N¹⁰-nitrosopteroyl azide | 197151-80-7

• 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: N¹⁰-nitrosopteroyl azide
• 英文别名: 4-[(2-amino-4-oxo-3H-pteridin-6-yl)methyl-nitrosoamino]benzoyl azide
• CAS: 197151-80-7
• 化学式: C₁₄H₁₀N₁₀O₃
• 分子量: 366.299
• InChiKey: VLWBXZFEQVVJDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N¹⁰-nitrosopteroyl azide 在 sodium azide 作用下， 以 三氟乙酸 为溶剂， 生成 pteroyl azide
  参考文献：
  名称：

  Efficient Syntheses of Pyrofolic Acid and Pteroyl Azide, Reagents for the Production of Carboxyl-Differentiated Derivatives of Folic Acid

  摘要：

  Reaction of folic acid (1) with excess trifluoroacetic anhydride provides access to both the previously unknown N-10-(trifluoroacetyl)pyrofolic acid (8) and pyrofolic acid (9). Reaction of either of these materials with hydrazine selectively affords pteroyl hydrazide (13), which may be oxidized to pteroyl azide (27) on a large scale (62% overall from 1 without the need for chromatography). Treatment of 27 with differentially protected glutamates provides a convenient and high-yielding synthesis of differentially protected, optically pure folates.

  DOI：

  10.1021/ja971568j
• 作为产物：
  描述：

  pteroyl azide 在 亚硝酸特丁酯 、 1,1,2,3-四甲基胍 、 potassium thioacyanate 、 肼 作用下， 以 四氢呋喃 、 二甲基亚砜 、 三氟乙酸 为溶剂， 反应 34.5h， 生成 N¹⁰-nitrosopteroyl azide
  参考文献：
  名称：

  Efficient Syntheses of Pyrofolic Acid and Pteroyl Azide, Reagents for the Production of Carboxyl-Differentiated Derivatives of Folic Acid

  摘要：

  Reaction of folic acid (1) with excess trifluoroacetic anhydride provides access to both the previously unknown N-10-(trifluoroacetyl)pyrofolic acid (8) and pyrofolic acid (9). Reaction of either of these materials with hydrazine selectively affords pteroyl hydrazide (13), which may be oxidized to pteroyl azide (27) on a large scale (62% overall from 1 without the need for chromatography). Treatment of 27 with differentially protected glutamates provides a convenient and high-yielding synthesis of differentially protected, optically pure folates.

  DOI：

  10.1021/ja971568j

文献信息

• Folate-modified cholesterol-bearing pullulan as a drug carrier
  申请人：Sunamoto Junzo

  公开号：US20070042970A1

  公开（公告）日：2007-02-22

  Folate modified cholesterol-bearing pullulan (FA-CHP) was synthesized by the reaction of folic acid γ-2-aminoethylamide and 4-nitorophenyl chloroformate-activated cholesterol-bearing pullulan, wherein folate and pullulan are connected through a NH—CH 2 —CH 2 —NH group. Approximately 0.5-1 folates are connected per about 100 glycoside units of pullulan. Then, several combinations of FA-CHP, cholesterol-bearing pullulan (CHP) and doxorubicin (DOX) mixture were tested for cancer selective cytotoxicity. A mixture of FA-CHP, CHP and DOX of 1:4:0.02 (weight ratio) gave sharp and selective damage to cells of a human epidermoid cancer KB known as expressing a high level of folate receptor. The same mixture inhibited the growth of HuH7 cells, which is a human hepatocellular carcinoma and is unknown as a folate receptor.

  叶酸修饰的胆固醇载体泊洛聚糖（FA-CHP）是通过叶酸γ-2-氨基乙酰胺和4-硝基苯基氯甲酸酯活化的胆固醇载体泊洛聚糖反应合成的，其中叶酸和泊洛聚糖通过一个NH—CH2—CH2—NH基团连接。每约100个葡糖苷单元中连接了大约0.5-1个叶酸。然后，对叶酸修饰的胆固醇载体泊洛聚糖（FA-CHP）、胆固醇载体泊洛聚糖（CHP）和阿霉素（DOX）混合物进行了多种组合的癌症选择性细胞毒性测试。FA-CHP、CHP和DOX的混合物比例为1:4:0.02（重量比）对人表皮癌KB细胞具有高叶酸受体表达水平的细胞造成了明显和选择性的损伤。同样的混合物抑制了HuH7细胞的生长，这是一种人类肝细胞癌，并且未知是否具有叶酸受体。
• US6291673B1
  申请人：——

  公开号：US6291673B1

  公开（公告）日：2001-09-18
• Efficient Syntheses of Pyrofolic Acid and Pteroyl Azide, Reagents for the Production of Carboxyl-Differentiated Derivatives of Folic Acid
  作者：Jin Luo、Michael D. Smith、Douglas A. Lantrip、Susan Wang、P. L. Fuchs

  DOI：10.1021/ja971568j

  日期：1997.10.1

  Reaction of folic acid (1) with excess trifluoroacetic anhydride provides access to both the previously unknown N-10-(trifluoroacetyl)pyrofolic acid (8) and pyrofolic acid (9). Reaction of either of these materials with hydrazine selectively affords pteroyl hydrazide (13), which may be oxidized to pteroyl azide (27) on a large scale (62% overall from 1 without the need for chromatography). Treatment of 27 with differentially protected glutamates provides a convenient and high-yielding synthesis of differentially protected, optically pure folates.