5-formamido-1-(3-formyloxypropyl)pyrazole | 131654-78-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-formamido-1-(3-formyloxypropyl)pyrazole
• 英文别名: 3-(5-formamidopyrazol-1-yl)propyl formate
• CAS: 131654-78-9
• 化学式: C₈H₁₁N₃O₃
• 分子量: 197.194
• InChiKey: VPASZIUKRKKSQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  424.2±25.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-formamido-1-(3-formyloxypropyl)pyrazole 在 盐酸 、 碳酸氢钠 、 苯甲醚 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[3-amino-2-(3-hydroxypropyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate
  参考文献：
  名称：

  Studies on 3′-quaternary ammonium cephalosporins—IV. Synthesis and antibacterial activity of 3′-(2-alkyl-3-aminopyrazolium)cephalosporins related to FK037

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(97)00092-8
• 作为产物：
  描述：

  5-amino-1-(2-methoxycarbonylethyl)pyrazole 在 lithium aluminium tetrahydride 、 乙酸酐 、 sodium fluoride 作用下， 反应 4.0h， 生成 5-formamido-1-(3-formyloxypropyl)pyrazole
  参考文献：
  名称：

  Studies on 3′-quaternary ammonium cephalosporins—IV. Synthesis and antibacterial activity of 3′-(2-alkyl-3-aminopyrazolium)cephalosporins related to FK037

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(97)00092-8

文献信息

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

  公开号：US05187160A1

  公开（公告）日：1993-02-16

  The invention relates to antimicrobial compounds of the formula: ##STR1## wherein R.sup.1 is amino or a protected amino, R.sup.2 is ethyl, propyl or lower alkenyl, R.sup.3 is COO .theta., carboxy or a protected carboxy, R.sup.4 is hydroxy(lower)alkyl or protected hydroxy(lower)alkyl, R.sup.5 is amino or a protected amino, X.sup..theta. is an anion, and n is 0 or 1, or, R.sup.1, R.sup.3, R.sup.5, X.sup..theta. and n are each as defined above, R.sup.2 is lower alkyl, and R.sup.4 is 3-hydroxypropyl, with proviso that (i) when R.sup.3 is COO.sup..theta., then n is 0, and (ii) when R.sup.3 is carboxy or a protected carboxy, then n is 1, or a pharmaceutically acceptable salt thereof.

  该发明涉及一种抗菌化合物，其化学式为：##STR1## 其中R.sup.1是氨基或受保护的氨基，R.sup.2是乙基、丙基或较低烯烃基，R.sup.3是COO .theta.、羧基或受保护的羧基，R.sup.4是羟基(较低)烷基或受保护的羟基(较低)烷基，R.sup.5是氨基或受保护的氨基，X.sup..theta.是阴离子，n为0或1，或者R.sup.1、R.sup.3、R.sup.5、X.sup..theta.和n分别如上定义，R.sup.2为较低烷基，R.sup.4为3-羟基丙基，但需满足以下条件：(i)当R.sup.3为COO.sup..theta.时，n为0，(ii)当R.sup.3为羧基或受保护的羧基时，n为1，或其药用可接受盐。
• New cephem compound and a process for preparation thereof
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0386689A1

  公开（公告）日：1990-09-12

  A cephem compound of the formula : wherein R1 is amino or a protected amino, R2 is ethyl, propyl or lower alkenyl, R3 is COOe, carboxy or a protected carboxy, R4 is hydroxy(lower)alkyl or protected hydroxy(lower)alkyl, RS is amino or a protected amino, X⊖ is an anion, and n is 0 or 1, or, R1, R3, RS, Xe and n are each as defined above, R2 is lower alkyl, and R4 is 3-hydroxypropyl, with proviso that (i) when R3 is COOe, then n is 0, and (ii) when R3 is carboxy or a protected carboxy, then n is 1, or a pharmaceutically acceptable salt thereof, processes for their preparation and pharmaceutical compositions comprising them as an active ingredient in admixture with pharmaceutically acceptable carriers.

  一种分子式为......的 cephem 化合物 其中 R1 是氨基或受保护的氨基 R2 是乙基、丙基或低级烯基 R3 是 COOe、羧基或受保护的羧基，R4 是羟基（低级）烷基或受保护的羟基（低级）烷基、 RS 是氨基或受保护的氨基、 X⊖ 是阴离子，以及 n 为 0 或 1、 或 R1、R3、RS、Xe 和 n 均如上定义、 R2 是低级烷基，以及 R4 是 3-羟基丙基、 但条件是 (i) 当 R3 是 COOe 时，n 为 0，和 (ii) 当 R3 为羧基或受保护的羧基时，则 n 为 1，或其药学上可接受的盐、其制备方法以及将其作为活性成分与药学上可接受的载体混合的药物组合物。
• US5187160A
  申请人：——

  公开号：US5187160A

  公开（公告）日：1993-02-16
• 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.