4-(2-Phenyltetrazol-5-yl)benzenesulfonyl chloride | 203639-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2-Phenyltetrazol-5-yl)benzenesulfonyl chloride
• CAS: 203639-66-1
• 化学式: C₁₃H₉ClN₄O₂S
• 分子量: 320.759
• InChiKey: QRATUBXVWQOGAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-Phenyltetrazol-5-yl)benzenesulfonyl chloride 在 N-甲基吗啉 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-3-Methyl-2-[4-(2-phenyl-2H-tetrazol-5-yl)-benzenesulfonylamino]-butyric 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：

  5-(4-bromophenyl)-2-phenyl-2H-tetrazole 在 正丁基锂 、 磺酰氯 、 二氧化硫 作用下， 生成 4-(2-Phenyltetrazol-5-yl)benzenesulfonyl chloride
  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

• 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.