Design, synthesis and antitrypanosomal activities of 2,6-disubstituted-4,5,7-trifluorobenzothiophenes

Bhambra, Avninder S.; Edgar, Mark; Elsegood, Mark R. J.; Li, Yuqi; Weaver, George W.; Arroo, Randolph; Yardley, Vanessa; Burrell‐Saward, Hollie; Kryštof, Vladimír

doi:10.1016/j.ejmech.2015.11.043

Cited by 17 publications

(7 citation statements)

References 25 publications

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“…Compounds of different class heterocycles are included in Table 5 as potent agents against Trypanosoma species and the results of their assessments were compared to those of standard drugs Tryparsamide, melarsoprol, difluoromethylornitithine, pentamidine, diminazene, suramin, benznidazole and nifurtimox. Among the substituted benzothiophene derivatives developed by Bhambra et al [217], compound 14a and 114b were found to be the most active candidates for HAT treatment with IC 50 values of 0.60 and 0.53 µM, respectively. In another series of imidazole compounds synthesized by Trunz et al [218], compounds 115a and 115b demonstrated good potency against T.b.rhodesiense and their reported IC 50 values were 0.16 and 0.10 µM, respectively.…”

Section: Recent Progress Of Antiprotozoan Agentsmentioning

confidence: 99%

Recent Advances in the Discovery of Novel Antiprotozoal Agents

et al. 2019

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Parasitic diseases have serious health, social, and economic impacts, especially in the tropical regions of the world. Diseases caused by protozoan parasites are responsible for considerable mortality and morbidity, affecting more than 500 million people worldwide. Globally, the burden of protozoan diseases is increasing and is been exacerbated because of a lack of effective medication due to the drug resistance and toxicity of current antiprotozoal agents. These limitations have prompted many researchers to search for new drugs against protozoan parasites. In this review, we have compiled the latest information (2012–2017) on the structures and pharmacological activities of newly developed organic compounds against five major protozoan diseases, giardiasis, leishmaniasis, malaria, trichomoniasis, and trypanosomiasis, with the aim of showing recent advances in the discovery of new antiprotozoal drugs.

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Section: Recent Progress Of Antiprotozoan Agentsmentioning

confidence: 99%

Recent Advances in the Discovery of Novel Antiprotozoal Agents

et al. 2019

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“…Compound 99 (Filho et al 2017) showed activity against the promastigote form of T. cruzi (IC 50 = 0.37 μM), compound 100 (Thompson et al 2017) with IC 50 = 0.055 μM against T. cruzi, and compounds 101 and 102 with IC 50 values 1.2 and 1.6 μM, respectively against the trypomastigote form of T. cruzi (Figure 36). Bhambra et al (2016) reported the synthesis of a small library of 2,6-disubstituted-4,5,7trifluorobenzothiophenes. Compounds 103 and 104 ( Figure 37) demonstrated interesting antitrypanosomal activity against T. b. rhodesiense with IC 50 values 0.60 and 0.53 μM, respectively and no toxicity to mammalian cells.…”

Section: Thiazole Derivativesmentioning

confidence: 99%

Hits and Lead Discovery in the Identification of New Drugs against the Trypanosomatidic Infections

Calogeropoulou¹,

Magoulas²,

Pöhner³

et al. 2019

Medicinal Chemistry of Neglected and Tropical Diseases

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The Neglected Tropical Diseases (NTDs) are a group of 17 pathologies, recognized by the World Health Organization (WHO), which are endemic in 149 countries of tropical and subtropical areas of the globe, and affect more than one billion people overall (Feasey et al. 2010). The pathologies are all caused by microparasites or macroparasites. Among the diseases provoked by microparasites, three are caused by kinetoplastidae, a group of flagellated protozoa transmitted by insect vectors: Chagas disease, Human African Trypanosomiasis and leishmaniasis. The focus of the present chapter is on the identification of new drugs for the treatment of trypanosomatidic infections such as Chagas disease, caused by Trypanosoma cruzi, and Human African Trypanosomiasis, caused by Trypanosoma brucei (Filardy et al. 2018).

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“…Among these, benzothiophenes constitute an important category of heterocyclic compounds due to their wide range of biological properties and also various applications in material sciences [11] . In particular, 2‐acyl benzothiophenes are privileged scaffolds in medicinal chemistry and display diverse pharmacological activities such as anti‐mitotic, [12] 17 β ‐HSD1 inhibition, [13] anti‐proliferative, [14] and anti‐trypanosomal (Figure 1). [15] Due to their broad range of pharmacological applications; their structure activity relationships have developed interest among medicinal chemists resulting in development of novel and elegant approaches [16]…”

Section: Introductionmentioning

confidence: 99%

KI‐assisted Sulfur Activation/Insertion/Denitration Strategy towards Dual C−S Bond Formation for One‐pot Synthesis of β‐Carboline‐tethered 2‐Acylbenzothiophenes

Singh

Jamra

et al. 2022

Asian J Org Chem

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A simple and efficient KI promoted sulfur activation‐insertion/de‐nitration strategy has been developed for the synthesis of β‐carboline C1 tethered 2‐acylbenzothiophenes via one‐pot assembly of 1‐acetyl β‐carbolines (an alkaloid based scaffold), 2‐nirobenzaldehydes and elemental sulfur. This expeditious reaction proceeds through the formation of β‐carboline linked nitro‐chalcones followed by embodiment of elemental sulfur to generate the multifunctional β‐carboline linked benzothiophene derivatives. The highlighted features of this efficient methodology are transition metal‐free conditions, use of inexpensive and non‐toxic catalyst, easy procedure, short reaction time, and broad substrate scope with good yields. The scope of this protocol has been extended for the synthesis of a range of novel compounds with significant diversity.

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Design, synthesis and antitrypanosomal activities of 2,6-disubstituted-4,5,7-trifluorobenzothiophenes

Cited by 17 publications

References 25 publications

Recent Advances in the Discovery of Novel Antiprotozoal Agents

Recent Advances in the Discovery of Novel Antiprotozoal Agents

Hits and Lead Discovery in the Identification of New Drugs against the Trypanosomatidic Infections

KI‐assisted Sulfur Activation/Insertion/Denitration Strategy towards Dual C−S Bond Formation for One‐pot Synthesis of β‐Carboline‐tethered 2‐Acylbenzothiophenes

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