(Z)-5-(4-aminobenzylidene)-2-iminothiazolidin-4-one | 1310744-67-2

• 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: (Z)-5-(4-aminobenzylidene)-2-iminothiazolidin-4-one
• 英文别名: (5Z)-5-[(4-aminophenyl)methylidene]-2-imino-1,3-thiazolidin-4-one
• CAS: 1310744-67-2
• 化学式: C₁₀H₉N₃OS
• 分子量: 219.267
• InChiKey: QXOIZYPBCJHYLN-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-dimethyl 2-(3-formylbenzamido)pentanedioate 、 (Z)-5-(4-aminobenzylidene)-2-iminothiazolidin-4-one 在 三乙酰氧基硼氢化钠 、 三氟乙酸 、 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 36.67h， 生成 (R,Z)-2-(3-(((4-((2-imino-4-oxothiazolidin-5-ylidene)methyl)phenyl)amino)methyl)benzamido)pentanedioic acid
  参考文献：
  名称：

  Structure-Based Design of a New Series of d-Glutamic Acid Based Inhibitors of Bacterial UDP-N-acetylmuramoyl-l-alanine:d-glutamate Ligase (MurD)

  摘要：

  MurD ligase is one of the key enzymes participating in the intracellular steps of peptidoglycan biosynthesis and constitutes a viable target in the search for novel antibacterial drugs to combat bacterial drug-resistance. We have designed, synthesized, and evaluated a new series of D-glutamic acid-based Escherichia colt MurD inhibitors incorporating the 5-benzylidenethiazolidin-4-one scaffold. The crystal structure of 16 in the MurD active site has provided a good starting point for the design of structurally optimized inhibitors 73-75 endowed with improved MurD inhibitory potency (IC50 between 3 and 7 mu M). Inhibitors 74 and 75 showed weak activity against Gram-positive Staphylococcus aureus and Enterococcus faecalis. Compounds 73-75, with IC50 values in the low micromolar range, represent the most potent D-Glu-based MurD inhibitors reported to date.

  DOI：

  10.1021/jm2002525
• 作为产物：
  描述：

  对硝基苯甲醛 在 tin(II) chloride dihdyrate 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 (Z)-5-(4-aminobenzylidene)-2-iminothiazolidin-4-one
  参考文献：
  名称：

  Structure-Based Design of a New Series of d-Glutamic Acid Based Inhibitors of Bacterial UDP-N-acetylmuramoyl-l-alanine:d-glutamate Ligase (MurD)

  摘要：

  MurD ligase is one of the key enzymes participating in the intracellular steps of peptidoglycan biosynthesis and constitutes a viable target in the search for novel antibacterial drugs to combat bacterial drug-resistance. We have designed, synthesized, and evaluated a new series of D-glutamic acid-based Escherichia colt MurD inhibitors incorporating the 5-benzylidenethiazolidin-4-one scaffold. The crystal structure of 16 in the MurD active site has provided a good starting point for the design of structurally optimized inhibitors 73-75 endowed with improved MurD inhibitory potency (IC50 between 3 and 7 mu M). Inhibitors 74 and 75 showed weak activity against Gram-positive Staphylococcus aureus and Enterococcus faecalis. Compounds 73-75, with IC50 values in the low micromolar range, represent the most potent D-Glu-based MurD inhibitors reported to date.

  DOI：

  10.1021/jm2002525

文献信息

• [EN] THIAZOLIDINE DERIVATIVES FOR THE TREATMENT AND PREVENTION OF METABOLIC BONE DISORDERS<br/>[FR] DERIVES DE THIAZOLIDINE UTILES POUR LE TRAITEMENT ET LA PREVENTION DE TROUBLES METABOLIQUES DES OS
  申请人：ROCHE DIAGNOSTICS GMBH

  公开号：WO2000018746A1

  公开（公告）日：2000-04-06

  The object of the present invention are compounds of general formula (I), in which: m signifies a number between 0-8; q signifies a number between 0-8; A signifies a single or double bond; R1 signifies hydrogen or, when X and Z are oxygen, also -(CH2)-COR4 with a =0-6; R2, R3 signify hydrogen or lower alkyl, whereby R2 and R3 can be the same or different and, when m signifies 2-8, R2 and R3 in the group CR2=CR3 can have various significances within the following sequence; R4 signifies hydroxyl, lower alkoxy or the NR1R2 residue, whereby R1 and R2 can be the same or different; X signifies oxygen or imino; Z signifies oxygen, sulfur or imino; W signifies an optionally mono- or polysubstituted saturated or unsaturated mono-, bi- or tricycle which can contain one or more hetero atoms, as well as their physiologically compatible salts, esters, optically active forms, racemates, tautomers, as well as derivatives which can be metabolized in vivo to compounds of general formula (I), as well as the use of these compounds for the production of medicaments for the prophylaxis or therapy of metabolic bone disorders.
• Structure-Based Design of a New Series of <scp>d</scp>-Glutamic Acid Based Inhibitors of Bacterial UDP-<i>N</i>-acetylmuramoyl-<scp>l</scp>-alanine:<scp>d</scp>-glutamate Ligase (MurD)
  作者：Tihomir Tomašić、Nace Zidar、Roman Šink、Andreja Kovač、Didier Blanot、Carlos Contreras-Martel、Andréa Dessen、Manica Müller-Premru、Anamarija Zega、Stanislav Gobec、Danijel Kikelj、Lucija Peterlin Mašič

  DOI：10.1021/jm2002525

  日期：2011.7.14

  MurD ligase is one of the key enzymes participating in the intracellular steps of peptidoglycan biosynthesis and constitutes a viable target in the search for novel antibacterial drugs to combat bacterial drug-resistance. We have designed, synthesized, and evaluated a new series of D-glutamic acid-based Escherichia colt MurD inhibitors incorporating the 5-benzylidenethiazolidin-4-one scaffold. The crystal structure of 16 in the MurD active site has provided a good starting point for the design of structurally optimized inhibitors 73-75 endowed with improved MurD inhibitory potency (IC50 between 3 and 7 mu M). Inhibitors 74 and 75 showed weak activity against Gram-positive Staphylococcus aureus and Enterococcus faecalis. Compounds 73-75, with IC50 values in the low micromolar range, represent the most potent D-Glu-based MurD inhibitors reported to date.