Clofarabine

CAT#: H100180

CAS#: 123318-82-1


Description: 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.

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Synthetic Routes

Clofarabine - Synthetic Route 1

Clofarabine route01

Synthetic reference

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

Clofarabine - Synthetic Route 2

Clofarabine route02

Synthetic reference

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

Clofarabine - Synthetic Route 3

Clofarabine route03

Synthetic reference

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

Clofarabine - Synthetic Route 4

Clofarabine route04

Synthetic reference

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

Clofarabine - Synthetic Route 5

Clofarabine route05

Synthetic reference

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

Clofarabine - Synthetic Route 6

Clofarabine route06

Synthetic reference

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

Clofarabine - Synthetic Route 7

Clofarabine route07

Synthetic reference

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

Clofarabine - Synthetic Route 8

Clofarabine route08

Synthetic reference

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

Clofarabine - Synthetic Route 9

Clofarabine route09

Synthetic reference

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