benzyl 2,3,5-tri-O-benzyl-4-deoxy-4-thio-D-thioarabinofuranoside | 169736-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 2,3,5-tri-O-benzyl-4-deoxy-4-thio-D-thioarabinofuranoside
• 英文别名: (3S,4S,5R)-2-benzylsulfanyl-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)thiolane
• CAS: 169736-19-0
• 化学式: C₃₃H₃₄O₃S₂
• 分子量: 542.763
• InChiKey: HWRDLVHHHOIMJE-JOYOFOISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,5-tri-O-benzyl-4-deoxy-4-thio-D-thioarabinofuranoside 在 苯磺酰胺 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 21.0h， 生成 1-(2,3,5-tri-O-benzyl-4-thio-β-D-arabinofuranosyl)cytosine
  参考文献：
  名称：

  Synthesis of 4′-Thio-β-D-arabinofuranosylcytosine (4′-Thio-ara-C) and Comparison of Its Anticancer Activity with That of Ara-C

  摘要：

  4'-thio-beta-D-arabinofuranosylcytosine was synthesized by a facile route in high yields. It was evaluated for antitumor activity against a panel of human tumors, both in vitro and in vivo.

  DOI：

  10.1080/15257770008033012
• 作为产物：
  描述：

  2,3,5-tri-O-benzyl-L-xylose-dibenzyl dithioacetal 在 咪唑 、 碘 、 三苯基膦 作用下， 以83%的产率得到benzyl 2,3,5-tri-O-benzyl-4-deoxy-4-thio-D-thioarabinofuranoside
  参考文献：
  名称：

  某些4'-硫代核苷的合成及生物活性

  摘要：

  摘要介绍了几种类型的4'-硫代核苷作为潜在抗癌剂的合成和生物学活性。还介绍了有关4'-硫代胸苷的作用机理的详细研究。

  DOI：

  10.1080/15257779508012449

文献信息

• Synthesis and Biological Activity of Certain 4‘-Thio-<scp>d</scp>-arabinofuranosylpurine Nucleosides
  作者：John A. Secrist、Kamal N. Tiwari、Anita T. Shortnacy-Fowler、Lea Messini、James M. Riordan、John A. Montgomery、Scott C. Meyers、Steven E. Ealick

  DOI：10.1021/jm980195+

  日期：1998.9.1

  A series of 4'-thio-D-arabinofuranosylpurine nucleosides was prepared and evaluated as potential anticancer agents. The details of a convenient and high-yielding synthesis of the carbohydrate precursor 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-D-arabinofuranose (6) are presented. Proof of structure and configuration at all chiral centers of the nucleosides was obtained through an X-ray crystal structure

  制备了一系列的4'-硫代-D-阿拉伯呋喃糖基嘌呤核苷，并将其评估为潜在的抗癌药。给出了碳水化合物前体1-O-乙酰基-2,3,5-三-O-苄基-4-硫代-D-阿拉伯呋喃糖的方便且高产合成的细节（6）。通过9alpha的X射线晶体结构以及在9beta和9alpha上进行的NOE实验，获得了核苷所有手性中心的结构和构型的证明。在培养的一系列人类癌细胞系中评估了所有六个目标化合物。两种目标化合物，以二氨基嘌呤（12）和鸟嘌呤（16）为基础的β端基异构体，具有明显的细胞毒性。选择了其中一种化合物（12）用于动物研究，但在鼠结肠36肿瘤模型中发现在最大耐受剂量下没有选择性。
• Preparation of thioarabinofuranosyl compounds and use thereof
  申请人：——

  公开号：US20030203872A1

  公开（公告）日：2003-10-30

  Patients suffering from cancer are treated by being administered a compound represented by the following formula: 1 wherein each R individually is H or an aliphatic or aromatic acyl group; A is selected from the group consisting of 2 wherein X is selected from the group consisting of hydrogen, fluorine, alkoxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, amino, monoalkylamino, dialkylamino, cyano and nitro. The above compounds also inhibit DNA replication in mammalian cells.

  患有癌症的患者通过接受以下式子所表示的化合物治疗： 其中每个R分别为H或脂肪族或芳香族酰基；A选自以下组合的群体： 式中X从氢、氟、烷氧基、烷基、卤代烷基、烯基、卤代烯基、炔基、氨基、单烷基氨基、双烷基氨基、氰基和硝基中选取。上述化合物还能抑制哺乳动物细胞中的DNA复制。
• Thioarabinofuranosyl compounds and use thereof
  申请人：Secrist A. John

  公开号：US20050038025A1

  公开（公告）日：2005-02-17

  Patients suffering from cancer are treated by being administered a compound represented by the following formula: wherein each R individually is H or an aliphatic or aromatic acyl group; A is selected from the group consisting of wherein X is selected from the group consisting of hydrogen, fluorine, alkoxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, amino, monoalkylamino, dialkylamino, cyano and nitro. The above compounds also inhibit DNA replication in mammalian cells.

  患有癌症的患者被给予以下化学式代表的化合物治疗：其中每个R单独为H或脂肪族或芳香族酰基；A从以下组中选择：其中X从氢，氟，烷氧基，烷基，卤代烷基，烯基，卤代烯基，炔基，氨基，单烷基氨基，双烷基氨基，氰基和硝基中选择。上述化合物还抑制哺乳动物细胞中的DNA复制。
• PREPARATION OF THIOARABINOFURANOSYL COMPOUNDS AND USE THEREOF
  申请人：Secrist, III John A.

  公开号：US20100216797A1

  公开（公告）日：2010-08-26

  Patients suffering from cancer are treated by being administered a compound represented by the following formula: wherein each R individually is H or an aliphatic or aromatic acyl group; A is selected from the group consisting of wherein X is selected from the group consisting of hydrogen, fluorine, alkoxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, amino, monoalkylamino, dialkylamino, cyano and nitro. The above compounds also inhibit DNA replication in mammalian cells.

  患有癌症的患者通过接受以下公式所代表的化合物治疗：其中每个R分别为H或脂肪族或芳香族酰基；A从以下群体中选择：其中X从氢、氟、烷氧基、烷基、卤代烷基、烯基、卤代烯基、炔基、氨基、单烷基氨基、二烷基氨基、氰基和硝基中选择。上述化合物还可抑制哺乳动物细胞中的DNA复制。
• Use of thioarabinofuranosyl compounds
  申请人：Southern Research Institute

  公开号：EP2332551A1

  公开（公告）日：2011-06-15

  Patients suffering from cancer are treated by being administered a compound represented by formula: (1), wherein each R individually is H or an aliphatic or aromatic acyl group; A is selected from the group consisting of formulae (IIa, IIb, IIc, IId), wherein X is selected from the group consisting of hydrogen, fluorine, alkoxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, amino, monoalkylamino, dialkylamino, cyano and nitro. The above compounds also inhibit DNA replication in mammalian cells.

  癌症患者可通过服用由式表示的化合物进行治疗：(1)，其中每个 R 单独为 H 或脂肪族或芳香族酰基；A 选自由式（IIa、IIb、IIc、IId）组成的组，其中 X 选自由氢、氟、烷氧基、烷基、卤代烷基、烯基、卤代烯基、炔基、氨基、单烷基氨基、二烷基氨基、氰基和硝基组成的组。上述化合物还能抑制哺乳动物细胞中 DNA 的复制。