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methyl 5-O-ethyl-2,3-O-isopropylidene-D-ribofuranoside | 185453-50-3

中文名称
——
中文别名
——
英文名称
methyl 5-O-ethyl-2,3-O-isopropylidene-D-ribofuranoside
英文别名
(3aR,6R,6aR)-6-(ethoxymethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
methyl 5-O-ethyl-2,3-O-isopropylidene-D-ribofuranoside化学式
CAS
185453-50-3
化学式
C11H20O5
mdl
——
分子量
232.277
InChiKey
MWGGYLATHFTSAO-PBVVMKELSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    0.5
  • 重原子数:
    16
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    46.2
  • 氢给体数:
    0
  • 氢受体数:
    5

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    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:
    参考文献:
    名称:
    Holy, Antonin; Koenig, Joachim; Vesely, Jiri, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 6, p. 1589 - 1608
    摘要:
    DOI:
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文献信息

  • C2,5'-disubstituted and N6,C2,5'-trisubstituted adenosine derivatives and pharmaceutical compositions containing them
    申请人:UNIVERSITEIT LEIDEN
    公开号:US20040127452A1
    公开(公告)日:2004-07-01
    The present invention concerns novel C2,5′-disubstituted and N6,C2,5′-trisubstituted adenosine derivatives and their different uses. These adenosine derivatives were found to be potent adenosine receptor agonists and thus are of a therapeutic value in the treatment and prophylaxis of diseases and disorders affected by adenosine receptor agonists.
    本发明涉及新型C2,5'-二取代和N6,C2,5'-三取代腺苷衍生物及其不同用途。这些腺苷衍生物被发现是有效的腺苷受体激动剂,因此在治疗和预防受腺苷受体激动剂影响的疾病和障碍方面具有治疗价值。
  • 5'-SUBSTITUTED-RIBOFURANOSYL BENZIMIDAZOLES AS ANTIVIRAL AGENTS
    申请人:——
    公开号:US20010011075A1
    公开(公告)日:2001-08-02
    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。
  • US5874413A
    申请人:——
    公开号:US5874413A
    公开(公告)日:1999-02-23
  • US7189706B2
    申请人:——
    公开号:US7189706B2
    公开(公告)日:2007-03-13
  • Holy, Antonin; Koenig, Joachim; Vesely, Jiri, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 6, p. 1589 - 1608
    作者:Holy, Antonin、Koenig, Joachim、Vesely, Jiri、Cech, Dieter、Votruba, Ivan、Clercq, Erik de
    DOI:——
    日期:——
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