1-methyl-5-ureidopyrazole | 116856-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-5-ureidopyrazole
• 英文别名: (2-methylpyrazol-3-yl)urea
• CAS: 116856-17-8
• 化学式: C₅H₈N₄O
• 分子量: 140.145
• InChiKey: XSGPCKRUVVAWNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-5-ureidopyrazole 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-ureido-2-methyl-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：

  1-甲基-5-氨基吡唑 以 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 生成 1-methyl-5-ureidopyrazole
  参考文献：
  名称：

  Cephem compounds and processes for preparation thereof

  摘要：

  制备了7.β.-[2-5氨基-1，2，4-噻二唑-3-基)2(羧基较低烷氧基亚氨基)乙酰胺]-3-(3-氨基-2-烷基-1-吡唑啉)甲基3头孢烯4羧酸盐。它们是抗生素。

  公开号：

  US04927818A1

文献信息

• Intermediates for cephem compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05162520A1

  公开（公告）日：1992-11-10

  The invention relates to intermediate compounds of the formula: ##STR1## wherein R.sup.3 is a lower alkyl, hydroxy(lower)alkyl or a protected hydroxy(lower)alkyl, R.sup.4 is amino or a protected amino group, and R.sup.5 is hydrogen or lower alkyl, or a salt thereof, useful in the preparation of compounds of antimicrobial activity.

  本发明涉及式为：##STR1##的中间化合物，其中R.sup.3是较低的烷基，羟基（较低）烷基或保护羟基（较低）烷基，R.sup.4是氨基或保护氨基团，R.sup.5是氢或较低的烷基，或其盐，在制备抗微生物活性化合物方面有用。
• Cephem compounds
  申请人：Fujisawa Pharmaceuticals Co., Ltd.

  公开号：US05108997A1

  公开（公告）日：1992-04-28

  The invention relates to a compound, of antimicrobial activity, of the formula: ##STR1## wherein R.sup.1 and R.sup.4 are each amino or a protected amino group, R.sup.2 is carboxy(lower) alkyl or a protected carboxy(lower) alkyl, R.sup.3 is lower alkyl, and R.sup.5 is hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof.

  本发明涉及一种具有抗微生物活性的化合物，其化学式为：##STR1## 其中R.sup.1和R.sup.4都是氨基或受保护的氨基基团，R.sup.2是羧基（低级）烷基或受保护的羧基（低级）烷基，R.sup.3是低级烷基，R.sup.5是氢或低级烷基，或其药学上可接受的盐。
• Studies on 3′-quaternary ammonium cephalosporins—III. Synthesis and antibacterial activity of 3′-(3-aminopyrazolium)cephalosporins
  作者：Hidenori Ohki、Kohji Kawabata、Yoshiko Inamoto、Shinya Okuda、Toshiaki Kamimura、Kazuo Sakane

  DOI：10.1016/s0968-0896(96)00270-2

  日期：1997.3

  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.
• Cephem compounds and processes for preparation thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04927818A1

  公开（公告）日：1990-05-22

  7 .beta.-[2-5 amino-1, 2, 4 thiadiazol-3yl) 2(carboxy lower alkyleneoxyimino) acetamido]-3-(3-amino-2-alkyl-1-pyrazolio) methyl 3 cephem 4 carboxylates are prepared. They are antibiotics.

  制备了7.β.-[2-5氨基-1，2，4-噻二唑-3-基)2(羧基较低烷氧基亚氨基)乙酰胺]-3-(3-氨基-2-烷基-1-吡唑啉)甲基3头孢烯4羧酸盐。它们是抗生素。