Intramolecular azide to alkene cycloadditions for the construction of pyrrolobenzodiazepines and azetidino-benzodiazepines

Karl Hemming, Christopher S Chambers, Faisal Jamshaid, Paul A O'Gorman

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrrolo[1,4]benzodiazepines (PBDs), pyrrolo[1,2,5]benzothiadiazepines (PBTDs), and azetidino[1,4]benzodiazepines. The imines and aziridines are formed after loss of nitrogen from a triazoline cycloadduct. The PBDs are a potent class of antitumour antibiotics.

Original languageEnglish
Pages (from-to)16737-56
Number of pages20
JournalMolecules
Volume19
Issue number10
DOIs
Publication statusPublished - 2014

Fingerprint

Azides
Cycloaddition
Cycloaddition Reaction
cycloaddition
Alkenes
Benzodiazepines
imines
alkenes
Imines
antibiotics
Aziridines
Proline
nitrogen
acids
Nitrogen
Anti-Bacterial Agents
Acids
Bz-423
pyrrolo(2,1-c)(1,4)benzodiazepine

Cite this

Hemming, Karl ; Chambers, Christopher S ; Jamshaid, Faisal ; O'Gorman, Paul A. / Intramolecular azide to alkene cycloadditions for the construction of pyrrolobenzodiazepines and azetidino-benzodiazepines. In: Molecules. 2014 ; Vol. 19, No. 10. pp. 16737-56.
@article{8c8877a33ee444838a28da0f0e34a16f,
title = "Intramolecular azide to alkene cycloadditions for the construction of pyrrolobenzodiazepines and azetidino-benzodiazepines",
abstract = "The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrrolo[1,4]benzodiazepines (PBDs), pyrrolo[1,2,5]benzothiadiazepines (PBTDs), and azetidino[1,4]benzodiazepines. The imines and aziridines are formed after loss of nitrogen from a triazoline cycloadduct. The PBDs are a potent class of antitumour antibiotics.",
keywords = "Alkenes, Antibiotics, Antineoplastic, Azides, Benzodiazepines, Cycloaddition Reaction, Molecular Structure, Pyrroles, Journal Article, Research Support, Non-U.S. Gov't",
author = "Karl Hemming and Chambers, {Christopher S} and Faisal Jamshaid and O'Gorman, {Paul A}",
year = "2014",
doi = "10.3390/molecules191016737",
language = "English",
volume = "19",
pages = "16737--56",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "10",

}

Intramolecular azide to alkene cycloadditions for the construction of pyrrolobenzodiazepines and azetidino-benzodiazepines. / Hemming, Karl; Chambers, Christopher S; Jamshaid, Faisal; O'Gorman, Paul A.

In: Molecules, Vol. 19, No. 10, 2014, p. 16737-56.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Intramolecular azide to alkene cycloadditions for the construction of pyrrolobenzodiazepines and azetidino-benzodiazepines

AU - Hemming, Karl

AU - Chambers, Christopher S

AU - Jamshaid, Faisal

AU - O'Gorman, Paul A

PY - 2014

Y1 - 2014

N2 - The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrrolo[1,4]benzodiazepines (PBDs), pyrrolo[1,2,5]benzothiadiazepines (PBTDs), and azetidino[1,4]benzodiazepines. The imines and aziridines are formed after loss of nitrogen from a triazoline cycloadduct. The PBDs are a potent class of antitumour antibiotics.

AB - The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrrolo[1,4]benzodiazepines (PBDs), pyrrolo[1,2,5]benzothiadiazepines (PBTDs), and azetidino[1,4]benzodiazepines. The imines and aziridines are formed after loss of nitrogen from a triazoline cycloadduct. The PBDs are a potent class of antitumour antibiotics.

KW - Alkenes

KW - Antibiotics, Antineoplastic

KW - Azides

KW - Benzodiazepines

KW - Cycloaddition Reaction

KW - Molecular Structure

KW - Pyrroles

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.3390/molecules191016737

DO - 10.3390/molecules191016737

M3 - Article

VL - 19

SP - 16737

EP - 16756

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 10

ER -