N-<3-(1-piperidinyl)-4-nitrophenyl>methanesulfonamide | 88413-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-<3-(1-piperidinyl)-4-nitrophenyl>methanesulfonamide
• 英文别名: N-(4-nitro-3-piperidin-1-yl-phenyl)methanesulfonamide；N-(4-nitro-3-piperidin-1-ylphenyl)methanesulfonamide
• CAS: 88413-05-2
• 化学式: C₁₂H₁₇N₃O₄S
• 分子量: 299.351
• InChiKey: IPEUUSOEFMGBIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-<3-(1-piperidinyl)-4-nitrophenyl>methanesulfonamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 N-[4-(acridin-9-ylamino)-3-piperidin-1-ylphenyl]methanesulfonamide
  参考文献：
  名称：

  Potential antitumor agents. 41. Analogs of amsacrine with electron-donor substituents in the anilino ring

  摘要：

  The preparation and antitumor activity of a series of 3'-alkylamino and 3'-dialkylamino analogues of amsacrine are reported. The results support previous work suggesting that the presence of electron-donating groups in the 3'-position of the anilino ring substantially enhance the antitumor activity of amsacrine analogues, possibly by the provision of high levels of electron density at the 6'-position. The alkylamino derivatives generally possess tighter DNA binding, higher levels of in vitro and in vivo antileukemic activity, and greater aqueous solubility than the corresponding amsacrine analogues.

  DOI：

  10.1021/jm00369a022
• 作为产物：
  描述：

  3-chloro-4-nitroacetanilide 在 吡啶 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 N-<3-(1-piperidinyl)-4-nitrophenyl>methanesulfonamide
  参考文献：
  名称：

  Potential antitumor agents. 41. Analogs of amsacrine with electron-donor substituents in the anilino ring

  摘要：

  The preparation and antitumor activity of a series of 3'-alkylamino and 3'-dialkylamino analogues of amsacrine are reported. The results support previous work suggesting that the presence of electron-donating groups in the 3'-position of the anilino ring substantially enhance the antitumor activity of amsacrine analogues, possibly by the provision of high levels of electron density at the 6'-position. The alkylamino derivatives generally possess tighter DNA binding, higher levels of in vitro and in vivo antileukemic activity, and greater aqueous solubility than the corresponding amsacrine analogues.

  DOI：

  10.1021/jm00369a022

文献信息

• WO2006/47504
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery of novel FMS kinase inhibitors as anti-inflammatory agents
  作者：Carl R. Illig、Jinsheng Chen、Mark J. Wall、Kenneth J. Wilson、Shelley K. Ballentine、M. Jonathan Rudolph、Renee L. DesJarlais、Yanmin Chen、Carsten Schubert、Ioanna Petrounia、Carl S. Crysler、Christopher J. Molloy、Margery A. Chaikin、Carl L. Manthey、Mark R. Player、Bruce E. Tomczuk、Sanath K. Meegalla

  DOI：10.1016/j.bmcl.2008.01.059

  日期：2008.3

  The optimization of the arylamide lead 2 resulted in identification of a highly potent series of 2,4-disubstituted arylamides. Compound 8 (FMS kinase IC50 = 0.0008 mu M) served as a proof-of-concept candidate in a collagen-induced model of arthritis in mice. (c) 2008 Elsevier Ltd. All rights reserved.