tert-butyl (R)-2-(4-nitrophenylsulfonamido)-3-methylbutanoate | 193810-39-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (R)-2-(4-nitrophenylsulfonamido)-3-methylbutanoate
• 英文别名: tert-butyl (2R)-3-methyl-2-[(4-nitrophenyl)sulfonylamino]butanoate
• CAS: 193810-39-8
• 化学式: C₁₅H₂₂N₂O₆S
• 分子量: 358.415
• InChiKey: JIDSYRXYRRXFFE-CYBMUJFWSA-N

物化性质

• 沸点：
  478.6±55.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-2-(4-nitrophenylsulfonamido)-3-methylbutanoate 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (2R)-3-methyl-2-[[4-[(4-methylsulfanylbenzoyl)amino]phenyl]sulfonylamino]butanoic Acid
  参考文献：
  名称：

  Highly Selective and Orally Active Inhibitors of Type IV Collagenase (MMP-9 and MMP-2):  N-Sulfonylamino Acid Derivatives

  摘要：

  Various N-sulfonylamino acid derivatives were synthesized and evaluated for their in vitro and in vivo activities to inhibit type IV collagenase (MMP-9 and MMP-2). When the amino acid residue and the sulfonamide moiety were modified, their inhibitory activities were greatly affected by the structure of the sulfonamide moiety. A series of aryl sulfonamide derivatives containing biaryl, tetrazole, amide, and triple bond were found to be potent and highly selective inhibitors of MMP-9 and MMP-2 In addition, these compounds were orally active in animal models of tumor growth and metastasis. These results revealed the potential of the N-sulfonylamino acid derivatives as a new type of candidate drug for the treatment of cancer.

  DOI：

  10.1021/jm9707582
• 作为产物：
  描述：

  D-valine t-butyl ester 、 对硝基苯磺酰氯 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl (R)-2-(4-nitrophenylsulfonamido)-3-methylbutanoate
  参考文献：
  名称：

  Highly Selective and Orally Active Inhibitors of Type IV Collagenase (MMP-9 and MMP-2):  N-Sulfonylamino Acid Derivatives

  摘要：

  Various N-sulfonylamino acid derivatives were synthesized and evaluated for their in vitro and in vivo activities to inhibit type IV collagenase (MMP-9 and MMP-2). When the amino acid residue and the sulfonamide moiety were modified, their inhibitory activities were greatly affected by the structure of the sulfonamide moiety. A series of aryl sulfonamide derivatives containing biaryl, tetrazole, amide, and triple bond were found to be potent and highly selective inhibitors of MMP-9 and MMP-2 In addition, these compounds were orally active in animal models of tumor growth and metastasis. These results revealed the potential of the N-sulfonylamino acid derivatives as a new type of candidate drug for the treatment of cancer.

  DOI：

  10.1021/jm9707582

文献信息

• Novel Fluorinated Derivatives of the Broad-Spectrum MMP Inhibitors <i>N</i>-Hydroxy-2(<i>R</i>)-[[(4-methoxyphenyl)sulfonyl](benzyl)- and (3-picolyl)-amino]-3-methyl-butanamide as Potential Tools for the Molecular Imaging of Activated MMPs with PET
  作者：Stefan Wagner、Hans-Jörg Breyholz、Marilyn P. Law、Andreas Faust、Carsten Höltke、Sandra Schröer、Günter Haufe、Bodo Levkau、Otmar Schober、Michael Schäfers、Klaus Kopka

  DOI：10.1021/jm0708533

  日期：2007.11.1

  An approach to the in vivo imaging of locally upregulated and activated matrix metalloproteinases (MMPs) found in many pathological processes is offered by positron emission tomography (PET). Hence, appropriate PET radioligands for MMP imaging are required. Here, we describe the syntheses of novel fluorinated MMP inhibitors (MMPIs) based on lead structures of the broad-spectrum inhibitors N-hydrox

  正电子发射断层扫描（PET）提供了一种在许多病理学过程中发现的局部上调和激活的基质金属蛋白酶（MMP）的体内成像方法。因此，需要用于MMP成像的合适的PET放射性配体。在这里，我们描述了基于广谱抑制剂N-hydroxy-2（R）-[[（（4-甲氧基苯基）磺酰基]（苄基）-氨基] -3的前导结构的新型氟化MMP抑制剂（MMPI）的合成-甲基-丁酰胺（CGS 25966）和N-羟基-2（R）-[[（（4-甲氧基苯基）磺酰基]（3-吡啶甲基）-氨基] -3-甲基-丁酰胺（CGS 27023A）。另外，合成了用于用正电子发射体18F进行放射性标记的量身定制的前体化合物。所有制备的异羟肟酸酯目标化合物对MMP-2，MMP-8，MMP-9和MMP-13均显示出较高的体外MMP抑制能力。作为结果，通过两种不同的方法重新合成了有前途的氟化异羟肟酸衍生物1f，使其具有18F标记的形式，从而产生了潜在的PET放射性配体[18F]
• Highly Selective and Orally Active Inhibitors of Type IV Collagenase (MMP-9 and MMP-2):  <i>N</i>-Sulfonylamino Acid Derivatives
  作者：Yoshinori Tamura、Fumihiko Watanabe、Takuji Nakatani、Ken Yasui、Masahiro Fuji、Tadafumi Komurasaki、Hiroshige Tsuzuki、Ryuji Maekawa、Takayuki Yoshioka、Kenji Kawada、Kenji Sugita、Mitsuaki Ohtani

  DOI：10.1021/jm9707582

  日期：1998.2.1

  Various N-sulfonylamino acid derivatives were synthesized and evaluated for their in vitro and in vivo activities to inhibit type IV collagenase (MMP-9 and MMP-2). When the amino acid residue and the sulfonamide moiety were modified, their inhibitory activities were greatly affected by the structure of the sulfonamide moiety. A series of aryl sulfonamide derivatives containing biaryl, tetrazole, amide, and triple bond were found to be potent and highly selective inhibitors of MMP-9 and MMP-2 In addition, these compounds were orally active in animal models of tumor growth and metastasis. These results revealed the potential of the N-sulfonylamino acid derivatives as a new type of candidate drug for the treatment of cancer.