N⁴-acetyl-1-(2-C-cyano-2-deoxy-β-D-arabinofuranosyl)cytosine | 135598-72-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N⁴-acetyl-1-(2-C-cyano-2-deoxy-β-D-arabinofuranosyl)cytosine
• 英文别名: 1-(2'-cyano-2'-deoxy-β-D-arabinofuranosyl)-N4-acetylcytosine；N-[1-[(2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
• CAS: 135598-72-0
• 化学式: C₁₂H₁₄N₄O₅
• 分子量: 294.267
• InChiKey: ZVJRUYLDONXPQT-GISOBZBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N⁴-acetyl-1-(2-C-cyano-2-deoxy-β-D-arabinofuranosyl)cytosine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以35%的产率得到(2R,3S,4S,5R)-2-(4-氨基-2-氧代嘧啶-1-基)-4-羟基-5-(羟基甲基)四氢呋喃-3-甲腈盐酸盐
  参考文献：
  名称：

  NOVEL STABLE CRYSTAL OF 1-(2'-CYANO-2'-DEOXY-BETA-D-ARABINOFURANOSYL)CYTOSINE MONOHYDROCHLORIDE

  摘要：

  揭示了1-(2′-氰基-2′-脱氧-β-D-阿拉伯呋喃核糖基)胞嘧啶单盐酸盐的稳定晶体。提供了一种1-(2′-氰基-2′-脱氧-β-D-阿拉伯呋喃核糖基)胞嘧啶单盐酸盐的晶体，其在粉末X射线衍射中的特征峰为13.7°、15.7°、16.0°、18.6°、20.3°和22.7°（2θ±0.1°），熔点为192°C至197°C。

  公开号：

  US20120029182A1
• 作为产物：
  描述：

  N-[1-[(8R,9S,9aS)-9-cyano-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxopyrimidin-4-yl]acetamide 以84的产率得到N⁴-acetyl-1-(2-C-cyano-2-deoxy-β-D-arabinofuranosyl)cytosine
  参考文献：
  名称：

  J. Med. Chem. 1993, 36, 4183-4189

  摘要：

  DOI：

文献信息

• PREPARATION OF INTERMEDIATES USEFUL IN THE SYNTHESIS OF 2'-CYANO-2'-DEOXY-N4-PALMI-TOYL-1-BETA-D-ARABINOFURANOSYLCYTOSINE
  申请人：Wood Gavin

  公开号：US20110224421A1

  公开（公告）日：2011-09-15

  The present invention relates to a process for preparing a compound of formula 682-4, said process comprising the steps of: (i) converting a compound of formula 682-1 into a compound of formula 682-2; (ii) converting said compound of formula 682-2′ into a compound of formula 682-3; and (iii) converting said compound of formula 682-3 into a compound of formula 682-4. Further aspects of the invention relate to the use of the above process in the preparation of 2′-cyano-2′-deoxy-N 4 -palmitoyl-1-β-D-arabmofuranosylcytosine, a pyrimidine nucleoside which is therapeutically useful in the treatment and/or prevention of cancer.

  本发明涉及一种制备式682-4化合物的方法，该方法包括以下步骤：（i）将式682-1化合物转化为式682-2化合物；（ii）将式682-2化合物转化为式682-3化合物；以及（iii）将式682-3化合物转化为式682-4化合物。本发明的其他方面涉及上述方法在制备2'-氰基-2'-脱氧-N4-棕榈酰-1-β-D-阿拉伯呋喃糖基胞嘧啶中的应用，该嘧啶核苷在治疗和/或预防癌症方面具有治疗作用。
• Azuma; Nakajima; Nishizono, Journal of Medicinal Chemistry, 1993, vol. 36, # 26, p. 4183 - 4189
  作者：Azuma、Nakajima、Nishizono、Minakawa、Suzuki、Hanaoka、Kobayashi、Tanaka、Sasaki、Matsuda

  DOI：——

  日期：——
• Nucleosides and nucleotides. 100. 2'-C-Cyano-2'-deoxy-1-.beta.-D-arabinofuranosylcytosine (CNDAC): design of a potential mechanism-based DNA-strand-breaking antineoplastic nucleoside
  作者：Akira Matsuda、Yuki Nakajima、Atsushi Azuma、Motohiro Tanaka、Takuma Sasaki

  DOI：10.1021/jm00113a034

  日期：1991.9
• PREPARATION OF INTERMEDIATES USEFUL IN THE SYNTHESIS OF 2'-CYANO-2'-DEOXY-N4-PALMITOYL-1-BETA-D-ARABINOFURANOSYLCYTOSINE
  申请人：Cyclacel Limited

  公开号：EP2291193B1

  公开（公告）日：2018-08-08
• Combination of a Cdk Inhibitor and Cs-682 or a Metabolite Thereof
  申请人：Green Richard Simon

  公开号：US20070270442A1

  公开（公告）日：2007-11-22

  A first aspect of the invention relates to a combination comprising a CDK inhibitor and 1-(2-C-cyano-2-dioxy-β-D-arabino-pentofuranosyl)-N4-palmitoyl cytosine, or a metabolite thereof. A second aspect of the invention relates to a pharmaceutical product comprising a CDK inhibitor and 1-(2-C-cyano-2-dioxy-β-D-arabino-pentofuranosyl)-N4-palmitoyl cytosine, or a metabolite thereof, as a combined preparation for simultaneous, sequential or separate use in therapy. A third aspect of the invention relates to a method of treating a proliferative disorder, said method comprising simultaneously, sequentially or separately administering a CDK inhibitor and 1-(2-C-cyano-2-dioxy-β-D-arabino-pentofuranosyl)-N4-palmitoyl cytosine, or a metabolite thereof, to a subject.