5-formamido-1-(2-hydroxyethyl)pyrazole | 122589-40-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-formamido-1-(2-hydroxyethyl)pyrazole
• 英文别名: 1-(2-hydroxyethyl)-5-formamidopyrazole；N-[2-(2-hydroxyethyl)pyrazol-3-yl]formamide
• CAS: 122589-40-6
• 化学式: C₆H₉N₃O₂
• 分子量: 155.156
• InChiKey: SBGVMZDALRWZPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-formamido-1-(2-hydroxyethyl)pyrazole 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 1-formyl-2,3-dihydro-1H-imidazo[1,2-b]pyrazole
  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：

  5-氨基-1-(2-羟乙基)吡唑 在 甲酸 、 乙酸酐 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 5-formamido-1-(2-hydroxyethyl)pyrazole
  参考文献：
  名称：

  Cephem compound and a process for preparation thereof

  摘要：

  本发明的对象是一种具有抗微生物活性的新的头孢菌素化合物，用于治疗一般式的传染性疾病：##STR1## 其中，R1是氨基或保护氨基，R2是较低的烷基，可以有1到3个卤素，R3是COO.sup..crclbar.，羧基或保护羧基，R4是羟基(较低)烷基或保护羟基(较低)烷基，R5是氨基或保护氨基，R6是氢或较低的烷基，X.sup..crclbar.是阴离子，n为0或1，但需注意：(i)当R3为COO.sup..crclbar.时，n为0；(ii)当R3为羧基或保护羧基时，n为1，以及其药学上可接受的盐。

  公开号：

  US04952578A1

文献信息

• Cephem compound and a process for preparation thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04952578A1

  公开（公告）日：1990-08-28

  The object of the invention is a new cephem compound with antimicrobial activity used for the treatment of infectious diseases of the general formula: ##STR1## wherein R1 is amino or a protected amino R2 is lower alkyl which may have 1 to 3 halogens R3 is COO.sup..crclbar., carboxy or a protected carboxy R4 is hydroxy(lower)alkyl or protected hydroxy(lower)alkyl R5 is amino or a protected amino R6 is hydrogen or lower alkyl X.sup..crclbar. is an anion, and n is 0 or 1 with proviso that (i) when R3 is COO.sup..crclbar., then n is 0, and (ii) when R3 is carboxy or a protected carboxy, then n is 1, and pharmaceutically acceptable salt thereof.

  本发明的对象是一种具有抗微生物活性的新的头孢菌素化合物，用于治疗一般式的传染性疾病：##STR1## 其中，R1是氨基或保护氨基，R2是较低的烷基，可以有1到3个卤素，R3是COO.sup..crclbar.，羧基或保护羧基，R4是羟基(较低)烷基或保护羟基(较低)烷基，R5是氨基或保护氨基，R6是氢或较低的烷基，X.sup..crclbar.是阴离子，n为0或1，但需注意：(i)当R3为COO.sup..crclbar.时，n为0；(ii)当R3为羧基或保护羧基时，n为1，以及其药学上可接受的盐。
• Cephem compounds and processes for preparation thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05663163A1

  公开（公告）日：1997-09-02

  The present invention relates to new cephem compounds, pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising the same and anti-bacterial methods of using the same. The subject cephem compounds comprise a thiadiazine ring bonded to the cephem through an iminoacetamido chain and a pyarzolium ring bonded to the cephem through a methylene chain.

  本发明涉及新的头孢菌素化合物，其药学上可接受的盐，包含其的制药组合物以及使用其的抗菌方法。该头孢菌素化合物由通过亚氨基乙酰胺链与头孢菌素结合的噻二嗪环和通过亚甲基链与头孢菌素结合的吡唑环组成。
• Cephem compounds and pharmaceutically acceptable salts thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05366970A1

  公开（公告）日：1994-11-22

  The invention relates to a compound of the formula: ##STR1## of antimicrobial activity.

  该发明涉及一种具有抗微生物活性的化合物，其化学式为：##STR1##。
• 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.
• US4952578A
  申请人：——

  公开号：US4952578A

  公开（公告）日：1990-08-28