Parasiticidal 2-alkoxy- and 2-aryloxyiminoalkyl trifluoromethanesulfonanilides

Ali, Abdelselam; Altamore, Timothy M.; Bliese, Marianne; Fisara, Petr; Liepa, Andris J.; Meyer, Adam G.; Nguyen, Oahn; Sargent, Roger M.; Sawutz, David G.; Winkler, David A.; Winzenberg, Kevin N.; Ziebell, Angela

doi:10.1016/j.bmcl.2007.10.090

Cited by 7 publications

(7 citation statements)

References 6 publications

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“…Several compounds from a series of 2-phenyl-3-(1 H -pyrrol-2-yl) acrylonitrile derivatives exhibited contact toxicity against adult C. felis [ 370 ]. Topical applications to adult cat fleas of a number of 2-alkoxy- and 2-aryl-oxyimino-aryl trifluoromethansulfoonanilides were very active [ 371 ]. An extract of neem seeds showed contact activity against both larvae and adult C. felis [ 372 ].…”

Section: Pest Managementmentioning

confidence: 99%

The Biology and Ecology of Cat Fleas and Advancements in Their Pest Management: A Review

Rust

2017

Insects

113

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The cat flea Ctenocephalides felis felis (Bouché) is the most important ectoparasite of domestic cats and dogs worldwide. It has been two decades since the last comprehensive review concerning the biology and ecology of C. f. felis and its management. Since then there have been major advances in our understanding of the diseases associated with C. f. felis and their implications for humans and their pets. Two rickettsial diseases, flea-borne spotted fever and murine typhus, have been identified in domestic animal populations and cat fleas. Cat fleas are the primary vector of Bartonella henselae (cat scratch fever) with the spread of the bacteria when flea feces are scratched in to bites or wounds. Flea allergic dermatitis (FAD) common in dogs and cats has been successfully treated and tapeworm infestations prevented with a number of new products being used to control fleas. There has been a continuous development of new products with novel chemistries that have focused on increased convenience and the control of fleas and other arthropod ectoparasites. The possibility of feral animals serving as potential reservoirs for flea infestations has taken on additional importance because of the lack of effective environmental controls in recent years. Physiological insecticide resistance in C. f. felis continues to be of concern, especially because pyrethroid resistance now appears to be more widespread. In spite of their broad use since 1994, there is little evidence that resistance has developed to many of the on-animal or oral treatments such as fipronil, imidacloprid or lufenuron. Reports of the perceived lack of performance of some of the new on-animal therapies have been attributed to compliance issues and their misuse. Consequentially, there is a continuing need for consumer awareness of products registered for cats and dogs and their safety.

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Section: Pest Managementmentioning

confidence: 99%

The Biology and Ecology of Cat Fleas and Advancements in Their Pest Management: A Review

Rust

2017

Insects

113

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“…As shown in Table 4B, 3 ik was converted to the corresponding aldoxime compound 10 a , which is a dual inhibitor of neutrophil elastase and proteinase 3 [11e] . In addition, the derivative product 10 b , which displays excellent vitro activity against C. felis and R. sanguineus, was obtained in an equivalent yield from 3 pf [11c] …”

Section: Resultsmentioning

confidence: 99%

“…N ‐(2‐carbonylaryl) benzenesulfonamides are key structural units found in biologically active molecules, as well as in organic synthesis [11] . Their derivatives have also been reported to display potent insecticidal properties, [11a] and function as protease inhibitors [11b–f] . They are also used in the synthesis of high‐value heterocycles such as dihydroquinoline and indole derivatives [12] .…”

Section: Introductionmentioning

confidence: 99%

“…[12] Typically, benzenesulfonamides are prepared from the reaction of o-carbonylanilines and sulfonyl chlorides with pyridine as a base. [11] Additionally, the oxidative coupling of anilines and sulfinates has been developed for the synthesis of these compounds. [13] Nevertheless, these processes required the use of a large number of environmentally unfriendly pyridines or stoichiometric oxidants, with low atom economy.…”

Section: Introductionmentioning

confidence: 99%

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Iron‐Catalyzed Electrophilic Amination of Sodium Sulfinates with Anthranils

et al. 2021

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A practical method for the synthesis of N‐(2‐carbonylaryl) benzenesulfonamides via an iron‐catalyzed electrophilic amination of sodium sulfinates with anthranils is described. This redox‐neutral transformation has high atom efficiency and is achieved under simple and mild reaction conditions. A wide range of anthranils and sodium sulfinates were compatible in this transformation. Moreover, the synthetic potential of this methodology was further demonstrated by the synthesis of various useful N‐heterocycles and derivatives.

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“…These methods have been used to design and optimise green pesticides [16][17][18][19][20] in collaboration with Du Pont and Schering Plough, have discovered new peptides and small molecules to control stem cells and cancers, [21][22][23][24][25][26][27] are accelerating the development of biomaterials for implantation and stem cell culture, [28][29][30][31][32][33] have provided new scientific insight into the potential adverse properties of nanomaterials, [34][35][36][37][38] have yielded clinical candidates for Australian SMEs and international companies, and were instrumental in the discovery of antibiotics [39,40] with a novel mode of action for the biotechnology spin off company, Betabiotics. Some of this research is discussed in more detail in the following sections.…”

Section: The Threat and Promise Of The Vastness Of Chemical Spacementioning

confidence: 99%

Adrien Albert Award: How to Mine Chemistry Space for New Drugs and Biomedical Therapies

Winkler

2015

Aust. J. Chem.

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It is clear that the sizes of chemical, 'drug-like', and materials spaces are enormous. If scientists working in established therapeutic, and newly established regenerative medicine fields are to discover better molecules or materials, they must find better ways of probing these enormous spaces. There are essentially five ways that this can be achieved: combinatorial and high throughput synthesis and screening approaches; fragment-based methods; de novo molecular design, design of experiments, diversity libraries; supramolecular approaches; evolutionary approaches. These methods either synthesise materials and screen them more quickly, or constrain chemical spaces using biology or other types of 'fitness functions'. High throughput experimental approaches cannot explore more than a minute part of chemical space. We are nevertheless entering into an era that is data dominated. High throughput experiments, robotics, automated crystallographic beam lines, combinatorial and flow synthesis, high content screening, and the 'omics' technologies are providing a flood of data, and efficient methods for extracting meaning from it are essential. This paper describes how new developments in mathematics have provided excellent, robust computational modelling tools for exploring large chemical spaces, for extracting meaning from large datasets, for designing new bioactive agents and materials, and for making truly predictive, quantitative models of the properties of molecules and materials for use in therapeutic and regenerative medicine. We describe these broadly applicable modelling tools and provide examples of their application to serum free stem cell culture, pathogen resistant polymers for implantable devices, new markers and biological mechanisms derived from mathematical analyses of gene array data, and pharmacokinetically important physicochemical properties of small molecules. We also discuss biologically conserved peptide motifs as a design framework for small molecule drugs and give examples of the application of this concept to drug design.

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Parasiticidal 2-alkoxy- and 2-aryloxyiminoalkyl trifluoromethanesulfonanilides

Cited by 7 publications

References 6 publications

The Biology and Ecology of Cat Fleas and Advancements in Their Pest Management: A Review

The Biology and Ecology of Cat Fleas and Advancements in Their Pest Management: A Review

Iron‐Catalyzed Electrophilic Amination of Sodium Sulfinates with Anthranils

Adrien Albert Award: How to Mine Chemistry Space for New Drugs and Biomedical Therapies

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