N⁴-palmitoyl-2',3'-dideoxycytidine-5'-monophosphate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N⁴-palmitoyl-2',3'-dideoxycytidine-5'-monophosphate
• 英文别名: [(2s,5r)-5-[4-(Hexadecanoylamino)-2-oxo-pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl dihydrogen phosphate；[(2S,5R)-5-[4-(hexadecanoylamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate
• 化学式: C₂₅H₄₄N₃O₇P
• 分子量: 529.614
• InChiKey: DANRWCHAADIUTO-XUZZJYLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N⁴-palmitoyl-2',3'-dideoxycytidine 在 磷酸三甲酯 、 三氯氧磷 作用下， 反应 2.0h， 生成 N⁴-palmitoyl-2',3'-dideoxycytidine-5'-monophosphate
  参考文献：
  名称：

  Synthesis and in vitro anti-HIV activities of amphiphilic heterodinucleoside phosphate derivatives containing the 2',3'-dideoxynucleosides ddC, AZT and ddI

  摘要：

  N-4-Palmitoyl-2',3'-dideoxycytidine-5'-hydrogenphosphonate was condensed with 2',3'-dideoxyinosine (ddI) and 3'-azido-2',3'-dideoxythymidine (AZT) to the amphiphilic heterodimers 2',3'-dideoxyinosinylyl-(5'-->5')-N-4-palmitoyl-2',3'-dideoxycytidine (2) and 3'-azido-2',3'-dideoxythymidylyl-(5'-->5') 2',3'-dideoxycytidine (3) which was also converted to the hydrophilic heterodimer 3'-azido-2',3'-dideoxythymidylyl-(5'-->5')-2',3'-dideoxycytidine (3a). The heterodimers exhibit strong activity against HIV wild type and an AZT-resistant virus variant. The anti-HIV activity of 3 combining AZT with pN(4)-pamddC was lower than that of 2'-deoxythymidylyl-(3'-->5')-N-4-palmitoyl-2',3'-dideoxycytidine (4) linking pN(4)-pamddC as the only antiviral monomer unit to the inactive thymidine. It is expected that the anti-HIV activities and selectivities of ddNs can be varied by their dimerization to heterodimers offering the prospect of new therapeutic modalities. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80084-1

文献信息

• Amphiphilic nucleosidephosphate analogues
  申请人：——

  公开号：US05679652A1

  公开（公告）日：1997-10-21

  Amphiphilic nucleoside phosphate analogues of formula I ##STR1## wherein R.sup.1 denotes a hydroxyl or amino group or an acylated or alkylated or polyoxyethylene-substituted amino group, the acyl or alkyl group of which is straight-chained or branched, has 1 to 24 carbon atoms and up to 2 double bonds and may be substituted by an aromatic group; R.sup.2 denotes H, F, a 2-bromo vinyl group or a straight-chained or branched C.sub.1-24 -alkyl group; R.sup.3 and R.sup.4 are identical or different and denote H, hydroxyl, halogen and azido; R.sup.5 denotes a nucleoside group of formula II ##STR2## wherein R.sup.6 denotes a hydroxyl or amino group or an acylated or alkalized amino group, the acyl or alkyl group of which is straight-chained or branched, contains 1 to 24 carbon atoms and up to 2 double bonds and may be substituted by an aromatic group, whilst R.sup.6 and R.sup.1 are different and one of the groups denotes acylamino or alkylamino groups having 12 to 24 carbon atoms, R.sup.1, R.sup.2, R.sup.6 and R.sup.7 are selected so that, together, they impart an amphiphilic nature to a dinucleotide phosphate analogue; and the corresponding salts of the acid forms of these compounds.

  公式I的两性亲合性核苷酸磷酸类似物，其中R.sup.1表示羟基或氨基或酰化或烷基化或聚氧乙烯取代的氨基基团，其酰基或烷基基团是直链或支链，具有1到24个碳原子和最多2个双键，并且可以被芳香基团取代; R.sup.2表示H，F，2-溴乙烯基团或直链或支链C.sub.1-24-烷基基团; R.sup.3和R.sup.4相同或不同，表示H，羟基，卤素和偶氮基; R.sup.5表示公式II的核苷酸基团##STR2##其中R.sup.6表示羟基或氨基或酰化或烷基化的氨基基团，其酰基或烷基基团是直链或支链，含有1到24个碳原子和最多2个双键，并且可以被芳香基团取代，而R.sup.6和R.sup.1不同，其中一个基团表示具有12到24个碳原子的酰基氨基或烷基氨基基团，R.sup.1，R.sup.2，R.sup.6和R.sup.7被选择为，它们共同赋予二核苷酸磷酸类似物一个两性亲合性的性质;以及这些化合物的酸形式的对应盐。
• AMPHIPHILE NUCLEOSIDPHOSPHATANALOGA
  申请人：SCHOTT, Herbert

  公开号：EP0642527B1

  公开（公告）日：1996-01-10