4-(3-Methoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester | 350604-54-5

• 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: 4-(3-Methoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 4-(3-methoxyphenyl)sulfonylpiperazine-1-carboxylate
• CAS: 350604-54-5
• 化学式: C₁₆H₂₄N₂O₅S
• 分子量: 356.443
• InChiKey: WGOPCDWQNGUFOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3-Methoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Evaluation of Substituted N,N′-Diarylsulfonamides as Activators of the Tumor Cell Specific M2 Isoform of Pyruvate Kinase

  摘要：

  The metabolism of cancer cells is altered to support rapid proliferation. Pharmacological activators of a tumor cell specific pyruvate kinase isozyme (PKM2) may be an approach for altering the classic Warburg effect characteristic of aberrant metabolism in cancer cells yielding a novel anti proliferation strategy. In this manuscript, we detail the discovery of a series of Substituted N,N'-diarylsulfonamides as activators of PKM2. The synthesis of numerous analogues and the evaluation of structure-activity relationships are presented as well as assessments of mechanism and selectivity. Several agents are found that have good potencies and appropriate solubility for use as chemical probes of PKM2 including 55 (AC(50) = 43 nM, maximum response = 84%; solubility = 7.3 mu g/mL), 56 (AC(50) = 99 nM, maximum response 84%; solubility = 5.7 mu g/mL), and 58 (AC(50) = 38 nM, maximum response = 82%; solubility 51.2 mu g/mL). The small molecules described here represent first-in-class activators of PKM2

  DOI：

  10.1021/jm901577g
• 作为产物：
  描述：

  3-甲氧基苯磺酰氯 、 N-Boc-哌嗪 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-(3-Methoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Evaluation of Substituted N,N′-Diarylsulfonamides as Activators of the Tumor Cell Specific M2 Isoform of Pyruvate Kinase

  摘要：

  The metabolism of cancer cells is altered to support rapid proliferation. Pharmacological activators of a tumor cell specific pyruvate kinase isozyme (PKM2) may be an approach for altering the classic Warburg effect characteristic of aberrant metabolism in cancer cells yielding a novel anti proliferation strategy. In this manuscript, we detail the discovery of a series of Substituted N,N'-diarylsulfonamides as activators of PKM2. The synthesis of numerous analogues and the evaluation of structure-activity relationships are presented as well as assessments of mechanism and selectivity. Several agents are found that have good potencies and appropriate solubility for use as chemical probes of PKM2 including 55 (AC(50) = 43 nM, maximum response = 84%; solubility = 7.3 mu g/mL), 56 (AC(50) = 99 nM, maximum response 84%; solubility = 5.7 mu g/mL), and 58 (AC(50) = 38 nM, maximum response = 82%; solubility 51.2 mu g/mL). The small molecules described here represent first-in-class activators of PKM2

  DOI：

  10.1021/jm901577g

文献信息

• Inhibitors of prenyl-protein transferase
  申请人：——

  公开号：US06413964B1

  公开（公告）日：2002-07-02

  The present invention is directed to peptidomimetic macrocyclic compounds of the formula A: wherein W is a heterocycle, V is a heterocycle or aryl moiety and Z1 is a suitably substituted aryl or heterocycle moiety. The instant compounds inhibit prenyl-protein transferase and the prenylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting prenyl-protein transferase and the prenylation of the oncogene protein Ras.

  本发明涉及公式A的肽类类似物大环化合物，其中W为杂环，V为杂环或芳基基团，Z1为适当取代的芳基或杂环基团。该化合物可抑制异戊烷-蛋白质转移酶和致癌基因蛋白Ras的异戊烷化。本发明还涉及含有本发明化合物的化疗组合物以及抑制异戊烷-蛋白质转移酶和致癌基因蛋白Ras的方法。
• US6413964B1
  申请人：——

  公开号：US6413964B1

  公开（公告）日：2002-07-02
• [EN] INHIBITORS OF PRENYL-PROTEIN TRANSFERASE<br/>[FR] INHIBITEURS DE LA PRENYL-PROTEINE TRANSFERASE
  申请人：MERCK & CO INC

  公开号：WO2001051125A1

  公开（公告）日：2001-07-19

  The present invention is directed to peptidomimetic macrocyclic compounds which inhibit prenyl-protein transferase and the prenylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting prenyl-protein transferase and the prenylation of the oncogene protein Ras.
• Evaluation of Substituted <i>N</i>,<i>N</i>′-Diarylsulfonamides as Activators of the Tumor Cell Specific M2 Isoform of Pyruvate Kinase
  作者：Matthew B. Boxer、Jian-kang Jiang、Matthew G. Vander Heiden、Min Shen、Amanda P. Skoumbourdis、Noel Southall、Henrike Veith、William Leister、Christopher P. Austin、Hee Won Park、James Inglese、Lewis C. Cantley、Douglas S. Auld、Craig J. Thomas

  DOI：10.1021/jm901577g

  日期：2010.2.11

  The metabolism of cancer cells is altered to support rapid proliferation. Pharmacological activators of a tumor cell specific pyruvate kinase isozyme (PKM2) may be an approach for altering the classic Warburg effect characteristic of aberrant metabolism in cancer cells yielding a novel anti proliferation strategy. In this manuscript, we detail the discovery of a series of Substituted N,N'-diarylsulfonamides as activators of PKM2. The synthesis of numerous analogues and the evaluation of structure-activity relationships are presented as well as assessments of mechanism and selectivity. Several agents are found that have good potencies and appropriate solubility for use as chemical probes of PKM2 including 55 (AC(50) = 43 nM, maximum response = 84%; solubility = 7.3 mu g/mL), 56 (AC(50) = 99 nM, maximum response 84%; solubility = 5.7 mu g/mL), and 58 (AC(50) = 38 nM, maximum response = 82%; solubility 51.2 mu g/mL). The small molecules described here represent first-in-class activators of PKM2