C-3'-deoxycytidine | 74560-43-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: C-3'-deoxycytidine
• 英文别名: (+/-)-4-amino-1-<(1α,2β,4α)-2-hydroxy-4-(hydroxymethyl)cyclopentyl>-2-(1H)pyrimidinone；4-amino-1-[(1R,2R,4S)-2-hydroxy-4-(hydroxymethyl)cyclopentyl]pyrimidin-2-one
• CAS: 74560-43-3
• 化学式: C₁₀H₁₅N₃O₃
• 分子量: 225.247
• InChiKey: ADZISMWWECFDDR-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  C-3'-deoxycytidine 在 氢碘酸 、 碘 、 溶剂黄146 作用下， 以 四氯化碳 、 水 为溶剂， 反应 6.0h， 以43%的产率得到C-5-iodo-3'-deoxycytidine
  参考文献：
  名称：

  Carbocyclic analogs of 5-halocytosine nucleosides

  摘要：

  Carbocyclic analogues of 5-halocytosine nucleosides were prepared by direct halogenation of the carbocyclic analogues of cytidine, 2'-deoxycytidine, 3'-deoxycytidine, or ara-C. The 5-chloro and 5-bromo derivatives of the cytidine (carbodine) and of the 2'-deoxycytidine analogues and the 5-iodo derivatives of all four of the cytosine nucleoside analogues were prepared. All of the C-5-halocytosine nucleosides, as well as the parent C-cytosine nucleosides, were tested against a strain of herpes simplex virus type 1 (HSV-1) that induces thymidine kinase in host cells. Carbodine, 5-bromocarbodine, C-2'-deoxycytidine, C-5-bromo-2'-deoxycytidine, the four C-5-iodocytosine nucleosides, and C-ara-C inhibited replication of this strain of HSV-1 in cultured cells. Most of these compounds were tested also against the type 2 virus (HSV-2) in vitro and were active. The greatest activity observed was exerted by C-5-iodo-2'-deoxycytidine in inhibiting replication of HSV-1 in L929 cells. In tests against these DNA viruses, carbodine, a ribofuranoside analogue that had been shown previously to be highly active against human influenza A virus in vitro, was the most active compound against HSV-2 and one of the most active compounds against HSV-1 in Vero cells. 5-Bromocarbodine was active against influenza virus, but it was less active than carbodine.

  DOI：

  10.1021/jm00159a026
• 作为产物：
  描述：

  (+/-)-1-<(1β,2α,4β)-2-hydroxy-4-(hydroxymethyl)cyclopentyl>-2,4-(1H,3H)-pyrimidinedione 在 盐酸 、 氯化亚砜 、 氨 作用下， 反应 86.0h， 生成 C-3'-deoxycytidine
  参考文献：
  名称：

  胞嘧啶核苷的碳环类似物

  摘要：

  由类似的尿嘧啶衍生物合成了胞苷，2'-脱氧胞苷和3'-脱氧胞苷的碳环类似物。该途径包括尿嘧啶衍生物的完全苯甲酰化，选择性除去连接在嘧啶环上的苯甲酰基，用二甲基甲酰胺-亚硫酰氯试剂将4-氧代转化为4-氯基以及用氯代氨酯取代氯基。甲醇氨中的氨基 当使用脱氧氯化反应的总产物时，所需的胞嘧啶衍生物常常伴随着少量的相应的N，N-二甲基胞嘧啶衍生物，可以通过离子交换色谱法除去。从纯的4-氯嘧啶酮中间体通过在四氯化碳中进行脱氧氯化制备后，以84％的收率获得了胞嘧啶核苷的类似物卡铂（VIa）。卡博定具有抗白血病，抗病毒和抗菌活性。

  DOI：

  10.1002/jhet.5570170228

文献信息

• Carbocyclic analogs of cytosine nucleosides
  作者：Y. Fulmer Shealy、C. Allen O'Dell

  DOI：10.1002/jhet.5570170228

  日期：1980.3

  cytosine derivatives were frequently accompanied by small amounts of the corresponding N,N-dimethylcytosine derivatives, which could be removed by ion-exchange chromatography. Carbodine (VIa), the carbocyclic analog of cytidine, was obtained in 84% yield from the pure 4-chloropyrimidinone intermediate, after the latter was prepared by deoxychlorination in carbon tetrachloride. Carbodine has antileukemic

  由类似的尿嘧啶衍生物合成了胞苷，2'-脱氧胞苷和3'-脱氧胞苷的碳环类似物。该途径包括尿嘧啶衍生物的完全苯甲酰化，选择性除去连接在嘧啶环上的苯甲酰基，用二甲基甲酰胺-亚硫酰氯试剂将4-氧代转化为4-氯基以及用氯代氨酯取代氯基。甲醇氨中的氨基 当使用脱氧氯化反应的总产物时，所需的胞嘧啶衍生物常常伴随着少量的相应的N，N-二甲基胞嘧啶衍生物，可以通过离子交换色谱法除去。从纯的4-氯嘧啶酮中间体通过在四氯化碳中进行脱氧氯化制备后，以84％的收率获得了胞嘧啶核苷的类似物卡铂（VIa）。卡博定具有抗白血病，抗病毒和抗菌活性。
• Carbocyclic analogs of 5-halocytosine nucleosides
  作者：Y. Fulmer Shealy、C. Allen O'Dell、Gussie Arnett、William M. Shannon、Martha C. Thorpe、James M. Riordan、William C. Coburn

  DOI：10.1021/jm00159a026

  日期：1986.9

  Carbocyclic analogues of 5-halocytosine nucleosides were prepared by direct halogenation of the carbocyclic analogues of cytidine, 2'-deoxycytidine, 3'-deoxycytidine, or ara-C. The 5-chloro and 5-bromo derivatives of the cytidine (carbodine) and of the 2'-deoxycytidine analogues and the 5-iodo derivatives of all four of the cytosine nucleoside analogues were prepared. All of the C-5-halocytosine nucleosides, as well as the parent C-cytosine nucleosides, were tested against a strain of herpes simplex virus type 1 (HSV-1) that induces thymidine kinase in host cells. Carbodine, 5-bromocarbodine, C-2'-deoxycytidine, C-5-bromo-2'-deoxycytidine, the four C-5-iodocytosine nucleosides, and C-ara-C inhibited replication of this strain of HSV-1 in cultured cells. Most of these compounds were tested also against the type 2 virus (HSV-2) in vitro and were active. The greatest activity observed was exerted by C-5-iodo-2'-deoxycytidine in inhibiting replication of HSV-1 in L929 cells. In tests against these DNA viruses, carbodine, a ribofuranoside analogue that had been shown previously to be highly active against human influenza A virus in vitro, was the most active compound against HSV-2 and one of the most active compounds against HSV-1 in Vero cells. 5-Bromocarbodine was active against influenza virus, but it was less active than carbodine.