L-methyl folate (γ) | 53464-60-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: L-methyl folate (γ)
• 英文别名: folic acid γ-methyl ester；(2S)-2-[(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)amino]-5-methoxy-5-oxopentanoic acid；Folic acid, methyl-；(2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoyl]amino]-5-methoxy-5-oxopentanoic acid
• CAS: 53464-60-1
• 化学式: C₂₀H₂₁N₇O₆
• 分子量: 455.43
• InChiKey: BNZPKFAGFVCCMO-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  198
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙二胺 、 L-methyl folate (γ) 以72%的产率得到ethylelediamine-folate
  参考文献：
  名称：

  Folate-modified cholesterol-bearing pullulan as a drug carrier

  摘要：

  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。

  公开号：

  US20070042970A1
• 作为产物：
  描述：

  pteroyl hydrazide 在 亚硝酸特丁酯 、 t-butyltetramethyl-guanidine 、 potassium thioacyanate 作用下， 以 二甲基亚砜 、 三氟乙酸 为溶剂， 反应 13.0h， 生成 L-methyl folate (γ)
  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

• Novel compositions magnetic particles covered with gem-bisphosphonate derivatives
  申请人：Port Marc

  公开号：US20100297025A1

  公开（公告）日：2010-11-25

  The invention relates to a composition comprising acid magnetic particles (p) based on an iron compound, the acid magnetic particles (p) being complexed by one or more gem-bisphosphonate compounds, of formula I: X-L-CH(PO 3 H 2 ) 2 (I) in which: L represents an organic group connecting the X group to the gem-bisphosphonate group —CH(PO 3 H 2 ) 2 ; X represents a chemical group capable of reacting with a biovector; all or some of the X groups of the particles optionally being coupled to a biovector. The invention relates also to a process for the preparation of the compositions and their use, in particular as contrast products for Magnetic Resonance Imaging (MRI).

  这项发明涉及一种包含基于铁化合物的酸性磁性颗粒（p）的组合物，所述酸性磁性颗粒（p）被一个或多个式I的双膦酸盐化合物络合： X-L-CH(PO3H2)2(I) 其中： L代表将X基团连接到双膦酸盐基团—CH(PO3H2)2的有机基团； X代表能够与生物载体发生反应的化学基团；颗粒的一个或多个X基团可选择地与生物载体偶联。 该发明还涉及一种制备所述组合物的方法及其用途，特别是作为磁共振成像（MRI）对比剂。
• US7780953B2
  申请人：——

  公开号：US7780953B2

  公开（公告）日：2010-08-24
• US9744204B1
  申请人：——

  公开号：US9744204B1

  公开（公告）日：2017-08-29
• 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.
• 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。