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K-182

中文名称
——
中文别名
——
英文名称
K-182
英文别名
N-hydroxy-4-[[2-hydroxyethyl(naphthalen-2-ylmethyl)amino]methyl]benzamide
K-182化学式
CAS
——
化学式
C21H22N2O3
mdl
——
分子量
350.417
InChiKey
AIEQYWORJOFHKE-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):
    2.6
  • 重原子数:
    26
  • 可旋转键数:
    7
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.19
  • 拓扑面积:
    72.8
  • 氢给体数:
    3
  • 氢受体数:
    4

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:
    K-182月桂酸4-二甲氨基吡啶N,N'-二环己基碳二亚胺 作用下, 以 二氯甲烷 为溶剂, 反应 5.0h, 以24.3%的产率得到K-182-DD
    参考文献:
    名称:
    Histone deacetylase inhibitor prodrugs in nanoparticle vector enhanced gene expression in human cancer cells
    摘要:
    We developed histone deacetylase inhibitor (HDACI) prodrugs to enhance the expression of the external genes transfected into human cells with cationic nanoparticles (NPs). We synthesized five kinds of lipid-linked HDACI prodrugs in which n-dodecanoic acid or cholesterol is linked with a potent HDACI, K-182, by an ester bond or a disulfide carbonate linker. The prodrugs were able to admix as a component of NPs, although the intact K-182 was not incorporated into NPs. Namely, NPs composed of cholesteryl-3 beta-carboxyamidoethylene-N-hydroxyethylamine and Tween 80 with the 10 mol% K-182 prodrug were prepared as a DNA vector to transfect plasmid DNAs into human prostate cancer cells, PC-3, or human breast cancer cells, Sk-Br-3. The NPs containing K-182 prodrugs with n-dodecanoic acid exhibited two to four times higher the gene expression than the original NPs. The enhancement of the gene expression will be due to the hyperacetylation of core histories caused by intact K-182 degraded from the prodrug in the vector incorporated into the cells. (C) 2009 Elsevier Masson SAS. All rights reserved.
    DOI:
    10.1016/j.ejmech.2009.06.036
  • 作为产物:
    描述:
    4-氨甲基苯甲酸甲酯盐酸盐氢氧化钾 、 sodium tetrahydroborate 、 羟胺potassium carbonate三乙胺 作用下, 以 甲醇二氯甲烷乙腈 为溶剂, 反应 11.0h, 生成 K-182
    参考文献:
    名称:
    新型组蛋白脱乙酰基酶抑制剂的合成及其抗癌活性:亲水性异羟肟酸酯和含2-氨基苯甲酰胺的衍生物。
    摘要:
    合成了包含异羟肟酸或2-氨基苯甲酰胺基团作为锌螯合功能的新系列组蛋白脱乙酰酶抑制剂,并评估了其对一组人类癌细胞的抗增殖活性。2-氨基苯甲酰胺系列抑制剂通常具有与MS-275相当的对细胞生长的抑制作用。其中,在分子的一端具有(3,4-二氟苄基)(2-羟乙基)氨基,另一侧具有2-氨基苯甲酰胺基的化合物显示出作为抗癌候选药物最有前景的特征。与MS-275对正常成纤维细胞CCD-1059SK相比毒性较低。另外,该衍生物在人血浆稳定性测试中显示出高回收率。
    DOI:
    10.1016/j.ejmech.2006.02.002
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文献信息

  • Histone deacetylase inhibitor prodrugs in nanoparticle vector enhanced gene expression in human cancer cells
    作者:Yuta Ishii、Yoshiyuki Hattori、Toshiharu Yamada、Shinichi Uesato、Yoshie Maitani、Yasuo Nagaoka
    DOI:10.1016/j.ejmech.2009.06.036
    日期:2009.11
    We developed histone deacetylase inhibitor (HDACI) prodrugs to enhance the expression of the external genes transfected into human cells with cationic nanoparticles (NPs). We synthesized five kinds of lipid-linked HDACI prodrugs in which n-dodecanoic acid or cholesterol is linked with a potent HDACI, K-182, by an ester bond or a disulfide carbonate linker. The prodrugs were able to admix as a component of NPs, although the intact K-182 was not incorporated into NPs. Namely, NPs composed of cholesteryl-3 beta-carboxyamidoethylene-N-hydroxyethylamine and Tween 80 with the 10 mol% K-182 prodrug were prepared as a DNA vector to transfect plasmid DNAs into human prostate cancer cells, PC-3, or human breast cancer cells, Sk-Br-3. The NPs containing K-182 prodrugs with n-dodecanoic acid exhibited two to four times higher the gene expression than the original NPs. The enhancement of the gene expression will be due to the hyperacetylation of core histories caused by intact K-182 degraded from the prodrug in the vector incorporated into the cells. (C) 2009 Elsevier Masson SAS. All rights reserved.
  • Synthesis and cancer antiproliferative activity of new histone deacetylase inhibitors: hydrophilic hydroxamates and 2-aminobenzamide-containing derivatives
    作者:Y. Nagaoka、T. Maeda、Y. Kawai、D. Nakashima、T. Oikawa、K. Shimoke、T. Ikeuchi、H. Kuwajima、S. Uesato
    DOI:10.1016/j.ejmech.2006.02.002
    日期:2006.6
    New series histone deacetylase inhibitors comprising a hydroxamic acid or 2-aminobenzamide group as a zinc-chelating function were synthesized and evaluated for antiproliferative activities against a panel of human cancer cells. The 2-aminobenzamide series inhibitors generally had the potency in cell growth inhibitions comparable to that of MS-275. Among them, the compound having a (3,4-difluorobe
    合成了包含异羟肟酸或2-氨基苯甲酰胺基团作为锌螯合功能的新系列组蛋白脱乙酰酶抑制剂,并评估了其对一组人类癌细胞的抗增殖活性。2-氨基苯甲酰胺系列抑制剂通常具有与MS-275相当的对细胞生长的抑制作用。其中,在分子的一端具有(3,4-二氟苄基)(2-羟乙基)氨基,另一侧具有2-氨基苯甲酰胺基的化合物显示出作为抗癌候选药物最有前景的特征。与MS-275对正常成纤维细胞CCD-1059SK相比毒性较低。另外,该衍生物在人血浆稳定性测试中显示出高回收率。
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