cytarabine | 7428-39-9

• 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: cytarabine
• 英文别名: 4-Amino-1-alpha-D-arabinofuranosyl-2(1H)-pyrimidinone；4-amino-1-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 7428-39-9
• 化学式: C₉H₁₃N₃O₅
• 分子量: 243.219
• InChiKey: UHDGCWIWMRVCDJ-GVYWOMJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cytarabine 在 咪唑 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、137.9 kPa 条件下， 反应 4.0h， 生成 N⁴-(1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-D-asparagine
  参考文献：
  名称：

  WO2023/228177

  摘要：

  公开号：
• 作为产物：
  描述：

  N⁴-acetyl-1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)cytosine 在 氨 作用下， 以 甲醇 为溶剂， 反应 28.0h， 以66%的产率得到cytarabine
  参考文献：
  名称：

  Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides

  摘要：

  The 5 alpha-D-arabinofuranosylnucleosides alpha-araU (15), alpha-araT (18), alpha-araC (22), alpha-araA (25), and alpha-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2'-hydroxy group at the sugar moiety were protected by the 2-(4-nitro-phenyl) ethoxycarbonyl (npeoc) group (37-40) and the amide function in alpha-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5'-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3'-OH group led to the monomeric building blocks 66-75 as well as the 3'-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-alpha-arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between alpha-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-alpha-D-arabinonucleotide with a complementary oligo-2'-deoxy-beta-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-alpha-arabinonucleotide synthesis were furthermore demonstrated by the synthesis of the t alpha-ANA(his) a structural analog of the natural tRNA(his) of the phage T5.

  DOI：

  10.1080/15257770500267113

文献信息

• Synthesis and hybridization studies of α-configured arabino nucleic acids
  作者：Pankaj Gupta、Jyotirmoy Maity、Gaurav Shakya、Ashok K. Prasad、Virinder S. Parmar、Jesper Wengel

  DOI：10.1039/b905019c

  日期：——

  Synthesis of α-L-arabino- and α-D-arabino-configured pentofuranosyl nucleosides of four of the natural bases [thymine (ara-T), adenine (ara-A), cytosine (ara-C) and guanine (ara-G)] is reported together with hybridization properties of oligonucleotides containing α-L-ara-T and -A, α-D-ara-T and -A, and 2′-amino-α-L-ara-T monomers. 2′-O-Acetylated α-L-ara-T, -A, -C and -G, α-D-ara-T, -A, -C and -G,

  四个天然碱的α-L-阿拉伯糖和α-D-阿拉伯糖构型的呋喃呋喃糖基核苷的合成[胸腺嘧啶 （一只老鼠）， 腺嘌呤 （ara-A）， 胞嘧啶 （ara-C） 和 鸟嘌呤（ara-G）]与含有α-L-ara-T和-A，α-D-ara-T和-A以及2'-氨基-α-L-ara-T的寡核苷酸的杂交特性一起报道。单体。2' - O-乙酰化的α-L-ara-T，-A，-C和-G，α-D-ara-T，-A，-C和-G和N2'-酰化的α-L-合成了ara-T亚磷酰胺结构单元，并将其与标准DNA亚磷酰胺一起用于18-mer寡核苷酸的固相合成。热变性实验表明，掺入了三到六种阿拉伯糖-配置成DNA-寡核苷酸的单体降低了对反平行DNA / RNA补体的结合亲和力。完全修饰的α-L-ara-寡核苷酸不与DNA / RNA互补序列杂交，而证实了完全修饰的α-D-ara-寡核苷酸与互补DNA / RNA在平行链方向上的杂交。
• Enhancer of anti-tumor effect
  申请人：Yamasa Shoyu Kabushiki Kaisha

  公开号：EP0045944A1

  公开（公告）日：1982-02-17

  A nucleoside selected from the group consisting of 3'-deoxyguanosine and 3'-deoxyuridine enhances, when administered to a tumor-bearing animal under the anti-tumor treatment, anti-tumor effect due to the anti-tumor treatment. The anti-tumor treatment comprises irradiation to a tumor site of the animal or administration of an anti-tumor agent to the animal.

  选自 3'-脱氧鸟苷和 3'-脱氧尿苷组成的组的核苷，在给接受抗肿瘤治疗的肿瘤动物用药时，可增强抗肿瘤治疗的抗肿瘤效果。抗肿瘤治疗包括对动物的肿瘤部位进行照射或对动物施用抗肿瘤剂。
• Methods for delivering nucleic acid molecules into cells and assessment thereof
  申请人：——

  公开号：US20030224522A1

  公开（公告）日：2003-12-04

  Methods for delivering nucleic acid molecules into cells and methods for measuring nucleic acid delivery into cells and the expression of the nucleic acids are provided. The methods are designed for introduction of large nucleic acid molecules, including artificial chromosomes, into cells.

  提供了将核酸分子送入细胞的方法和测量核酸送入细胞及核酸表达的方法。这些方法设计用于将大型核酸分子（包括人工染色体）导入细胞。
• LIPOSOME DELIVERY METHOD FOR DECREASING THE TOXICITY OF AN ANTITUMOR DRUG
  申请人：HEALTH RESEARCH, INC.

  公开号：EP0153955A1

  公开（公告）日：1985-09-11
• OLIGO(ALPHA-ARABINOFURANOSYL NUCLEOTIDES) AND ALPHA-ARABINOFURANOSYL PRECURSORS THEREOF
  申请人：MICROPROBE CORPORATION

  公开号：EP0543913A1

  公开（公告）日：1993-06-02