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ChemicalBook CAS DataBase List Clofarabine
123318-82-1

Clofarabine synthesis

12synthesis methods
Clofarabine is a second generation purine nucleoside analog with antineoplastic activity. Clofarabine is phosphorylated intracellularly to the cytotoxic active 5'-triphosphate metabolite, which inhibits the enzymatic activities of ribonucleotide reductase and DNA polymerase, resulting in inhibition of DNA repair and synthesis of DNA and RNA. This nucleoside analog also disrupts mitochondrial function and membrane integrity, resulting in the release of pre-apoptotic factors, including cytochrome C and apoptotic-inducing factor, which activate apoptosis.
Synthetic Routes
  • ROUTE 1

    • Clofarabine synthesis

    Cen, Yana; Sauve, Anthony A. Efficient Syntheses of Clofarabine and Gemcitabine From 2-Deoxyribonolactone. Nucleosides, Nucleotides & Nucleic Acids. Department of Pharmacology. Weill Medical College of Cornell University. New York, USA. Volume 29. Issue 2. Pages 113-122. 2010

  • ROUTE 2

    • Clofarabine synthesis

    Bauta, William E.; Schulmeier, Brian E.; Burke, Brian; Puente, Jose F.; Cantrell, William R., Jr.; Lovett, Dennis; Goebel, James; Anderson, Bruce; Ionescu, Dumitru; Guo, Ruichao. A New Process for Antineoplastic Agent Clofarabine. Organic Process Research & Development. Department of Process Chemistry and Department of Analytical Chemistry. ILEX Products, Inc. San Antonio, USA 78245. Volume 8. Issue 6. Pages 889-896. 2004

  • ROUTE 3

    • Clofarabine synthesis

    Fateev, Ilja V.; Antonov, Konstantin V.; Konstantinova, Irina D.; Muravyova, Tatyana I.; Seela, Frank; Esipov, Roman S.; Miroshnikov, Anatoly I.; Mikhailopulo, Igor A. The chemoenzymic synthesis of clofarabine and related 2'-deoxyfluoroarabinosyl nucleosides: the electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases. Beilstein Journal of Organic Chemistry. Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry. Russian Academy of Sciences. Moscow, Russia. Volume 10. Pages 1657-1669, 13 pp. 2014

  • ROUTE 4

    • Clofarabine synthesis

    Montgomery, John A.; Shortnacy-Fowler, Anita T.; Clayton, Sarah D.; Riordan, James M.; Secrist, John A., III. Synthesis and biological activity of 2'-fluoro-2-halo derivatives of 9-β-D-arabinofuranosyladenine. Journal of Medicinal Chemistry. South. Res. Inst. Birmingham, USA 35255-5305. Volume 35. Issue 2. Pages 397-401. 1992

  • ROUTE 5

    • Clofarabine synthesis

    Chen, Yunhua; Yang, Weiqiang; Bai, Hua. Synthesis of clofarabine. Zhongguo Yiyao Gongye Zazhi. Taizhou Vocational and Technical College. Taizhou, Zhejiang Province, Peop. Rep. China 318000 Volume 42. Issue 6. Pages 404-407. 2011

  • ROUTE 6

    • Clofarabine synthesis

    Ding, Haixin; Li, Chuang; Zhou, Yirong; Hong, Sanguo; Zhang, Ning; Xiao, Qiang. Stereoselective synthesis of 2'-modified nucleosides by using ortho-alkynyl benzoate as a gold(I)-catalyzed removable neighboring participation group. RSC Advances. Department of Chemistry. Nanchang University. Jiangxi, Peop. Rep. China 330031. Volume 7. Issue 4. Pages 1814-1817. 2017

  • ROUTE 7

    • Clofarabine synthesis

    Chai, Yuzhu; Niu, Ben; Lu, Yazhou; Zhu, Xianfeng; Chen, Yanbo. Synthesis of antileukemia drug clofarabine. Huagong Shikan. Volume 24. Issue 8. Pages 36-38. 2010. Medical Research Institute. Jiangsu Jumpcan Pharmaceutical Co., Ltd. Taixing, Peop. Rep. China 225441

  • ROUTE 8

    • Clofarabine synthesis

    Sauve, Anthony A.; Cen, Yana. Preparation and SirT activity of halogenated 2-deoxy-lactones, 2'-deoxy-D-nucleosides. Assignee Cornell University, USA. WO 2011003018. 2011

  • ROUTE 9

    • Clofarabine synthesis

    Zabudkin, Alexander; Matvienko, Victor; Matviienko, Iaroslav; Sypchenko, Volodymyr. Chemoenzymic synthesis of clofarabine. Assignee Synbias Pharma AG, Switz. WO 2015162175. 2015

Clofarabine synthesis

Cen, Yana; Sauve, Anthony A. Efficient Syntheses of Clofarabine and Gemcitabine From 2-Deoxyribonolactone. Nucleosides, Nucleotides & Nucleic Acids. Department of Pharmacology. Weill Medical College of Cornell University. New York, USA. Volume 29. Issue 2. Pages 113-122. 2010

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Yield:123318-82-1 95.41%

Reaction Conditions:

with methanol;sodium methylate at 15 - 20; for 2 h;

Steps:

2

The last step intermediate obtained clofarabine added 10mL of anhydrous methanol,After stirring, NaOCH3 / CH3OH solution (193.41mg dissolved in 2mL anhydrous methanol) was added, and the mixture was stirred at 15-20 for 2h. The reaction was complete by TLC. After completion of the reaction, the insoluble matter was removed by filtration, and a large amount of solid was precipitated from the filtrate. The pH was adjusted to 6.5 to 7.5 by adding acetic acid under stirring. After adjustment, the mixture was stirred at room temperature for 30 minutes, filtered and the cake was washed with a small amount of cold methanol to obtain clofarabine, which was vacuum dried at 50C to obtain 1.73 g of clofarabine product in a yield of 95.41%. Result of liquid phase: 99.85%.

References:

CN105601688,2016,A Location in patent:Paragraph 0049- 0058

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