4-(N)-palmitoyl cytidine | 60107-19-9

• 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: 4-(N)-palmitoyl cytidine
• 英文别名: N4-palmitoylcytidine；N-Hexadecanoylcytidine；N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]hexadecanamide
• CAS: 60107-19-9
• 化学式: C₂₅H₄₃N₃O₆
• 分子量: 481.633
• InChiKey: XEFNBUBDJCJOGM-OTUUDDROSA-N

物化性质

• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  34
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 、 4-(N)-palmitoyl cytidine 在 1,3二氯-1,1,3,3-四异丙基二硅氧烷 作用下， 生成 N-[1-[(6aR,8R,9R,9aS)-9-hydroxy-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]hexadecanamide
  参考文献：
  名称：

  Pyrimidine nucleoside derivatives having anti-tumor activity, their preparation and use

  摘要：

  式子（I）的化合物：[其中：R¹、R²和R³相同或不同，每个代表氢原子、可选取代的脂肪酰基团或烯基羰基团，前提是至少有一个R¹、R²和R³代表有5到24个碳原子的未取代脂肪酰基团，或者是所述取代的脂肪酰基团或所述烯基羰基团；R⁴和R⁵中的一个代表氢原子，另一个代表氰基]，具有有价值的抗肿瘤活性。

  公开号：

  EP0536936A1
• 作为产物：
  描述：

  棕榈酸 在 N-甲基吗啉 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-(N)-palmitoyl cytidine
  参考文献：
  名称：

  Gelation properties of self-assembling N-acyl modified cytidine derivatives

  摘要：

  一个含有胞嘧啶的自组装凝胶体的新设计，其中包含有机溶剂和水的二元混合物，被证明为高分子量和低分子量分子提供了合适的传递平台。

  DOI：

  10.1039/c4tb01375a

文献信息

• Pyrimidine nucleoside derivatives having anti-tumor activity, their
  申请人：Sankyo Company, Limited

  公开号：US05691319A1

  公开（公告）日：1997-11-25

  Compounds of formula (I): ##STR1## wherein: R.sup.1, R.sup.2 and R.sup.3 are independently selected from the group consisting of hydrogen atoms, optionally substituted alkanoyl groups and alkenylcarbonyl groups, PROVIDED THAT at least one of R.sup.1, R.sup.2 and R.sup.3 represents an unsubstituted alkanoyl group having from 5 to 24 carbon atoms, said substituted alkanoyl group or said alkenylcarbonyl group; and one of R.sup.4 and R.sup.5 represents a hydrogen atom and the other represents a cyano group; have valuable anti-tumor activity.

  化合物的化学式（I）：##STR1##其中：R.sup.1、R.sup.2和R.sup.3分别选自氢原子、可选择取代的烷酰基团和烯基羰基团的组，前提是R.sup.1、R.sup.2和R.sup.3中至少有一个代表具有5至24个碳原子的未取代烷酰基团，所述取代烷酰基团或所述烯基羰基团；R.sup.4和R.sup.5中的一个代表氢原子，另一个代表氰基；具有有价值的抗肿瘤活性。
• Cytidine nucleotide derivatives
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US04086417A1

  公开（公告）日：1978-04-25

  A nucleotide derivative represented by the general formula: ##STR1## wherein R represents an acyl group having 14 - 22 carbon atoms and having an aliphatic acyl moiety; X represents a hydrogen atom, a halogen atom, an alkyl group having 1 - 4 carbon atoms, or a trifluoromethyl group; and at least one, but not all, of Y.sub.1, Y.sub.2, and Y.sub.3 represents a phosphate, a pyrophosphate, a triphosphate, or a salt thereof, the balance of Y.sub.1, Y.sub.2 and Y.sub.3 representing a hydroxyl group; or in case of ribosyl, Y.sub.1 and Y.sub.3, or Y.sub.2 and Y.sub.3 represent, at the same time, the aforesaid phosphate, pyrophosphate, triphosphate or salt thereof and the remaining group of Y.sub.1, Y.sub.2 or Y.sub.3 represents a hydroxyl group; or in case of arabinosyl, Y.sub.1 and Y.sub.2, or Y.sub.2 and Y.sub.3 represent, at the same time, the aforesaid phosphate, pyrophosphate, triphosphate or salt therof and the remaining group of Y.sub.1, Y.sub.2 or Y.sub.3 represents a hydroxyl group. The nontoxic salts of these phosphates are useful as an antileukemialagent for mice which is soluble in water and has high stability.

  一种核苷酸衍生物，其通式表示为：##STR1## 其中R代表具有14-22个碳原子和具有脂肪族酰基的酰基基团；X代表氢原子、卤素原子、具有1-4个碳原子的烷基基团或三氟甲基基团；至少一个但不是全部的Y.sub.1、Y.sub.2和Y.sub.3代表磷酸盐、焦磷酸盐、三磷酸盐或其盐，Y.sub.1、Y.sub.2和Y.sub.3的平衡代表羟基；在核糖基的情况下，Y.sub.1和Y.sub.3，或者Y.sub.2和Y.sub.3同时代表上述磷酸盐、焦磷酸盐、三磷酸盐或其盐，而Y.sub.1、Y.sub.2或Y.sub.3的其余基团代表羟基；在阿拉伯糖基的情况下，Y.sub.1和Y.sub.2，或者Y.sub.2和Y.sub.3同时代表上述磷酸盐、焦磷酸盐、三磷酸盐或其盐，而Y.sub.1、Y.sub.2或Y.sub.3的其余基团代表羟基。这些磷酸盐的无毒盐在水中溶解并具有高稳定性，可用作小鼠的抗白血病剂。
• 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。
• Preparation of intermediates useful in the synthesis of 2′-cyano-2′-deoxy-N4-palmi-toyl-1-β-D-arabinofuranosylcytosine
  申请人：Wood Gavin

  公开号：US08884001B2

  公开（公告）日：2014-11-11

  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-N4-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化合物的过程，该过程包括以下步骤：(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过程在制备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。
• Gelation properties of self-assembling N-acyl modified cytidine derivatives
  作者：K. J. Skilling、A. Ndungu、B. Kellam、M. Ashford、T. D. Bradshaw、M. Marlow

  DOI：10.1039/c4tb01375a

  日期：——

  A new design for a self-assembling gelator of cytidine containing a binary mixture of organic solvent and water, shown to provide a suitable delivery platform for high and lowM_wmolecules.

  一个含有胞嘧啶的自组装凝胶体的新设计，其中包含有机溶剂和水的二元混合物，被证明为高分子量和低分子量分子提供了合适的传递平台。