2-phenyl-5,6-dihydro-1H-thieno[3,2-c]pyrazol-3-one | 31657-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-5,6-dihydro-1H-thieno[3,2-c]pyrazol-3-one
• 英文别名: 2-phenyl-1,2,5,6-tetrahydro-thieno[3,2-c]pyrazol-3-one
• CAS: 31657-22-4
• 化学式: C₁₁H₁₀N₂OS
• 分子量: 218.279
• InChiKey: QPIOQQGEZUTTHO-UHFFFAOYSA-N

物化性质

• 沸点：
  386.5±42.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.05
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  对甲苯磺酸甲酯 、 2-phenyl-5,6-dihydro-1H-thieno[3,2-c]pyrazol-3-one 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-methoxy-2-phenyl-5,6-dihydro-2H-thieno[3,2-c]pyrazole
  参考文献：
  名称：

  噻吩并（3,4-c）-和-（3,2-c）吡唑的合成，烷基化和氧化。

  摘要：

  DOI：

  10.1021/jm00287a025
• 作为产物：
  描述：

  3-[(2-甲氧基-2-乙氧基)硫醇]甲基丙酸 在 sodium methylate 、 四氯化钛 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2-phenyl-5,6-dihydro-1H-thieno[3,2-c]pyrazol-3-one
  参考文献：
  名称：

  2-Phenyl-5,6-dihydro-2H-thieno[3,2-c]pyrazol-3-ol derivatives as new inhibitors of bacterial cell wall biosynthesis

  摘要：

  Twenty-five 2-phenyl-5,6-dihydro-2H-thieno[3,2-c]pyrazol-3-ol derivatives were synthesized for evaluation as new inhibitors of bacterial cell wall biosynthesis. Many of them demonstrated good inhibitory activity against Staphylococcus aureus MurB. MurC and MurD enzymes in vitro and antimicrobial activity against gram-positive bacteria including MRSA, VRE and PRSP, However. when they were tested in the presence of 4% bovine serum albumin, the MIC values increased to greater than 128 mug/mL against PRSP. None of the compounds demonstrated activity against gram-negative bacteria at MIC <32 mug/mL. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00471-2

文献信息

• New arylsulfonohydrazide inhibitors of enzymes MurC and MurD
  申请人：UNIVERZA V LJUBLJANI, FAKULTETA ZA FARMACIJO

  公开号：EP1845083A2

  公开（公告）日：2007-10-17

  This invention belongs to the field of pharmaceutical chemistry and relates to new arylsulfonohydrazides as inhibitors of UDP-N-acetylmuramyl:L-alanine ligaze (MurC) and UDP-N-acetylmuramyl-L-alanine:D-glutamate ligaze (MurD), to procedures for their preparation and pharmaceutical preparations containing the same. The enzymes MurC and MurD are the key enzymes involved in the synthesis of bacterial peptidoglycan, so arylsulfonohydrazide inhibitors possess antibacterial activity. Compounds of general formula I and the pharmaceutically acceptable salts are described. The appropriate substituents are clearly presented in the body of the text and in claims.

  本发明属于药物化学领域，涉及作为 UDP-N-乙酰基氨酰基：L-丙氨酸连接酶（MurC）和 UDP-N-乙酰基氨酰基-L-丙氨酸：D-谷氨酸连接酶（MurD）抑制剂的新型芳基磺酰肼、其制备方法以及含有这些抑制剂的药物制剂。MurC 和 MurD 是参与合成细菌肽聚糖的关键酶，因此芳基磺酰肼抑制剂具有抗菌活性。通式 I 的化合物 及其药学上可接受的盐类。适当的取代基在正文和权利要求中均有清楚的表述。
• 2-Phenyl-5,6-dihydro-2H-thieno[3,2-c]pyrazol-3-ol derivatives as new inhibitors of bacterial cell wall biosynthesis
  作者：Zhong Li、Gerardo D. Francisco、William Hu、Pornpen Labthavikul、Peter J. Petersen、Anatoly Severin、Guy Singh、Youjun Yang、Beth A. Rasmussen、Yang-I Lin、Jerauld S. Skotnicki、Tarek S. Mansour

  DOI：10.1016/s0960-894x(03)00471-2

  日期：2003.8

  Twenty-five 2-phenyl-5,6-dihydro-2H-thieno[3,2-c]pyrazol-3-ol derivatives were synthesized for evaluation as new inhibitors of bacterial cell wall biosynthesis. Many of them demonstrated good inhibitory activity against Staphylococcus aureus MurB. MurC and MurD enzymes in vitro and antimicrobial activity against gram-positive bacteria including MRSA, VRE and PRSP, However. when they were tested in the presence of 4% bovine serum albumin, the MIC values increased to greater than 128 mug/mL against PRSP. None of the compounds demonstrated activity against gram-negative bacteria at MIC <32 mug/mL. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis, alkylation, and oxidation of thieno[3,4-c]- and -[3,2-c]pyrazoles
  作者：Victor J. Bauer、Richard P. Williams、S. R. Safir

  DOI：10.1021/jm00287a025

  日期：1971.5