Diethyl 2',3'-O-isopropylidenecytidine 5'-phosphate | 89539-20-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Diethyl 2',3'-O-isopropylidenecytidine 5'-phosphate
• 英文别名: (6-(4-amino-2-oxopyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl diethyl phosphate；[(3aR,4R,6R,6aR)-4-(4-amino-2-oxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl diethyl phosphate
• CAS: 89539-20-8
• 化学式: C₁₆H₂₆N₃O₈P
• 分子量: 419.371
• InChiKey: WGWFUZJMQWKZAY-FMKGYKFTSA-N

物化性质

• 沸点：
  534.5±60.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Diethyl 2',3'-O-isopropylidenecytidine 5'-phosphate 在 甲酸 、 羟胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 132.0h， 生成
  参考文献：
  名称：

  [EN] N4-HYDROXYCYTIDINE AND DERIVATIVES AND ANTI-VIRAL USES RELATED THERETO
  [FR] N4-HYDROXYCYTIDINE, SES DÉRIVÉS ET UTILISATIONS ANTI-VIRALES

  摘要：

  这项披露涉及N4-羟基胞嘧啶衍生物、组合物以及相关方法。在某些实施方式中，该披露涉及治疗和预防病毒感染。

  公开号：

  WO2016106050A1
• 作为产物：
  描述：

  胞苷 在 吡啶 、 硫酸 作用下， 反应 1.0h， 生成 Diethyl 2',3'-O-isopropylidenecytidine 5'-phosphate
  参考文献：
  名称：

  [EN] N4-HYDROXYCYTIDINE AND DERIVATIVES AND ANTI-VIRAL USES RELATED THERETO
  [FR] N4-HYDROXYCYTIDINE, SES DÉRIVÉS ET UTILISATIONS ANTI-VIRALES

  摘要：

  这项披露涉及N4-羟基胞嘧啶衍生物、组合物以及相关方法。在某些实施方式中，该披露涉及治疗和预防病毒感染。

  公开号：

  WO2016106050A1

文献信息

• [EN] N4-HYDROXYCYTIDINE AND DERIVATIVES AND ANTI-VIRAL USES RELATED THERETO<br/>[FR] N4-HYDROXYCYTIDINE ET DÉRIVÉS ET LEURS UTILISATIONS ANTI-VIRALES
  申请人：UNIV EMORY

  公开号：WO2017156380A1

  公开（公告）日：2017-09-14

  This disclosure relates to certain N4-hydroxycytidine derivatives, compositions, and methods related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of a Zika virus infection.

  这项披露涉及某些N4-羟基胞嘧啶衍生物，相关组合物和方法。在某些实施例中，该披露涉及治疗或预防寨卡病毒感染。
• Novel Cytidine-Based Orotidine-5′-Monophosphate Decarboxylase Inhibitors with an Unusual Twist
  作者：Meena K. Purohit、Ewa Poduch、Lianhu William Wei、Ian Edward Crandall、Terrence To、Kevin C. Kain、Emil F. Pai、Lakshmi P. Kotra

  DOI：10.1021/jm301176r

  日期：2012.11.26

  Orotidine-5'-monophosphate decarboxylase (ODCase) is an interesting enzyme with an unusual catalytic activity and a potential drug target in Plasmodium falciparum, which causes malaria. ODCase has been shown to exhibit unusual and interesting interactions with a variety of nucleotide ligands. Cytidine-5'-monophosphate (CMP) is a poor ligand of ODCase, and CMP binds to the active site of ODCase with an unusual orientation and conformation. We designed N3- and N4-modified CMP derivatives as novel ligands to ODCase. These novel CMP derivatives and their corresponding nucleosides were evaluated against Plasmodium falciparum ODCase and parasitic cultures, respectively. These derivatives exhibited improved inhibition of the enzyme catalytic activity displayed interesting binding conformations and unusual molecular rearrangements of the ligands. These findings with the modified CMP nucleotides underscored the potential of transformation of poor ligands to ODCase into novel inhibitors of this drug target.
• Chemoselective phosphorylation of -unprotected nucleosides via aluminum alkoxides
  作者：Y. Hayakawa、Y. Aso、M. Uchiyama、R. Noyori

  DOI：10.1016/s0040-4039(00)94162-5

  日期：1983.1
• O-selective phosphorylation of nucleosides without N-protection
  作者：Mamoru Uchiyama、Yoshio Aso、Ryoji Noyori、Yoshihiro Hayakawa

  DOI：10.1021/jo00054a020

  日期：1993.1

  A facile chemoselective O-phosphorylation of N-unprotected nucleosides has been achieved via metal alkoxide formation. Sequential treatment of N-unprotected nucleosides with an equimolar amount of a metallo-organic base such as an alkyllithium, potassium tert-butoxide, tert-butylmagnesium chloride, LiAl[N(CH3)2]4, Al[N(CH3)2]3, (i-C4H9)2AlH, etc., and a phosphorochloridate or p-nitrophenyl phosphate results in rapid O-phosphorylation to give the corresponding nucleotides in high yield. The method using magnesium alkoxides is among the best, considering its chemoselectivity, generality, and operational simplicity. The origin of the observed chemoselectivity is discussed.