Synthetic, structural, and conformational studies of methylated ring-expanded nucleosides containing the imidazo[4,5-e] [1, 4]diazepine ring system

Ramachandra S. Hosmane; Anila Bhan; Martin Hulce; Hongming Zhang; Narayan S. Hosmane

doi:10.1080/07328319108046664

Synthetic, structural, and conformational studies of methylated ring-expanded nucleosides containing the imidazo[4,5-e] [1, 4]diazepine ring system

Ramachandra S. Hosmane, Anila Bhan, Martin Hulce, Hongming Zhang, Narayan S. Hosmane

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

Syntheses of 4- and 7-methyl 4, 5, 7, 8-tetrahydro-6H-3-(β-D-ribofuranosyl)imidazo[4, 5-e] [1, 4]diazepine-5, 8-dione, 3 and 4, respectively, are reported. Single-crystal X-ray diffraction analysis of the aglycon of 3 aided in confirming the site of methylation in 3, and that of 4 in elucidating the solid state conformation of 4. Solution conformations of 3 and 4, along with their parent nucleoside 1 and the latter's 1-glycosyl regioisomer 2, were investigated by NOE and CD measurements.

Original language	English (US)
Pages (from-to)	819-836
Number of pages	18
Journal	Nucleosides and Nucleotides
Volume	10
Issue number	4
DOIs	https://doi.org/10.1080/07328319108046664
State	Published - Jun 1 1991
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Genetics

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10.1080/07328319108046664

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@article{c4b3f2c826c84981a80f360370a100cb,

title = "Synthetic, structural, and conformational studies of methylated ring-expanded nucleosides containing the imidazo[4,5-e] [1, 4]diazepine ring system",

abstract = "Syntheses of 4- and 7-methyl 4, 5, 7, 8-tetrahydro-6H-3-(β-D-ribofuranosyl)imidazo[4, 5-e] [1, 4]diazepine-5, 8-dione, 3 and 4, respectively, are reported. Single-crystal X-ray diffraction analysis of the aglycon of 3 aided in confirming the site of methylation in 3, and that of 4 in elucidating the solid state conformation of 4. Solution conformations of 3 and 4, along with their parent nucleoside 1 and the latter's 1-glycosyl regioisomer 2, were investigated by NOE and CD measurements.",

author = "Hosmane, {Ramachandra S.} and Anila Bhan and Martin Hulce and Hongming Zhang and Hosmane, {Narayan S.}",

note = "Funding Information: Acknowledgments. This investigation was supported by the National Institutes of Health (R.S.H. # CA 361541, the American Cancer Society Institutional Research Grant (A.B. # IN-l47H), MD Cancer PrograqAJniv. of Maryland, the American Cancer Society-Maryland Div., Inc. (M.H.), and the National Science Foundation (N.S.H. # CHE-88-00328).",

year = "1991",

month = jun,

day = "1",

doi = "10.1080/07328319108046664",

language = "English (US)",

volume = "10",

pages = "819--836",

journal = "Nucleosides, Nucleotides and Nucleic Acids",

issn = "1525-7770",

publisher = "Marcel Dekker Inc.",

number = "4",

}

TY - JOUR

T1 - Synthetic, structural, and conformational studies of methylated ring-expanded nucleosides containing the imidazo[4,5-e] [1, 4]diazepine ring system

AU - Hosmane, Ramachandra S.

AU - Bhan, Anila

AU - Hulce, Martin

AU - Zhang, Hongming

AU - Hosmane, Narayan S.

N1 - Funding Information: Acknowledgments. This investigation was supported by the National Institutes of Health (R.S.H. # CA 361541, the American Cancer Society Institutional Research Grant (A.B. # IN-l47H), MD Cancer PrograqAJniv. of Maryland, the American Cancer Society-Maryland Div., Inc. (M.H.), and the National Science Foundation (N.S.H. # CHE-88-00328).

PY - 1991/6/1

Y1 - 1991/6/1

N2 - Syntheses of 4- and 7-methyl 4, 5, 7, 8-tetrahydro-6H-3-(β-D-ribofuranosyl)imidazo[4, 5-e] [1, 4]diazepine-5, 8-dione, 3 and 4, respectively, are reported. Single-crystal X-ray diffraction analysis of the aglycon of 3 aided in confirming the site of methylation in 3, and that of 4 in elucidating the solid state conformation of 4. Solution conformations of 3 and 4, along with their parent nucleoside 1 and the latter's 1-glycosyl regioisomer 2, were investigated by NOE and CD measurements.

AB - Syntheses of 4- and 7-methyl 4, 5, 7, 8-tetrahydro-6H-3-(β-D-ribofuranosyl)imidazo[4, 5-e] [1, 4]diazepine-5, 8-dione, 3 and 4, respectively, are reported. Single-crystal X-ray diffraction analysis of the aglycon of 3 aided in confirming the site of methylation in 3, and that of 4 in elucidating the solid state conformation of 4. Solution conformations of 3 and 4, along with their parent nucleoside 1 and the latter's 1-glycosyl regioisomer 2, were investigated by NOE and CD measurements.

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Synthetic, structural, and conformational studies of methylated ring-expanded nucleosides containing the imidazo[4,5-e] [1, 4]diazepine ring system

Abstract

All Science Journal Classification (ASJC) codes

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