1,2,3-tri-O-acetyl-5-deoxy-5-chloro-β-D-ribofuranose | 185453-73-0

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3-tri-O-acetyl-5-deoxy-5-chloro-β-D-ribofuranose
• 英文别名: 1,2,3-tri-O-acetyl-5-deoxy-5-chloro-beta-D-ribofuranose；[(2S,3S,4R,5S)-4,5-diacetyloxy-2-(chloromethyl)oxolan-3-yl] acetate
• CAS: 185453-73-0
• 化学式: C₁₁H₁₅ClO₇
• 分子量: 294.689
• InChiKey: ICEXMBAGIAETTO-GWOFURMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2,3-tri-O-acetyl-5-deoxy-5-chloro-β-D-ribofuranose 在 三氟甲磺酸三甲基硅酯 、 sodium carbonate 、 牛血清白蛋白 作用下， 以 乙醇 为溶剂， 反应 4.75h， 生成 2,5,6-trichloro-1-(5-chloro-5-deoxy-β-D-ribofuranosyl)benzimidazole
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Certain 5‘-Modified Analogs of 2,5,6-Trichloro-1-(β-d-ribofuranosyl)benzimidazole

  摘要：

  A series of 5'-modified 2,5,6-trichlorobenzimidazole ribonucleosides has been synthesized and tested for activity against two human herpesviruses and for cytotoxicity. The 5'-methoxy, 5'-ethoxy, and 5'-butoxy analogs of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) were prepared by coupling the appropriate 5-O-alkyl-1,2,3-tri-O-acetyl-beta-D-ribose derivatives with 2,5,6-trichlorobenzimidazole followed by removal of the protecting groups. The 5'-deoxy-5'-fluoro, -5'-chloro, -5'-bromo, -5'-iodo, -5'-azido, and -5'-thiomethyl derivatives were synthesized in a similar fashion. All of these 5'-modified derivatives had significant activity against HCMV in plaque and yield reduction assays (IC50's = 0.5-14.2 mu M) but had little activity (IC50's > 100 mu M) against HSV-1. This pattern is similar to the antiviral activity profile observed for TCRB. The 5'-halogenated derivatives were more active than the other 5'-modified derivatives with antiviral activity well separated from cytotoxicity. In general, cytotoxicity of all the 5'-modified derivatives was greater in human foreskin fibroblasts (HFF cells) than in L1210 or K-B tumor cells. These results indicate that the viral target tolerates significant modifications of TCRB at the 5'-position without adversely affecting activity against HCMV, whereas the 5'-modifications increased cytotoxicity in human diploid cells.

  DOI：

  10.1021/jm9604888
• 作为产物：
  描述：

  卡培他滨中间体 在 吡啶 、 盐酸 作用下， 反应 26.0h， 生成 1,2,3-tri-O-acetyl-5-deoxy-5-chloro-β-D-ribofuranose
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Certain 5‘-Modified Analogs of 2,5,6-Trichloro-1-(β-d-ribofuranosyl)benzimidazole

  摘要：

  A series of 5'-modified 2,5,6-trichlorobenzimidazole ribonucleosides has been synthesized and tested for activity against two human herpesviruses and for cytotoxicity. The 5'-methoxy, 5'-ethoxy, and 5'-butoxy analogs of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) were prepared by coupling the appropriate 5-O-alkyl-1,2,3-tri-O-acetyl-beta-D-ribose derivatives with 2,5,6-trichlorobenzimidazole followed by removal of the protecting groups. The 5'-deoxy-5'-fluoro, -5'-chloro, -5'-bromo, -5'-iodo, -5'-azido, and -5'-thiomethyl derivatives were synthesized in a similar fashion. All of these 5'-modified derivatives had significant activity against HCMV in plaque and yield reduction assays (IC50's = 0.5-14.2 mu M) but had little activity (IC50's > 100 mu M) against HSV-1. This pattern is similar to the antiviral activity profile observed for TCRB. The 5'-halogenated derivatives were more active than the other 5'-modified derivatives with antiviral activity well separated from cytotoxicity. In general, cytotoxicity of all the 5'-modified derivatives was greater in human foreskin fibroblasts (HFF cells) than in L1210 or K-B tumor cells. These results indicate that the viral target tolerates significant modifications of TCRB at the 5'-position without adversely affecting activity against HCMV, whereas the 5'-modifications increased cytotoxicity in human diploid cells.

  DOI：

  10.1021/jm9604888

文献信息

• PROCESS FOR PRODUCTION OF RIBOFURANOSE DERIVATIVES
  申请人：API Corporation

  公开号：EP2210896A1

  公开（公告）日：2010-07-28

  It is an object of the present Invention to provide a process for producing 1,2,3-tri-O-acetyl-5-deoxy-ribofuranose in an industrially appropriate manner. The present invention provides a process for producing a 1,2,3-tri-O-acetyl-5-deoxy-ribofuranose which comprises hydrogenating a compound represented by the formula (1) or formula (2) in the presence of a metal catalyst: wherein P1 and P2 independently represent a hydrogen atom or an acyl group OP1 and OP2 may together form an acetal group, and R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, or an acyl group; wherein X1 represents Br or I, P3 and P4 independently represent a hydrogen atom or an acryl group, and R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, or an acyl group.

  本发明的目的是以工业适当的方式提供一种生产1,2,3-三-O-乙酰-5-去氧-核糖呋喃糖的方法。本发明提供了一种生产1,2,3-三-O-乙酰-5-去氧-核糖呋喃糖的方法，其包括在金属催化剂的存在下氢化由化合物表示的化合物（1）或化合物（2）：其中P1和P2独立地表示氢原子或酰基OP1和OP2可以共同形成缩醛基，R表示氢原子、烷基、芳基、芳基烷基或酰基；其中X1表示Br或I，P3和P4独立地表示氢原子或丙烯酰基，R表示氢原子、烷基、芳基、芳基烷基或酰基。
• Probing the molecular determinants of fluorinase specificity
  作者：W. L. Yeo、X. Chew、D. J. Smith、K. P. Chan、H. Sun、H. Zhao、Y. H. Lim、E. L. Ang

  DOI：10.1039/c6cc09213f

  日期：——

  Probing the structural determinants of fluorinase enzyme specificity with 5′-chloro-5′-deoxyadenosine (5′-ClDA) analog substrates generated fluorinases with improved and novel activity.

  用5'-氯-5'-脱氧腺苷（5'-ClDA）类似底物探究氟化酶酶特异性的结构决定因素，产生了具有改进和新活性的氟化酶。
• 5'-substituted-ribofuranosyl benzimidazoles as antiviral agents
  申请人：——

  公开号：US20030119762A1

  公开（公告）日：2003-06-26

  The present invention relates to polysubstituted benzimidazoles, having the following formula: 1 wherein Q is a substituted benzimidazole group attached at the benzimidazole 1-position; R is a halogen of atomic number 9 to 53, inclusive (i.e., —F, —Cl, —Br, or —I); azido (i.e., —N 3 ); or —X—R 1 , wherein X is a chalcogen of atomic number 8 to 16, inclusive (i.e., —O— or —S—), and R 1 may be straight or branched chain alkyl of 1 to 8 carbon atoms; and R 2 and R 3 may be the same or different and are separately —O—C(═O)CH 3 (i.e., —OAc) or hydroxy (i.e., —OH); and pharmaceutically acceptable salts and operative combinations thereof. Also provided by this invention are compositions comprising a polysubstituted benzimidazole as defined above and methods of use thereof.

  本发明涉及具有下式的多取代苯并咪唑： 1 其中 Q 是连接在苯并咪唑 1 位上的取代苯并咪唑基团；R 是原子序数为 9 至 53（含）的卤素（即 -F、-Cl、-Br 或 -I）；叠氮（即 -N 3 ）；或 -X-R 1 其中 X 是原子序数为 8 至 16（包括 8 和 16）的缩醛（即 -O- 或 -S-），而 R 1 可以是 1 至 8 个碳原子的直链或支链烷基；以及 R 2 和 R 3 可以相同或不同，并分别为-O-C(═O)CH 3 (即-OAc)或羟基(即-OH)；以及药学上可接受的盐及其作用组合。本发明还提供了包含如上定义的多取代苯并咪唑的组合物及其使用方法。
• 5'-SUBSTITUTED-RIBOFURANOSYL BENZIMIDAZOLES AS ANTIVIRAL AGENTS
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：EP0845001A1

  公开（公告）日：1998-06-03
• US5874413A
  申请人：——

  公开号：US5874413A

  公开（公告）日：1999-02-23