CAS: 36804-95-2; Deoxyharringtonine
该化合物是一种天然的藻类,产自植物物种Cephalotaxus harringtonia,通称为harringingia树,其特点是结构复杂,包括四环核心和各种功能组,有助于其生物活动,该化合物主要因其强大的抗肿瘤特性而得到承认,特别是在治疗某些种类的白血病和其他恶性肿瘤方面;脱氧哈林顿因子作为蛋白综合抑制剂的功能,具体针对破坏癌症细胞生长的产卵翻译启动过程;其行动机制涉及eIF4F综合体的抑制,导致减少对肿瘤的转化;此外,对脱氧哈林顿因子对流行性疾病和细胞循环调节的潜在影响进行了研究;由于其治疗潜力,它引起了对药物研究的兴趣,尽管其临床用途可能受到毒性和可获性等因素的限制.
- 英文名称Deoxyharringtonine
- 中文名称去氧哈林通碱
- 其它别名Cephalotaxine,4-methyl (2R)-2-hydroxy-2-(3-methylbutyl)butanedioate (ester) (9CI); Cephalotaxine,4-methyl 2-hydroxy-2-(3-methylbutyl)butanedioate (ester), [3(R)]-; 4H-Cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepine, cephalotaxinederiv.; (-)-Deoxyharringtonine; 3(R)-Deoxyharringtonine; Deoxyharringtonine; Desoxyharringtonin; Harringtonine, deoxy-
- CAS编号36804-95-2
- 分子式:C28H37NO8分子量:515.6
- 产品CID: 1377280
- 产品分类生物化工 → 中草药成分
物理性质
MSDS等安全信息
上下游产品
(-)-deoxyharringtonine β-lactone sodium methylate (2R,4R)-[2-tert-butyl-4-(3-methylbut-2-enyl)-5-oxo-1,3-dioxolan-4-yl]acetic acid 6-chloro-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one合成工艺路线路线简述
📜(+/-)-2,2-Dimethyl-3αβ,6αβ-Dihydro-4H-Cyclopenta-1,3-Dioxol-4-One置于palladium On Activated Charcoal Chromium Dichloride,盐酸,甲醇,六甲基磷酰三胺,Sodium Tetrahydroborate,Samarium Diiodide,Cerium(Iii) Chloride,Schwartz'S Reagent,2,4,6-三氯苯甲酰氯,氢气,Silver Trifluoromethanesulfonate,双(三甲基硅烷基)氨基钾,Caesium Carbonate,戴斯-马丁氧化剂,对甲苯磺酸,三乙胺,间氯过氧苯甲酸,Ytterbium(Iii) Triflate体系中,用 四氢呋喃,1,4-二氧六环,甲醇,二氯甲烷,水,乙酸乙酯,丙酮,乙腈,叔丁醇 作为反应溶剂,化学反应 209.92H,反应生成 去氧哈林通碱
参考文献:N-乙烯基-2-芳基氮丙啶的应变释放重排.抗白血病生物碱 (-)-Deoxyharringtonine 的全合成
标题:N-乙烯基-2-芳基氮丙啶的应变释放重排.抗白血病生物碱 (-)-Deoxyharringtonine 的全合成
摘要:Deoxyharringtonine (1) 是从 Cephalotaxus 属中分离出的最有效的抗白血病生物碱之一.报道了 (-)-1 的收敛全合成,涉及新的合成方法和策略,包括 (1) 用于 [3] 苯并氮杂合成的 N-芳基-2-乙烯基氮丙啶的应变释放重排,(2) 一种乙烯基酰胺用于螺-吡咯烷构建的酰化-环加成级联反应,以及 (3) α-(β-内酯) 羧酸衍生物对头孢菌素核心的有效酰化,以获得具有生物活性的头孢菌酯.这些创新不仅应允许快速获取其他三尖杉生物碱,而且还应允许快速获取具有潜在治疗效用的非天然类似物.
DOI:10.1021/ja063304F
海关参考信息
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2901220000-丙烯
2902600000-乙苯
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专利信息
专利号:US-3959312-A
优先权日:1974-12-20
标 题 :Synthesis of antitumor alkaloid deoxyharringtonine and its precursor 3'-0-(5-methyl-2-oxohexanoyl)-cephalotaxine
发明人：MIKOLAJCZAK KENNETH L; SMITH JR CECIL R
权利人:US AGRICULTURE
摘要:The alkaloid deoxyharringtonine and its precursor 3'-O-(5-methyl-2-oxohexanoyl)-cephalotaxine were synthesized according to the following preferred series of reactions: Ethyl t-butyl oxalate + 1-lithio-3-methylbut-1-yne -> t-butyl 5-methyl-2-oxohex-3-ynoate -> t-butyl 5-methyl-2-oxohexanoate -trifluoroacetic acid 5-methyl-2-oxohexanoic acid (COCl)+402 5-methyl-2-oxohexanoyl chloride cephalotaxine 3'-O-(5-methyl-2-oxohexanoyl)-cephalotaxine lithio methyl acetate deoxyharringtonine.
专利号:US-9006231-B2
优先权日:2008-03-03
标 题:Cephalotaxus esters, methods of synthesis, and uses thereof
发明人：GIN DAVID Y; WILMOT JEREMY; DJABALLAH HAKIM
权利人:SLOAN KETTERING INST CANCER
摘要:The present invention provides novel cephalotaxus esters, syntheses thereof, and intermediates thereto. The invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of using said compounds or compositions in the treatment of proliferative diseases (e.g., benign neoplasm, cancer, inflammatory disease, autoimmune disease, diabetic retinopathy) and infectious disease. The invention further provides methods of using said compounds or compositions in the treatment of multidrug resistant cancer.
专利号:WO-2009148654-A2
优先权日:2008-03-03
标 题:Cephalotaxus esters, methods of synthesis, and uses thereof
专利号:CN-102976924-A
优先权日:2012-12-14
标 题 :Total Synthesis Method of Homoharringtonine Side Chain Acid and Its Analogs
专利号:US-2011071097-A1
优先权日:2008-03-03
标题:Cephalotaxus esters, methods of synthesis, and uses thereof
专利号:US-2014171416-A1
优先权日:2008-03-03
标 题 :Cephalotaxus esters, methods of synthesis, and uses thereof
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合成参考文献
摘要:Journal of Ethnopharmacology., 24(1), 1988 []
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