The Curtius Rearrangement: Applications in Modern Drug Discovery and Medicinal Chemistry
Publication type: Journal Article
Publication date: 2018-10-11
scimago Q1
wos Q2
SJR: 0.717
CiteScore: 6.7
Impact factor: 3.4
ISSN: 18607179, 18607187
PubMed ID:
30187672
Organic Chemistry
Drug Discovery
Biochemistry
Pharmacology
Molecular Medicine
General Pharmacology, Toxicology and Pharmaceutics
Abstract
The Curtius rearrangement is the thermal decomposition of an acyl azide derived from carboxylic acid to produce an isocyanate as the initial product. The isocyanate can undergo further reactions to provide amines and their derivatives. Due to its tolerance for a large variety of functional groups and complete retention of stereochemistry during rearrangement, the Curtius rearrangement has been used in the synthesis of a wide variety of medicinal agents with amines and amine-derived functional groups such as ureas and urethanes. The current review outlines various applications of the Curtius rearrangement in drug discovery and medicinal chemistry. In particular, the review highlights some widely used rearrangement methods, syntheses of some key agents for popular drug targets and FDA-approved drugs. In addition, the review highlights applications of the Curtius rearrangement in continuous-flow protocols for the scale-up of active pharmaceutical ingredients.
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Total citations:
90
Citations from 2024:
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(32.22%)
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GOST
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Ghosh A. K., Brindisi M., Sarkar A. The Curtius Rearrangement: Applications in Modern Drug Discovery and Medicinal Chemistry // ChemMedChem. 2018. Vol. 13. No. 22. pp. 2351-2373.
GOST all authors (up to 50)
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Ghosh A. K., Brindisi M., Sarkar A. The Curtius Rearrangement: Applications in Modern Drug Discovery and Medicinal Chemistry // ChemMedChem. 2018. Vol. 13. No. 22. pp. 2351-2373.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/cmdc.201800518
UR - https://doi.org/10.1002/cmdc.201800518
TI - The Curtius Rearrangement: Applications in Modern Drug Discovery and Medicinal Chemistry
T2 - ChemMedChem
AU - Ghosh, Arun K
AU - Brindisi, Margherita
AU - Sarkar, Anindya
PY - 2018
DA - 2018/10/11
PB - Wiley
SP - 2351-2373
IS - 22
VL - 13
PMID - 30187672
SN - 1860-7179
SN - 1860-7187
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2018_Ghosh,
author = {Arun K Ghosh and Margherita Brindisi and Anindya Sarkar},
title = {The Curtius Rearrangement: Applications in Modern Drug Discovery and Medicinal Chemistry},
journal = {ChemMedChem},
year = {2018},
volume = {13},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/cmdc.201800518},
number = {22},
pages = {2351--2373},
doi = {10.1002/cmdc.201800518}
}
Cite this
MLA
Copy
Ghosh, Arun K., et al. “The Curtius Rearrangement: Applications in Modern Drug Discovery and Medicinal Chemistry.” ChemMedChem, vol. 13, no. 22, Oct. 2018, pp. 2351-2373. https://doi.org/10.1002/cmdc.201800518.