Enantiomerically pure synthesis and antiviral evaluation of [(2′S, 3′S)-bis(hydroxymethyl)azetidin-1-yl] purine nucleosides: Analogs of oxetanocin-A

Nishiyama, Shigeru; Kikuchi, Yo; Kurata, H.; Yamamura, Shosuke; Izawa, Takeshi; Nagahata, Takemitsu; Ikeda, Ryuji; Kato, Kuniki

doi:10.1016/0960-894x(95)00395-a

Cited by 18 publications

(7 citation statements)

References 10 publications

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“…The formation of 3 in an ionic liquid proceeded in a shorter reaction time, but it has been suggested to occur in a manner similar to that previously proposed for typical Lewis acids (BF 3 .OEt 2 ) in molecular solvent such as hexane in 15h at 25 o C [10]. more, some of other compounds incorporating azetidine structure have been reported to exhibit remarkable biological activity against influenza virus [12], and possesses anti-HIV-1, anti-HSV-2 potential [13]. Whereas the strain associated with the azetidine ring system leads to difficulties in its synthesis, functionalizations, and modifications.…”

Section: Aziridinesmentioning

confidence: 89%

Ionic Liquids: A Class of Versatile Green Reaction Media for the Syntheses of Nitrogen Heterocycles

Chaturvedi

2011

COS

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Ionic liquids have been emerging as a versatile class of green solvents with many projected advantages compared with conventional media. They have been described as "designer solvents" whose properties such as solubility, density, refractive index, and viscosity can be adjusted to suit requirements simply by making changes to the structure of either anion or cation or both. In organic synthesis, ionic liquids have been extensively used for the variety of synthetic transformations. Recently, plethoras of nitrogen heterocycles have been synthesized using variety of structurally diverse ionic liquids. In the present review, I would account the synthesis of various kinds of nitrogen heterocycles using variety of ionic liquids from the beginning to the recent reports.

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Section: Aziridinesmentioning

confidence: 89%

Ionic Liquids: A Class of Versatile Green Reaction Media for the Syntheses of Nitrogen Heterocycles

Chaturvedi

2011

COS

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“…The azetidine ring‐containing molecules are noticeably active against influenza A H2N2 virus and have the potential to act as anti‐HIV‐1, anti‐HSV‐1, and HSV‐2 agents. [ 12 ]…”

Section: Introductionmentioning

confidence: 99%

Azetidines of pharmacological interest

Parmar

Soni²,

Guduru

et al. 2021

Archiv der Pharmazie

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Azetidines are almost unexplored among nitrogen‐containing saturated heterocycles due to difficulties associated with their synthesis. However, over the past few years, attempts have been made by scientists to advance their synthetic feasibility. Compounds with the azetidine moiety display an important and diverse range of pharmacological activities, such as anticancer, antibacterial, antimicrobial, antischizophrenic, antimalarial, antiobesity, anti‐inflammatory, antidiabetic, antiviral, antioxidant, analgesic, and dopamine antagonist activities, and are also useful for the treatment of central nervous system disorders and so forth. Owing to its satisfactory stability, molecular rigidity, and chemical and biological properties, azetidine has emerged as a valuable scaffold and it has drawn the attention of medicinal researchers. The present review sheds light on the traditional method of synthesis of azetidine and advancements in synthetic methodology over the past few years, along with its application with various examples, and its biological significance.

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“…Azetidines are fascinating synthetic targets because of their remarkable chemical and biological properties [2][3][4][5][6][7][8][9][10][11] . The azetidine ring system prominently features in many medicinally important molecules some of which are markedly active against influenza A H2N2 virus 12 and have anti-HIV-1, anti-HSV-1 and HSV-2 potential 13 . Although the inherent strain associated with the azetidine ring leads to difficulties in its construction, functionalization and modifications, it is advantageous for its synthetic applications involving ring-opening reactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Substituted Phenyl Azetidines as Potential Antimicrobial Agents

Doraswamy¹,

Ramana²

2013

Chem Sci Trans

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The reaction of 2-(4-bromo phenyl) methyl cyanide (1a) with ethylchloroformate in the presence of n-butyl lithium gave ethyl-2-(4-bromo phenyl)-2-cyano acetate (2a). 2a on reduction with sodium borohydride yields 3-amino-2-(4-bromo phenyl) propan-1-ol (3a). Compound 3a on further reaction with tert butyloxy anhydride in presence of triethylamine afford tert-butyl-2-(4-bromo phenyl)-3hydroxy propyl carbamate (4a). 4a on treatment with tosyl chloride gave 2-(4-bromo phenyl)-3-(tertiarybutyloxy carbonyl amino)-propan-1-ol-(4-toluene sulphonate) (5a). Compound 5a on cyclization followed by hydrolysis gave 3-(4-bromo phenyl) azetidine (7a). Compounds 2b-2e, 3b-3e, 4b-4e, 5b-5e, 6b-6e and 7b-e were synthesized by a similar method. The compounds are characterized by elemental analysis, IR, 1 H NMR and Mass spectral analysis and screened for antimicrobial activity.

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Enantiomerically pure synthesis and antiviral evaluation of [(2′S, 3′S)-bis(hydroxymethyl)azetidin-1-yl] purine nucleosides: Analogs of oxetanocin-A

Cited by 18 publications

References 10 publications

Ionic Liquids: A Class of Versatile Green Reaction Media for the Syntheses of Nitrogen Heterocycles

Ionic Liquids: A Class of Versatile Green Reaction Media for the Syntheses of Nitrogen Heterocycles

Azetidines of pharmacological interest

Synthesis and Characterization of Substituted Phenyl Azetidines as Potential Antimicrobial Agents

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