diphenylmethyl 7β-amino-3-(1,2,3-thiadiazol-5-ylthio)methyl-3-cephem-4-carboxylate | 70380-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diphenylmethyl 7β-amino-3-(1,2,3-thiadiazol-5-ylthio)methyl-3-cephem-4-carboxylate
• 英文别名: (6R)-7t-amino-8-oxo-3-[1,2,3]thiadiazol-5-ylsulfanylmethyl-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester；benzhydryl (6R,7R)-7-amino-8-oxo-3-(thiadiazol-5-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 70380-13-1
• 化学式: C₂₃H₂₀N₄O₃S₃
• 分子量: 496.635
• InChiKey: SNDOFBGEHSAWEJ-XMSQKQJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  98.41
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  diphenylmethyl 7β-amino-3-(1,2,3-thiadiazol-5-ylthio)methyl-3-cephem-4-carboxylate 生成 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-8-oxo-3-[1,2,3]thiadiazol-5-ylsulfanylmethyl-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  3-[(1,2,3-Thiadiazol-5-ylthio)methyl]cephalosporins

  摘要：

  The syntheses of ten 3-](1,2,3-thiadiazol-5-ylthio)methyl]cephalosporins, made by displacement of the 3'-acetoxy group by the novel thiol derivatives, potassium 1,2,3-thiadiazole-5-thiolate and dipotassium 1,2,3-thiadiazole-4-carboxylate-5-thiolate, are described. Several of the compounds showed good in vitro antibacterial activity against both Gram-positive and Gram-negative organisms. The subcutaneous in vivo activities against Staphylococcus aureus were generally less than that of cafazolin. Four of the compounds were administered orally and all were active; the 7 beta-(thiophen-2-acetamido) and 7 beta-(D-2-amino-2-phenylacetamido)-3-[(1,2,3-thiadiazol-5-ylthio)methyl] compounds were equally active by either route, with a PD50 of ca. 1 mg/kg.

  DOI：

  10.1021/jm00196a012
• 作为产物：
  描述：

  7-氨基头孢烷酸 在 碳酸氢钠 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 diphenylmethyl 7β-amino-3-(1,2,3-thiadiazol-5-ylthio)methyl-3-cephem-4-carboxylate
  参考文献：
  名称：

  3-[(1,2,3-Thiadiazol-5-ylthio)methyl]cephalosporins

  摘要：

  The syntheses of ten 3-](1,2,3-thiadiazol-5-ylthio)methyl]cephalosporins, made by displacement of the 3'-acetoxy group by the novel thiol derivatives, potassium 1,2,3-thiadiazole-5-thiolate and dipotassium 1,2,3-thiadiazole-4-carboxylate-5-thiolate, are described. Several of the compounds showed good in vitro antibacterial activity against both Gram-positive and Gram-negative organisms. The subcutaneous in vivo activities against Staphylococcus aureus were generally less than that of cafazolin. Four of the compounds were administered orally and all were active; the 7 beta-(thiophen-2-acetamido) and 7 beta-(D-2-amino-2-phenylacetamido)-3-[(1,2,3-thiadiazol-5-ylthio)methyl] compounds were equally active by either route, with a PD50 of ca. 1 mg/kg.

  DOI：

  10.1021/jm00196a012

文献信息

• Synthesis and structure-activity relationships of 7.BETA.-((Z)-2-(2-aminothiazol-4-yl)-3-(substituted)-2-propenoylamino)-3-cephems with C-3 substitutions.
  作者：KOJI ISHIKURA、TADASHI KUBOTA、KYOJI MINAMI、YOSHIO HAMASHIMA、HIROMU NAKASHIMIZU、KIYOSHI MOTOKAWA、YASUO KIMURA、HIDEAKI MIWA、TADASHI YOSHIDA

  DOI：10.7164/antibiotics.47.466

  日期：——

  Synthesis and biological activity of a series of 7 beta-[(Z)-2-(2- aminothiazol-4-yl)-3-(substituted)-2-propenoylamino]-3-cephe m-4-carboxylic acids with C-3 substitutions and their pivaloyloxymethyl esters are described. These acid compounds exhibited potent antibacterial activity against both Gram-positive and Gram-negative bacteria. Pivaloyloxymethyl esters of selected compounds in this series were

  一系列7个β-[（（Z）-2-（2-氨基噻唑-4-基）-3-（取代）-2-丙烯酰基氨基] -3- Cephe m-4-羧酸的合成及生物活性描述了-3个取代及其新戊酰氧基甲基酯。这些酸化合物对革兰氏阳性和革兰氏阴性细菌均显示出有效的抗菌活性。发现该系列中所选化合物的新戊酰氧基甲基酯在小鼠中被小肠很好吸收。最终选择了新戊酰氧基甲基7β-[（（Z）-2-（2-氨基噻唑-4-基）-2-戊烯酰氨基] -3-氨基甲酰氧基甲基-3-cephem-4-羧化酶盐酸盐水合物（S-1108）用于临床评估。
• CURRAN, WILLIAM V.
  作者：CURRAN, WILLIAM V.

  DOI：——

  日期：——
• 3-[(1,2,3-Thiadiazol-5-ylthio)methyl]cephalosporins
  作者：Graham S. Lewis、Peter H. Nelson

  DOI：10.1021/jm00196a012

  日期：1979.10

  The syntheses of ten 3-](1,2,3-thiadiazol-5-ylthio)methyl]cephalosporins, made by displacement of the 3'-acetoxy group by the novel thiol derivatives, potassium 1,2,3-thiadiazole-5-thiolate and dipotassium 1,2,3-thiadiazole-4-carboxylate-5-thiolate, are described. Several of the compounds showed good in vitro antibacterial activity against both Gram-positive and Gram-negative organisms. The subcutaneous in vivo activities against Staphylococcus aureus were generally less than that of cafazolin. Four of the compounds were administered orally and all were active; the 7 beta-(thiophen-2-acetamido) and 7 beta-(D-2-amino-2-phenylacetamido)-3-[(1,2,3-thiadiazol-5-ylthio)methyl] compounds were equally active by either route, with a PD50 of ca. 1 mg/kg.