羟基苯并三氮唑活性酰胺 | 78162-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 羟基苯并三氮唑活性酰胺
• 中文别名: 1-[2-(Z)-甲氧亚氨基-2-(2-氨基噻唑-4-基)乙酰基]苯并三氮唑-3-氧化物；羟基苯并三氮活性酰胺
• 英文名称: 1-<(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetyl>-benzotriazol-3-oxide
• 英文别名: MABO:1-[2-(2)-Methoxyimino-2-(2-aminothiazol-4-yl)-acetyl] Benzotriazole-3-oxide DMF solvate；(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-1-(3-oxidobenzotriazol-3-ium-1-yl)ethanone
• CAS: 78162-04-6
• 化学式: C₁₂H₁₀N₆O₃S
• 分子量: 318.316
• InChiKey: BOOZZGFERNQMGC-GDNBJRDFSA-N

物化性质

• 熔点：
  156-159 °C
• 沸点：
  573.7±42.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  8

制备方法与用途

用途：医药中间体。

反应信息

• 作为反应物：
  描述：

  羟基苯并三氮唑活性酰胺 、 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid 以95%的产率得到
  参考文献：
  名称：

  LIM, SUNG;MOON, SOON;LEE, GWAN

  摘要：

  DOI：
• 作为产物：
  描述：

  1-羟基苯并三唑 、 氨噻肟酸 以92%的产率得到
  参考文献：
  名称：

  LIM, SUNG;MOON, SOON;LEE, GWAN

  摘要：

  DOI：

文献信息

• 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。
• Studies on 3′-quaternary ammonium cephalosporins—IV. Synthesis and antibacterial activity of 3′-(2-alkyl-3-aminopyrazolium)cephalosporins related to FK037
  作者：Hidenori Ohki、Kohji Kawabata、Yoshiko Inamoto、Shinya Okuda、Toshiaki Kamimura、Kazuo Sakane

  DOI：10.1016/s0968-0896(97)00092-8

  日期：1997.8

  The synthesis and in vitro antibacterial activity of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido] cephalosporins bearing various 2-alkyl-3-aminopyrazolium groups at the 3-position are described. Antibacterial activity against MRSA was affected by the nature of the substituent at the 2-position on the 3'-aminopyrazolium groups. Among the cephalosporins prepared in this study, 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[3-amino-2-(2-hydroxyethyl)-pyrazolio]methyl-3-cephem-4-carboxylate sulfate (23e, FK037) showed extremely potent broad-spectrum activity against both Gram-positive bacteria including MRSA, and Gram-negative bacteria including Pseudomonas aeruginosa. In particular, the in vivo activity against MRSA of FK037 was the highest of all the beta-lactam antibiotics tested. (C) 1997 Elsevier Science Ltd.
• 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：EP0332156B1

  公开（公告）日：1996-12-18
• US5173485A
  申请人：——

  公开号：US5173485A

  公开（公告）日：1992-12-22