4-acetyl-1-(2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranosyl)cytosine | 221552-93-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 4-acetyl-1-(2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranosyl)cytosine
• 英文别名: [(2R,3S,4S)-5-(4-acetamido-2-oxopyrimidin-1-yl)-3-benzoyloxy-4-fluorothiolan-2-yl]methyl benzoate
• CAS: 221552-93-8
• 化学式: C₂₅H₂₂FN₃O₆S
• 分子量: 511.531
• InChiKey: LXSKTKHOBCFOGC-LXGGTWNRSA-N

物化性质

• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-acetyl-1-(2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranosyl)cytosine 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1-(2-deoxy-2-fluoro-4-thio-β-D-arabinofuranosyl)cytosine
  参考文献：
  名称：

  SOLID FORM OF 4'-THIO-2'-FLUORONUCLEOSIDE PHOSPHAMIDE COMPOUND AND PREPARATION METHOD THEREFOR AND USE THEREOF

  摘要：

  本发明涉及化合物Formula (I)的固体形式，制备该固体形式的方法，包含该固体形式的药物组合物，以及在治疗涉及异常细胞增殖或病毒感染疾病中使用该固体形式的用途。

  公开号：

  US20190241603A1
• 作为产物：
  描述：

  3-deoxy-5,6-di-O,S-acetyl-3-fluoro-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose 在 硫酸 、 氢溴酸 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-acetyl-1-(2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranosyl)cytosine
  参考文献：
  名称：

  SOLID FORM OF 4'-THIO-2'-FLUORONUCLEOSIDE PHOSPHAMIDE COMPOUND AND PREPARATION METHOD THEREFOR AND USE THEREOF

  摘要：

  本发明涉及化合物Formula (I)的固体形式，制备该固体形式的方法，包含该固体形式的药物组合物，以及在治疗涉及异常细胞增殖或病毒感染疾病中使用该固体形式的用途。

  公开号：

  US20190241603A1

文献信息

• SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-ß-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME
  申请人：FUJIFILM Corporation

  公开号：US20150152131A1

  公开（公告）日：2015-06-04

  A compound represented by a formula [1D] as shown below (wherein R 1A , R 1B , R 2A , R 2B , R 3A and R 3B represent a hydrogen atom, an optionally substituted C 1-6 alkyl group, and the like) is useful as an intermediate for producing a thionucleoside, and the production method of the present invention is useful as a method for producing a thionucleoside.

  下列的化合物，其化学式为[1D]（其中R1A、R1B、R2A、R2B、R3A和R3B代表氢原子、可选择取代的C1-6烷基等），可作为生产硫代核苷的中间体，本发明的生产方法可作为一种生产硫代核苷的方法。
• Solid form of 4′-thio-2′-fluoronucleoside phosphamide compound and preparation method therefor and use thereof
  申请人：SICHUAN KELUN-BIOTECH BIOPHARMACEUTICAL CO., LTD.

  公开号：US10787477B2

  公开（公告）日：2020-09-29

  The present invention relates to a solid form of a compound of Formula (I), a method for preparing the solid form, a pharmaceutical composition comprising the solid form, and the use of the solid form in the treatment of a disease involving abnormal cell proliferation or a viral infectious disease.

  本发明涉及一种式（I）化合物的固体形式、一种制备该固体形式的方法、一种包含该固体形式的药物组合物，以及该固体形式在治疗涉及异常细胞增殖的疾病或病毒性传染病中的用途。
• An alternative synthesis of antineoplastic 4′-thiocytidine analogue 4′-thioFAC
  作者：Yuichi Yoshimura、Mikari Endo、Shinji Sakata

  DOI：10.1016/s0040-4039(99)00048-9

  日期：1999.3

  We have developed an alternative method for the synthesis of 2'-modified 4'-thionucleosides. The fusion of 3,5-di-O-benzoyl-1-bromo-2-deoxy-2-fluoro-4-thio-alpha-D-arabinofuranose, prepared from 1,2:5,6-diisopropylidene-alpha-D-allofuranose, with persilylated N-4-acetylcytosine predominantly gave a beta-anomer of protected 4'-thionucleoside, which was then deprotected to give 4'-thioFAC. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthetic Studies on 2′-Substituted-4′-thiocytidine Derivatives as Antineoplastic Agents
  作者：Yuichi Yoshimura、Mikari Endo、Kenji Kitano、Kohei Yamada、Shinji Sakata、Shinji Miura、Haruhiko Machida

  DOI：10.1080/15257779908041569

  日期：1999.4

  As potential antineoplastic agents, we have synthesized 4'-thioFAC and 4'-thiocytarazid by developing an alternative synthetic method. 4'-ThioFAC showed potent antineoplastic activities in vivo as well as in vitro.
• An Alternative Synthesis of the Antineoplastic Nucleoside 4‘-ThioFAC and Its Application to the Synthesis of 4‘-ThioFAG and 4‘-Thiocytarazid
  作者：Yuichi Yoshimura、Mikari Endo、Shinji Miura、Shinji Sakata

  DOI：10.1021/jo990958g

  日期：1999.10.1

  Previously, we synthesized 4'-thioFAC, a novel antineoplastic cytosine nucleoside, by developing an original method. However, several problems remained. To overcome these problems, we have developed an alternative method far the synthesis of 4'-thionucleosides. In the original synthesis, carbons from C1 to C5 of D-glucose were used. The new method also starts from D-glucose but uses carbons closer to the tail (C2-C6). A dibenzoyl derivative obtained by this approach was brominated at the anomeric position to give a 1-bromide derivative. Fusion of the I-bromide and persilylated acetylcytosine, followed by deprotection, predominantly gave a beta-anomer of 4'-thioFAC. The reaction of 2,6-diaminopurine with the I-bromide in the presence of TMS triflate gave a glycosylated product in good yield. After deprotection, the resulting 1:1 anomeric mixture of free nucleosides was treated with adenosine deaminase to give a beta-anomer of 4'-thioFAG, a guanine congener of 4'-thioFAC, selectively. Using a similar approach, we synthesized 4'-thiocytarazid, which was not possible using the original method.