[(Z)-Methoxyimino]-thieno[2,3-b]thiophen-2-yl-acetic acid | 104251-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: [(Z)-Methoxyimino]-thieno[2,3-b]thiophen-2-yl-acetic acid
• 英文别名: 2-Methoxyimino-2-thieno[2,3-b]thiophen-5-ylacetic acid
• CAS: 104251-97-0
• 化学式: C₉H₇NO₃S₂
• 分子量: 241.291
• InChiKey: GXSAFRCWWWRQBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(Z)-Methoxyimino]-thieno[2,3-b]thiophen-2-yl-acetic acid 在 草酰氯 、 N,O-双(三甲基硅烷基)三氟乙酰胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 (6R,7R)-7-{2-[(Z)-Methoxyimino]-2-thieno[2,3-b]thiophen-2-yl-acetylamino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid

  摘要：

  Three positional analogues (4-, 5-, and 7-) of benzothienylglycine and (N-acetylindolinyl)-5-glycine were prepared and coupled to 7-aminodeacetoxycephalosporanic acid (7-ADCA) to give the cephalosporins 17a-c. In addition two isomeric (2,3-b and 3,2-b) thienothiopheneglycines were synthesized and coupled to 7-ADCA to yield cephalosporins 30d and 30e. In vitro testing of these new cephalosporins indicates good activity against Gram-positive bacteria. Against Streptococcus pneumoniae infections compound 25 displayed better mouse protection (both orally and subcutaneously) than cephalexin.

  DOI：

  10.1021/jm00150a023
• 作为产物：
  描述：

  噻吩酮[2,3-b]噻吩-2-羧酸 在 盐酸 、 sodium hydroxide 、 sodium periodate 、 甲酸 、 乙酸酐 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.33h， 生成 [(Z)-Methoxyimino]-thieno[2,3-b]thiophen-2-yl-acetic acid
  参考文献：
  名称：

  Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid

  摘要：

  Three positional analogues (4-, 5-, and 7-) of benzothienylglycine and (N-acetylindolinyl)-5-glycine were prepared and coupled to 7-aminodeacetoxycephalosporanic acid (7-ADCA) to give the cephalosporins 17a-c. In addition two isomeric (2,3-b and 3,2-b) thienothiopheneglycines were synthesized and coupled to 7-ADCA to yield cephalosporins 30d and 30e. In vitro testing of these new cephalosporins indicates good activity against Gram-positive bacteria. Against Streptococcus pneumoniae infections compound 25 displayed better mouse protection (both orally and subcutaneously) than cephalexin.

  DOI：

  10.1021/jm00150a023

文献信息

• Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid
  作者：Stjepan Kukolja、Susan E. Draheim、Bernard J. Graves、David C. Hunden、Janice L. Pfeil、Robin D. G. Cooper、John L. Ott、Fred T. Counter

  DOI：10.1021/jm00150a023

  日期：1985.12

  Three positional analogues (4-, 5-, and 7-) of benzothienylglycine and (N-acetylindolinyl)-5-glycine were prepared and coupled to 7-aminodeacetoxycephalosporanic acid (7-ADCA) to give the cephalosporins 17a-c. In addition two isomeric (2,3-b and 3,2-b) thienothiopheneglycines were synthesized and coupled to 7-ADCA to yield cephalosporins 30d and 30e. In vitro testing of these new cephalosporins indicates good activity against Gram-positive bacteria. Against Streptococcus pneumoniae infections compound 25 displayed better mouse protection (both orally and subcutaneously) than cephalexin.