CAS: 873436-91-0; 8-((6-Iodobenzo[d][1,3]Dioxol-5-yl)Thio)-9-(3-(Isopropylamino)Propyl)-9H-Purin-6-Amine

该化合物是属于纯分子类分子的合成有机化合物.该化合物具有纯核核心特征,其特点是含有氮原子的结合双环结构.在6位置上存在一个氨基组和一个丙胺侧链,有助于其潜在的生物活动.该化合物还含有一种与苯并二甲酚(Benzodooxole)运动的硫醚联系,这可能会加强其药理特性.苯并二甲醇环上的碘亚化物会影响该化合物的活性和生物相互作用.

结构式图片

物理性质

MSDS等安全信息

上下游产品

{3-[6-amino-8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-purin-9-yl]-propyl}-isopropyl-carbamic acid tert-butyl ester tert-butyl N-(3-hydroxypropyl)-N-(isopropyl)carbamate 3-(tert-butoxycarbonyl-isopropylamino)propyl tosylate 8-(benzo[1,3]dioxol-5-ylsulfanyl)adenine

合成工艺路线路线简述

  • 873436-88-5 = 873436-91-0
    反应条件:1.1 Reagents: Trifluoroacetic Acid,N-Iodosuccinimide Solvents: Acetonitrile; Overnight,Rt2.1 Reagents: Cesium Carbonate Solvents: Dimethylformamide; Rt3.1 Solvents: Dimethylformamide; Overnight,Rt
    标题:A Facile And Efficient Synthesis Of D6-Labeled Pu-H71,A Purine-Scaffold Hsp90 Inhibitor
    作者:Taldone,Tony; Et Al
    参考文献:Journal Of Labelled Compounds And Radiopharmaceuticals 日期:2010 卷标:53(1) 页码:47-49]

    5876-51-7 + 7390-62-7 = 873436-91-0
    反应条件:1.1 Reagents: 2,9-Dimethyl-1,10-Phenanthroline,Sodium Tert-Butoxide Catalysts: Cuprous Iodide Solvents: Dimethylformamide; 48 H,115 °C2.1 Reagents: Trifluoroacetic Acid,N-Iodosuccinimide Solvents: Acetonitrile; Overnight,Rt3.1 Reagents: Cesium Carbonate Solvents: Dimethylformamide; Rt4.1 Solvents: Dimethylformamide; Overnight,Rt
    标题:A Facile And Efficient Synthesis Of D6-Labeled Pu-H71,A Purine-Scaffold Hsp90 Inhibitor
    作者:Taldone,Tony; Et Al
    参考文献:Journal Of Labelled Compounds And Radiopharmaceuticals 日期:2010 卷标:53(1) 页码:47-49]

    118-70-7 = 873436-91-0
    反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Ethanol,Water; 72 H,Reflux2.1 Reagents: 2,9-Dimethyl-1,10-Phenanthroline,Sodium Tert-Butoxide Catalysts: Cuprous Iodide Solvents: Dimethylformamide; 48 H,115 °C3.1 Reagents: Trifluoroacetic Acid,N-Iodosuccinimide Solvents: Acetonitrile; Overnight,Rt4.1 Reagents: Cesium Carbonate Solvents: Dimethylformamide; Rt5.1 Solvents: Dimethylformamide; Overnight,Rt
    标题:A Facile And Efficient Synthesis Of D6-Labeled Pu-H71,A Purine-Scaffold Hsp90 Inhibitor
    作者:Taldone,Tony; Et Al
    参考文献:Journal Of Labelled Compounds And Radiopharmaceuticals 日期:2010 卷标:53(1) 页码:47-49]

    1240419-78-6 + 75-31-0 = 873436-91-0
    反应条件:1.1 Solvents: Dimethylformamide; Overnight,Rt
    标题:A Facile And Efficient Synthesis Of D6-Labeled Pu-H71,A Purine-Scaffold Hsp90 Inhibitor
    作者:Taldone,Tony; Et Al
    参考文献:Journal Of Labelled Compounds And Radiopharmaceuticals 日期:2010 卷标:53(1) 页码:47-49]

    873436-89-6 + 905449-67-4 = 873436-91-0
    反应条件:1.1 Reagents: Cesium Carbonate Solvents: Dimethylformamide; 24 H,80 °C1.2 Reagents: Trifluoroacetic Acid Solvents: Trifluoroacetic Acid; 1.5 H,0 °C
    标题:Identification Of Potent Water Soluble Purine-Scaffold Inhibitors Of The Heat Shock Protein 90
    作者:He,Huazhong; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2006 卷标:49(1) 页码:381-390]

    873436-89-6 = 873436-91-0
    反应条件:1.1 Reagents: Cesium Carbonate Solvents: Dimethylformamide; Rt2.1 Solvents: Dimethylformamide; Overnight,Rt
    标题:A Facile And Efficient Synthesis Of D6-Labeled Pu-H71,A Purine-Scaffold Hsp90 Inhibitor
    作者:Taldone,Tony; Et Al
    参考文献:Journal Of Labelled Compounds And Radiopharmaceuticals 日期:2010 卷标:53(1) 页码:47-49]

    873436-88-5 = 873436-91-0
    反应条件:1.1 Reagents: Trifluoroacetic Acid,N-Iodosuccinimide Solvents: Acetonitrile; 24 H,Rt2.1 Reagents: Cesium Carbonate Solvents: Dimethylformamide; 24 H,80 °C2.2 Reagents: Trifluoroacetic Acid Solvents: Trifluoroacetic Acid; 1.5 H,0 °C
    标题:Identification Of Potent Water Soluble Purine-Scaffold Inhibitors Of The Heat Shock Protein 90
    作者:He,Huazhong; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2006 卷标:49(1) 页码:381-390]

    873437-13-9 = 873436-91-0
    反应条件:1.1 Reagents: Pyridine Solvents: Pyridine; Overnight,Rt2.1 Reagents: Cesium Carbonate Solvents: Dimethylformamide; 24 H,80 °C2.2 Reagents: Trifluoroacetic Acid Solvents: Trifluoroacetic Acid; 1.5 H,0 °C
    标题:Identification Of Potent Water Soluble Purine-Scaffold Inhibitors Of The Heat Shock Protein 90
    作者:He,Huazhong; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2006 卷标:49(1) 页码:381-390]

    24424-99-5 + 75-31-0 + 627-18-9 = 873436-91-0
    反应条件:1.1 Overnight,50 °C1.2 Reagents: Triethylamine; Overnight,Rt2.1 Reagents: Pyridine Solvents: Pyridine; Overnight,Rt3.1 Reagents: Cesium Carbonate Solvents: Dimethylformamide; 24 H,80 °C3.2 Reagents: Trifluoroacetic Acid Solvents: Trifluoroacetic Acid; 1.5 H,0 °C
    标题:Identification Of Potent Water Soluble Purine-Scaffold Inhibitors Of The Heat Shock Protein 90
    作者:He,Huazhong; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2006 卷标:49(1) 页码:381-390]

    5876-51-7 + 7390-62-7 = 873436-91-0
    反应条件:1.1 Reagents: Sodium Tert-Butoxide Catalysts: 2,9-Dimethyl-1,10-Phenanthroline,Cuprous Iodide Solvents: Dimethylformamide; 24 H,110 °C2.1 Reagents: Trifluoroacetic Acid,N-Iodosuccinimide Solvents: Acetonitrile; 24 H,Rt3.1 Reagents: Cesium Carbonate Solvents: Dimethylformamide; 24 H,80 °C3.2 Reagents: Trifluoroacetic Acid Solvents: Trifluoroacetic Acid; 1.5 H,0 °C
    标题:Identification Of Potent Water Soluble Purine-Scaffold Inhibitors Of The Heat Shock Protein 90
    作者:He,Huazhong; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2006 卷标:49(1) 页码:381-390]

    14268-66-7 = 873436-91-0
    反应条件:1.1 Reagents: Sodium Nitrite,Hydrochloric Acid Solvents: Water; 15 Min,0 °C; 10 Min,0 °C1.2 Reagents: Urea; 10 Min,0 °C1.3 Reagents: Potassium Iodide Solvents: Water; Overnight,0 °C2.1 Reagents: Sodium Tert-Butoxide Catalysts: 2,9-Dimethyl-1,10-Phenanthroline,Cuprous Iodide Solvents: Dimethylformamide; 24 H,110 °C3.1 Reagents: Trifluoroacetic Acid,N-Iodosuccinimide Solvents: Acetonitrile; 24 H,Rt4.1 Reagents: Cesium Carbonate Solvents: Dimethylformamide; 24 H,80 °C4.2 Reagents: Trifluoroacetic Acid Solvents: Trifluoroacetic Acid; 1.5 H,0 °C
    标题:Identification Of Potent Water Soluble Purine-Scaffold Inhibitors Of The Heat Shock Protein 90
    作者:He,Huazhong; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2006 卷标:49(1) 页码:381-390]

    118-70-7 = 873436-91-0
    反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Ethanol,Water; 3 D,Reflux2.1 Reagents: Sodium Tert-Butoxide Catalysts: 2,9-Dimethyl-1,10-Phenanthroline,Cuprous Iodide Solvents: Dimethylformamide; 24 H,110 °C3.1 Reagents: Trifluoroacetic Acid,N-Iodosuccinimide Solvents: Acetonitrile; 24 H,Rt4.1 Reagents: Cesium Carbonate Solvents: Dimethylformamide; 24 H,80 °C4.2 Reagents: Trifluoroacetic Acid Solvents: Trifluoroacetic Acid; 1.5 H,0 °C
    标题:Identification Of Potent Water Soluble Purine-Scaffold Inhibitors Of The Heat Shock Protein 90
    作者:He,Huazhong; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2006 卷标:49(1) 页码:381-390
📜8-巯基腺嘌呤置于n-碘代丁二酰亚胺,Copper(L) Iodide,新铜试剂,Caesium Carbonate,三氟乙酸,Sodium T-Butanolate体系中,用 二氯甲烷,N,N-二甲基甲酰胺,乙腈 作为反应溶剂,化学反应 73.5H,反应生成 6-氨基-8-[(6-碘-1,3-苯并二茂-5-基)硫基]-N-异丙基-9H-嘌呤-9-丙胺
参考文献:Identification Of Potent Water Soluble Purine-Scaffold Inhibitors Of The Heat Shock Protein 90
标题:Identification Of Potent Water Soluble Purine-Scaffold Inhibitors Of The Heat Shock Protein 90
摘要:Hsp90 Is A Chaperone Protein That Allows Cancer Cells To Tolerate The Many Components Of Dysregulated Pathways. Its Inactivation May Result In Targeting Multiple Molecular Alterations And,Thus,In Reverting The Transformed Phenotype. The Pu-Class,A Purine-Scaffold Hsp90 Inhibitor Series,Has Been Reported To Be Potent And Selective Against Hsp90 Both In Vitro And In Vivo Models Of Cancer. Here,A Series Of This Class Was Synthesized And Evaluated As Inhibitors Of The Chaperone. The Structure-Activity Relationship And Selectivity For Tumor Hsp90 Of Compounds Within The Series Is Presented. The Study Identifies Water Soluble Derivatives (> 5 Mm In Pbs Ph 7.4) Of Nanomolar Potency (Ic50 Similar To 50 Nm) In Cellular And Animal Models Of Cancer. Binding Affinities Of These Compounds For Hsp90 Correlate Well With Their Biological Activities. When Administered In Vivo To Mice Bearing Mda-Mb-468 Human Breast Cancer Xenocyrafted Tumors,These Agents Result In Pharmacologically Relevant Concentrations And,Accordingly,In Modulation Of Hsp90-Client Proteins In Tumors.
DOI:10.1021/jm0508078

海关参考信息

专利信息


专利号:WO-2014018862-A1
优先权日:2012-07-27
标 题 :Pharmaceutical compositions comprising a heat shock protein inhibitor and a; purine de novo synthesis inhibitor for treating rheumatoid arthritis or cancer
发明人：FANG YE
权利人:CORNING INC; FANG YE
摘要:A pharmaceutical composition including an effective amount of the combination of: an heat shock protein (HSP) inhibitor, and a purine de novo biosynthesis inhibitor, or a pharmaceutically acceptable salt thereof. Also disclosed is a method of treating rheumatoid arthritis or cancer including administering an effective amount of the above mentioned pharmaceutical composition to a patient in need of such treatment, as defined herein.

专利号:US-9994573-B2
优先权日:2013-12-23
标 题 :Methods and reagents for radiolabeling
发明人：OCHIANA STEFAN O; PILLARSETTY NAGAVARAKISHORE; TALDONE TONY; CHIOSIS GABRIELA
权利人:MEMORIAL SLOAN KETTERING CANCER CENTER
摘要:The present invention provides methods for radiolabeling compounds useful as Hsp90 inhibitors. The present invention also provides intermediates useful in such methods, and compositions of radiolabeled compounds. The present invention provides, among other things, novel methods for the synthesis of radiolabeled compounds. In certain embodiments, the present invention provides compounds of formula I.

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主要参考文献


1: Taldone T, Zatorska D, Ochiana SO, Smith-Jones P, Koziorowski J, Dunphy MP, Zanzonico P, Bolaender A, Lewis JS, Larson SM, Chiosis G, Pillarsetty NV. Radiosynthesis of the iodine-124 labeled Hsp90 inhibitor PU-H71. J Labelled Comp Radiopharm. 2016 Mar;59(3):129-32. doi: 10.1002/jlcr.3369.
2: Trendowski M. PU-H71: An improvement on nature's solutions to oncogenic Hsp90 addiction. Pharmacol Res. 2015 Sep;99:202-16. doi: 10.1016/j.phrs.2015.06.007. Review. doi: 10.1016/j.radonc.2016.08.029.
4: Li HK, Matsumoto Y, Furusawa Y, Kamada T. PU-H71, a novel Hsp90 inhibitor, as a potential cancer-specific sensitizer to carbon-ion beam therapy. J Radiat Res. 2016 Sep;57(5):572-575.

合成参考文献


参考文献:10.1523/jneurosci.0185-08.2008
摘要:Wang L, Xie C, Greggio E, Parisiadou L, Shim H, Sun L, Chandran J, Lin X, Lai C, Yang W, Moore DJ, Dawson TM, Dawson VL, Chiosis G, Cookson MR, Cai H. The Chaperone Activity of Heat Shock Protein 90 Is Critical for Maintaining the Stability of Leucine-Rich Repeat Kinase 2. J. Neurosci. 2008 Mar 26;28(13):3384–91. doi: 10.1523/jneurosci.0185-08.2008.
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