Pentamidine congeners. 3. Crystal structure and molecular modeling studies of trans‐1,4‐bis(4‐amidinophenoxy)‐2‐butene

Isaac Donkor, Cheryl L. Klein, Li Liang, G. Craig Hill

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Abstract

X‐ray diffraction was used to confirm the geometry of trans‐1,4‐bis(4‐amidinophenoxy)‐2‐butene dihydrochloride dihydrate (trans‐butenamidine). trans‐Butenamidine is a semirigid analogue of pentamidine that has demonstrated good anti‐Pneumocystis carinii activity in rats. Molecular modeling studies revealed that unlike pentamidine or propamidine, trans‐butenamidine does not discriminate between AT and TA sequences in its binding to the minor groove of DNA. Crystal data: [C18H22N4O22+][Cl]2[H2O]2, triclinic space group, P1, a = 9.443(1) Å, b = 11.400(1) Å, c = 11.919(1) Å, α = 62.19(1) Å, β = 81.10(1)°, γ = 72.19(1)°, V = 1080.3(3) Å3, Z = 2, R = 0.054 for 1149 observed reflections with I > 3σ(I).

Original languageEnglish (US)
Pages (from-to)448-455
Number of pages8
JournalJournal of Pharmaceutical Sciences
Volume84
Issue number4
DOIs
StatePublished - Jan 1 1995

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Pentamidine
Molecular Structure
X-Ray Diffraction
DNA
propamidine

All Science Journal Classification (ASJC) codes

  • Pharmaceutical Science

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Pentamidine congeners. 3. Crystal structure and molecular modeling studies of trans‐1,4‐bis(4‐amidinophenoxy)‐2‐butene. / Donkor, Isaac; Klein, Cheryl L.; Liang, Li; Hill, G. Craig.

In: Journal of Pharmaceutical Sciences, Vol. 84, No. 4, 01.01.1995, p. 448-455.

Research output: Contribution to journalArticle

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abstract = "X‐ray diffraction was used to confirm the geometry of trans‐1,4‐bis(4‐amidinophenoxy)‐2‐butene dihydrochloride dihydrate (trans‐butenamidine). trans‐Butenamidine is a semirigid analogue of pentamidine that has demonstrated good anti‐Pneumocystis carinii activity in rats. Molecular modeling studies revealed that unlike pentamidine or propamidine, trans‐butenamidine does not discriminate between AT and TA sequences in its binding to the minor groove of DNA. Crystal data: [C18H22N4O22+][Cl−]2[H2O]2, triclinic space group, P1, a = 9.443(1) {\AA}, b = 11.400(1) {\AA}, c = 11.919(1) {\AA}, α = 62.19(1) {\AA}, β = 81.10(1)°, γ = 72.19(1)°, V = 1080.3(3) {\AA}3, Z = 2, R = 0.054 for 1149 observed reflections with I > 3σ(I).",
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