(6R,7R)-7-amino-3-<(3-methyl-1,2,4-triazol-5-yl)-thiomethyl>-8-oxo-5-thia-1-zabicyclo<4.2.0>oct-2-ene-2-carboxylic acid | 51646-81-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6R,7R)-7-amino-3-<(3-methyl-1,2,4-triazol-5-yl)-thiomethyl>-8-oxo-5-thia-1-zabicyclo<4.2.0>oct-2-ene-2-carboxylic acid
• 英文别名: (6R)-7t-amino-3-(5-methyl-1H-[1,2,4]triazol-3-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 51646-81-2
• 化学式: C₁₁H₁₃N₅O₃S₂
• 分子量: 327.388
• InChiKey: VNNJNTZHOWNSOH-HZGVNTEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  125.2
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (6R,7R)-7-amino-3-<(3-methyl-1,2,4-triazol-5-yl)-thiomethyl>-8-oxo-5-thia-1-zabicyclo<4.2.0>oct-2-ene-2-carboxylic acid 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and structure—activity relationship of C-3 substituted triazolylthiomethyl cephems

  摘要：

  A series of C-3 substituted triazolylthiomethyl cephems with an aminothiazolemethoxyiminoacetamido side chain at C-7 were synthesized and tested for antimicrobial activity against clinically-relevant isolates. The compound with 3-pyridyl at C-5 and methyl at N-4 of the triazole moiety exhibited good antibacterial activity against both Gram-positive and Gram-negative bacteria, with the exception of pseudomonas spp against which none of the derivatives exhibited favorable activity.

  DOI：

  10.1016/0223-5234(96)80367-9
• 作为产物：
  描述：

  3-巯基-5-甲基-1,2,4-三氮唑 、 7-氨基头孢烷酸 在 phosphate buffer 、 碳酸氢钠 作用下， 生成 (6R,7R)-7-amino-3-<(3-methyl-1,2,4-triazol-5-yl)-thiomethyl>-8-oxo-5-thia-1-zabicyclo<4.2.0>oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure—activity relationship of C-3 substituted triazolylthiomethyl cephems

  摘要：

  A series of C-3 substituted triazolylthiomethyl cephems with an aminothiazolemethoxyiminoacetamido side chain at C-7 were synthesized and tested for antimicrobial activity against clinically-relevant isolates. The compound with 3-pyridyl at C-5 and methyl at N-4 of the triazole moiety exhibited good antibacterial activity against both Gram-positive and Gram-negative bacteria, with the exception of pseudomonas spp against which none of the derivatives exhibited favorable activity.

  DOI：

  10.1016/0223-5234(96)80367-9

文献信息

• Semisynthetic cephalosporins. Synthesis and structure-activity relations of 7-sulfonylacetamido-3-cephem-4-carboxylic acids
  作者：R. M. DeMarinis、J. R. E. Hoover、L. L. Lam、J. V. Uri、J. R. Guarini、L. Phillips、P. Actor、J. A. Weisbach

  DOI：10.1021/jm00228a003

  日期：1976.6

  The synthesis and in vitro and in vivo activities of a series of 7-sulfonylacetamido-3-cephem-4-carboxylic acids with acetoxymethyl or heterocyclic thiomethyl substituents at the 3 position are described. Lengthening the alkyl chain attached to the sulfonyl group increased gram-positive activity but the effect on gram-negative activity was variable. Other structural changes on the 7-acyl side chain

  描述了一系列在3位带有乙酰氧基甲基或杂环硫代甲基取代基的7-磺酰基乙酰氨基-3-cephem-4-羧酸的合成以及体外和体内活性。延长连接至磺酰基的烷基链可提高革兰氏阳性活性，但对革兰氏阴性活性的影响却是可变的。7-酰基侧链上的其他结构变化仅导致体外活性的微小变化。除了丁基磺酰基衍生物的保护作用不如体外活性所预测的那样，在感染小鼠中的保护效果通常与体外活性相当。用3-杂环硫代甲基取代3-乙酰氧基甲基导致体外和体内活性的总体提高。
• Nannini; Molgora; Biasoli, Arzneimittel-Forschung/Drug Research, 1977, vol. 27, # 2, p. 343 - 352
  作者：Nannini、Molgora、Biasoli

  DOI：——

  日期：——
• Malabarba; Cavalleri; Berti, Farmaco, Edizione Scientifica, 1977, vol. 32, # 9, p. 650 - 664
  作者：Malabarba、Cavalleri、Berti、Arioli

  DOI：——

  日期：——