New possibilities of 1,2,4-triazines functionalization: first examples of synthesis and structure of boron-containing 1,2,4-triazines

Azev, Yuri A.; Lork, Enno; Duelcks, Thomas; Gabel, Detlef

doi:10.1016/j.tetlet.2004.02.121

Cited by 11 publications

(4 citation statements)

References 4 publications

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“…From X-ray crystal analysis (see, e.g., (37)), the van der Waals radius of the dodecaborate cluster can be determined to be approximately 4 Å, giving an unsolvated cross section area of the head group of about 0.5 nm 2 . This is close to the 0.6 nm 2 area occupied by lipids with saturated fatty acid chains in the gel phase (34).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, Liposomal Preparation, andin VitroToxicity of Two Novel Dodecaborate Cluster Lipids for Boron Neutron Capture Therapy

et al. 2007

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A new class of lipids, containing the closo-dodecaborate cluster, has been synthesized. Two lipids, S-(N, N-(2-dimyristoyloxyethyl)acetamido)thioundecahydro-closo-dodecaborate (2-) (B-6-14) and S-(N, N-(2-dipalmitoyloxyethyl)acetamido)thioundecahydro-closo-dodecaborate (2-) (B-6-16) are described. Both of them have a double-tailed lipophilic part and a headgroup carrying two negative charges. Differential scanning calorimetry shows that B-6-14 and B-6-16 bilayers have main phase transition temperatures of 18.8 and 37.9 degrees C, respectively. Above the transition temperature of 18.8 degrees C, B-6-14 can form liposomal vesicles, representing the first boron-containing lipid with this capability. Upon cooling below the transition temperature, stiff bilayers are formed. When incorporated into liposomal formulations with equimolar amounts of distearoyl phosphatidylcholine (DSPC) and cholesterol, stable liposomes are obtained. The zeta-potential measurements indicate that both B-6-14- and B-6-16-containing vesicles are negatively charged, with the most negative potential described of any liposome so far. The liposomes are of high potential value as transporters of boron to tumor cells in treatments based on boron neutron capture therapy (BNCT). Liposomes prepared from B-6-14 were slightly less toxic in V79 Chinese hamster cells (IC50 5.6 mM) than unformulated Na2B12H11SH (IC50 3.9 mM), while liposomes prepared from B-6-16 were not toxic even at 30 mM.

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Section: Chemistrymentioning

confidence: 99%

Synthesis, Liposomal Preparation, andin VitroToxicity of Two Novel Dodecaborate Cluster Lipids for Boron Neutron Capture Therapy

et al. 2007

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“…Alkylation with epichlorohydrin undergo epoxide ring opening to give compound 18. Interestingly, the end of these alkylation reactions could be observed visually by turn yellow starting thioxo derivative 10 into white precipitate of reaction products [15][16][17][18][19].…”

Section: Resultsmentioning

confidence: 99%

“…They exhibit various types of pharmacological properties, such as antibacterial, antiviral, and anticancer activities , they are referred as hypoglycemic agents or small molecule chaperone amplifiers . Pyrimidotriazine is the core structure of natural antibiotics as fervenuline, 2‐methylfervenuline, xantotricine, and reumicine, and this gives more attractivity to the said heterocyclic system .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Functionalization of 8‐Methyl‐2h‐pyrimido [2,1‐c][1,2,4]triazine‐3,6(1h,4h)‐dione

Jakubkienė

Cepla

Burbuliene

et al. 2012

Journal of Heterocyclic Chem

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6‐Methyl‐2‐methylthio‐4‐oxopyrimidin‐3(4H)‐yl)acetohydrazide on heating in benzylamine undergo cyclization to 8‐methyl‐2H‐pyrimido[2,1‐c][1,2,4]triazine‐3,6(1H, 4H)‐dione, which under treatment with bromine in glacial acetic acid was converted to 7‐bromo substituted derivative and at reflux with Lawesson's reagent yielded 3‐thioxo compound. The latter reacted with primary and secondary amines to give 3‐amino substituted pyrimidotriazines and on alkylation—the corresponding S‐alkyl derivatives.

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“…BSH is a water-soluble divalent anion cluster with significantly lowered toxicity and thus has been utilized for clinical treatment of BNCT. However, few synthetic examples of BSH derivatives as boron carriers have been reported so far due to the difficulty of their functionalizations. , Gabel and co-workers reported a novel “BSH activation” method, which enabled us to conduct S-alkylation of BSH under mild conditions . In this paper, we report synthesis of closo- dodecaborate containing boron lipids 4a − c and 5a − c and their liposomal property (Scheme 1).…”

mentioning

confidence: 95%

Synthesis of Boron Cluster Lipids: closo-Dodecaborate as an Alternative Hydrophilic Function of Boronated Liposomes for Neutron Capture Therapy

et al. 2006

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We succeeded in the synthesis of the double-tailed boron cluster lipids 4a-c and 5a-c, which have a B12H11S moiety as a hydrophilic function, by S-alkylation of B12H11SH (BSH) with bromoacetyl and chloroacetocarbamate derivatives of diacylglycerols for a liposomal boron delivery system on neutron capture therapy. Calcein encapsulation experiments revealed that the liposomes, prepared from the boron cluster lipid 4b, DMPC, PEG-DSPE, and cholesterol, are stable at 37 degrees C in FBS solution for 24 h. [reaction: see text].

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New possibilities of 1,2,4-triazines functionalization: first examples of synthesis and structure of boron-containing 1,2,4-triazines

Cited by 11 publications

References 4 publications

Synthesis, Liposomal Preparation, andin VitroToxicity of Two Novel Dodecaborate Cluster Lipids for Boron Neutron Capture Therapy

Synthesis, Liposomal Preparation, andin VitroToxicity of Two Novel Dodecaborate Cluster Lipids for Boron Neutron Capture Therapy

Synthesis and Functionalization of 8‐Methyl‐2h‐pyrimido [2,1‐c][1,2,4]triazine‐3,6(1h,4h)‐dione

Synthesis of Boron Cluster Lipids: closo-Dodecaborate as an Alternative Hydrophilic Function of Boronated Liposomes for Neutron Capture Therapy

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