1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxy-4-iminopyrimidin-2-one | 3310-47-2

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: 1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxy-4-iminopyrimidin-2-one
• 英文别名: 4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-pyrimidin-2-one-3-oxide；4-amino-1-(3,4-dihydroxy-5-hydroxymethyltetrahydrofuran-2-yl)pyrimidin-2(1H)-one 3-oxide；Cytidine N³-oxide；cytidine-N³-oxide；cytidine 3-oxide；cytidine N₃-oxide
• CAS: 3310-47-2
• 化学式: C₉H₁₃N₃O₆
• 分子量: 259.219
• InChiKey: GFFPFDZXIVTAHU-XVFCMESISA-N

物化性质

• 熔点：
  263-269 °C (decomp)(Solv: methanol (67-56-1))
• 沸点：
  607.8±65.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.32
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  144.88
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxy-4-iminopyrimidin-2-one 在 甲醇 、 phosphate buffer 、 lithium hydride 作用下， 以 甲醇 为溶剂， 生成 1-(3,4-dihydroxy-5-hydroxymethyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 4-(O-benzyloxime)
  参考文献：
  名称：

  15 N 3-标记的胞嘧啶核苷的一种新的高效合成方法：胞苷N 3-氧化物的Dimroth重排

  摘要：

  在三个反应步骤中，由苄基溴在过量甲醇甲醇存在下，处理由适当的未保护尿苷制备的15 N 4标记的胞苷N 3-氧化物和15 N 4标记的2'-脱氧胞苷N 3-氧化物即使在温和的条件下，其Dimroth重排的顺利发生也导致相应的15 N 3标记的尿苷4- O-苄基肟，它们很容易经历还原性N - O键断裂，得到所需的15 N 3标记的胞嘧啶核苷具有很高的总收率。

  DOI：

  10.1021/jo0486241
• 作为产物：
  描述：

  胞苷 在 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 以86%的产率得到1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxy-4-iminopyrimidin-2-one
  参考文献：
  名称：

  15 N 3-标记的胞嘧啶核苷的一种新的高效合成方法：胞苷N 3-氧化物的Dimroth重排

  摘要：

  在三个反应步骤中，由苄基溴在过量甲醇甲醇存在下，处理由适当的未保护尿苷制备的15 N 4标记的胞苷N 3-氧化物和15 N 4标记的2'-脱氧胞苷N 3-氧化物即使在温和的条件下，其Dimroth重排的顺利发生也导致相应的15 N 3标记的尿苷4- O-苄基肟，它们很容易经历还原性N - O键断裂，得到所需的15 N 3标记的胞嘧啶核苷具有很高的总收率。

  DOI：

  10.1021/jo0486241

文献信息

• [EN] PURINE AND PYRIMIDINE NUCLEOTIDES AS ECTO-5'-NUCLEOTIDASE INHIBITORS<br/>[FR] NUCLÉOTIDES DE PURINE ET DE PYRIMIDINE EN TANT QU'INHIBITEURS DE L'ECTO-5'-NUCLÉOTIDASE
  申请人：US HEALTH

  公开号：WO2020037275A1

  公开（公告）日：2020-02-20

  Disclosed is a compound of formula (I), wherein Q, U, T, A, a, b, c, and n are as defined herein. Also disclosed are methods of inhibiting ecto‑5'‑nucleotidase, inhibiting suppression of an antitumor immune response, inhibiting tumor growth of a cancerous tumor, inhibiting metastasis of cancer in a mammal afflicted with cancer, synergistically enhancing a response of a mammal afflicted with cancer undergoing treatment with an immunotherapeutic anti‑cancer agent, potentiating an activity of an inhibitor of nicotinamide phosphoribosyltransferase in a mammal undergoing treatment of a mammal with the inhibitor, and treating preeclampsia in a mammal in need thereof, comprising administering to an animal an effective amount of a compound of formula (I).

  揭示了一种具有式（I）的化合物，其中Q、U、T、A、a、b、c和n的定义如本文所述。还揭示了抑制外源性5'-核苷酸酶、抑制抗肿瘤免疫应答抑制、抑制癌症肿瘤生长、抑制哺乳动物患有癌症的转移、在接受免疫治疗抗癌剂治疗的患有癌症的哺乳动物的反应协同增强、在接受抑制剂治疗的哺乳动物中增强烟酰胺磷酸核糖转移酶的活性、以及治疗患有妊高症的哺乳动物的方法，包括向动物投与式（I）化合物的有效量。
• Oxidation of Cytosine and 5-Methylcytosine Nucleosides and 5-Methyl-2′-deoxycytidine 5′-Monophosphate with Peroxosulfate Ions
  作者：Toshio Itahara

  DOI：10.1246/cl.1991.1591

  日期：1991.9

  Reaction of 5-methylcytosine nucleosides and nucleotide with Na2S2O8 resulted in an oxidation of the 5-methyl group, while treatment of them and cytosine nucleosides with KHSO5 gave the corresponding N3-oxides.

  5-甲基胞嘧啶核苷和核苷酸与 Na2S2O8 反应导致 5-甲基基团氧化，而用 KHSO5 处理它们和胞嘧啶核苷产生相应的 N3-氧化物。
• Rhie, Soo Young; Ryu, Eung K., Heterocycles, 1995, vol. 41, # 2, p. 323 - 328
  作者：Rhie, Soo Young、Ryu, Eung K.

  DOI：——

  日期：——
• 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.
• 3-Hydroxyuridine, an allelopathic factor of an African tree, Baillonella toxisperma
  作者：Hajime Ohigashi、Mikio Kaji、Masaharu Sakaki、Koichi Koshimizu

  DOI：10.1016/s0031-9422(00)97747-1

  日期：——