileishmanial Agents

Abstract

Desnitro analogues of 4-chloro-3,5-dinitrobenzotrifluoride (chloralin) (2), an in vitro microtubule inhibitor of several Leishmania species, have been synthesized from 2-halo-5-(trifluoromethyl)benzenesulfonyl chlorides 4 and 5. The analogues exhibited moderate to excellent activity when tested against Leishmania donovani amastigotes in vitro. Two representative compounds, 7f and 8, were tested against the Khartoum strain of L. donovani in a hamster model using chloralin (2) and Glucantime (one of the current therapeutics of choice in the treatment of Leishmania) as standards, the results of which will be discussed herein.

High-performance liquid chromatographic method for determination of amino acids by precolumn derivatization with 4-chloro-3,5-dinitrobenzotrifluoride

“…The CNBF derivatization was rapid at moderate temperature, along with the resultant derivatives being very stable and of high ultraviolet and fluorescent absorption [41][42][43][44][45][46][47]. There were not any multiple derivatives and by-products except CNBF hydrolysis compound in the reaction, while excess reagent and its hydrolysis compound could not disturb the separation.…”

A rapid liquid chromatography method for determination of glufosinate residue in maize after derivatisation

“…4-Chloro-3,5-dinitrobenzotrifluoride (CNBF) is an important fine chemical, which has been known to react with primary or secondary amines in the presence of base to produce stable N-substituted-2,6-dinitro-4-(trifluoromethyl)-benzamine deriva-0308-8146/$ -see front matter Ó 2011 Elsevier Ltd. All rights reserved. doi:10.1016/j.foodchem.2010.12.132 tives, which display satisfactory ultraviolet absorption (Pitzer, Werbovetz, Brendle, & Scovill, 1998;Qian et al, 2009). For the determination of water-soluble herbicides, ion-pair liquid chromatography-tandem mass spectrometry and ion-pair liquid chromatography coupled to inductively coupled plasma mass spectrometry were ever used (Chen, He, Beer, Megharaj, & Naidu, 2009;Wang et al, 2008).…”

Residue determination of glyphosate in environmental water samples with high-performance liquid chromatography and UV detection after derivatization with 4-chloro-3,5-dinitrobenzotrifluoride

“…Thus for sensitive determination of glyphosate, many derivatization agents have been developed including 4-chloro-7-nitrobenzofurazan (NBD-Cl) [20], 2,2-dihydroxy-1h-indene-1,3-(2h)-dione (Ninhydrin) [21][22][23], lfluoro-2,4-dinitrobenzene (DNP) [24], 9-fluorenylmethyl chloroformate (FMOC-Cl) [25][26][27][28][29][30][31][32][33][34], o-phthalaldehyde-mercaptoethanol (OPA-MERC) [35,36], p-toluenesulphonyl chloride (TsCl) [37,38]. 4-Chloro-3,5-dinitrobenzotrifluoride (CNBF) is an important fine chemical, which has been known to react with primary or secondary amines in presence of base to produce stable N-substituted-2,6-dinitro-4-(trifluoromethyl)-benzamine derivatives which are satisfactory ultraviolet absorption [39][40][41][42][43].…”