N-(6-aminohexyl)-2-[(8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]acetamide | 179184-36-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: N-(6-aminohexyl)-2-[(8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]acetamide
• CAS: 179184-36-2
• 化学式: C₂₆H₄₀N₂O₃
• 分子量: 428.615
• InChiKey: RXAFJWIZUJBWDA-YWBWYGPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  95.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,11-dimethyl-6H-pyrido[4,3-b]carbazole-9-carboxylic acid 、 N-(6-aminohexyl)-2-[(8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]acetamide 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以45%的产率得到9-[[[N-(3,17beta-Dihydroxy-1,3,5-estratrien-17alpha-yl)acetamido]-N-hexyl]carbamoyl]ellipticine
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Ellipticine−Estradiol Conjugates

  摘要：

  Three ellipticine-estradiol conjugates were synthesized in an effort to target the cytotoxicity of ellipticine to estrogen-receptor positive cells. The three conjugates were prepared with linker chains extending from the 17 alpha position of the estradiol to N-2 (compound 3), N-6 (compound 4), and C-9 (compound 5) positions of ellipticine. The ellipticine-estradiol conjugates were evaluated for their abilities to bind to estrogen receptors, to inhibit topoisomerase II, and for their cytotoxicities in human cancer cell lines. Conjugates 3 and 5 displayed weak binding affinities of 0.132 and 0.303 for the estrogen receptor (relative to estradiol = 100), while conjugate 4 did not show any detectable binding to the estrogen receptor. Compound 3 was a moderate inhibitor of topoisomerase II (IC50 24.1 mu M), while 4 and 5 were inactive. Conjugate 3 was consistently more cytotoxic (GI(50) values 1-10 mu M) than compounds 4 and 5 (GI(50) values 10-100 mu M) in a variety of human cancer cell lines, None of the compounds displayed any selectivity for estrogen-receptor positive cell lines, which probably reflects their weak affinities for estrogen receptors.

  DOI：

  10.1021/jm9602930
• 作为产物：
  描述：

  ethyl 3,17β-dihydroxy-1,3,5-estratriene-17α-acetate 在 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 106.0h， 生成 N-(6-aminohexyl)-2-[(8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]acetamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Ellipticine−Estradiol Conjugates

  摘要：

  Three ellipticine-estradiol conjugates were synthesized in an effort to target the cytotoxicity of ellipticine to estrogen-receptor positive cells. The three conjugates were prepared with linker chains extending from the 17 alpha position of the estradiol to N-2 (compound 3), N-6 (compound 4), and C-9 (compound 5) positions of ellipticine. The ellipticine-estradiol conjugates were evaluated for their abilities to bind to estrogen receptors, to inhibit topoisomerase II, and for their cytotoxicities in human cancer cell lines. Conjugates 3 and 5 displayed weak binding affinities of 0.132 and 0.303 for the estrogen receptor (relative to estradiol = 100), while conjugate 4 did not show any detectable binding to the estrogen receptor. Compound 3 was a moderate inhibitor of topoisomerase II (IC50 24.1 mu M), while 4 and 5 were inactive. Conjugate 3 was consistently more cytotoxic (GI(50) values 1-10 mu M) than compounds 4 and 5 (GI(50) values 10-100 mu M) in a variety of human cancer cell lines, None of the compounds displayed any selectivity for estrogen-receptor positive cell lines, which probably reflects their weak affinities for estrogen receptors.

  DOI：

  10.1021/jm9602930

文献信息

• Design, Synthesis, and Biological Evaluation of Ellipticine−Estradiol Conjugates
  作者：Rajesh Devraj、John F. Barrett、Jeffrey A. Fernandez、John A. Katzenellenbogen、Mark Cushman

  DOI：10.1021/jm9602930

  日期：1996.1.1

  Three ellipticine-estradiol conjugates were synthesized in an effort to target the cytotoxicity of ellipticine to estrogen-receptor positive cells. The three conjugates were prepared with linker chains extending from the 17 alpha position of the estradiol to N-2 (compound 3), N-6 (compound 4), and C-9 (compound 5) positions of ellipticine. The ellipticine-estradiol conjugates were evaluated for their abilities to bind to estrogen receptors, to inhibit topoisomerase II, and for their cytotoxicities in human cancer cell lines. Conjugates 3 and 5 displayed weak binding affinities of 0.132 and 0.303 for the estrogen receptor (relative to estradiol = 100), while conjugate 4 did not show any detectable binding to the estrogen receptor. Compound 3 was a moderate inhibitor of topoisomerase II (IC50 24.1 mu M), while 4 and 5 were inactive. Conjugate 3 was consistently more cytotoxic (GI(50) values 1-10 mu M) than compounds 4 and 5 (GI(50) values 10-100 mu M) in a variety of human cancer cell lines, None of the compounds displayed any selectivity for estrogen-receptor positive cell lines, which probably reflects their weak affinities for estrogen receptors.