Evidence map›Paper›PMID 38025988›Full record

ArticleOrganic process research & development2023

Application of Chiral Transfer Reagents to Improve Stereoselectivity and Yields in the Synthesis of the Antituberculosis Drug Bedaquiline.

Juliana M S Robey, Sanjay Maity, Sarah L Aleshire, Angshuman Ghosh, Ajay K Yadaw, Subho Roy, Sarah Jane Mear, Timothy F Jamison, Gopal Sirasani, Chris H Senanayake and 5 more

Open access · hybridAbstract read
In one paragraph

Article in Organic process research & development, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing papers in PubMed
1.6field-weighted citation impact, top 17% of its field
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

5 citing papers in PubMed, 8 citations in OpenAlex.

  1. Article
  2. Review
  3. Bi(OTf)Organic letters · 2024
    Article
  4. Article
  5. 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

15 authors at 3 institutions in 2 countries.

Juliana M S RobeyMedicines for All Institute, Virginia Commonwealth University, Richmond, Virginia 23284-3068, United States.ORCID https://orcid.org/0000-0002-1002-5215
Sanjay MaityMedicines for All Institute, Virginia Commonwealth University, Richmond, Virginia 23284-3068, United States.
Sarah L AleshireMedicines for All Institute, Virginia Commonwealth University, Richmond, Virginia 23284-3068, United States.ORCID https://orcid.org/0000-0001-5353-4063
Angshuman GhoshR&D Centre, TCG Life Sciences Pvt. Limited, Kolkata, WB 700091, India.
Ajay K YadawR&D Centre, TCG Life Sciences Pvt. Limited, Kolkata, WB 700091, India.
Subho RoyR&D Centre, TCG Life Sciences Pvt. Limited, Kolkata, WB 700091, India.
Sarah Jane MearDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Timothy F JamisonDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID https://orcid.org/0000-0002-8601-7799
Gopal SirasaniTCG GreenChem, Inc., Richmond, Virginia 23219, United States.
Chris H SenanayakeTCG GreenChem, Inc., Richmond, Virginia 23219, United States.ORCID https://orcid.org/0009-0009-3170-0687
Rodger W StringhamMedicines for All Institute, Virginia Commonwealth University, Richmond, Virginia 23284-3068, United States.
B Frank GuptonMedicines for All Institute, Virginia Commonwealth University, Richmond, Virginia 23284-3068, United States.ORCID https://orcid.org/0000-0002-8165-1088
Kai O DonsbachMedicines for All Institute, Virginia Commonwealth University, Richmond, Virginia 23284-3068, United States.
Ryan C NelsonMedicines for All Institute, Virginia Commonwealth University, Richmond, Virginia 23284-3068, United States.
Charles S ShanahanMedicines for All Institute, Virginia Commonwealth University, Richmond, Virginia 23284-3068, United States.
Virginia Commonwealth University · USTCG Lifesciences (India) · INMassachusetts Institute of Technology · US

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Bedaquiline (BDQ) is an important drug for treating multidrug-resistant tuberculosis (MDR-TB), a worldwide disease that causes more than 1.6 million deaths yearly. The current synthetic strategy adopted by the manufacturers to assemble this molecule relies on a nucleophilic addition reaction of a quinoline fragment to a ketone, but it suffers from low conversion and no stereoselectivity, which subsequently increases the cost of manufacturing BDQ. The Medicines for All Institute (M4ALL) has developed a new reaction methodology to this process that not only allows high conversion of starting materials but also results in good diastereo- and enantioselectivity toward the desired BDQ stereoisomer. A variety of chiral lithium amides derived from amino acids were studied, and it was found that lithium (

Identifiers

PMID38025988
PMCPMC10661061
OpenAlexW4387617579

What OpenQuestion holds

Textmetadata
LicenceCC BY
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.