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Novel synthetic route for (parent) phosphetanes, phospholanes, phosphinanes and phosphepanes.

ABSTRACT: A novel synthetic route for (parent) phosphorus-containing cycloalkanes such as phosphetanes, phospholanes, phosphinanes and phosphepanes is reported. By using [K(dme)₂]₂[Cp*Fe(η⁴-P₅)] (I) in combination with α,ω-dibromoalkanes C _n H_2n Br₂ [n = 3-6], unique phosphetane, phospholane, phosphinane and phosphepane precursor complexes [Cp*Fe{η⁴-P₅(CH₂) _n }] [n = 3-6] (2-5) are synthesised. They act as P-atom carriers and the corresponding phosphetane, phospholane, phosphinane and phosphepanes (6-9) can be released by nucleophiles i.e., potassium benzyl (KBn) or LiAlH₄. The latter enables the selective synthesis of parent cyclic secondary phosphines (10) in an easy and straightforward way, including the first parent phospholane (10b).

SUBMITTER: Reichl S

PROVIDER: S-EPMC10074431 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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Novel synthetic route for (parent) phosphetanes, phospholanes, phosphinanes and phosphepanes.

Reichl Stephan S Balázs Gábor G Scheer Manfred M

Chemical science 20230313 14

A novel synthetic route for (parent) phosphorus-containing cycloalkanes such as phosphetanes, phospholanes, phosphinanes and phosphepanes is reported. By using [K(dme)2]2[Cp*Fe(η4-P5)] (I) in combination with α,ω-dibromoalkanes C n H2n Br2 [n = 3-6], unique phosphetane, phospholane, phosphinane and phosphepane precursor complexes [Cp*Fe{η4-P5(CH2) n ...[more]

PMID: 37035692

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Project description:IntroductionCancer is a big challenge of the 21 century, whose defeat requires efficient antitumor drugs.ObjectivesThe paper aims to investigate the synergistic effect of two structural building blocks, phenothiazine and poly(ethylene glycol), towards efficient antitumor drugs.MethodsTwo PEGylated phenothiazine derivatives were synthetized by attaching poly(ethylene glycol) of 550 Da to the nitrogen atom of phenothiazine by ether or ester linkage. Their antitumor activity has been investigated on five human tumour lines and a mouse tumor line as well, by determination of IC50. The in vivo toxicity was determined by measuring the LD50 in BALB/c mice by the sequential method and the in vivo antitumor potential was measured by the tumours growth test. The antitumor mechanism was investigated by complexation studies of zinc and magnesium ions characteristic to the farnesyltransferase enzyme, by studies of self-aggregation in the cells proximity and by investigation of the antitumor properties of the acid species resulted by enzymatic cleavage of the PEGylated derivatives.ResultsThe two compounds showed antitumor activity, with IC50 against mouse colon carcinoma cell line comparable with that of the traditional antitumor drugs 5-Fluorouracil and doxorubicin. The phenothiazine PEGylation resulted in a significant toxicity diminishing, the LD50 in BALB/c mice increasing from 952.38 up to 1450 mg/kg, in phenothiazine equivalents. Both compounds inflicted a 92% inhibition of the tumour growth for doses much smaller than LD50. The investigation of the possible tumour inhibition mechanism suggested the nanoaggregate formation and the cleavage of ester bonds as key factors for the inhibition of cancer cell proliferation and biocompatibility improvement.ConclusionPhenothiazine and PEG building blocks have a synergetic effect working for both tumour growth inhibition and biocompatibility improvement. All these findings recommend the PEGylated phenothiazine derivatives as a valuable workbench for a next generation of antitumor drugs.

Dataset Information

Novel synthetic route for (parent) phosphetanes, phospholanes, phosphinanes and phosphepanes.

Publications

Novel synthetic route for (parent) phosphetanes, phospholanes, phosphinanes and phosphepanes.

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