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Record W4396532702 · doi:10.1002/cmdc.202400220

N‐Pyrazolyl‐ and N‐Triazolylamines and ‐Ureas as Antileishmanial and Antitrypanosomal Drugs

2024· article· en· W4396532702 on OpenAlexfundno aff
Tobias Winge, Lukas Imberg, Benjamin Perry, An Matheeussen, Guy Caljon, Dmitrii V. Kalinin, Bernhard Wünsch

Bibliographic record

VenueChemMedChem · 2024
Typearticle
Languageen
FieldMedicine
TopicResearch on Leishmaniasis Studies
Canadian institutionsnot available
FundersDrugs for Neglected Diseases initiativeUniversiteit AntwerpenOntario Stroke Network
KeywordsPharmacologyChemistryTrypanocidal agentToxicologyStereochemistryTraditional medicineBiologyMedicineTrypanosoma bruceiBiochemistry

Abstract

fetched live from OpenAlex

Abstract Three types of modifications of antileishmanial pyrazole lead compounds 7 and 8 were conducted to expand understanding of the relationships between structural features and antileishmanial/antitrypanosomal activity: (1) the pyrazole core was retained or replaced by a 1,2,4‐triazole ring; (2) various aryl moieties including 2‐fluorophenyl, pyridin‐3‐yl and pyrazin‐2‐yl rings were attached at 3‐position of the core azole; (3) either arylmethylamino or ureido substituents were introduced at 5‐position of the azole core. The synthesis followed established routes starting with esters 9 or 15 and anhydride 21 . The synthesized 3‐arylpyrazoles and 3‐aryl‐1,2,4‐triazoles had only very low antileishmanial activity. The 2‐fluorophenyl‐substituted pyrazole 18c revealed the highest antileishmanial activity of this series of compounds, but its IC 50 value (20 μM) still indicates low activity. However, low micromolar antitrypanosomal activity was detected for the pyridin‐3‐yl‐substituted pyrazoles 12b ( IC 50 =4.7 μM) and 14a ( IC 50 =2.1 μM). Their IC 50 values are comparable with the IC 50 values of the reference compounds benznidazole and nifurtimox. Whereas only low unspecific cytotoxicity at the primary peritoneal mouse macrophages (PMM) was detected, considerable cytotoxicity at MRC‐5 human fibroblast cells was found for both pyrazoles 12b an 14a . The activity of pyrazole 12b against T. cruzi is 4‐fold higher than its unspecific MRC‐5 cytotoxicity.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.115
Threshold uncertainty score0.984

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.001
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.014
GPT teacher head0.302
Teacher spread0.288 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations1
Published2024
Admission routes1
Has abstractyes

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