Carboranes. II. An Analog of 1,4-(Dimethanesulfonoxy)butane<sup>1,2</sup>

Haslinger, F.; Ah, Soloway

doi:10.1021/jm00323a046

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Dna Binders1

Synthesis Of Ab 2 -Type 135-s-triazines1

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2011

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Cited by 9 publications

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“…a. Alkylating Agents. Since nitrogen mustards and other cancer chemotherapeutic alkylating agents are electrophiles that are covalently incorporated into tumor DNA and, as a result, interfere with tumor replication, the basis for the synthesis of such boron-containing analogues is understandable. , The following early structures were synthesized (Figure ). Preliminary biological studies at that time were not very promising, and in retrospect, those results may be explainable.…”

Section: Dna Bindersmentioning

confidence: 99%

The Chemistry of Neutron Capture Therapy

et al. 1998

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Section: Dna Bindersmentioning

confidence: 99%

The Chemistry of Neutron Capture Therapy

et al. 1998

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“…22 While nitrogen mustards have chloroalkyl units directly linked to the amine backbone, we were also interested in attaching the triazine units via an additional ethylene spacer. 23,24 The synthesis of the homologous 2-(o-carboranyl)-4,6-bis(chloroethyl)amino-1,3,5-s-triazine (7) started with N,N -bis(2-chloroethyl)amine, as shown in Scheme 4. Thus, compound 4 was aminated with chloroethylamine in the presence of potassium carbonate in THF to provide the desired AB 2 -type molecule in 44-45% yield.…”

Section: Synthesis Of Ab 2 -Type 135-s-triazinesmentioning

confidence: 99%

o‐Carboranyl derivatives of 1,3,5‐s‐triazines: structures, properties and in vitro activities

Lee

Lim

Lee

et al. 2003

Applied Organom Chemis

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Our objective was to design and synthesize substituted o-carboranes carrying the 1,3,5-s-triazine units as potential boron neutron capture therapy agents. The preliminary results indicated that selective substitution was successful, and the structural AB 2 (mono-o-carboranyl-1,3,5-s-triazine) or A 2 B (biso-carboranyl-1,3,5-s-triazine) type was used as the starting point for the generation of biologically active species. In the first series, the influence of the structural changes in the central core unit was investigated. Thus, a procedure for the sequential, selective derivatization of cyanuric chloride that allows for the incorporation of o-carborane was elucidated. As a result, a variety of mono-, di-, and tri-substituted triazines were produced in good yield. In the second series, the effect of additional amine substituents on the 1,3,5-s-triazine was studied.

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