연구된 수용성 작용기 bis(2-methoxyethyl)amino-, bis(2-hydoxyethyl)amino-, 그리고 bis(carboxymethyl)amino기를 가지는 carboranyl-s-triazine과 phenol유도체는 처음 시도된 안정한 수용성 carborane 유도체의 독특한 구조로서, 현재 임상에 사용되는 BPA 및 BSH에 비하여 암세포에 대한 세포독성과 boron-uptake의 성질도 매우 우수하여 BNCT 시약의 선도물질로서 기대할 수 있음. Cyanuric chloride와 하나 또는 두 개
연구된 수용성 작용기 bis(2-methoxyethyl)amino-, bis(2-hydoxyethyl)amino-, 그리고 bis(carboxymethyl)amino기를 가지는 carboranyl-s-triazine과 phenol유도체는 처음 시도된 안정한 수용성 carborane 유도체의 독특한 구조로서, 현재 임상에 사용되는 BPA 및 BSH에 비하여 암세포에 대한 세포독성과 boron-uptake의 성질도 매우 우수하여 BNCT 시약의 선도물질로서 기대할 수 있음. Cyanuric chloride와 하나 또는 두 개의 bis(2-methoxyethyl)amino-기를 도입하고 이어서 butyllithium으로 처리된 carborane을 반응시키는 방법과 4-carboranylphenol과 bis- (2-methoxyethyl)amine과 fomaldehyde의 Mannich 반응으로 목표의 화합물을 합성하였음. BNCT 시약의 개발로 원자력의 평화적 이용의 이해증진, 유기붕소 화합물을 이용한 방사선 진단의 조영제(contrast agent)의 발전, 그리고 핵화학과 영상진단 의학에 필요한 붕소원자를 함유하는 진단시약 제조의 정밀화학 전문 인력의 양성을 기대할 수 있음.
Abstract▼
A method for preparing triazinyl-substituted carboranyl systems using 1,2-, 1,7-, and 1,12-$\C_2B_10H_12$ as cores and [di(alkyl)amino]triazine as substituents is described. Reaction of 6-chloro- 2,4-bis[di(methoxyethyl)amino]-1,3,5-triazine with mono-anionic forms of three isomeric carbo
A method for preparing triazinyl-substituted carboranyl systems using 1,2-, 1,7-, and 1,12-$\C_2B_10H_12$ as cores and [di(alkyl)amino]triazine as substituents is described. Reaction of 6-chloro- 2,4-bis[di(methoxyethyl)amino]-1,3,5-triazine with mono-anionic forms of three isomeric carboranes produced the corresponding mono-substituted (triazinyl)carboranes. Subsequent de-methylation of the corresponding mono-substituted (triazinyl)carboranes produced the desired mono {bis[di- (hydroxyethyl)amino]triazinyl}carboranes. Methoxyethyl and hydroxy- ethyl functional groups on the amine units of triazine were identified by $^1H- and $^13C {$^1H}-NMR spectroscopy. Furthermore, an X-ray structural study of bis{di(methoxyethyl)amino}-s-triazinyl}-m-carborane, a typical example of a (triazinyl)carborane, confirmed the selective mono-substitution on the carboranyl carbon atoms. A sulfur-containing o-carboranyl cage compound was also incorporated into the 1,3,5-triazine network to generate new types of hybrid compounds having a thio-etherlinkage. Thus, the reaction of 1-chloro-bis{bis(2-methoxyethyl))amino-s-triazine with anionic o-carboranylthiolate produced mono-substituted (triazinyl)-o-carboranylthiolate. Two triazine units with bis[di(methoxyethyl)amino] functionalities were successfully introduced into the carboranyl scaffolds to generate a series of bis(triazinyl)carboranes by reacting 1-chloro-bis{bis(2-methoxyethyl))- amino-s-triazine with the dianionic forms of the o-, m- ,and p-carboranes. An X-ray structural study of 1,12-Bis[2,6-bis{bis(2-methoxyethyl)amino}-1,3,5-triazin-4-yl]-p-caborane (25) authenticated the bis- (triazinyl) substitution on the p-carboranyl scaffold. Within the series of synthesized compounds, 25 showed increased water-solubility arising from the effective camouflaging of the central p-carboranyl unit by the polar functional groups at the periphery. Furthermore, 25 exhibited high boron uptake in B-16 melanoma cells with low toxicity, showing promise as a BNCT agent.
※ AI-Helper는 부적절한 답변을 할 수 있습니다.