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rac-1-S-hexadecyl-2-O-palmitoyl-1-thioglycerol | 103612-83-5

中文名称
——
中文别名
——
英文名称
rac-1-S-hexadecyl-2-O-palmitoyl-1-thioglycerol
英文别名
(1-hexadecylsulfanyl-3-hydroxypropan-2-yl) hexadecanoate
rac-1-S-hexadecyl-2-O-palmitoyl-1-thioglycerol化学式
CAS
103612-83-5
化学式
C35H70O3S
mdl
——
分子量
571.005
InChiKey
CUTUXBYYLZYAJI-UHFFFAOYSA-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):
    11.59
  • 重原子数:
    39.0
  • 可旋转键数:
    33.0
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.97
  • 拓扑面积:
    46.53
  • 氢给体数:
    1.0
  • 氢受体数:
    4.0

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:
    描述:
    rac-1-S-hexadecyl-2-O-palmitoyl-1-thioglycerol吡啶三乙胺三氯氧磷 作用下, 以 正己烷甲苯 为溶剂, 反应 240.0h, 生成 ara-CDP-rac-1-S-hexadecyl-2-O-palmitoyl-1-thioglycerol disodium salt
    参考文献:
    名称:
    Nucleoside conjugates. 11. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine and cytidine conjugates of thioether lipids
    摘要:
    Five 1-beta-D-arabinofuranosylcytosine conjugates and two cytidine conjugates of thioether lipids (1-S-alkylthioglycerols) linked by a pyrophosphate diester bond have been prepared and their antitumor activity against an ara-C2 sensitive (L1210/0) and two ara-C resistant L1210 lymphoid leukemia sublines in mice were evaluated. These prodrugs of ara-C include ara-CDP-rac-1-S-hexadecyl-2-O-palmitoyl-1-thioglycerol (8a), ara-CDP-rac-1-S-octadecyl-2-O-palmitoylthioglycerol (8b), and ara-CDP-rac-1-S-octadecyl-2-O-methyl(or -ethyl, -hexadecyl)thioglycerols (8c-e). The cytidine conjugates include CDP-rac-1-S-octadecyl-2-O-palmitoyl(or -methyl)- 1-thioglycerols (9a and 9b). Sonicated solutions of the conjugates existed in the form of micellar disks (size 0.01-0.04 microns). Single doses (200-400 mg/kg) of 8a and 8b produced significant increase in life span (257-371%) in mice bearing ip implanted L1210/0 leukemia. In contrast, conjugates 8c-e were less effective (ILS 19-75%) and cytidine conjugates (9a and 9b) were ineffective. Even though 8a and 8b were found to be curative in a high percentage of mice bearing ip implanted partially ara-C resistant L1210 subline [L1210/ara-C(I)], they were completely ineffective against deoxycytidine kinase deficient ara-C resistant L1210 subline [L1210/ara-C(II)]. However, the present results, together with the previous, demonstrate that 8a and 8b are promising new prodrugs of ara-C with improved efficacy.
    DOI:
    10.1021/jm00167a016
  • 作为产物:
    描述:
    参考文献:
    名称:
    Nucleoside conjugates. 11. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine and cytidine conjugates of thioether lipids
    摘要:
    Five 1-beta-D-arabinofuranosylcytosine conjugates and two cytidine conjugates of thioether lipids (1-S-alkylthioglycerols) linked by a pyrophosphate diester bond have been prepared and their antitumor activity against an ara-C2 sensitive (L1210/0) and two ara-C resistant L1210 lymphoid leukemia sublines in mice were evaluated. These prodrugs of ara-C include ara-CDP-rac-1-S-hexadecyl-2-O-palmitoyl-1-thioglycerol (8a), ara-CDP-rac-1-S-octadecyl-2-O-palmitoylthioglycerol (8b), and ara-CDP-rac-1-S-octadecyl-2-O-methyl(or -ethyl, -hexadecyl)thioglycerols (8c-e). The cytidine conjugates include CDP-rac-1-S-octadecyl-2-O-palmitoyl(or -methyl)- 1-thioglycerols (9a and 9b). Sonicated solutions of the conjugates existed in the form of micellar disks (size 0.01-0.04 microns). Single doses (200-400 mg/kg) of 8a and 8b produced significant increase in life span (257-371%) in mice bearing ip implanted L1210/0 leukemia. In contrast, conjugates 8c-e were less effective (ILS 19-75%) and cytidine conjugates (9a and 9b) were ineffective. Even though 8a and 8b were found to be curative in a high percentage of mice bearing ip implanted partially ara-C resistant L1210 subline [L1210/ara-C(I)], they were completely ineffective against deoxycytidine kinase deficient ara-C resistant L1210 subline [L1210/ara-C(II)]. However, the present results, together with the previous, demonstrate that 8a and 8b are promising new prodrugs of ara-C with improved efficacy.
    DOI:
    10.1021/jm00167a016
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文献信息

  • HONG, CHUNG IL;KIRISITS, ALAN J.;NECHAEV, ALEXANDER;BUCHHEIT, DAVID J.;WE+, J. MED. CHEM., 33,(1990) N, C. 1380-1386
    作者:HONG, CHUNG IL、KIRISITS, ALAN J.、NECHAEV, ALEXANDER、BUCHHEIT, DAVID J.、WE+
    DOI:——
    日期:——
  • ——
    作者:HONG CHUNG I.、 WEST C. R.
    DOI:——
    日期:——
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