865838-26-2 ((RX-3117)

快速询单

结构式：

RX-3117MOL文件

CAS号：

865838-26-2

英文名称：

RX-3117

分子式：

C₁₀H₁₂FN₃O₄

分子量：

257.218385696411

简介：

RX-3117 (TV-1360) 是一种有效的口服活性抗癌和抗代谢物药剂。RX-3117 抑制 DNA 甲基转移酶 1 (DNMT1。RX-3117 显示出抗增殖和抗肿瘤活性。RX-3117 诱导细胞周期停滞在 S 期和细胞凋亡 (apoptosis)。

API：

Roducitabine

RX-3117(865838-26-2)名称与标识符

名称

中文别名：

RX-3117;氟环戊烯基胞嘧啶;

英文别名：

RX-3117;4-Amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-2(1H)-pyrimidinone (ACI);4-amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]pyrimidin-2(1H)-one;Roducitabine;RX 3117;UNII-0Z4A82I0JO;RX3117;Cytidine Analog RX-3117;4-Amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-2(1H)-pyrimidinone;4-amino-1-((1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-cyclopent-2-en-1-yl)-pyrimidin-2(1H)-one;fluorocyclopentenylcytosine;MS-23620;4-Amino-1-((1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl)pyrimidin-2(1H)-one;SCHEMBL4409591;BRD-K66213167-001-01-2;Roducitabine [USAN];NSC785657;4-AMINO-1-((1S,4R,5S)-2-FLUORO-4,5-DIHYDROXY-3-(HYDROXYMETHYL)CYCLOPENT-2-EN-1-YL)PYRIMIDIN-2-ONE;4-Amino-1-((1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl)-2(1H)-pyrimidinone;865838-26-2;4-amino-1-((1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl)-1,2-dihydropyrimidin-2-one;fluorocyclopentenyl-cytosine;NSC-785657;QLLGKCJUPWYJON-HLTSFMKQSA-N;4-amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]-1,2-dihydropyrimidin-2-one;4-AMINO-1-((1S,4R,5S)-2-FLUORO-4,5-DIHYDROXY-3-(HYDROXYMETHYL) CYCLOPENT-2-EN-1-YL) PYRIMIDIN-2-ONE;TV-1360;RODUCITABINE [INN];WHO 11374;0Z4A82I0JO;S900007480;AKOS027327327;NCGC00485875-02;EX-A4776;CHEMBL2064455;fluorocyclopentenyl cytosine;NCGC00485875-01;1-[(1S,4R,5S)-2-Fluoro-3-(hydroxymethyl)-4,5-dihydroxy-2-cyclopentenyl]cytosine;1-((1S,4R,5S)-2-fluoro-3-(hydroxymethyl)-4,5-dihydroxy-2-cyclopentenyl)cytosine;DTXSID101113297;CS-3947;Roducitabine (USAN);AC-35336;HY-15228;CHEBI:147412;2(1H)-PYRIMIDINONE, 4-AMINO-1-((1S,4R,5S)-2-FLUORO-4,5-DIHYDROXY-3-(HYDROXYMETHYL)-2-CYCLOPENTEN-1-YL)-;4-amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]pyrimidin-2-one;

标识符

MDL：

MFCD28502078

InChIKey：

QLLGKCJUPWYJON-HLTSFMKQSA-N

Inchi：

1S/C10H12FN3O4/c11-6-4(3-15)8(16)9(17)7(6)14-2-1-5(12)13-10(14)18/h1-2,7-9,15-17H,3H2,(H2,12,13,18)/t7-,8-,9+/m1/s1

SMILES：

FC1=C(CO)[C@@H](O)[C@@H](O)[C@@H]1N1C=CC(N)=NC1=O

RX-3117(865838-26-2)物化性质

计算特性

精确分子量 : 257.08118403g/mol
氢键供体数量 : 5
氢键受体数量 : 7
可旋转化学键数量 : 2
同位素质量 : 257.08118403g/mol
重原子数量 : 18
复杂度 : 474
同位素原子数量 : 0
确定原子立构中心数量 : 3
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 0
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : -2.6
拓扑分子极性表面积 : 119Å²

RX-3117(865838-26-2)安全信息

储存条件： Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month

RX-3117(865838-26-2)推荐厂家更多厂家(9)

公司名称	手机号/电话	联系人	QQ	询单
上海源叶生物科技有限公司	15026964105 15026964105	汤思磊	2881489226	询单
上海瀚思化工有限公司	18939883912 021-34536277	顾经理	3003949364	询单
北京索莱宝科技有限公司	18101056239 010-50973130	龚思雨	3193328036	询单
MedChemExpress（MCE 中国）	13611715263 021-58955995	MCE生命科学试剂	2881321772	询单
杭州六可生物科技有限公司	15658003402 0086-571-86912261	Susan	3671025517	询单
上海吉至生化科技有限公司	18117592386 021-57481218	吉至试剂	3007522982	询单
天津普西唐生物医药科技有限公司	15801484223 15801484223	唐召锋	3003463702	询单
上海源溪生物科技有限公司	13564518121	李经理	1724405207	询单

RX-3117(865838-26-2)合成路线

合成路线：1 步

865838-20-6

_40%

865838-26-2

反应条件：

1.1 Reagents: Acetic anhydride , Pyridine ; rt; 18 h, rt
1.2 Reagents: 1H-1,2,4-Triazole , Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 1 h, rt; rt → 0 °C
1.3 Reagents: Triethylamine Solvents: Acetonitrile ; 24 h, rt
1.4 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, rt
1.5 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Design, synthesis and anticancer activity of fluorocyclopentenyl-purines and - pyrimidines

Yoon, Ji-seong; et al, European Journal of Medicinal Chemistry, 2018, 155, 406-417

合成路线：1 步

865838-20-6

_40%

865838-26-2

反应条件：

1.1 Reagents: Acetic anhydride Solvents: Pyridine ; rt; 15 h, rt
1.2 Reagents: 1H-1,2,4-Triazole , Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 5 min, rt
1.3 Reagents: Triethylamine Solvents: Acetonitrile ; 0 °C; 24 h, 30 °C
1.4 Reagents: Triethylamine Solvents: Water ; 10 min
1.5 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, 30 °C
1.6 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Fluorocyclopentenyl-cytosine with Broad Spectrum and Potent Antitumor Activity

Choi, Won Jun; et al, Journal of Medicinal Chemistry, 2012, 55(9), 4521-4525

合成路线：1 步

2241279-06-9

865838-26-2

反应条件：

1.1 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, rt
1.2 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Design, synthesis and anticancer activity of fluorocyclopentenyl-purines and - pyrimidines

Yoon, Ji-seong; et al, European Journal of Medicinal Chemistry, 2018, 155, 406-417

合成路线：2 步

288-88-0

1119248-71-3

865838-26-2

反应条件：

1.1 Reagents: Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 1 h, rt; rt → 0 °C
1.2 Reagents: Triethylamine Solvents: Acetonitrile ; 24 h, rt
2.1 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, rt
2.2 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Design, synthesis and anticancer activity of fluorocyclopentenyl-purines and - pyrimidines

Yoon, Ji-seong; et al, European Journal of Medicinal Chemistry, 2018, 155, 406-417

合成路线：2 步

2241019-45-2

865838-26-2

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Methanol , Water ; 0 °C; 18 h, rt
2.1 Reagents: Acetic anhydride , Pyridine ; rt; 18 h, rt
2.2 Reagents: 1H-1,2,4-Triazole , Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 1 h, rt; rt → 0 °C
2.3 Reagents: Triethylamine Solvents: Acetonitrile ; 24 h, rt
2.4 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, rt
2.5 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Design, synthesis and anticancer activity of fluorocyclopentenyl-purines and - pyrimidines

Yoon, Ji-seong; et al, European Journal of Medicinal Chemistry, 2018, 155, 406-417

合成路线：2 步

944158-83-2

865838-26-2

反应条件：

1.1 Reagents: Ammonia Solvents: Methanol ; 3 h, rt
1.2 Reagents: Boron tribromide Solvents: Dichloromethane ; 30 min, -78 °C
1.3 Reagents: Methanol ; 1 h, -78 °C
1.4 Reagents: Pyridine ; neutralized
1.5 Reagents: Acetic anhydride Solvents: Pyridine ; rt; 15 h, rt
1.6 Reagents: Sodium bicarbonate Solvents: Water
2.1 Reagents: Acetic anhydride Solvents: Pyridine ; rt; 15 h, rt
2.2 Reagents: 1H-1,2,4-Triazole , Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 5 min, rt
2.3 Reagents: Triethylamine Solvents: Acetonitrile ; 0 °C; 24 h, 30 °C
2.4 Reagents: Triethylamine Solvents: Water ; 10 min
2.5 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, 30 °C
2.6 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Fluorocyclopentenyl-cytosine with Broad Spectrum and Potent Antitumor Activity

Choi, Won Jun; et al, Journal of Medicinal Chemistry, 2012, 55(9), 4521-4525

合成路线：2 步

944158-83-2

865838-26-2

反应条件：

1.1 Reagents: Ammonia Solvents: Methanol
1.2 Reagents: Boron trichloride Solvents: Dichloromethane
2.1 Reagents: Acetic anhydride , Pyridine Solvents: Pyridine
2.2 Reagents: Triethylamine , 1H-1,2,4-Triazole , Phosphorus oxychloride
2.3 Reagents: Ammonium hydroxide Solvents: 1,4-Dioxane
2.4 Reagents: Ammonia Solvents: Methanol

参考文献：

Synthesis and Antitumor Activity of Fluorocyclopentenyl-Pyrimidines

Jeong, Lak Shin; et al, Nucleosides, 2007, 26(6-7), 713-716

合成路线：2 步

944158-83-2

865838-26-2

反应条件：

1.1 Reagents: Ammonia Solvents: Methanol
1.2 Reagents: Boron trichloride Solvents: Dichloromethane
2.1 Reagents: Acetic anhydride , Pyridine Solvents: Pyridine ; rt
2.2 Reagents: Triethylamine , 1H-1,2,4-Triazole , Phosphorus oxychloride
2.3 Reagents: Ammonium hydroxide Solvents: 1,4-Dioxane , Water
2.4 Reagents: Ammonia Solvents: Methanol

参考文献：

Design, synthesis, and anticancer activity of fluorocyclopentenyl-pyrimidines

Zhao, Long Xuan; et al, Nucleic Acids Symposium Series, 2005, (49), 107-108

合成路线：3 步

865838-20-6

108-24-7

865838-26-2

反应条件：

1.1 Reagents: Pyridine ; rt; 18 h, rt
2.1 Reagents: Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 1 h, rt; rt → 0 °C
2.2 Reagents: Triethylamine Solvents: Acetonitrile ; 24 h, rt
3.1 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, rt
3.2 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Design, synthesis and anticancer activity of fluorocyclopentenyl-purines and - pyrimidines

Yoon, Ji-seong; et al, European Journal of Medicinal Chemistry, 2018, 155, 406-417

合成路线：3 步

491578-02-0

2775-87-3

865838-26-2

反应条件：

1.1 Reagents: Triphenylphosphine , Diisopropyl azodicarboxylate Solvents: Tetrahydrofuran ; 0 °C; 15 min, 0 °C; 12 h, rt
2.1 Reagents: Ammonia Solvents: Methanol ; 3 h, rt
2.2 Reagents: Boron tribromide Solvents: Dichloromethane ; 30 min, -78 °C
2.3 Reagents: Methanol ; 1 h, -78 °C
2.4 Reagents: Pyridine ; neutralized
2.5 Reagents: Acetic anhydride Solvents: Pyridine ; rt; 15 h, rt
2.6 Reagents: Sodium bicarbonate Solvents: Water
3.1 Reagents: Acetic anhydride Solvents: Pyridine ; rt; 15 h, rt
3.2 Reagents: 1H-1,2,4-Triazole , Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 5 min, rt
3.3 Reagents: Triethylamine Solvents: Acetonitrile ; 0 °C; 24 h, 30 °C
3.4 Reagents: Triethylamine Solvents: Water ; 10 min
3.5 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, 30 °C
3.6 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Fluorocyclopentenyl-cytosine with Broad Spectrum and Potent Antitumor Activity

Choi, Won Jun; et al, Journal of Medicinal Chemistry, 2012, 55(9), 4521-4525

合成路线：3 步

491578-02-0

2775-87-3

865838-26-2

反应条件：

1.1 Reagents: Triphenylphosphine , Diethyl azodicarboxylate Solvents: Tetrahydrofuran
2.1 Reagents: Ammonia Solvents: Methanol
2.2 Reagents: Boron trichloride Solvents: Dichloromethane
3.1 Reagents: Acetic anhydride , Pyridine Solvents: Pyridine
3.2 Reagents: Triethylamine , 1H-1,2,4-Triazole , Phosphorus oxychloride
3.3 Reagents: Ammonium hydroxide Solvents: 1,4-Dioxane
3.4 Reagents: Ammonia Solvents: Methanol

参考文献：

Synthesis and Antitumor Activity of Fluorocyclopentenyl-Pyrimidines

Jeong, Lak Shin; et al, Nucleosides, 2007, 26(6-7), 713-716

合成路线：3 步

491578-02-0

2775-87-3

865838-26-2

反应条件：

1.1 Reagents: Triphenylphosphine , Diethyl azodicarboxylate
2.1 Reagents: Ammonia Solvents: Methanol
2.2 Reagents: Boron trichloride Solvents: Dichloromethane
3.1 Reagents: Acetic anhydride , Pyridine Solvents: Pyridine ; rt
3.2 Reagents: Triethylamine , 1H-1,2,4-Triazole , Phosphorus oxychloride
3.3 Reagents: Ammonium hydroxide Solvents: 1,4-Dioxane , Water
3.4 Reagents: Ammonia Solvents: Methanol

参考文献：

Design, synthesis, and anticancer activity of fluorocyclopentenyl-pyrimidines

Zhao, Long Xuan; et al, Nucleic Acids Symposium Series, 2005, (49), 107-108

合成路线：3 步

2775-87-3

805245-42-5

865838-26-2

反应条件：

1.1 Reagents: Triphenylphosphine , Diisopropyl azodicarboxylate Solvents: Tetrahydrofuran ; 0 °C; 15 min, rt; rt → 0 °C
1.2 Solvents: Tetrahydrofuran ; 0 °C; 24 h, rt
1.3 Reagents: Ammonia Solvents: Methanol ; 15 h, rt
2.1 Reagents: Hydrochloric acid Solvents: Methanol , Water ; 0 °C; 18 h, rt
3.1 Reagents: Acetic anhydride , Pyridine ; rt; 18 h, rt
3.2 Reagents: 1H-1,2,4-Triazole , Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 1 h, rt; rt → 0 °C
3.3 Reagents: Triethylamine Solvents: Acetonitrile ; 24 h, rt
3.4 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, rt
3.5 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Design, synthesis and anticancer activity of fluorocyclopentenyl-purines and - pyrimidines

Yoon, Ji-seong; et al, European Journal of Medicinal Chemistry, 2018, 155, 406-417

合成路线：4 步

491577-97-0

865838-26-2

反应条件：

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
2.1 Reagents: Triphenylphosphine , Diethyl azodicarboxylate Solvents: Tetrahydrofuran
3.1 Reagents: Ammonia Solvents: Methanol
3.2 Reagents: Boron trichloride Solvents: Dichloromethane
4.1 Reagents: Acetic anhydride , Pyridine Solvents: Pyridine
4.2 Reagents: Triethylamine , 1H-1,2,4-Triazole , Phosphorus oxychloride
4.3 Reagents: Ammonium hydroxide Solvents: 1,4-Dioxane
4.4 Reagents: Ammonia Solvents: Methanol

参考文献：

Synthesis and Antitumor Activity of Fluorocyclopentenyl-Pyrimidines

Jeong, Lak Shin; et al, Nucleosides, 2007, 26(6-7), 713-716

合成路线：4 步

491578-01-9

865838-26-2

反应条件：

1.1 Reagents: Butyllithium , N-Fluorobenzenesulfonimide Solvents: Tetrahydrofuran , Hexane ; -78 °C; 1 h, -78 °C
1.2 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; rt; 1 h, rt
2.1 Reagents: Triphenylphosphine , Diisopropyl azodicarboxylate Solvents: Tetrahydrofuran ; 0 °C; 15 min, 0 °C; 12 h, rt
3.1 Reagents: Ammonia Solvents: Methanol ; 3 h, rt
3.2 Reagents: Boron tribromide Solvents: Dichloromethane ; 30 min, -78 °C
3.3 Reagents: Methanol ; 1 h, -78 °C
3.4 Reagents: Pyridine ; neutralized
3.5 Reagents: Acetic anhydride Solvents: Pyridine ; rt; 15 h, rt
3.6 Reagents: Sodium bicarbonate Solvents: Water
4.1 Reagents: Acetic anhydride Solvents: Pyridine ; rt; 15 h, rt
4.2 Reagents: 1H-1,2,4-Triazole , Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 5 min, rt
4.3 Reagents: Triethylamine Solvents: Acetonitrile ; 0 °C; 24 h, 30 °C
4.4 Reagents: Triethylamine Solvents: Water ; 10 min
4.5 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, 30 °C
4.6 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Fluorocyclopentenyl-cytosine with Broad Spectrum and Potent Antitumor Activity

Choi, Won Jun; et al, Journal of Medicinal Chemistry, 2012, 55(9), 4521-4525

合成路线：4 步

491578-01-9

865838-26-2

反应条件：

1.1 Reagents: Butyllithium , N-Fluorobenzenesulfonimide Solvents: Tetrahydrofuran ; -78 °C
1.2 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
2.1 Reagents: Triphenylphosphine , Diethyl azodicarboxylate
3.1 Reagents: Ammonia Solvents: Methanol
3.2 Reagents: Boron trichloride Solvents: Dichloromethane
4.1 Reagents: Acetic anhydride , Pyridine Solvents: Pyridine ; rt
4.2 Reagents: Triethylamine , 1H-1,2,4-Triazole , Phosphorus oxychloride
4.3 Reagents: Ammonium hydroxide Solvents: 1,4-Dioxane , Water
4.4 Reagents: Ammonia Solvents: Methanol

参考文献：

Design, synthesis, and anticancer activity of fluorocyclopentenyl-pyrimidines

Zhao, Long Xuan; et al, Nucleic Acids Symposium Series, 2005, (49), 107-108

合成路线：5 步

491578-01-9

865838-26-2

反应条件：

1.1 Reagents: Butyllithium , N-Fluorobenzenesulfonimide Solvents: Tetrahydrofuran ; -78 °C
2.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
3.1 Reagents: Triphenylphosphine , Diethyl azodicarboxylate Solvents: Tetrahydrofuran
4.1 Reagents: Ammonia Solvents: Methanol
4.2 Reagents: Boron trichloride Solvents: Dichloromethane
5.1 Reagents: Acetic anhydride , Pyridine Solvents: Pyridine
5.2 Reagents: Triethylamine , 1H-1,2,4-Triazole , Phosphorus oxychloride
5.3 Reagents: Ammonium hydroxide Solvents: 1,4-Dioxane
5.4 Reagents: Ammonia Solvents: Methanol

参考文献：

Synthesis and Antitumor Activity of Fluorocyclopentenyl-Pyrimidines

Jeong, Lak Shin; et al, Nucleosides, 2007, 26(6-7), 713-716

合成路线：4 步

805245-41-4

865838-26-2

反应条件：

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 0 °C; 2 h, rt
2.1 Reagents: Triphenylphosphine , Diisopropyl azodicarboxylate Solvents: Tetrahydrofuran ; 0 °C; 15 min, rt; rt → 0 °C
2.2 Solvents: Tetrahydrofuran ; 0 °C; 24 h, rt
2.3 Reagents: Ammonia Solvents: Methanol ; 15 h, rt
3.1 Reagents: Hydrochloric acid Solvents: Methanol , Water ; 0 °C; 18 h, rt
4.1 Reagents: Acetic anhydride , Pyridine ; rt; 18 h, rt
4.2 Reagents: 1H-1,2,4-Triazole , Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 1 h, rt; rt → 0 °C
4.3 Reagents: Triethylamine Solvents: Acetonitrile ; 24 h, rt
4.4 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, rt
4.5 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Design, synthesis and anticancer activity of fluorocyclopentenyl-purines and - pyrimidines

Yoon, Ji-seong; et al, European Journal of Medicinal Chemistry, 2018, 155, 406-417

合成路线：5 步

491578-00-8

58479-61-1

865838-26-2

反应条件：

1.1 Reagents: Imidazole Solvents: Dimethylformamide ; rt; overnight, 40 - 50 °C
1.2 Reagents: Water
2.1 Reagents: Butyllithium , N-Fluorobenzenesulfonimide Solvents: Tetrahydrofuran , Hexane ; -78 °C; 1 h, -78 °C
2.2 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; rt; 1 h, rt
3.1 Reagents: Triphenylphosphine , Diisopropyl azodicarboxylate Solvents: Tetrahydrofuran ; 0 °C; 15 min, 0 °C; 12 h, rt
4.1 Reagents: Ammonia Solvents: Methanol ; 3 h, rt
4.2 Reagents: Boron tribromide Solvents: Dichloromethane ; 30 min, -78 °C
4.3 Reagents: Methanol ; 1 h, -78 °C
4.4 Reagents: Pyridine ; neutralized
4.5 Reagents: Acetic anhydride Solvents: Pyridine ; rt; 15 h, rt
4.6 Reagents: Sodium bicarbonate Solvents: Water
5.1 Reagents: Acetic anhydride Solvents: Pyridine ; rt; 15 h, rt
5.2 Reagents: 1H-1,2,4-Triazole , Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 5 min, rt
5.3 Reagents: Triethylamine Solvents: Acetonitrile ; 0 °C; 24 h, 30 °C
5.4 Reagents: Triethylamine Solvents: Water ; 10 min
5.5 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, 30 °C
5.6 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Fluorocyclopentenyl-cytosine with Broad Spectrum and Potent Antitumor Activity

Choi, Won Jun; et al, Journal of Medicinal Chemistry, 2012, 55(9), 4521-4525

合成路线：5 步

491578-00-8

58479-61-1

865838-26-2

反应条件：

1.1 Reagents: Imidazole Solvents: Dimethylformamide
2.1 Reagents: Butyllithium , N-Fluorobenzenesulfonimide Solvents: Tetrahydrofuran ; -78 °C
2.2 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
3.1 Reagents: Triphenylphosphine , Diethyl azodicarboxylate
4.1 Reagents: Ammonia Solvents: Methanol
4.2 Reagents: Boron trichloride Solvents: Dichloromethane
5.1 Reagents: Acetic anhydride , Pyridine Solvents: Pyridine ; rt
5.2 Reagents: Triethylamine , 1H-1,2,4-Triazole , Phosphorus oxychloride
5.3 Reagents: Ammonium hydroxide Solvents: 1,4-Dioxane , Water
5.4 Reagents: Ammonia Solvents: Methanol

参考文献：

Design, synthesis, and anticancer activity of fluorocyclopentenyl-pyrimidines

Zhao, Long Xuan; et al, Nucleic Acids Symposium Series, 2005, (49), 107-108

合成路线：6 步

491578-00-8

58479-61-1

865838-26-2

反应条件：

1.1 Reagents: Imidazole Solvents: Dimethylformamide
2.1 Reagents: Butyllithium , N-Fluorobenzenesulfonimide Solvents: Tetrahydrofuran ; -78 °C
3.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
4.1 Reagents: Triphenylphosphine , Diethyl azodicarboxylate Solvents: Tetrahydrofuran
5.1 Reagents: Ammonia Solvents: Methanol
5.2 Reagents: Boron trichloride Solvents: Dichloromethane
6.1 Reagents: Acetic anhydride , Pyridine Solvents: Pyridine
6.2 Reagents: Triethylamine , 1H-1,2,4-Triazole , Phosphorus oxychloride
6.3 Reagents: Ammonium hydroxide Solvents: 1,4-Dioxane
6.4 Reagents: Ammonia Solvents: Methanol

参考文献：

Synthesis and Antitumor Activity of Fluorocyclopentenyl-Pyrimidines

Jeong, Lak Shin; et al, Nucleosides, 2007, 26(6-7), 713-716

合成路线：5 步

805245-40-3

865838-26-2

反应条件：

1.1 Reagents: Butyllithium , N-Fluorobenzenesulfonimide Solvents: Tetrahydrofuran , Hexane , Heptane , tert-Butyl methyl ether ; 1 h, -78 °C; 30 min, -78 °C
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 0 °C; 2 h, rt
3.1 Reagents: Triphenylphosphine , Diisopropyl azodicarboxylate Solvents: Tetrahydrofuran ; 0 °C; 15 min, rt; rt → 0 °C
3.2 Solvents: Tetrahydrofuran ; 0 °C; 24 h, rt
3.3 Reagents: Ammonia Solvents: Methanol ; 15 h, rt
4.1 Reagents: Hydrochloric acid Solvents: Methanol , Water ; 0 °C; 18 h, rt
5.1 Reagents: Acetic anhydride , Pyridine ; rt; 18 h, rt
5.2 Reagents: 1H-1,2,4-Triazole , Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 1 h, rt; rt → 0 °C
5.3 Reagents: Triethylamine Solvents: Acetonitrile ; 24 h, rt
5.4 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, rt
5.5 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Design, synthesis and anticancer activity of fluorocyclopentenyl-purines and - pyrimidines

Yoon, Ji-seong; et al, European Journal of Medicinal Chemistry, 2018, 155, 406-417

合成路线：6 步

491577-99-2

865838-26-2

反应条件：

1.1 Reagents: Cerium trichloride , Sodium borohydride Solvents: Methanol ; 1 h, 0 °C
1.2 Reagents: Water
2.1 Reagents: Imidazole Solvents: Dimethylformamide ; rt; overnight, 40 - 50 °C
2.2 Reagents: Water
3.1 Reagents: Butyllithium , N-Fluorobenzenesulfonimide Solvents: Tetrahydrofuran , Hexane ; -78 °C; 1 h, -78 °C
3.2 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; rt; 1 h, rt
4.1 Reagents: Triphenylphosphine , Diisopropyl azodicarboxylate Solvents: Tetrahydrofuran ; 0 °C; 15 min, 0 °C; 12 h, rt
5.1 Reagents: Ammonia Solvents: Methanol ; 3 h, rt
5.2 Reagents: Boron tribromide Solvents: Dichloromethane ; 30 min, -78 °C
5.3 Reagents: Methanol ; 1 h, -78 °C
5.4 Reagents: Pyridine ; neutralized
5.5 Reagents: Acetic anhydride Solvents: Pyridine ; rt; 15 h, rt
5.6 Reagents: Sodium bicarbonate Solvents: Water
6.1 Reagents: Acetic anhydride Solvents: Pyridine ; rt; 15 h, rt
6.2 Reagents: 1H-1,2,4-Triazole , Phosphorus oxychloride Solvents: Acetonitrile ; 0 °C; 5 min, rt
6.3 Reagents: Triethylamine Solvents: Acetonitrile ; 0 °C; 24 h, 30 °C
6.4 Reagents: Triethylamine Solvents: Water ; 10 min
6.5 Reagents: Ammonia Solvents: 1,4-Dioxane , Water ; 16 h, 30 °C
6.6 Reagents: Ammonia Solvents: Methanol ; 15 h, rt

参考文献：

Fluorocyclopentenyl-cytosine with Broad Spectrum and Potent Antitumor Activity

Choi, Won Jun; et al, Journal of Medicinal Chemistry, 2012, 55(9), 4521-4525

合成路线：6 步

491577-99-2

865838-26-2

反应条件：

1.1 Reagents: Cerium trichloride , Sodium borohydride
2.1 Reagents: Imidazole Solvents: Dimethylformamide
3.1 Reagents: Butyllithium , N-Fluorobenzenesulfonimide Solvents: Tetrahydrofuran ; -78 °C
3.2 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
4.1 Reagents: Triphenylphosphine , Diethyl azodicarboxylate
5.1 Reagents: Ammonia Solvents: Methanol
5.2 Reagents: Boron trichloride Solvents: Dichloromethane
6.1 Reagents: Acetic anhydride , Pyridine Solvents: Pyridine ; rt
6.2 Reagents: Triethylamine , 1H-1,2,4-Triazole , Phosphorus oxychloride
6.3 Reagents: Ammonium hydroxide Solvents: 1,4-Dioxane , Water
6.4 Reagents: Ammonia Solvents: Methanol

参考文献：

Design, synthesis, and anticancer activity of fluorocyclopentenyl-pyrimidines

Zhao, Long Xuan; et al, Nucleic Acids Symposium Series, 2005, (49), 107-108

合成路线：7 步

491577-99-2

865838-26-2

反应条件：

1.1 Reagents: Cerium trichloride , Sodium borohydride
2.1 Reagents: Imidazole Solvents: Dimethylformamide
3.1 Reagents: Butyllithium , N-Fluorobenzenesulfonimide Solvents: Tetrahydrofuran ; -78 °C
4.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
5.1 Reagents: Triphenylphosphine , Diethyl azodicarboxylate Solvents: Tetrahydrofuran
6.1 Reagents: Ammonia Solvents: Methanol
6.2 Reagents: Boron trichloride Solvents: Dichloromethane
7.1 Reagents: Acetic anhydride , Pyridine Solvents: Pyridine
7.2 Reagents: Triethylamine , 1H-1,2,4-Triazole , Phosphorus oxychloride
7.3 Reagents: Ammonium hydroxide Solvents: 1,4-Dioxane
7.4 Reagents: Ammonia Solvents: Methanol

参考文献：

Synthesis and Antitumor Activity of Fluorocyclopentenyl-Pyrimidines

Jeong, Lak Shin; et al, Nucleosides, 2007, 26(6-7), 713-716