5-氨基-1-(2-羟乙基)吡唑-4-甲酸乙酯 | 58046-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1-(2-羟乙基)吡唑-4-甲酸乙酯
• 中文别名: 5-氨基-1-(2-羟基乙基)-1H-吡唑-4-羧酸乙酯；5-氨基-1-(2-羟乙基)-4-乙氧羰基吡唑
• 英文名称: 5-amino-4-ethoxycarbonyl-1-(2'-hydroxyethyl)-pyrazole
• 英文别名: 5-amino-4-ethoxycarbonyl-1-(2-hydroxyethyl)pyrazole；1-(2-hydroxyethyl)-4-ethoxycarbonyl-5-aminopyrazole；5-amino-1-(2-hydroxy-ethyl)-1H-pyrazole-4-carboxylic acid ethyl ester；5-Amino-1-(2-hydroxy-aethyl)-1H-pyrazol-4-carbonsaeure-aethylester；3-Amino-2-(2-hydroxy-aethyl)-4-aethoxycarbonyl-pyrazol；Ethyl 5-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carboxylate；ethyl 5-amino-1-(2-hydroxyethyl)pyrazole-4-carboxylate
• CAS: 58046-49-4
• 化学式: C₈H₁₃N₃O₃
• mdl: MFCD02676875
• 分子量: 199.21
• InChiKey: PTHDVPPLPCACPF-UHFFFAOYSA-N

物化性质

• 熔点：
  84-87 °C
• 沸点：
  180 °C(Press: 0.3 Torr)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.4
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933199090

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-amino-1-(2-methoxyethyl)-1H-pyrazole-4-carboxylic acid ethyl ester	144991-34-4	C9H15N3O3	213.236
  ——	1-(2-methylsulfonyloxyethyl)-4-ethoxycarbonyl-5-aminopyrazole	126352-83-8	C9H15N3O5S	277.301
  5-氨基-(2-羟乙基)-4-吡唑甲酸	N-hydroxyethyl-5-amino-1H-pyrazole-4-carboxylic acid	58046-50-7	C6H9N3O3	171.156
  ——	5-amino-1-(2-methoxyethyl)pyrazole-4-carboxylic acid	144991-36-6	C7H11N3O3	185.183
  ——	Ethyl 5-bromo-1-(2-hydroxyethyl)pyrazole-4-carboxylate	1085802-36-3	C8H11BrN2O3	263.091

反应信息

• 作为反应物：
  描述：

  5-氨基-1-(2-羟乙基)吡唑-4-甲酸乙酯 在 sodium hydroxide 、 sodium methylate 、 三乙胺 作用下， 以 二苯醚 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 1-(2-甲氧基乙基)-1H-吡唑-5-胺
  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：

  2-肼基乙醇 、 2-氰基-3-乙氧基丙烯酸乙酯 以 乙醇 为溶剂， 反应 3.0h， 以to give 5-amino-4-ethoxycarbonyl-1-(2′-hydroxyethyl)-pyrazole (I)的产率得到5-氨基-1-(2-羟乙基)吡唑-4-甲酸乙酯
  参考文献：
  名称：

  Preparation of 4,5-diamino-1-(2′-hydroxyethyl)-pyrazole and acid addition salts thereof

  摘要：

  本发明公开了一种改进的制备4,5-二氨基-1-(2'-羟乙基)吡唑及其酸加成盐（如硫酸加成盐）的方法。该方法包括一系列新颖的步骤，从烷基（烷氧甲基）氰乙酸酯和2-羟乙基肼开始，形成中间化合物5-氨基-4-烷氧羰基-1-(2'-羟乙基)吡唑（I）、5-氨基-4-羧基-1-(2'-羟乙基)吡唑（II）、5-氨基-1-(2'-羟乙基)吡唑（III）、5-氨基-1-(2'-羟乙基)4-硝基吡唑（IV）。

  公开号：

  US06452019B1

文献信息

• Heilmittelchemische Studien in der heterocyclischen Reihe. 26. Mitteilung
  作者：P. Schmidt、K. Eichenberger、M. Wilhelm、J. Druey

  DOI：10.1002/hlca.19590420318

  日期：——

  Syntheses of pyrazolo [3,4-d]pyrimidines with an amino group in 3- or 4-position are described. For the preparation of the 3-amino derivatives a 4-chloro-5-cyano-pyrimidine is condensed with various hydrazines. The 4-amino-pyrazolo [3,4-d]pyrimidines are obtained by reacting 3-amino-4-carbethoxy-pyrazoles with formamide, chlorinating thc 4-hydroxy-pyrazolo [3,4-d]pyrimidines, and substituting the halogen

  描述了在3-或4-位具有氨基的吡唑并[3,4-d]嘧啶的合成。为了制备3-氨基衍生物，将4-氯-5-氰基-嘧啶与各种肼缩合。4-氨基-吡唑并[3,4-d]嘧啶是通过使3-氨基-4-碳乙氧基-吡唑与甲酰胺反应，氯化4-羟基-吡唑并[3,4-d]嘧啶并取代卤素而获得的。通过氨基。一些化合物表现出利尿和心脏活性，另一些则抑制肿瘤的生长。
• Cephem compounds
  申请人：Fujisawa Pharmaceutical Company, Ltd.

  公开号：US05173485A1

  公开（公告）日：1992-12-22

  The invention relates to an antimicrobial compound of the formula: ##STR1## wherein R.sup.1 is amino or a protected amino group, R.sup.2 is lower alkyl, lower alkenyl, carboxy (lower) alkyl or protected carboxy(lower)alkyl, R.sup.3 is hydrogen, lower alkyl, hydroxy(lower)alkyl, protected hydroxy(lower)alkyl, amino(lower)alkyl, protected amino(lower)alkyl or lower alkanoyl, R.sup.4 is hydrogen, lower alkyl or lower alkylthio, and Z is N or CH or a pharmaceutically acceptable salt thereof.

  本发明涉及一种抗微生物化合物，其化学式为：##STR1##其中R.sup.1是氨基或保护氨基基团，R.sup.2是较低的烷基、较低的烯基、羧基（较低的）烷基或保护羧基（较低的）烷基，R.sup.3是氢、较低的烷基、羟基（较低的）烷基、保护羟基（较低的）烷基、氨基（较低的）烷基、保护氨基（较低的）烷基或较低的烷酰基，R.sup.4是氢、较低的烷基或较低的烷硫基，Z是N或CH或其药学上可接受的盐。
• Preparation of 4,5-diamino-1-(substituted)-pyrazole and acid addition salts thereof
  申请人：Chamberlin Steven Kim

  公开号：US20070037987A1

  公开（公告）日：2007-02-15

  Disclosed is an improved process for the preparation of 4,5-diamino-1-(substituted)pyrazoles and acid addition salts thereof by coupling the corresponding 5-amino-1-(substituted)pyrazole with an aromatic diazonium compound to produce an intermediate azo compound and contacting the intermediate azo compound with hydrogen in the presence of a hydrogenation catalyst to produce 4,5-diamino-1-(substituted)pyrazoles. Also disclosed is a decarboxylation process for the preparation of a 5-amino-1-(substituted)pyrazole by heating a solution comprising a 5-amino-4-carboxy-1-(substituted)pyrazole, an inorganic acid and an inert solvent.

  本发明公开了一种改进的工艺，用于制备4,5-二氨基-1-(取代)吡唑及其酸加成盐，其方法是将相应的5-氨基-1-(取代)吡唑与芳香族重氮化合物偶联，生成中间偶氮化合物，然后在氢化催化剂的存在下将中间偶氮化合物与氢接触，制备4,5-二氨基-1-(取代)吡唑。本发明还公开了一种脱羧工艺，以制备5-氨基-1-(取代)吡唑，其方法是通过加热包含5-氨基-4-羧基-1-(取代)吡唑、无机酸和惰性溶剂的溶液进行脱羧反应。
• 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##。
• Cephem compounds and processes for preparation thereof
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0332156A2

  公开（公告）日：1989-09-13

  A compound of the formula : wherein R1 is amino or a protected amino group, R2 is an organic group, R3 is hydrogen, lower alkyl, hydroxy(lower)alkyl, protected hydroxy(lower)alkyl, amino(lower)alkyl, protected amino(lower)alkyl or an imino protective group, R4 is hydrogen, lower alkyl or lower alkylthio, A is lower alkylene which may be substituted with suitable substituent(s) and Z is N or CH, and a pharmaceutically acceptable salt thereof, processes for its preparation and pharmaceutical compositions comprising them or a pharmaceutically acceptable salt thereof in admixture with pharmaceutically acceptable carriers.

  式中的化合物 其中 R1 是氨基或受保护的氨基、 R2 是有机基团 R3 是氢、低级烷基、羟基（低级）烷基、受保护羟基（低级）烷基、氨基（低级）烷基、受保护氨基（低级）烷基或亚氨基保护基团、 R4 是氢、低级烷基或低级硫代烷基、 A 是可被适当取代基取代的低级亚烷基，以及 Z 是 N 或 CH、 及其药学上可接受的盐、其制备方法以及由它们或其药学上可接受的盐与药学上可接受的载体混合组成的药物组合物。