1H-咪唑并[1,2-b]吡唑-1-甲醛 | 188998-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1H-咪唑并[1,2-b]吡唑-1-甲醛
• 英文名称: 1-formyl-1H-imidazo[1,2-b]pyrazole
• 英文别名: 1h-Imidazo[1,2-b]pyrazole-1-carbaldehyde；imidazo[1,2-b]pyrazole-1-carbaldehyde
• CAS: 188998-04-1
• 化学式: C₆H₅N₃O
• mdl: MFCD18808090
• 分子量: 135.125
• InChiKey: DHEDMKADEUKAIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H-咪唑并[1,2-b]吡唑-1-甲醛 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-[1-formyl-5-(1H-imidazo[1,2-b]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-(2,2-diethoxyethyl)-4-carboxy-5-aminopyrazole 在 盐酸 、 乙酸酐 作用下， 反应 2.25h， 生成 1H-咪唑并[1,2-b]吡唑-1-甲醛
  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

• Cephem compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05215982A1

  公开（公告）日：1993-06-01

  Cephem compounds of the following formula are disclosed: ##STR1## wherein R.sup.1 is amino or protected amino group. R.sup.2 is H or an organic group, R.sup.3 is H or an organic group, R.sup.4 is H, lower alkyl, carboxy, protected carboxy, amino, protected amino or carbamoyl, Z=N or CH. The compounds are useful as antimicrobial agents.

  公开了以下式子的头孢菌素化合物：##STR1## 其中，R.sup.1是氨基或保护氨基基团。R.sup.2是氢或有机基团，R.sup.3是氢或有机基团，R.sup.4是氢、低碳基、羧基、保护羧基、氨基、保护氨基或氨基甲酰基，Z=N或CH。这些化合物可用作抗微生物剂。
• Intermediates for cephem compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05302712A1

  公开（公告）日：1994-04-12

  The invention relates to compounds, useful as intermediates in the preparation of products of antimicrobial activity, of the formula: ##STR1## wherein R.sup.3 is hydrogen, lower alkyl, hydroxy(lower)alkyl, protected hydroxy(lower)alkyl, amino(lower)alkyl, protected amino (lower) alkyl, carbamoyl)lower)alkyl, N,N-di(lower) alkylcarbamoyl(lower)alkyl or an amino protective group, and R.sup.4 is hydrogen, lower alkyl, carboxy, protected carboxy, amino, protected amino or carbamoyl, or a salt thereof.

  本发明涉及化合物，其在制备具有抗微生物活性的产物中作为中间体有用，其化学式为：##STR1## 其中R.sup.3是氢，低烷基，羟基（低）烷基，保护羟基（低）烷基，氨基（低）烷基，保护氨基（低）烷基，氨基甲酰（低）烷基，N，N-二（低）烷基氨基甲酰（低）烷基或氨基保护基，R.sup.4是氢，低烷基，羧基，保护羧基，氨基，保护氨基或氨基甲酰，或其盐。
• New cephem compounds and processes for preparation thereof
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0427248A2

  公开（公告）日：1991-05-15

  A compound of the formula wherein R1 is amino or a protected amino group, R2 is hydrogen or an organic group, R3 is hydrogen, lower alkyl, hydrory(lower)alkyl, protected hydroxy(lower)alkyl, amino(lower)alkyl, protected amino(lower)alkyl, carbamoyl-(lower)alkyl, N,N-di(lower)alkylcarbamoyl(lower)alkyl or an imino protective group, R4 is hydrogen, lower alkyl, carboxy, protected carboxy, amino,protected amino or carbamoyl, and Z is N or CH, and a pharmaceutically acceptable salt thereof, processes for their preparation and pharmaceutical compositions comprising them as an active ingredient in admixture with pharmaceutically acceptable carriers. The invention also relates to intermediates of the formula and processes for their preparation.

  式中的化合物 其中 R1 是氨基或受保护的氨基、 R2 是氢或有机基团 R3 是氢、低级烷基 R3是氢、低级烷基、羟基（低级）烷基、受保护的羟基（低级）烷基、氨基（低级）烷基、受保护的氨基（低级）烷基、氨基甲酰基（低级）烷基、N,N-二（低级）烷基氨基甲酰基（低级）烷基或亚胺保护基团、 R4 是氢、低级烷基、羧基、保护羧基、氨基、保护氨基或氨基甲酰基，以及 Z 是 N 或 CH、 及其药学上可接受的盐、 它们的制备工艺，以及将它们作为活性成分与药学上可接受的载体混合的药物组合物。本发明还涉及式 及其制备工艺。
• US5215982A
  申请人：——

  公开号：US5215982A

  公开（公告）日：1993-06-01
• US5302712A
  申请人：——

  公开号：US5302712A

  公开（公告）日：1994-04-12