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Record W1992246106 · doi:10.1021/ml400466p

Novel Quinoline-Based P2–P4 Macrocyclic Derivatives As Pan-Genotypic HCV NS3/4a Protease Inhibitors

2014· article· en· W1992246106 on OpenAlexaff
Unmesh Shah, Charles Jayne, Samuel Chackalamannil, Francisco Velázquez, Zhuyan Guo, Alexei V. Buevich, John A. Howe, Robert A. Chase, Aileen Soriano, Sony Agrawal, Michael T. Rudd, John A. McCauley, Nigel J. Liverton, Joseph J. Romano, Kimberly J. Bush, Paul J. Coleman, Christiane Grisé-Bard, Marie‐Christine Brochu, Sylvie Charron, Virender S. Aulakh, Benoit Bachand, Patrick Beaulieu, Helmi Zaghdane, Sathesh Bhat, Yongxin Han, Joseph P. Vacca, Ian W. Davies, Ann E. Weber, Srikanth Venkatraman

Bibliographic record

VenueACS Medicinal Chemistry Letters · 2014
Typearticle
Languageen
FieldMedicine
TopicHepatitis C virus research
Canadian institutionsMerck Canada Inc. (Canada)
Fundersnot available
KeywordsQuinolineProteaseNS3VirologyCombinatorial chemistryChemistryMedicineEnzymeBiochemistryOrganic chemistry

Abstract

fetched live from OpenAlex

We have previously reported the discovery of our P2-P4 macrocyclic HCV NS3/4a protease inhibitor MK-5172, which in combination with the NS5a inhibitor MK-8742 recently received a breakthrough therapy designation from the US FDA for treatment of chronic HCV infection. Our goal for the next generation NS3/4a inhibitor was to achieve pan-genotypic activity while retaining the pharmacokinetic profile of MK-5172. One of the areas for follow-up investigation involved replacement of the quinoxaline moiety in MK-5172 with a quinoline and studying the effect of substitution at 4-position of the quinoline. The rationale for this effort was based on molecular modeling, which indicated that such modifications would improve interactions with the S2 subsite, in particular with D79. We wish to report herein the discovery of highly potent inhibitors with pan-genotypic activity and an improved profile over MK-5172, especially against gt-3a and A156 mutants.

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation 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 score0.002
Threshold uncertainty score0.007

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0020.001

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 head0.019
GPT teacher head0.291
Teacher spread0.272 · 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 source (direct Gemma or distilled Codex), 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

Citations25
Published2014
Admission routes1
Has abstractyes

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Same venueACS Medicinal Chemistry LettersSame topicHepatitis C virus researchFrench-language works237,207