Four Pyrrole Derivatives Used as Building Blocks in the Synthesis of Minor-Groove Binders

Alan R. Kennedy, Abedawn I. Khalaf, Fraser Scott, Colin J. Suckling

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The title nitro­pyrrole-based compounds, C7H8N2O4, (I) (ethyl 4-nitro-1H-pyrrole-2-carboxyl­ate), its derivative C12H14N2O4, (II) [ethyl 4-nitro-1-(4-pent­yn­yl)-1H-pyrrole-2-carboxyl­ate], C15H26N4O3, (III) {N-[3-(di­methyamino)prop­yl]-1-isopentyl-4-nitro-1H-pyrrole-2-carboxamide}, and C20H27N9O5, (IV) {1-(3-azido­prop­yl)-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-N-[2-(morpholin-4-yl)eth­yl]-1H-pyrrole-2-carboxamide}, are inter­mediates used in the synthesis of modified DNA minor-groove binders. In all four compounds, the nitro groups lie in the plane of the pyrrole ring. In compounds (I) and (II), the ester groups also lie in the plane of the pyrrole ring. In compound (III), both of the other substituents lie out of the plane of the pyrrole ring. In the case of compound (IV), the coplanarity extends to the second pyrrole ring and through both amide groups. In the crystals of all four compounds, layer-like structures are formed, via a combination of N—H⋯O and C—H⋯O hydrogen bonds for (I), (III) and (IV), but by only C—H⋯O hydrogen bonds for (II).
LanguageEnglish
Pages254-259
Number of pages6
JournalActa Crystallographica Section E: Crystallographic Communications
Volume73
Issue number2
DOIs
Publication statusPublished - 27 Jan 2017
Externally publishedYes

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Pyrroles
pyrroles
grooves
Binders
Hydrogen bonds
Derivatives
synthesis
Amides
Esters
DNA
Crystals
rings
Nitro Compounds
hydrogen bonds
coplanarity
amides
esters
deoxyribonucleic acid

Cite this

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title = "Four Pyrrole Derivatives Used as Building Blocks in the Synthesis of Minor-Groove Binders",
abstract = "The title nitro­pyrrole-based compounds, C7H8N2O4, (I) (ethyl 4-nitro-1H-pyrrole-2-carboxyl­ate), its derivative C12H14N2O4, (II) [ethyl 4-nitro-1-(4-pent­yn­yl)-1H-pyrrole-2-carboxyl­ate], C15H26N4O3, (III) {N-[3-(di­methyamino)prop­yl]-1-isopentyl-4-nitro-1H-pyrrole-2-carboxamide}, and C20H27N9O5, (IV) {1-(3-azido­prop­yl)-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-N-[2-(morpholin-4-yl)eth­yl]-1H-pyrrole-2-carboxamide}, are inter­mediates used in the synthesis of modified DNA minor-groove binders. In all four compounds, the nitro groups lie in the plane of the pyrrole ring. In compounds (I) and (II), the ester groups also lie in the plane of the pyrrole ring. In compound (III), both of the other substituents lie out of the plane of the pyrrole ring. In the case of compound (IV), the coplanarity extends to the second pyrrole ring and through both amide groups. In the crystals of all four compounds, layer-like structures are formed, via a combination of N—H⋯O and C—H⋯O hydrogen bonds for (I), (III) and (IV), but by only C—H⋯O hydrogen bonds for (II).",
keywords = "Crystal structure, Nitropyrrole, Minor-groove binders, Hydrogen bonding",
author = "Kennedy, {Alan R.} and Khalaf, {Abedawn I.} and Fraser Scott and Suckling, {Colin J.}",
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pages = "254--259",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",
number = "2",

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Four Pyrrole Derivatives Used as Building Blocks in the Synthesis of Minor-Groove Binders. / Kennedy, Alan R.; Khalaf, Abedawn I.; Scott, Fraser; Suckling, Colin J.

In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 73, No. 2, 27.01.2017, p. 254-259.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Four Pyrrole Derivatives Used as Building Blocks in the Synthesis of Minor-Groove Binders

AU - Kennedy, Alan R.

AU - Khalaf, Abedawn I.

AU - Scott, Fraser

AU - Suckling, Colin J.

PY - 2017/1/27

Y1 - 2017/1/27

N2 - The title nitro­pyrrole-based compounds, C7H8N2O4, (I) (ethyl 4-nitro-1H-pyrrole-2-carboxyl­ate), its derivative C12H14N2O4, (II) [ethyl 4-nitro-1-(4-pent­yn­yl)-1H-pyrrole-2-carboxyl­ate], C15H26N4O3, (III) {N-[3-(di­methyamino)prop­yl]-1-isopentyl-4-nitro-1H-pyrrole-2-carboxamide}, and C20H27N9O5, (IV) {1-(3-azido­prop­yl)-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-N-[2-(morpholin-4-yl)eth­yl]-1H-pyrrole-2-carboxamide}, are inter­mediates used in the synthesis of modified DNA minor-groove binders. In all four compounds, the nitro groups lie in the plane of the pyrrole ring. In compounds (I) and (II), the ester groups also lie in the plane of the pyrrole ring. In compound (III), both of the other substituents lie out of the plane of the pyrrole ring. In the case of compound (IV), the coplanarity extends to the second pyrrole ring and through both amide groups. In the crystals of all four compounds, layer-like structures are formed, via a combination of N—H⋯O and C—H⋯O hydrogen bonds for (I), (III) and (IV), but by only C—H⋯O hydrogen bonds for (II).

AB - The title nitro­pyrrole-based compounds, C7H8N2O4, (I) (ethyl 4-nitro-1H-pyrrole-2-carboxyl­ate), its derivative C12H14N2O4, (II) [ethyl 4-nitro-1-(4-pent­yn­yl)-1H-pyrrole-2-carboxyl­ate], C15H26N4O3, (III) {N-[3-(di­methyamino)prop­yl]-1-isopentyl-4-nitro-1H-pyrrole-2-carboxamide}, and C20H27N9O5, (IV) {1-(3-azido­prop­yl)-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-N-[2-(morpholin-4-yl)eth­yl]-1H-pyrrole-2-carboxamide}, are inter­mediates used in the synthesis of modified DNA minor-groove binders. In all four compounds, the nitro groups lie in the plane of the pyrrole ring. In compounds (I) and (II), the ester groups also lie in the plane of the pyrrole ring. In compound (III), both of the other substituents lie out of the plane of the pyrrole ring. In the case of compound (IV), the coplanarity extends to the second pyrrole ring and through both amide groups. In the crystals of all four compounds, layer-like structures are formed, via a combination of N—H⋯O and C—H⋯O hydrogen bonds for (I), (III) and (IV), but by only C—H⋯O hydrogen bonds for (II).

KW - Crystal structure

KW - Nitropyrrole

KW - Minor-groove binders

KW - Hydrogen bonding

UR - http://journals.iucr.org/e/

U2 - 10.1107/S2056989017001177

DO - 10.1107/S2056989017001177

M3 - Article

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EP - 259

JO - Acta Crystallographica Section E: Crystallographic Communications

T2 - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

IS - 2

ER -