An efficient synthesis of novel deoxy phospha sugar pyrimidine nucleosides

Yamashita, Mitsuji; Reddy, Valluru Krishna; Reddy, P. Jayarama; Kato, Y.; Haritha, Buchammagari; Suzuki, Keijiro; Takahashi, Masaki; Oshikawa, Tatsuo

doi:10.1016/s0040-4039(03)00678-6

Cited by 13 publications

(7 citation statements)

References 19 publications

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“…The bis(2,5-dihydro-1H-phosphol-1-yl)amine P,P′-dioxides 6a-g and 7a,e were obtained in 72-95% yields after purification by chromatography. The structures of the products were supported by 31 P, 13 C, and 1 H NMR, as well as mass spectral parameters.…”

Section: Methodsmentioning

confidence: 99%

“…[5][6][7][8][9] Yamashita synthesized 'phospha-sugars' on the basis of 2,3-and 3,4dihydrophosphole oxides. [10][11][12][13] Keglevich et al developed the ring opening of 2,5-dihydro-1H-phosphole oxides. Dichlorocarbene addition to the double bond of 2,5-dihydro-1H-phosphole oxides afforded 6,6-dichloro-3-phosphabicyclo[3.1.0]hexane 3-oxides that were converted into 1,2dihydrophosphinine oxides by thermolysis.…”

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confidence: 99%

“…This method was then applied to the synthesis of other amino-dihydrophosphole oxides 5a and 5b by the reaction of chloro-dihydrophosphole oxide 3 with butylamine and isobutylamine (Scheme 1). The 1-amino-2,5-dihydro-1H-phosphole 1-oxides 5a-e were obtained in 76-88% yields after purification by column chromatography and were characterized by 31 P, 13 C, and 1 H NMR, as well as mass spectral data.…”

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confidence: 99%

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Synthesis of 1-Amino-2,5-dihydro-1H-phosphole 1-Oxides and Their N-Phosphinoyl Derivatives, Bis(2,5-dihydro-1H-phosphol-1-yl)amine P,P′-Dioxides

et al. 2012

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Depending on the molar ratio of the reactants and on the order of mixing, the reactions of a series of primary amines with 1-chloro-2,5-dihydro-1H-phosphole 1-oxides prepared in situ from the corresponding hydroxy-dihydrophosphole oxides afforded 1-amino-2,5-dihydro-1H-phosphole 1-oxides, or their N-phosphinoyl derivatives, bis(2,5-dihydro-1H-phosphol-1-yl)amine P,P′-dioxides. The latter family of P-heterocycles could also be synthesized by the reaction of 1-amino-2,5-dihydro-1H-phosphole oxides with chloro-dihydrophosphole oxides.

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Section: Methodsmentioning

confidence: 99%

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Synthesis of 1-Amino-2,5-dihydro-1H-phosphole 1-Oxides and Their N-Phosphinoyl Derivatives, Bis(2,5-dihydro-1H-phosphol-1-yl)amine P,P′-Dioxides

et al. 2012

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“…Uracil derivatives can be prepared by addition of primary amines to 3-ethoxyacryloylisocyanate [114], methoxyacryloylisothiocyanate [115], or acryloylcarbamates [116] by addition and intramolecular displacement of the vinylic alkoxy group (Schemes 19. 81 and 19.82).…”

Section: From Hetero-12-diazepinesmentioning

confidence: 99%

Six‐Membered Heterocycles: 1,2‐, 1,3‐, and 1,4‐Diazines and Related Systems

Cabal

2011

Modern Heterocyclic Chemistry

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“…Further, nucleic acid bases such as uracil were formed by the cyclization reaction of acrylamide intermediates to prepare phospha sugar nucleosides (6). We are continuously searching biologically active phosphorus heterocycles, phospha sugars and phospholanes, for a couple often years.…”

Section: Introductionmentioning

confidence: 99%

Preparation And Characterization Of Phospholanes And Phospha Sugars As Novel Anti-Cancer Agents

Ito¹,

Yamashita²,

Niimi³

et al. 2009

Heterocyclic Communications

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Diastereo isomericerythro and threo forms of 2,3-epoxy-l-phenylphospholane 1-oxides were synthesized from threo and erythro forms of 2-bromo-3-hydroxy-l-phenylphospholane 1-oxides being prepared from l-phenyl-2-phospholene 1-oxide. Alternatively, the epoxides were also prepared by the epoxidation of the 2-phospholene with peroxides such as sodium peroxide and hydrogen peroxide. The reactivity and regioselectivity for the reaction of erythro and threo forms of the 2,3-epoxides with nucleophiles were investigated by using amines, and the reaction afforded 2-amino-3-hydroxy-l-phenylphospholane 1-oxides, which correspond to phospha sugar N-glycosides.2,3-Dibromo-3-methyl-l-phenylphospholane 1-oxides were first prepared from 3-methyl-l-phenyl-2-phospholene 1-oxide. The prepared phospholanes or phospha sugars were biologically qualified by ΜΤΓ(3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium bromide) in vitro method to find that some of these phosphorus heterocycles or phospha sugars have quite efficient anti-cancer activity for leukemia cells in manners of (i) wide spectra, (ii) high activities, and (iii) high specificities.

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An efficient synthesis of novel deoxy phospha sugar pyrimidine nucleosides

Cited by 13 publications

References 19 publications

Synthesis of 1-Amino-2,5-dihydro-1H-phosphole 1-Oxides and Their N-Phosphinoyl Derivatives, Bis(2,5-dihydro-1H-phosphol-1-yl)amine P,P′-Dioxides

Synthesis of 1-Amino-2,5-dihydro-1H-phosphole 1-Oxides and Their N-Phosphinoyl Derivatives, Bis(2,5-dihydro-1H-phosphol-1-yl)amine P,P′-Dioxides

Six‐Membered Heterocycles: 1,2‐, 1,3‐, and 1,4‐Diazines and Related Systems

Preparation And Characterization Of Phospholanes And Phospha Sugars As Novel Anti-Cancer Agents

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