Synthesis and biological properties of carboranylaziridines bearing cascade polyols

Yamamoto, Yoshinori; Sadayori, Naoki

doi:10.1016/0960-894x(95)00545-5

Cited by 14 publications

(14 citation statements)

References 8 publications

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“…Soloway and Butler prepared and evaluated the biological activity of the 1,2- carborane-containing nitrogen mustard 8 for the delivery of boron to chromosomal DNA, the first example of a DNAbinding agent containing boron which was developed 40 years ago. The addition of the water-solubilising element decreased the cytotoxicity of the aziridine derivatives towards B16 cells, however, the cellular uptake was higher for the cascade-polyol modified aziridines [38]. Although the levels of boron in the mice 48 hr after administration showed that the compound was retained in the body, the compound did not show any significant tumour selectivity [35].…”

Section: Alkylating Agentsmentioning

confidence: 99%

Boronated DNA-Binding Compounds as Potential Agents for Boron Neutron Capture Therapy

Crossley¹,

Ziolkowski²,

Coderre³

et al. 2007

MRMC

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Boron Neutron Capture Therapy (BNCT) is a binary cancer treatment that exploits the short range particles released from a nuclear fission reaction involving the non-radioactive 10B nucleus and low-energy (thermal) neutrons for the destruction of tumour cells. If boronated agents are targeted towards chromosomal DNA, the efficiency of BNCT is greatly enhanced. This article presents a concise review of DNA-binding compounds that have been functionalised with boron.

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Section: Alkylating Agentsmentioning

confidence: 99%

Boronated DNA-Binding Compounds as Potential Agents for Boron Neutron Capture Therapy

Crossley¹,

Ziolkowski²,

Coderre³

et al. 2007

MRMC

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“…Moving to this path boron-containing analogues of various cellular building blocks have been synthesized [34][35][36][37]. Variety of heterocyclic compounds has been used as transporters for anticancer agents to target cancer cells.…”

Section: Quinazolinones: New Horizons In Cancer Therapymentioning

confidence: 99%

Quinazolinone Analogs as Potential Therapeutic Agents

Sharma¹,

Kaur²,

Pahwa

et al. 2011

CMC

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Quinazolinone scaffold has been considered as a magic moiety possessing myriad spectrum of medicinal activities. Diversity of biological response profile has attracted considerable interest of several researchers across the globe to explore this skeleton for its assorted therapeutic significance. Various novel classes of structurally different quinazolinones have been designed and synthesized depicting potential interventions such as antibacterial, antifungal, antiviral, anticonvulsant, CNS depressant, antiinflammatory, antihistaminic, anticancer and so on. Moreover, the nucleus constitutes an integral structural component in a number of drugs currently employed in several clinical therapies. The present paper is an earnest attempt to provide an insight view on the current medicinal aspects of quinazolinone heterocycles alongwith brief discussion of their chemistry.

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“…The conversion of 4-o-carboranylanisole to 4-o-carboranylphenol 1 (91%) was achieved by BBr 3 in CH 2 Cl 2 . 9 The general synthetic strategy for the preparation of 4-o-carboranyl-2-[bis(methyl propionato)aminomethyl]phenol (2), 10 4-ocarboranyl-2-[bis(ethyl propionato)aminomethyl]phenol (3), 11 N-[(5-o-carboranyl-2-hydroxyphenyl)methyl]iminodiacetic acid (4), 12 4-o-carboranyl-2-[bis(methoxyethyl)aminomethyl]phenol (5), 13 N-[(5-o-carboranyl-2-hydroxyphenyl)methyl]amino diethanol (6), 14 4-o-carboranyl-2,6-bis{2-[bis(methoxyethyl)aminomethyl]} phenol (7), 15 and 7,16-bis[(5-o-carboranyl-2-hydroxyphenyl)aminomethyl]-1,4,10,13-tetraoxadiazacyclooctadecane (8) 16 was developed using the Mannich reaction 17 (see Supplementary data for details). The hydroxyl proton in the -OH unit of 2-8 was removed via an intramolecular NÁÁÁH-O hydrogen bonding interaction.…”

Section: Introductionmentioning

confidence: 99%

“…Yamamoto et al demonstrated that cascade polyol 4 units resulted in good water solubility, low cytotoxicity, and high cellular uptake of MACB(OH) 2 and MACB(OH) 4 . 5 In this study, the bis(hydroxyethyl)aminomethylphenol unit was introduced into o-carborane as a multi-functional group to improve the biological properties. The amine nitrogen of the o-bis(hydroxyethyl)amine unit coordinated to the phenolic hydrogen through an intra-molecular hydrogen bond.…”

mentioning

confidence: 99%