Synthesis of novel phytosphingosine derivatives and their preliminary biological evaluation for enhancing radiation therapy

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 23, 2007, Pages 6643-6646

  Moon, Byung Seok ^a,c   Park, Moon Taek ^a   Park, Jeong Hoon ^b   Kim, Sang Wook ^b   Lee, Kyo Chul ^a   An, Gwang Il ^a   Yang, Seung Dae ^b   Chi, Dae Yoon ^c   Cheon, Gi Jeong ^a   Lee, Su Jae ^a,d  

^a Korea Institute of Radiation and Medical Science   (South Korea)

^b Korea Atomic Energy Research Institute   (South Korea)

^c Inha University   (South Korea)

^d Hanyang University   (South Korea)

Author keywords

Phytoceramide; Phytosphingosine; Radiosensitizer; Sphingolipids

Indexed keywords

PHYTOSPHINGOSINE; TETRAHYDROFURAN;

ARTICLE; CANCER CELL; CELL DEATH; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INFRARED RADIATION; RADIOSENSITIZATION; ROOM TEMPERATURE;

APOPTOSIS; COMBINED MODALITY THERAPY; DRUG EVALUATION, PRECLINICAL; HUMANS; JURKAT CELLS; LEUKEMIA, T-CELL; RADIATION-SENSITIZING AGENTS; SPHINGOSINE;

EID: 35648950005     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.09.037     Document Type: Article

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26. 2). The mixture was stirred at 40-50 °C for 3 h, followed by removal of extra thionyl chloride in vacuo. After the acid chloride was dissolved in THF, the mixture was added dropwise in THF solution containing phytosphingosine and DIEA at 0 °C. The reaction mixture was stirred at 0 °C for 15 min and continuously stirred at room temperature for 45 min. This solution was quenched by small amounts of water and dried with sodium sulfate. Flash column chromatography (80-100% EtOAc/hexane) gave a white solid 3a-h in 35-88% yield.
27. +) 446.3482, found 446.3475.