2-acetamido-6-methylpteridin-4(3H)-one | 19962-30-2

• 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: 2-acetamido-6-methylpteridin-4(3H)-one
• 英文别名: 2-Acetamido-4-hydroxy-6-methylpteridine；N-(6-methyl-4-oxo-3H-pteridin-2-yl)acetamide
• CAS: 19962-30-2
• 化学式: C₉H₉N₅O₂
• 分子量: 219.203
• InChiKey: KRQNOGLLAFAABS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetamido-6-methylpteridin-4(3H)-one 在 溴 、 sodium acetate 、 溶剂黄146 、 nickel dichloride 作用下， 生成 2-氨基-4-羟基蝶啶-6-甲醛
  参考文献：
  名称：

  Synthesis of 6-formylpterin

  摘要：

  DOI：

  10.1007/bf01418018
• 作为产物：
  描述：

  2-氨基-6-甲基-4(3H)-蝶啶酮 、 乙酸酐 生成 2-acetamido-6-methylpteridin-4(3H)-one
  参考文献：
  名称：

  2-Amino-4-hydroxy-6-pteridinecarboxaldehyde

  摘要：

  DOI：

  10.1021/ja01166a081

文献信息

• Pteridines, Part CXIII
  作者：Qizheng Yao、Wolfgang Pfleiderer

  DOI：10.1002/hlca.200390025

  日期：2003.1

  compounds can be alkylated under Mitsunobu conditions to form from N2-acylpterins (see 2 and 3) and their derivatives (see 5, 6, 8, 9, 11, 13, 15, and 17) selectively the O4-alkyl derivatives 22–31, whereas the electron-donating [(dimethylamino)methyleneamino function in 46–51 gives, in a selective reaction, the N(3)-substitution (52–61). N2,N2-Dimethylpterins and 18 and 19 and N2-methylpterins 20 and 21

  蝶呤的低溶解度可通过N 2-酰化或形成N 2 -[（（二甲基氨基）亚甲基]衍生物而大大改善。这两种类型的化合物可以下被烷基化的Mitsunobu条件从到形式Ñ 2 -acylpterins（参照2和3）和它们的衍生物（参见图5，6，8，9，11，13，15，和17）选择性地将Ò 4 -烷基衍生物22 – 31，而给电子体[[（二甲基氨基）亚甲基氨基]在46 – 51在选择性反应中给出N（3）取代（52 – 61）。Ñ 2，Ñ 2个-Dimethylpterins和18个19和Ñ 2 -methylpterins 20和21直接烷基化还向Ò 4位上（32 - 35，38和39）。脱酰可以在非常温和的条件下通过溶剂解用MeOH（实现22 40，26 41），和所述的位移Ò 4- [2-（4-硝基苯基）乙基]基团在室温下，以相应的蝶啶-2,4-二胺氨前进42 - 45。N 2 -[（（二甲基氨基）亚甲基]基团的裂解可很好地与氨（62
• The Synthesis of 6-Aminomethyl-5,6,7,8-Tetrahydropterin
  作者：P Waring

  DOI：10.1071/ch9880667

  日期：——

  6-Aminomethyl-5,6,7,8-tetrahydropterin has been prepared by reduction of 2-acetamido-6-cyanopteridin-4(3H)-one* to 2-acetamido-6-aminomethyl- 5,6,7,8-tetrahydropteridin-4(3H)-one followed by acid hydrolysis. The hitherto undescribed 6-cyanopterin was prepared by careful hydrolysis of the 2-acetamido compound prepared by dehydration of the oxime derived from 2-acetamido-6-formylpteridin-4(3H)-one. The latter was prepared by selenium dioxide oxidation of the methyl compound. Oxidation of 6-aminomethyl-5,6,7,8-tetrahydropterin at neutral pH appears to proceed with significant side-chain loss in Tris buffer but not in phosphate buffer.

  通过将 2-乙酰氨基-6-氰基蝶啶-4(3H)-酮*还原为 2-乙酰氨基-6-氨基甲基-5,6,7,8-四氢蝶啶-4(3H)-酮，然后进行酸水解，制备出了 6-氨基甲基-5,6,7,8-四氢蝶啶。通过对 2-乙酰氨基-6-甲酰基蝶啶-4(3H)-酮肟脱水制备的 2-乙酰氨基化合物进行仔细水解，制备出了迄今为止尚未发现的 6-氰基蝶呤。后者是通过二氧化硒氧化甲基化合物制备的。在中性 pH 值下，6-氨甲基-5,6,7,8-四氢蝶呤的氧化似乎是在三羟甲基丙烷缓冲液中进行的，但在磷酸盐缓冲液中侧链损失不大。
• Folic Acid-Conjugated Europium Complexes as Luminescent Probes for Selective Targeting of Cancer Cells
  作者：Silvio Quici、Alessandro Casoni、Francesca Foschi、Lidia Armelao、Gregorio Bottaro、Roberta Seraglia、Cristina Bolzati、Nicola Salvarese、Debora Carpanese、Antonio Rosato

  DOI：10.1021/jm501945w

  日期：2015.2.26

  We report the synthesis of three optical probes (Eu3+subset of 1, Eu3+subset of 2, and Eu3+subset of 3) having a luminescent Eu complex (signaling unit) bonded in different positions to folic acid (FA), the folate receptor (FR) targeting unit. The structures of the two regioisomers Eu3+subset of 1 and Eu3+subset of 2 were assigned by mass spectrometric experiments. The optical properties and stability of these probes were assessed in phosphate-buffered saline, cell culture medium, rat serum, and cellular lysate, and results indicated that they are chemically and photophysically stable. Cytotoxicity was studied with ovarian cancer cells having high (SKOV-3), intermediate (OVCAR-3), low (IGROV-1), or null (A2780) expression of FRs. The internalized probe, evaluated in SKOV-3, IGROV-1, and A2780 cells, was in the order Eu3+subset of 2 > Eu3+subset of 1 > Eu3+subset of 3. No internalization was observed for A2780 cells. Such results, together with those obtained in competition experiments of FA versus Eu3+subset of 2 and FA or Eu3+subset of 2 versus H-3-FA, indicate that internalization is receptor-mediated and that Eu3+subset of 2 shows high selectivity and specificity for FR.
• Waring, Paul; Armarego, Wilfred, L. F., Australian Journal of Chemistry, 1985, vol. 38, # 4, p. 629 - 631
  作者：Waring, Paul、Armarego, Wilfred, L. F.

  DOI：——

  日期：——
• WARING, PAUL, AUSTRAL. J. CHEM., 41,(1988) N 5, C. 667-676
  作者：WARING, PAUL

  DOI：——

  日期：——