(S)-22-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)-1-(6-(((di(pyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)methyl)pyridin-3-yl)-1,7,14,19-tetraoxo-10,11-dithia-2,6,15,18-tetraazatricosan-23-oic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: (S)-22-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)-1-(6-(((di(pyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)methyl)pyridin-3-yl)-1,7,14,19-tetraoxo-10,11-dithia-2,6,15,18-tetraazatricosan-23-oic acid
• 英文别名: (2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoyl]amino]-5-[2-[3-[[3-[3-[[6-[[dipyridin-2-ylmethyl(pyridin-2-ylmethyl)amino]methyl]pyridine-3-carbonyl]amino]propylamino]-3-oxopropyl]disulfanyl]propanoylamino]ethylamino]-5-oxopentanoic acid
• 化学式: C₅₄H₆₀N₁₆O₈S₂
• 分子量: 1125.3
• InChiKey: NDTGDHOXKYLDSN-QLKFWGTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  80
• 可旋转键数：
  31
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  394
• 氢给体数：
  9
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  ferrous perchlorate 、 谷胱甘肽 、 (S)-22-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)-1-(6-(((di(pyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)methyl)pyridin-3-yl)-1,7,14,19-tetraoxo-10,11-dithia-2,6,15,18-tetraazatricosan-23-oic acid 以 二甲基亚砜 、 乙腈 为溶剂， 反应 0.33h， 生成 、 、 、 (2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoyl]amino]-5-oxo-5-[2-(3-sulfanylpropanoylamino)ethylamino]pentanoic acid 、
  参考文献：
  名称：

  Folic acid conjugates of a bleomycin mimic for selective targeting of folate receptor positive cancer cells

  摘要：

  A major challenge in the application of cytotoxic anti-cancer drugs is their general lack of selectivity, which often leads to systematic toxicity due to their inability to discriminate between malignant and healthy cells. A particularly promising target for selective targeting are the folate receptors (FR) that are often over-expressed on cancer cells. Here, we report on a conjugate of the pentadentate nitrogen ligand N4Py to folic acid, via a cleavable disulphide linker, which shows selective cytotoxicity against folate receptor expressing cancer cells.

  DOI：

  10.1016/j.bmcl.2019.05.047
• 作为产物：
  描述：

  5-(methoxycarbonyl)-2-methylpyridine 1-oxide 在 sodium cyanide 、 N,N-二异丙基乙胺 、 对甲苯磺酰氯 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 生成 (S)-22-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)-1-(6-(((di(pyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)methyl)pyridin-3-yl)-1,7,14,19-tetraoxo-10,11-dithia-2,6,15,18-tetraazatricosan-23-oic acid
  参考文献：
  名称：

  Folic acid conjugates of a bleomycin mimic for selective targeting of folate receptor positive cancer cells

  摘要：

  A major challenge in the application of cytotoxic anti-cancer drugs is their general lack of selectivity, which often leads to systematic toxicity due to their inability to discriminate between malignant and healthy cells. A particularly promising target for selective targeting are the folate receptors (FR) that are often over-expressed on cancer cells. Here, we report on a conjugate of the pentadentate nitrogen ligand N4Py to folic acid, via a cleavable disulphide linker, which shows selective cytotoxicity against folate receptor expressing cancer cells.

  DOI：

  10.1016/j.bmcl.2019.05.047