Synthesis and characterization of the novel l‐(substituted phenoxy/phenyl)‐2‐phospholene and phospholane 1‐oxide derivatives

Reddy, Valluru Krishna; Onogawa, Jun-Ichi; Rao, Lakonda Nagaprasada; Oshikawa, Tatsuo; Takahashi, Masaki; Yamashita, Mitsuji

doi:10.1002/jhet.5570390109

Cited by 14 publications

(2 citation statements)

References 19 publications

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“…The cis dibromide must be formed by the isomerization of the c/s-fused dibromide via a stable tertially carbonium intermediate by S N 1 mechanism, which was observed for 3-methylphospholane 1-oxides. 10 Table 2. Diastereomers la to Id of 2.3-dibromo-3-methyl-l-phenylphospholane 1-oxide (1).…”

Section: Leukemia Cell Lines Of Ks62 and U937 From The Results Of Thmentioning

confidence: 98%

A Novel Phospha Sugar Analogue: Synthesis And Evaluation Of 2,3-Dibromo-3-Methyl-1-Phenylphospholane 1-Oxide As A New Class Of Potential Anti-Proliferative Materials For Leukemia Cells

Fujie¹,

Nakamura²,

Asai³

et al. 2009

Heterocyclic Communications

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A novel dideoxydibromophospha sugar analogue, 2,3-dibromo-3-methyl-l-phenylphospholane 1-oxide (1), was prepared from l-phenyl-3-methyl-2-phospholene 1-oxide (2) and evaluated by MTT in vitro methods for leukemia cells. The evaluation of dibromide 1 (mixture of diastereomers) as well as the separated diastereomer of dibromides la to Id from the diastereomer mixtures revealed clearly that the synthesized phospha sugar analogues have competent potentials and excellent anti-tumor activities for the human leukemia cells of K562 and U937 in selective and specific manner. The cell cycle analyses by flow cytometry for K562 and U937 cells clearly demonstrated that the mechanism of the anti-proliferative effect on the human tumor cells is apoptosis induced by the phospha sugar. Introduction Well known typical pseudo sugars are carba-, aza-, and /Aia-sugars, 1 " 3 with a carbon, nitrogen, and sulphur atom, respectively, instead of the oxygen atom in the hemiacetal ring of the normal sugars. These pseudo sugars are known to exist in nature and are also prepared by synthetic sugar chemistry. Pseudo sugars exert important biological activities, therefore, many studies on the isolation, synthesis, characterization, etc., are actively performed. On the other hand, phospha sugars, one new category of the pseudo sugars which have a phosphorus atom in the hemiacetal ring of sugars, are not yet found in nature and the synthesis of them are rather difficult compared with the typical pseudo sugars. 4 " 7 We have been searching biologically active phospha sugars and/or phosphorus heterocycles, and we have first found new anti-tumor phospha sugar derivatives by using 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl-2//-tetrazolium bromide (MTT) in vitro evaluation methods for some of these phospha sugars or phosphorus heterocycles against leukemia cells. 8 In this paper we will deal with the research on the synthesis, separation, and in vitro evaluation for 2,3-dibromo-3-methyl-l-phenylphospholane 1-oxide (1), one of dibromodideoxyphospha sugars, against human 273 Brought to you by | Purdue University Libraries Authenticated Download Date | 6/7/15 3:12 PM

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Section: Leukemia Cell Lines Of Ks62 and U937 From The Results Of Thmentioning

confidence: 98%

A Novel Phospha Sugar Analogue: Synthesis And Evaluation Of 2,3-Dibromo-3-Methyl-1-Phenylphospholane 1-Oxide As A New Class Of Potential Anti-Proliferative Materials For Leukemia Cells

Fujie¹,

Nakamura²,

Asai³

et al. 2009

Heterocyclic Communications

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“…The methyl group on the third position [C(3)CH 3 ] was also shifted by the anisotropy effect to the higher or lower magnetic field depending on the same or opposite side of the phenyl group, respectively. 13 The largest retention time for 2d may be supported by the large dipole moment (7.05 D) calculated by MOPAC. Evaluations of 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide (2; mixture of diastereomers) and the separated four diastereomers 2a to 2d as inhibitors on proliferation of leukemia cells were carried out by the in vitro MTT assay method.…”

Section: Resultsmentioning

confidence: 99%

Preparation and Characterization of Phospha Sugar Analogues, 2,3-Dibromo-3-methyl-1- phenylphospholane 1-Oxide Derivatives, as Novel Anticancer Agents

Yamada

Asai

Yamashita

et al. 2010

Phosphorus, Sulfur, and Silicon and the Related Elements

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The synthesis of new phospha sugar analogues or phosphorus heterocycles and their biological activities as novel anticancer agents are reported in this article. A 1,2-dibromo-1,2-dideoxy phospha sugar derivative, 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide (2), was prepared from 1-phenyl-3-methyl-2-phospholene 1-oxide (1), and the yield and ratio of diastereomers 2a to 2d were changed by a catalyst such as manganese(IV) oxide and manganese(II) bromide. The antitumor activities of the mixture of dibromides 2 and the separated diastereomeric components 2a to 2d of the dibromides were evaluated by MTT in vitro method against the human leukemia cell lines of K562 and U937. The results showed that all of the diastereomers 2a to 2d as well as the diastereomer mixture exert excellent anticancer activity, and moreover, among them, diastereomer 2d showed the highest antitumor activity.

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ChemInform Abstract: Synthesis and Characterization of the Novel 1‐(Substituted phenoxy/phenyl)‐2‐phospholene and Phospholane 1‐Oxide Derivatives.

et al. 2002

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Synthesis and characterization of the novel l‐(substituted phenoxy/phenyl)‐2‐phospholene and phospholane 1‐oxide derivatives

Cited by 14 publications

References 19 publications

A Novel Phospha Sugar Analogue: Synthesis And Evaluation Of 2,3-Dibromo-3-Methyl-1-Phenylphospholane 1-Oxide As A New Class Of Potential Anti-Proliferative Materials For Leukemia Cells

A Novel Phospha Sugar Analogue: Synthesis And Evaluation Of 2,3-Dibromo-3-Methyl-1-Phenylphospholane 1-Oxide As A New Class Of Potential Anti-Proliferative Materials For Leukemia Cells

Preparation and Characterization of Phospha Sugar Analogues, 2,3-Dibromo-3-methyl-1- phenylphospholane 1-Oxide Derivatives, as Novel Anticancer Agents

ChemInform Abstract: Synthesis and Characterization of the Novel 1‐(Substituted phenoxy/phenyl)‐2‐phospholene and Phospholane 1‐Oxide Derivatives.

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