p-Cl-C6H4-SO2-Val-ONSu | 68147-86-4

• 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: p-Cl-C6H4-SO2-Val-ONSu
• 英文别名: (2,5-dioxopyrrolidin-1-yl) (2S)-2-[(4-chlorophenyl)sulfonylamino]-3-methylbutanoate
• CAS: 68147-86-4
• 化学式: C₁₅H₁₇ClN₂O₆S
• 分子量: 388.829
• InChiKey: NFRMEWYICAFWKL-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-Cl-C6H4-SO2-Val-ONSu 在 pyridine-SO3 complex 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.67h， 生成 N-(4-chlorophenylsulfonyl)-L-valyl-L-leucinal
  参考文献：
  名称：

  Structure−Activity Relationship Study and Drug Profile of N-(4-Fluorophenylsulfonyl)-l-valyl-l-leucinal (SJA6017) as a Potent Calpain Inhibitor

  摘要：

  Novel N-arylsulfonyldipeptidyl aldehyde derivatives were prepared by DMSO oxidation from the corresponding dipeptide alcohol, and their potencies as calpain inhibitors were evaluated in vitro. Among them, N-(4-fluorophenylsulfonyl)-L-valyl-L-leucinal (8, SJA6017) potently inhibited calpains. 8 also inhibited cathepsin B and L but did not inhibit other cysteine proteases (interleukin 1beta-converting enzyme), serine proteases (trypsin, chymotrypsin, thrombin, factor VIIa, factor Xa), or proteasome. Preliminary cytotoxicity studies of 8 exhibited a relatively safe profile.

  DOI：

  10.1021/jm0201924
• 作为产物：
  描述：

  4-氯苯磺酰氯 在 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 p-Cl-C6H4-SO2-Val-ONSu
  参考文献：
  名称：

  Structure−Activity Relationship Study and Drug Profile of N-(4-Fluorophenylsulfonyl)-l-valyl-l-leucinal (SJA6017) as a Potent Calpain Inhibitor

  摘要：

  Novel N-arylsulfonyldipeptidyl aldehyde derivatives were prepared by DMSO oxidation from the corresponding dipeptide alcohol, and their potencies as calpain inhibitors were evaluated in vitro. Among them, N-(4-fluorophenylsulfonyl)-L-valyl-L-leucinal (8, SJA6017) potently inhibited calpains. 8 also inhibited cathepsin B and L but did not inhibit other cysteine proteases (interleukin 1beta-converting enzyme), serine proteases (trypsin, chymotrypsin, thrombin, factor VIIa, factor Xa), or proteasome. Preliminary cytotoxicity studies of 8 exhibited a relatively safe profile.

  DOI：

  10.1021/jm0201924

文献信息

• Angiogenesis inhibitor
  申请人：Senju Pharmaceutical Co., Ltd.

  公开号：EP0771565B1

  公开（公告）日：2003-01-02
• US6057290A
  申请人：——

  公开号：US6057290A

  公开（公告）日：2000-05-02
• US6214800B1
  申请人：——

  公开号：US6214800B1

  公开（公告）日：2001-04-10
• US6551999B1
  申请人：——

  公开号：US6551999B1

  公开（公告）日：2003-04-22
• Structure−Activity Relationship Study and Drug Profile of <i>N</i>-(4-Fluorophenylsulfonyl)-<scp>l</scp>-valyl-<scp>l</scp>-leucinal (SJA6017) as a Potent Calpain Inhibitor
  作者：Jun Inoue、Masayuki Nakamura、Ying-She Cui、Yusuke Sakai、Osamu Sakai、Jeanette R. Hill、Kevin K. W. Wang、Po-Wai Yuen

  DOI：10.1021/jm0201924

  日期：2003.2.1

  Novel N-arylsulfonyldipeptidyl aldehyde derivatives were prepared by DMSO oxidation from the corresponding dipeptide alcohol, and their potencies as calpain inhibitors were evaluated in vitro. Among them, N-(4-fluorophenylsulfonyl)-L-valyl-L-leucinal (8, SJA6017) potently inhibited calpains. 8 also inhibited cathepsin B and L but did not inhibit other cysteine proteases (interleukin 1beta-converting enzyme), serine proteases (trypsin, chymotrypsin, thrombin, factor VIIa, factor Xa), or proteasome. Preliminary cytotoxicity studies of 8 exhibited a relatively safe profile.