(+/-)-phenyl-phenylcarbamoyl-methanesulfonic acid | 858004-74-7

• 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: (+/-)-phenyl-phenylcarbamoyl-methanesulfonic acid
• 英文别名: (+/-)-phenyl-phenylcarbamoyl-methanesulfonic acid ; (+/-)-α-sulfo-phenylacetic acid anilide；(+/-)-Phenyl-phenylcarbamoyl-methansulfonsaeure; (+/-)-α-Sulfo-phenylessigsaeure-anilid；Inaktives Phenyl-phenylcarbamoyl-methansulfonsaeure；Inaktives α-Sulfo-phenylessigsaeure-anilid；(+/-)-Phenyl-phenylcarbamoyl-methansulfonsaeure；2-Anilino-2-oxo-1-phenyl-ethanesulfonic acid；2-anilino-2-oxo-1-phenylethanesulfonic acid
• CAS: 858004-74-7
• 化学式: C₁₄H₁₃NO₄S
• 分子量: 291.328
• InChiKey: PCEDFPTYRADALF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-phenyl-phenylcarbamoyl-methanesulfonic acid 在 奎宁 作用下， 生成 (-)-phenyl-phenylcarbamoyl-methanesulfonic acid
  参考文献：
  名称：

  Brust, Recueil des Travaux Chimiques des Pays-Bas, 1928, vol. 47, p. 166

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-2-氧代-1-苯基乙烷磺酸 、 苯胺 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (+/-)-phenyl-phenylcarbamoyl-methanesulfonic acid
  参考文献：
  名称：

  Cefsulodin Inspired Potent and Selective Inhibitors of mPTPB, a Virulent Phosphatase from Mycobacterium tuberculosis

  摘要：

  mPTPB is a virulent phosphatase from Mycobacterium tuberculosis and a promising therapeutic target for tuberculosis. To facilitate mPTPB-based drug discovery, we identified alpha-sulfophenylacetic amide (SPAA) from cefsulodin, a third generation beta-lactam cephalosporin antibiotic, as a novel pTyr pharmacophore for mPTPB. Structure-guided and fragment-based optimization of SPAA led to the most potent and selective mPTPB inhibitor 9, with a K-i of 7.9 nM and more than 10,000-fold preference for mPTPB over a large panel of 25 phosphatases. Compound 9 also exhibited excellent cellular activity and specificity in blocking mPTPB function in macrophage. Given its novel structure, modest molecular mass, and extremely high ligand efficiency (0.46), compound 9 represents an outstanding lead compound for anti-TB drug discovery targeting mPTPB.

  DOI：

  10.1021/acsmedchemlett.5b00373

文献信息

• Inhibition of Low Molecular Weight Protein Tyrosine Phosphatase by an Induced-Fit Mechanism
  作者：Rongjun He、Jifeng Wang、Zhi-Hong Yu、Ruo-Yu Zhang、Sijiu Liu、Li Wu、Zhong-Yin Zhang

  DOI：10.1021/acs.jmedchem.6b00993

  日期：2016.10.13

  The low molecular weight protein tyrosine phosphatase (LMW-PTP) is a regulator of a number of signaling pathways and has been implicated as a potential target for oncology and diabetes/obesity. There is significant therapeutic interest in developing potent and selective inhibitors to control LMW-PTP activity. We report the discovery of a novel class of LMW-PTP inhibitors derived from sulfophenyl acetic

  低分子量蛋白酪氨酸磷酸酶（LMW-PTP）是许多信号通路的调节剂，并被认为是肿瘤和糖尿病/肥胖症的潜在靶标。在开发有效和选择性的抑制剂以控制LMW-PTP活性方面具有重大的治疗兴趣。我们报告发现了新的一类衍生自磺基苯乙酰胺（SPAA）的LMW-PTP抑制剂，其中有些抑制剂对LMW-PTP的偏好超过一大批PTP的50倍以上。X射线晶体学分析表明，基于SPAA的抑制剂的结合在LMW-PTP活性位点引起明显的构象变化，从而导致形成一个以前未公开的疏水性口袋，以适应配体中的α-苯环。
• Brust, Recueil des Travaux Chimiques des Pays-Bas, 1928, vol. 47, p. 166
  作者：Brust

  DOI：——

  日期：——
• Cefsulodin Inspired Potent and Selective Inhibitors of mPTPB, a Virulent Phosphatase from <i>Mycobacterium tuberculosis</i>
  作者：Rongjun He、Zhi-Hong Yu、Ruo-Yu Zhang、Li Wu、Andrea M. Gunawan、Zhong-Yin Zhang

  DOI：10.1021/acsmedchemlett.5b00373

  日期：2015.12.10

  mPTPB is a virulent phosphatase from Mycobacterium tuberculosis and a promising therapeutic target for tuberculosis. To facilitate mPTPB-based drug discovery, we identified alpha-sulfophenylacetic amide (SPAA) from cefsulodin, a third generation beta-lactam cephalosporin antibiotic, as a novel pTyr pharmacophore for mPTPB. Structure-guided and fragment-based optimization of SPAA led to the most potent and selective mPTPB inhibitor 9, with a K-i of 7.9 nM and more than 10,000-fold preference for mPTPB over a large panel of 25 phosphatases. Compound 9 also exhibited excellent cellular activity and specificity in blocking mPTPB function in macrophage. Given its novel structure, modest molecular mass, and extremely high ligand efficiency (0.46), compound 9 represents an outstanding lead compound for anti-TB drug discovery targeting mPTPB.