5-Formamido-1,4-dimethylpyrazole | 112029-00-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-Formamido-1,4-dimethylpyrazole
• 英文别名: N-(1,4-Dimethyl-1H-pyrazol-5-yl)formamide；N-(2,4-dimethylpyrazol-3-yl)formamide
• CAS: 112029-00-2
• 化学式: C₆H₉N₃O
• mdl: MFCD19220419
• 分子量: 139.157
• InChiKey: XQQVJXUYCQEULE-UHFFFAOYSA-N

物化性质

• 沸点：
  334.9±22.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Formamido-1,4-dimethylpyrazole 在 苯甲醚 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 7β-amino-3-(3-formamido-2,4-dimethyl-1-pyrazolio)methyl-3-cephem-4-carboxylate bistrifluoroacetate
  参考文献：
  名称：

  Studies on 3′-quaternary ammonium cephalosporins—III. Synthesis and antibacterial activity of 3′-(3-aminopyrazolium)cephalosporins

  摘要：

  The synthesis and in vitro antibacterial activity of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]cephalosporins bearing N-mono or dialkyl and carbamoyl aminopyrazolium, and five- or six-membered rings fused to the 3-aminopyrazolium methyl groups at the 3-position, are described. Aminopyrazolium methyl cephalosporins (23e, f, i), with fused saturated and unsaturated rings were especially effective against Staphylococcus strains compared to 3-amino-2-methylpyrazolium methyl cephalosporin (1). Among the cephalosporins prepared in this work, 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]pyrimidino)methyl-3-cephem-4-carboxylate (23f) showed a good balance of antibacterial activity against both Gram-positive bacteria including Staphylococcus aureus and Gram-negative bacteria including P. aeruginosa. An imidazopyrazolium group at the 3-position in, for example, cephalosporin (23i) was particularly effective for improving antibacterial activity against MRSA. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00270-2
• 作为产物：
  描述：

  甲酸 、 2,4-二甲基-3-氨基吡唑 在 乙酸酐 作用下， 生成 5-Formamido-1,4-dimethylpyrazole
  参考文献：
  名称：

  Studies on 3′-quaternary ammonium cephalosporins—III. Synthesis and antibacterial activity of 3′-(3-aminopyrazolium)cephalosporins

  摘要：

  The synthesis and in vitro antibacterial activity of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]cephalosporins bearing N-mono or dialkyl and carbamoyl aminopyrazolium, and five- or six-membered rings fused to the 3-aminopyrazolium methyl groups at the 3-position, are described. Aminopyrazolium methyl cephalosporins (23e, f, i), with fused saturated and unsaturated rings were especially effective against Staphylococcus strains compared to 3-amino-2-methylpyrazolium methyl cephalosporin (1). Among the cephalosporins prepared in this work, 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]pyrimidino)methyl-3-cephem-4-carboxylate (23f) showed a good balance of antibacterial activity against both Gram-positive bacteria including Staphylococcus aureus and Gram-negative bacteria including P. aeruginosa. An imidazopyrazolium group at the 3-position in, for example, cephalosporin (23i) was particularly effective for improving antibacterial activity against MRSA. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00270-2

文献信息

• New cephem compounds and processes for preparation thereof
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0223246A2

  公开（公告）日：1987-05-27

  A new cephem compound of the formula: wherein R' is amino or protected amino, R2 is hydrogen, hydroxy protective group, lower alkyl, dihalogenated lower alkyl, cyclo(lower)alkenyl, thietanyl, carboxy(lower)alkyl or protected carboxy(lower)alkyl, R3 is lower alkyl, R4 and R5 are each hydrogen, lower alkyl, hydroxy (lower)alkyl, lower alkoxy, amino or protected amino, R6 is COOe, carboxy or protected carboxy, X⊖ is an anion, and n is 0 or 1, with certain provisions, processes for their preparation and pharmaceutical compositions containing them. The invention relates also to compounds of the formula and of the formula in which Z is an acid residue.

  式中 R' 为氨基或保护氨基，R2 为氢、羟基保护基、低级烷基、二卤代低级烷基、环（低）烯基、硫杂环丁基、羧基（低）烷基或保护羧基（低）烷基，R3 为低级烷基，R4 和 R5 分别为氢、低级烷基、羟基（低）烷基、低级烷氧基、氨基或保护氨基，R6 为 COOe、羧基或保护羧基，X⊖ 为阴离子，n 为 0 或 1。 本发明还涉及式中和式中 Z 为酸残基的化合物。
• Cephem compounds, processes for preparation thereof and pharmaceutical compositions comprising them
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0261615A2

  公开（公告）日：1988-03-30

  A compound of the formula : wherein R1 and R4 are each amino or a protected amino group, R2 is carboxy(lower)alkyl or a protected carboxy(lower)alky], R3 is lower alkyl, hydroxy(lower)alkyl or a protected hydroxy(lower)alkyl, and R5 is hydrogen or lower alkyl, and a pharmaceutically acceptable salt thereof, processes for their preparation and pharmaceutical compositions comprising them as an active ingredient. The invention further relates to intermediate compounds of the formula and their preparation.

  式中的化合物： 其中 R1 和 R4 分别为氨基或受保护的氨基、 R2 是羧基（低级）烷基或受保护的羧基（低级）烷基、］ R3 是低级烷基、羟基（低级）烷基或受保护的羟基（低级）烷基，以及 R5 是氢或低级烷基、 及其药学上可接受的盐、它们的制备工艺和含有它们作为活性成分的药物组合物。本发明进一步涉及式 及其制备方法。
• US4927818A
  申请人：——

  公开号：US4927818A

  公开（公告）日：1990-05-22
• US4960766A
  申请人：——

  公开号：US4960766A

  公开（公告）日：1990-10-02
• US5108997A
  申请人：——

  公开号：US5108997A

  公开（公告）日：1992-04-28