Evidence map›Paper›PMID 36281761›Full record

ArticleAngewandte Chemie (International ed. in English)2023

Synthesis and Biological Evaluation of C(13)/C(13')-Bis(desmethyl)disorazole Z.

Christian Paul Bold, Daniel Lucena-Agell, María Ángela Oliva, José Fernando Díaz, Karl-Heinz Altmann

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.

0numbers the graph read from it
0cells of the map it votes in
8citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

8 citing papers in PubMed.

  1. Review
  2. Review
  3. Review
  4. Article
  5. Total Synthesis of (+)-Disorazole Z1.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Article
  6. Total Synthesis of Tosyl-Samroiyotmycin A and Its Biological Profiling.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024
    Article
  7. Synthesis of a Non-Symmetrical Disorazole CMolecules (Basel, Switzerland) · 2024
    Article
  8. Synthesis and Biological Evaluation of C(13)/C(13')-Bis(desmethyl)disorazole Z.Angewandte Chemie (International ed. in English) · 2023
    Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

5 authors.

Christian Paul BoldDepartment of Chemistry and Applied Biosciences, Institute of Pharmaceutical Sciences, ETH Zürich, Vladimir-Prelog-Weg 4, 8093, Zürich, Switzerland.ORCID 0000-0003-3810-8407
Daniel Lucena-AgellCentro de Investigaciones Biológicas Margarita Salas, Consejo Superior de Investigaciones Científicas, Ramiro de Maeztu 9, 28040, Madrid, Spain.ORCID 0000-0001-7314-8696
María Ángela OlivaCentro de Investigaciones Biológicas Margarita Salas, Consejo Superior de Investigaciones Científicas, Ramiro de Maeztu 9, 28040, Madrid, Spain.ORCID 0000-0002-2215-4639
José Fernando DíazCentro de Investigaciones Biológicas Margarita Salas, Consejo Superior de Investigaciones Científicas, Ramiro de Maeztu 9, 28040, Madrid, Spain.ORCID 0000-0003-2743-3319
Karl-Heinz AltmannDepartment of Chemistry and Applied Biosciences, Institute of Pharmaceutical Sciences, ETH Zürich, Vladimir-Prelog-Weg 4, 8093, Zürich, Switzerland.ORCID 0000-0002-0747-9734

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

We describe the total synthesis of the macrodiolide C(13)/C(13')-bis(desmethyl)disorazole Z through double inter-/intramolecular Stille cross-coupling of a monomeric vinyl stannane/vinyl iodide precursor to form the macrocycle. The key step in the synthesis of this precursor was a stereoselective aldol reaction of a formal Evans acetate aldol product with crotonaldehyde. As demonstrated by X-ray crystallography, the binding mode of C(13)/C(13')-bis(desmethyl)disorazole Z to tubulin is virtually identical with that of the natural product disorazole Z. Likewise, C(13)/C(13')-bis(desmethyl)disorazole Z inhibits tubulin assembly with at least the same potency as disorazole Z and it appears to be a more potent cell growth inhibitor.

Indexed as

MacrolidesTubulinAldehydesStereoisomerism3-hydroxybutanalAldehydesMacrolidesTubulinCross-CouplingCyclodimerizationDisorazolesMicrotubule-Interacting AgentsTotal Synthesis

Identifiers

PMID36281761
PMCPMC10107878

What OpenQuestion holds

Textmetadata
LicenceCC BY-NC-ND
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.