[4-[(2S)-3-(4-benzoylpiperazin-1-yl)-3-oxo-2-(phenylmethoxycarbonylamino)propyl]phenyl] 4-[4-[[4-[4-[(2S)-3-(4-benzoylpiperazin-1-yl)-3-oxo-2-(phenylmethoxycarbonylamino)propyl]phenoxy]sulfonylphenyl]carbamothioylamino]butylcarbamothioylamino]benzenesulfonate | 1011469-61-6

• 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: [4-[(2S)-3-(4-benzoylpiperazin-1-yl)-3-oxo-2-(phenylmethoxycarbonylamino)propyl]phenyl] 4-[4-[[4-[4-[(2S)-3-(4-benzoylpiperazin-1-yl)-3-oxo-2-(phenylmethoxycarbonylamino)propyl]phenoxy]sulfonylphenyl]carbamothioylamino]butylcarbamothioylamino]benzenesulfonate
• CAS: 1011469-61-6
• 化学式: C₇₄H₇₆N₁₀O₁₄S₄
• 分子量: 1457.74
• InChiKey: UBFCUCMMKHSJNH-XDVNEXBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  102
• 可旋转键数：
  29
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  374
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  MRS 2449 、 MRS 2483 以 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到[4-[(2S)-3-(4-benzoylpiperazin-1-yl)-3-oxo-2-(phenylmethoxycarbonylamino)propyl]phenyl] 4-[4-[[4-[4-[(2S)-3-(4-benzoylpiperazin-1-yl)-3-oxo-2-(phenylmethoxycarbonylamino)propyl]phenoxy]sulfonylphenyl]carbamothioylamino]butylcarbamothioylamino]benzenesulfonate
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of tyrosine-based antagonists at the human P2X7 receptor

  摘要：

  Analogues of the P2X(7) receptor antagonist KN-62, modified at the piperazine and arylsulfonyl groups, were synthesized and assayed at the human P2X(7) receptor for inhibition of BzATP-induced effects, that is, uptake of a fluorescent dye (ethidium bromide) in stably transfected HEK293 cells and IL-1 beta release in differentiated THP-1 cells. Substitution of the arylsulfonyl, moiety with a nitro group increased antagonistic potency relative to methyl substitution, such that compound 21 was slightly more potent than KN-62. Substitution with D-tyrosine in 36 and sterically bulky tyrosyl 3,5-dimethyl groups in 9 enhanced antagonistic potency. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.077

文献信息

• Synthesis and structure–activity relationship studies of tyrosine-based antagonists at the human P2X7 receptor
  作者：Ga Eun Lee、Bhalchandra V. Joshi、Wangzhong Chen、Lak Shin Jeong、Hyung Ryong Moon、Kenneth A. Jacobson、Yong-Chul Kim

  DOI：10.1016/j.bmcl.2007.11.077

  日期：2008.1

  Analogues of the P2X(7) receptor antagonist KN-62, modified at the piperazine and arylsulfonyl groups, were synthesized and assayed at the human P2X(7) receptor for inhibition of BzATP-induced effects, that is, uptake of a fluorescent dye (ethidium bromide) in stably transfected HEK293 cells and IL-1 beta release in differentiated THP-1 cells. Substitution of the arylsulfonyl, moiety with a nitro group increased antagonistic potency relative to methyl substitution, such that compound 21 was slightly more potent than KN-62. Substitution with D-tyrosine in 36 and sterically bulky tyrosyl 3,5-dimethyl groups in 9 enhanced antagonistic potency. (c) 2007 Elsevier Ltd. All rights reserved.