1-(tert-butyl) 4-ethyl 4-({[4-(2-butynyloxy)phenyl]sulfanyl}methyl)-1,4-piperidinedicarboxylate | 287202-23-7

• 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: 1-(tert-butyl) 4-ethyl 4-({[4-(2-butynyloxy)phenyl]sulfanyl}methyl)-1,4-piperidinedicarboxylate
• 英文别名: 1-O-tert-butyl 4-O-ethyl 4-[(4-but-2-ynoxyphenyl)sulfanylmethyl]piperidine-1,4-dicarboxylate
• CAS: 287202-23-7
• 化学式: C₂₄H₃₃NO₅S
• 分子量: 447.596
• InChiKey: XTHFVHOKAKIMAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(tert-butyl) 4-ethyl 4-({[4-(2-butynyloxy)phenyl]sulfanyl}methyl)-1,4-piperidinedicarboxylate 在 盐酸 、 Oxone tetrabutylammonium salt 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 4-[[[4-(2-butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic acid ethyl ester
  参考文献：
  名称：

  Design and synthesis of butynyloxyphenyl β-sulfone piperidine hydroxamates as TACE inhibitors

  摘要：

  A series of butynyloxyphenyl P-sulfone piperidine hydroxamate TACE inhibitors was designed and synthesized. The resulting structure-activity relationship and MMP selectivity of the series were examined. Of the compounds investigated, 17s has excellent in vitro potency against isolated TACE enzyme, shows good selectivity over MMP-1, -2, -7, -8, -9, -13, and -14, and oral activity in an in vivo mouse model of TNF-alpha production. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.026
• 作为产物：
  描述：

  N-Boc-4-哌啶甲酸乙酯 在 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 1-(tert-butyl) 4-ethyl 4-({[4-(2-butynyloxy)phenyl]sulfanyl}methyl)-1,4-piperidinedicarboxylate
  参考文献：
  名称：

  Design and synthesis of butynyloxyphenyl β-sulfone piperidine hydroxamates as TACE inhibitors

  摘要：

  A series of butynyloxyphenyl P-sulfone piperidine hydroxamate TACE inhibitors was designed and synthesized. The resulting structure-activity relationship and MMP selectivity of the series were examined. Of the compounds investigated, 17s has excellent in vitro potency against isolated TACE enzyme, shows good selectivity over MMP-1, -2, -7, -8, -9, -13, and -14, and oral activity in an in vivo mouse model of TNF-alpha production. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.026

文献信息

• Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors
  申请人：American Cyanamid Company

  公开号：US06358980B1

  公开（公告）日：2002-03-19

  Compounds of the formula: useful in the treatment of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection.

  该式化合物有助于治疗关节炎、肿瘤转移、组织溃疡、异常伤口愈合、牙周病、骨病、糖尿病（胰岛素抵抗）和HIV感染。
• Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/TACE inhibitors
  申请人：WYETH

  公开号：US20040229924A1

  公开（公告）日：2004-11-18

  Compounds of the formula: 1 useful in the treatment of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection.

  该式的化合物：1在治疗关节炎、肿瘤转移、组织溃疡、异常伤口愈合、牙周病、骨病、糖尿病（胰岛素抵抗）和HIV感染方面有用。
• ALKYNYL CONTAINING HYDROXAMIC ACID DERIVATIVES, THEIR PREPARATION AND THEIR USE AS MATRIX METALLOPROTEINASE (MMP) INHIBITORS / TNF-ALPHA CONVERTING ENZYME (TACE) INHIBITORS
  申请人：Wyeth Holdings Corporation

  公开号：EP1147085B1

  公开（公告）日：2005-11-16
• US6358980B1
  申请人：——

  公开号：US6358980B1

  公开（公告）日：2002-03-19
• US6753337B2
  申请人：——

  公开号：US6753337B2

  公开（公告）日：2004-06-22