2-chloroimidazoline hydrochloride | 54255-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-chloroimidazoline hydrochloride
• 英文别名: 2-chloro-2-imidazoline hydrochloride；2-Chloro-4,5-dihydro-1H-imidazole hydrochloride；2-chloro-4,5-dihydro-1H-imidazole;hydrochloride
• CAS: 54255-14-0
• 化学式: C₃H₅ClN₂*ClH
• 分子量: 141.0
• InChiKey: VRHFDEUVCIAOLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  24.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloroimidazoline hydrochloride 、 (6R,7R)-7-Amino-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 以 乙腈 为溶剂， 生成 (6R,7R)-7-(4,5-Dihydro-1H-imidazol-2-ylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and .beta.-lactamase stability on the pKa of the C-7 heterocycle

  摘要：

  Cephalosporins with new aminobenzimidazole and aminoimidazoline heterocycles at C-7 have been synthesized starting with versatile C-7 isocyanide dihalide synthons. The aminobenzimidazoles have a broad spectrum of antibacterial activity, including Gram-positive and Gram-negative organisms, but possess limited beta-lactamase stability. In contrast, the aminoimidazolines have a narrow spectrum of antibacterial activity, limited to Gram-negative strains only, but possess outstanding beta-lactamase stability. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-7 amino heterocycle, basic C-7 residues giving cephalosporins with exceptional beta-lactamase stability.

  DOI：

  10.1021/jm00107a035

文献信息

• Cephalosporin derivatives
  申请人：ICI Pharma

  公开号：US04463173A1

  公开（公告）日：1984-07-31

  A compound of the formula I: ##STR1## in which R.sup.1 is any C-3 substituent from antibacterially-active cephalosporins; R.sup.2 is any C-4 substituent from antibacterially-active cephalosporins; R.sup.3 is H, hydroxy, amino, 1-6C alkyl, 1-6C alkanoyl, 1-6C alkoxy, 1-6C alkanoylamino or 1-6C alkylamino, phenyl(1-6C)-alkyl or phenyl, each optionally substituted by methoxy; ##STR2## is of the formula II or III: ##STR3## in which R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 may have a variety of values, e.g. hydrogen, carboxy, cyano or alkyl; and the salts thereof. Manufacturing processes, pharmaceutical compositions and a method of treating a bacterial infection are also disclosed.

  公式I的化合物：##STR1##，其中R.sup.1是来自具有抗菌活性的头孢菌素的任何C-3取代基；R.sup.2是来自具有抗菌活性的头孢菌素的任何C-4取代基；R.sup.3是H、羟基、氨基、1-6C烷基、1-6C醇酰基、1-6C烷氧基、1-6C醇酰胺基或1-6C烷基胺基、苯基（1-6C）-烷基或苯基，每个基可选择地被甲氧基取代；##STR2##是公式II或III：##STR3##，其中R.sup.4、R.sup.5、R.sup.6、R.sup.7、R.sup.8和R.sup.9可以有多种取值，例如氢、羧基、氰基或烷基；及其盐。还公开了制造过程、药物组合物和治疗细菌感染的方法。
• 苯并噻二唑衍生物的制备方法
  申请人：四川科瑞德制药股份有限公司

  公开号：CN109535148B

  公开（公告）日：2023-04-25

  本发明公开了一种苯并噻二唑衍生物的制备方法，具体是盐酸替扎尼定的制备方法，包括以下步骤：(a)取化合物II与化合物III或其盐，使其在有机溶剂中、缚酸剂存在下反应，然后经碱化，过滤，精制，得到中间体IV；(b)以步骤(a)得到的中间体IV为原料制备得到式I所示盐酸替扎尼定。本发明方法同时具有较高的产率和纯度，并且操作简便、生产效率高、环保、安全，适用于工业化大生产，具有广阔的市场应用前景。
• Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and .beta.-lactamase stability on the pKa of the C-7 heterocycle
  作者：F. Jung、C. Delvare、D. Boucherot、A. Hamon、N. Ackerley、M. J. Betts

  DOI：10.1021/jm00107a035

  日期：1991.3

  Cephalosporins with new aminobenzimidazole and aminoimidazoline heterocycles at C-7 have been synthesized starting with versatile C-7 isocyanide dihalide synthons. The aminobenzimidazoles have a broad spectrum of antibacterial activity, including Gram-positive and Gram-negative organisms, but possess limited beta-lactamase stability. In contrast, the aminoimidazolines have a narrow spectrum of antibacterial activity, limited to Gram-negative strains only, but possess outstanding beta-lactamase stability. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-7 amino heterocycle, basic C-7 residues giving cephalosporins with exceptional beta-lactamase stability.