6-[(3,4,5-三甲氧基苯基)甲基]嘧啶-2,4-二胺 | 61550-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 6-[(3,4,5-三甲氧基苯基)甲基]嘧啶-2,4-二胺
• 英文名称: isotrimethoprim
• 英文别名: trimethoprim；2,4-Diamino-6-(3,4,5-trimethoxybenzyl)pyrimidine；6-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
• CAS: 61550-88-7
• 化学式: C₁₄H₁₈N₄O₃
• 分子量: 290.322
• InChiKey: ZQMPUWBQWRAQIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trans-dichlorobis(ethylenediamine)cobalt(III) chloride 、 6-[(3,4,5-三甲氧基苯基)甲基]嘧啶-2,4-二胺 、 [cis-Co(ethylenediamine)2Cl₂]Cl 以 乙醇 为溶剂， 生成 [Co(ethylenediamine)2(trimethoprim)2]Cl3
  参考文献：
  名称：

  Cobalt(III) Complexes of Some Antimalarial Drugs: Synthesis, Characterization, and in vitro Antiprotozoal Studies

  摘要：

  Cobalt(III) complexes of the antimalarial drugs amodiaquine, chloroquine, quinacrine and trimethoprim are presented. The complexes were characterized by elemental analyses, conductance, magnetic susceptibility measurement, IR and electronic spectroscopies. Their in vitro antiplasmodial and antitrypanosomal activity against Trypanosoma cruzi, L. donovani, T. b. rhodesiense and the resistant strain of Plasmodium falciparum showed that the cobalt(III) complexes of quinacrine, [CoQNC(en)2Cl]Cl2 and amodiaquine, CoAQ(en)2Cl]Cl2 are more active than chloroquine against the resistant strain of P. falciparum.

  DOI：

  10.1080/15533171003766691
• 作为产物：
  描述：

  3,4,5-trimethoxyphenylacetyl chloride 在 2,2'-联吡啶 、 calcium hydroxide 、 ammonium hydroxide 、 正丁基锂 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 生成 6-[(3,4,5-三甲氧基苯基)甲基]嘧啶-2,4-二胺
  参考文献：
  名称：

  通过迄今未知的6-苄基-2-（O-甲基）尿嘧啶生成潜在的二氢叶酸还原酶抑制剂的通用途径：异三甲氧苄啶的合成

  摘要：

  从2-（O-甲基）-6-（3,4,5-三甲氧基苄基）尿嘧啶开始，已经完成了2,4-二氨基-6-（3,4,5-三甲氧基苄基）嘧啶（异三甲氧苄啶）的合成。标准程序。苄基尿嘧啶衍生物是通过使O-甲基异脲硫酸盐与3,4,5-三甲氧基苯乙酰基乙酸乙酯反应而获得的。

  DOI：

  10.1002/jhet.5570260372

文献信息

• Synthesis, antimicrobial and antiviral activities of isotrimethoprim and some related derivatives
  作者：M Botta、M Artico、S Massa、A Gambacorta、ME Marongiu、A Pani、P La Colla

  DOI：10.1016/0223-5234(92)90009-p

  日期：1992.4

  The synthesis and the antimicrobial activities of 2,4-diamino-6-(3,4.5-trimethoxvbenzyl)pyrimidine (isotrimethoprim) and some related derivatives are reported. The new derivatives have been found scarcely active against bacteria and fungi, with the only exception of 4-chloro-2-methoxypyrimidinyl-3,4,5-trimethoxyphenyldichloromethane, which showed good antibacterial activity against Staphylococcus aureus. Cytotoxicity and antiviral assays, HIV included, have also been determined in comparison with TMP and AZT. Little but selective activity was shown by some derivatives against HIV retrovirus.
• Cobalt(III) Complexes of Some Antimalarial Drugs: Synthesis, Characterization, and <i>in vitro</i> Antiprotozoal Studies
  作者：Peter A. Ajibade、Gabriel A. Kolawole

  DOI：10.1080/15533171003766691

  日期：2010.5.11

  Cobalt(III) complexes of the antimalarial drugs amodiaquine, chloroquine, quinacrine and trimethoprim are presented. The complexes were characterized by elemental analyses, conductance, magnetic susceptibility measurement, IR and electronic spectroscopies. Their in vitro antiplasmodial and antitrypanosomal activity against Trypanosoma cruzi, L. donovani, T. b. rhodesiense and the resistant strain of Plasmodium falciparum showed that the cobalt(III) complexes of quinacrine, [CoQNC(en)2Cl]Cl2 and amodiaquine, CoAQ(en)2Cl]Cl2 are more active than chloroquine against the resistant strain of P. falciparum.
• BOTTA, MAURIZIO;ARTICO, MARINO;MASSA, SILVIO;GAMBACORTA, AUGUSTO, J. HETEROCYCL. CHEM., 26,(1989) N, C. 883-884
  作者：BOTTA, MAURIZIO、ARTICO, MARINO、MASSA, SILVIO、GAMBACORTA, AUGUSTO

  DOI：——

  日期：——
• A versatile route to potential dihydrofolate reductase inhibitors<i>via</i>the hitherto unknown 6-benzyl-2-(<i>O</i>-methyl)uracils: Synthesis of isotrimethoprim
  作者：Maurizio Botta、Marino Artico、Silvio Massa、Augusto Gambacorta

  DOI：10.1002/jhet.5570260372

  日期：1989.5

  The synthesis of 2, 4-diamino-6-(3, 4, 5-trimethoxybenzyl)pyrimidine (isotrimethoprim) has been accomplished starting from 2-(O-methyl)-6-(3, 4, 5-trimethoxybenzyl)uracil by standard procedures. The benzyluracil derivative has been obtained by reacting O-methylisourea sulphate and ethyl 3, 4, 5-trimethoxyphenacetylace-tate.

  从2-（O-甲基）-6-（3,4,5-三甲氧基苄基）尿嘧啶开始，已经完成了2,4-二氨基-6-（3,4,5-三甲氧基苄基）嘧啶（异三甲氧苄啶）的合成。标准程序。苄基尿嘧啶衍生物是通过使O-甲基异脲硫酸盐与3,4,5-三甲氧基苯乙酰基乙酸乙酯反应而获得的。