Tetrafluorobenzyl Alcohol-Oriented Novel (S)-Enantiomeric Esters: Synthesis and Structure-Activity Relationship

Background: Using constantly and widely chemistry insecticides has resulted in a selection burden and favored tolerance development in various insect species. Particularly, pyrethroids are the only one which can be used for net impregnation either ITNs or LLIN as yet, however, the excessive use of pyrethroids has led to many cases of insect resistance in worldwide. Therefore, it is urgent to develop novel insecticides fighting against this sort of resistance. Methods: Based on the preliminary studies, we explored a straightforward highly stereoselective method to achieve the novel chiral ester derivatives by using Oppolzer’s 10,2-camphorsultam as chiral controlling reagent. Results: A series of tetrafluorobenzyl alcohol oriented (S)-enantiomeric esters were designed and synthesized by the asymmetric synthesis. All the compounds exhibited moderate yields, and the original synthesized compounds have been evaluated for their potential insecticidal activity against Plutella xylostella compared with those of fenvalerate and D-trans-phenothrin, and some compounds presented excellent insecticidal activities. Conclusion: The bioassay illustrated that some of the compounds exhibit obviously insecticidal activities against Plutella xylostella, especially, the insecticidal activity of compound 5i was as good as commercial fenvalerate and D-trans-phenothrin, which can be used as a lead compound for further optimization.

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Antifeedant and Insecticidal Activity of Quassinoids against the Diamondback Moth(Plutella xylostella)and Structure—Activity Relationships

Bioscience Biotechnology and Biochemistry ◽

10.1271/bbb.59.974 ◽

1995 ◽

Vol 59 (6) ◽

pp. 974-979 ◽

Cited By ~ 11

Author(s):

Masayuki Daido ◽

Nobuhiro Ohno ◽

Kazunori Imamura ◽

Narihiko Fukamiya ◽

Makoto Hatakoshi ◽

...

Keyword(s):

Insecticidal Activity ◽

Plutella Xylostella ◽

Diamondback Moth ◽

Structure Activity Relationships ◽

Structure Activity

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Synthesis, insecticidal activity, structure–activity relationship (SAR) and density functional theory (DFT) of novel anthranilic diamides analogs containing 1,3,4-oxadiazole rings

RSC Advances ◽

10.1039/c4ra06356b ◽

2014 ◽

Vol 4 (98) ◽

pp. 55445-55451 ◽

Cited By ~ 12

Author(s):

Qi Liu ◽

Kai Chen ◽

Qiang Wang ◽

Jueping Ni ◽

Yufeng Li ◽

...

Keyword(s):

Density Functional Theory ◽

Insecticidal Activity ◽

Density Functional ◽

Activity Relationship ◽

Dft Studies ◽

Functional Theory ◽

Structure Activity ◽

Activity Structure ◽

The Density Functional Theory ◽

Insecticidal Activities

A series of anthranilic diamides analogs (5a–x) containing 1,3,4-oxadiazole rings were synthesized, and their insecticidal activities were evaluated. The density functional theory (DFT) studies was used to understand the various insecticidal activities.

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Synthesis and Insecticidal Activity of β-Dihydroagarofuran Acetal Derivatives

Natural Product Communications ◽

10.1177/1934578x1801300404 ◽

2018 ◽

Vol 13 (4) ◽

pp. 1934578X1801300

Author(s):

Xin Xi ◽

Ximei Zhao ◽

Feng Zhu ◽

Jielu Wei ◽

Zhan Hu ◽

...

Keyword(s):

Insecticidal Activity ◽

Structure Activity Relationship ◽

Positive Control ◽

Activity Relationship ◽

Structure Activity ◽

Mythimna Separate ◽

Relationship Of ◽

Insecticidal Compounds ◽

Insecticidal Activities

To search for improved insecticidal compounds based on β-dihydroagarofuran sesquiterpenoids, forty-four β-dihydroagarofuran acetal derivatives were designed and synthesized. Insecticidal activities and structure-activity relationship of these target compounds were evaluated. Some of the newly synthesized β-dihydroagarofuran acetal compounds were found to show higher insecticidal activity against sixth-instar larvae of Mythimna separate. Especially, compounds 2.2.9, 2.2.10, 2.2.11, 2.3.4, 2.3.6, 2.3.7, 2.5.4, 2.5.7 had great insecticidal activities with lower LD50 than that of the positive control celangulin-V (110.13 μg/g). It deserves mentioning that compound 2.2.11 showed the lowest LD50 (60.33 μg/g) among these compounds. Structure-activity relationship results suggested that the substituent groups of 1-, 6- and 9-positions of the target structures could greatly affect the insecticidal activity. Especially, when the substituent groups of 6-position were n-propyl, n-butyl, allyl, propargyl, o-fluorobenzyl, and p-fluorobenzyl, the compounds showed outstanding insecticidal activities.

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Asymmetric Synthesis of Photophore-Containing Lactisole Derivatives to Elucidate Sweet Taste Receptors

Molecules ◽

10.3390/molecules25122790 ◽

2020 ◽

Vol 25 (12) ◽

pp. 2790

Author(s):

Tomoya Nakagita ◽

Akiko Ishida ◽

Zetryana Puteri Tachrim ◽

Lei Wang ◽

Takumi Misaka ◽

...

Keyword(s):

Asymmetric Synthesis ◽

Chemical Biology ◽

Photoaffinity Labeling ◽

Sweet Taste ◽

Taste Receptors ◽

The Novel ◽

Synthetic Compounds ◽

Structure Activity ◽

Sweet Taste Receptors ◽

The Common

Lactisole, which has a 2-phenoxy propionic acid skeleton, is well-known as an inhibitor of sweet taste receptors. We recently revealed some of the structure–activity relationships of the aromatic ring and chiral center of lactisole. Photoaffinity labeling is one of the common chemical biology methods to elucidate the interaction between bioactive compounds and biomolecules. In this paper, the novel asymmetric synthesis of lactisole derivatives with common photophores (benzophenone, azide and trifluoromethyldiazirine) for photoaffinity labeling is described. The synthetic compounds are subjected to cell-based sweet taste receptors, and the substitution with trifluoromethyldiazirinyl photophore shows the highest affinity to the receptor of the synthesized compounds.

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Naldemedine: Peripherally Acting Opioid Receptor Antagonist for Treating Opioid-induced Adverse Effects

Current Topics in Medicinal Chemistry ◽

10.2174/1568026620666200710105953 ◽

2020 ◽

Vol 20 (31) ◽

pp. 2830-2842

Author(s):

Masanao Inagaki ◽

Toshiyuki Kanemasa ◽

Takaaki Yokota

Keyword(s):

Adverse Effects ◽

Adverse Events ◽

Severe Pain ◽

Lead Compound ◽

Inhibitory Effects ◽

Pharmacokinetic Profiles ◽

Structure Activity ◽

The Usa ◽

Relationship Study ◽

The Eu

Opioids are widely used for pain management in moderate-to-severe pain. However, opioids are associated with adverse events, such as constipation and emesis/vomiting. To reduce these undesired effects, a structure–activity relationship study of morphinan derivatives was conducted, and a promising lead compound with inhibitory effects on opioid receptors was obtained. Further improvement in the potency and pharmacokinetic profiles of the lead compound led to the discovery of naldemedine, which showed anti-constipation and anti-emetic effects against these adverse events that were induced by morphine without influencing morphine’s analgesic effect. Naldemedine was launched in Japan and the USA in 2017 and in the EU in 2019, for treating opioid-induced constipation.

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COVID-19 Vaccination: From Interesting Agent to the Patient

Vaccines ◽

10.3390/vaccines9020120 ◽

2021 ◽

Vol 9 (2) ◽

pp. 120

Author(s):

Anis Daou

Keyword(s):

Central Nervous System ◽

Nervous System ◽

Gastrointestinal Tract ◽

Circulatory System ◽

The Novel ◽

Lead Compound ◽

Fda Approval ◽

The World ◽

The Central Nervous System ◽

Novel Coronavirus

The vaccination for the novel Coronavirus (COVID-19) is undergoing its final stages of analysis and testing. It is an impressive feat under the circumstances that we are on the verge of a potential breakthrough vaccination. This will help reduce the stress for millions of people around the globe, helping to restore worldwide normalcy. In this review, the analysis looks into how the new branch of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2) came into the forefront of the world like a pandemic. This review will break down the details of what COVID-19 is, the viral family it belongs to and its background of how this family of viruses alters bodily functions by attacking vital human respiratory organs, the circulatory system, the central nervous system and the gastrointestinal tract. This review also looks at the process a new drug analogue undergoes, from (i) being a promising lead compound to (ii) being released into the market, from the drug development and discovery stage right through to FDA approval and aftermarket research. This review also addresses viable reasoning as to why the SARS-CoV-2 vaccine may have taken much less time than normal in order for it to be released for use.

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The Influence of Varying Fluorination Patterns on the Thermodynamics and Kinetics of Benzenesulfonamide Binding to Human Carbonic Anhydrase II

Biomolecules ◽

10.3390/biom10040509 ◽

2020 ◽

Vol 10 (4) ◽

pp. 509 ◽

Cited By ~ 2

Author(s):

Steffen Glöckner ◽

Khang Ngo ◽

Björn Wagner ◽

Andreas Heine ◽

Gerhard Klebe

Keyword(s):

Carbonic Anhydrase ◽

Carbonic Anhydrase Ii ◽

The Novel ◽

Binding Modes ◽

X Ray ◽

Structure Activity ◽

Small Set ◽

Novel Method ◽

Human Carbonic Anhydrase ◽

Kinetics Of

The fluorination of lead-like compounds is a common tool in medicinal chemistry to alter molecular properties in various ways and with different goals. We herein present a detailed study of the binding of fluorinated benzenesulfonamides to human Carbonic Anhydrase II by complementing macromolecular X-ray crystallographic observations with thermodynamic and kinetic data collected with the novel method of kinITC. Our findings comprise so far unknown alternative binding modes in the crystalline state for some of the investigated compounds as well as complex thermodynamic and kinetic structure-activity relationships. They suggest that fluorination of the benzenesulfonamide core is especially advantageous in one position with respect to the kinetic signatures of binding and that a higher degree of fluorination does not necessarily provide for a higher affinity or more favorable kinetic binding profiles. Lastly, we propose a relationship between the kinetics of binding and ligand acidity based on a small set of compounds with similar substitution patterns.

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