folic acid-hydrazide

• 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: folic acid-hydrazide
• 英文别名: 2-(4-(((2-Amino-4-oxo-4,8-dihydropteridin-6-yl)methyl)amino)benzamido)-5-hydrazinyl-5-oxopentanoic acid；2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoyl]amino]-5-hydrazinyl-5-oxopentanoic acid
• 化学式: C₁₉H₂₁N₉O₅
• 分子量: 455.433
• InChiKey: KGOZNLVSEDVQTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  227
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  葡糖二酸 、 folic acid-hydrazide 在 calcium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of receptor-based tumor imaging agent: 99mTc-folate-glucaric acid

  摘要：

  The aim of the present study was to prepare Tc-99m-folate-glucaric acid and investigate the radiopharmaceutical potential for tumors imaging that over express folate receptor. Folate-glucaric acid was synthesized and the synthesized folate conjugate was confirmed with H-1 NMR and LC-MS/MS methods. Folate-glucaric acid was labeled with Tc-99m, and its radiolabelling efficiency was found as 96 +/- 2.0%. Biodistribution study of Tc-99m-folate-glucaric acid was carried out in vivo using two groups of female Albino Wistar rats: folate receptor (FR) saturated and unsaturated. Biodistribution study showed that Tc-99m-folate-glucaric acid indicated high uptake in folate receptor rich tissues such as breast, ovary and uterus. Therefore, Tc-99m-folate-glucaric acid shows good radiolabeling and biodistribution in FR organs, the radiolabeled conjugate is a reason potentially useful radiopharmaceutical for detection of FR-positive tumors. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.07.010
• 作为产物：
  描述：

  L-谷氨酸 在 1,1,2,3-四甲基胍 、 caesium carbonate 、 肼 作用下， 以 四氢呋喃 、 氘代二甲亚砜 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 folic acid-hydrazide
  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

• 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.
• Synthesis and biological evaluation of receptor-based tumor imaging agent: 99mTc-folate-glucaric acid
  作者：Mehmet Onursal、Fatma Yurt Lambrecht、Aykut Ozgur

  DOI：10.1016/j.ijpharm.2011.07.010

  日期：2011.9

  The aim of the present study was to prepare Tc-99m-folate-glucaric acid and investigate the radiopharmaceutical potential for tumors imaging that over express folate receptor. Folate-glucaric acid was synthesized and the synthesized folate conjugate was confirmed with H-1 NMR and LC-MS/MS methods. Folate-glucaric acid was labeled with Tc-99m, and its radiolabelling efficiency was found as 96 +/- 2.0%. Biodistribution study of Tc-99m-folate-glucaric acid was carried out in vivo using two groups of female Albino Wistar rats: folate receptor (FR) saturated and unsaturated. Biodistribution study showed that Tc-99m-folate-glucaric acid indicated high uptake in folate receptor rich tissues such as breast, ovary and uterus. Therefore, Tc-99m-folate-glucaric acid shows good radiolabeling and biodistribution in FR organs, the radiolabeled conjugate is a reason potentially useful radiopharmaceutical for detection of FR-positive tumors. (C) 2011 Elsevier B.V. All rights reserved.