3671-61-2

Usage

Structure

Benzimidazole derivative with a trifluoromethyl group

Usage

Building block for the synthesis of bioactive molecules and crop protection agents in pharmaceutical and agrochemical industries

Importance

Valuable intermediate in organic synthesis, particularly in the development of new drugs and pesticides

Benefits

Presence of trifluoromethyl group enhances biological activity and metabolic stability of resulting compounds, making it desirable in drug design and discovery.

InChI:InChI=1/C9H4F3N3/c10-9(11,12)8-14-6-2-1-5(4-13)3-7(6)15-8/h1-3H,(H,14,15)

Upstream product

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Relevant academic research and scientific papers

Cyanato - benzimidazole salt and its preparation method

The present invention discloses a new metal cyano-substituted benzimidazolide salt having formula (I) and its preparation. This new cyano-substituted benzimidazole derivatives exhibited excellent thermal stability. The organic salt of the present inventio

Efficient syntheses of 2-fluoroalkylbenzimidazoles and -benzothiazoles

We report an efficient one-step route to 2-fluoroalkylbenzimidazoles and -benzothiazoles via the condensation of fluorinated carboxylic acids and aromatic diamines or aminothiophenols. Additionally, we describe the syntheses of fluoroalkyl-azabenzimidazoles, -purines, and -imidazolopyrazines. This method is high-yielding with broad scope and is operationally simple with potential application to parallel synthesis.

An efficient method to access 2-fluoroalkylbenzimidazoles by PIDA oxidation of amidines

A mild and practical strategy for the synthesis of 2-bromodifluoromethyl (or trifluoromethyl)-1H-benzimidazoles via PIDA-mediated oxidative intramolecular cyclization of the fluorinated amidines is described. The approach has the advantages of superior yi

Synthesis and antiprotozoal activity of some 2-(trifluoromethyl)-1H- benzimidazole bioisosteres

A series of 2-(trifluoromethyl)-1H-benzimidazole derivatives with various 5- and 6-position bioisosteric substituents (-Cl, -F, -CF3, -CN), namely 1-7, were prepared using a short synthetic route. Each analogue was tested in vitro against the protozoa Giardia intestinalis and Trichomonas vaginalis in comparison with albendazole and metronidazole. Several analogues had IC50 values 1 μM against both species, which make them significantly more potent than either standard. Compound 4 [2,5(6)- bis(trifluoromethyl)-1H-benzimidazole], was 14 times more active than albendazole against T.:vaginalis. This compound (4) also showed moderate antimalarial activity against W2 and D6 strains of Plasmodium falciparum (5.98 and 6.12 μM, respectively). Studying further structure activity relationships through the use of bioisosteric substitution in these benzimidazolic derivatives should provide new leads against protozoal and possibly malarial diseases.

Rapid one-pot preparation of 2-substituted benzimidazoles from 2-nitroanilines using microwave conditions

A high yielding one-pot procedure for the generation of 2-substituted benzimidazoles directly from 2-nitroanilines by in situ reduction and cyclization using a microwave procedure is described.

Heterocyclic topoisomerase poisons

The invention provides a topoisomerase poison of formula I: wherein R1-R8 have any of the meanings defined in the specification, or a pharmaceutically acceptable salt thereof, as well as pharmaceutical compositions comprising a compound of formula I or a salt thereof, intermediates useful for preparing a compound of formula I, and therapeutic methods comprising administering a compound of formula I or a salt thereof.

2'-Substituted 5-phenylterbenzimidazoles as topoisomerase I poisons

5-Phenylterbenzimidazole (1) is active as a topoisomerase I poison (topo I) and is cytotoxic to human tumor cells. No cross-resistance was observed for 1 when it was evaluated against the camptothecin-resistant cell line, CPT-K5. Derivatives of 1 substituted at the 2'-position, however, did exhibit cross-resistance to this cell line. The basis for the resistance of this cell line towards CPT is that it possesses a mutant form of topo I. These results suggest that substituents at the 2'-position may be in proximity to the wild-type enzyme. Therefore, we hypothesized that terbenzimidazoles with 2'-substituents could be capable of interacting with the enzyme and thereby influence activity within this class of topo I poisons. 5-Phenylterbenzimidazoles with a hydroxy, hydroxymethyl, mercapto, amino, N-benzoylaminomethyl, chloro, and trifluoromethyl group at the 2'-position were synthesized. In addition, several 2'-ethyl-5-phenylterbenzimidazoles were prepared containing either a methoxy, hydroxy, amino, or N-acetylamino group at the 2-position of the ethyl side-chain. These 2'-substituted 5-phenylterbenzimidazoles were evaluated as topo I poisons and for cytotoxic activity. The presence of a strong electron-withdrawing group at the 2'-position, such as a chloro or trifluoromethyl group, did enhance both topo I poisoning activity and cytotoxicity. Studies on the relative DNA binding affinity of 1 to its 2'-amino and 2'-trifluoromethyl derivatives did exhibit a correlation with their relative differences in biological activity. Copyright (C) 2000 Elsevier Science Ltd.

Topoisomerase I inhibition and cytotoxicity of 5-bromo- and 5-phenylterbenzimidazoles

Topoisomerase I is an enzyme that is essential for maintaining the three-dimensional structure of DNA during the processes of transcription, translation and mitosis. With the introduction of new clinical agents that are effective in poisoning topoisomeras