2-((4-bromophenyl)sulfonamido)-2-phenylacetic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((4-bromophenyl)sulfonamido)-2-phenylacetic acid
• 英文别名: (S)-2-((4-Bromophenyl)sulfonamido)-2-phenylaceticacid；(2S)-2-[(4-bromophenyl)sulfonylamino]-2-phenylacetic acid
• 化学式: C₁₄H₁₂BrNO₄S
• 分子量: 370.224
• InChiKey: AAMMHGXIMZVDDB-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((4-bromophenyl)sulfonamido)-2-phenylacetic acid 以 乙二醇 为溶剂， 以31%的产率得到1,4-bis((4-bromophenyl)sulfonyl)-3,6-diphenylpiperazine-2,5-dione
  参考文献：
  名称：

  Development of Piperazinediones as dual inhibitor for treatment of Alzheimer's disease

  摘要：

  Novel multifunctional 3,6-Diphenyl-1,4-bis(phenylsulfonyl)piperazine-2,5-dione derivatives were designed and synthesized for the treatment of Alzheimer's disease (AD). The designed scaffold has blood brain barrier penetrating ability, acetylcholinesterase (AChE) and matrix metalloproteinase-2 (MMP-2) inhibition potential. Compounds 52 and 46 showed very significant inhibition against AChE, IC50 = 32.45 +/- 0.044, 28.65 +/- 0.029, BuChE, IC50 = 157.95 +/- 0.264, 160.58 +/- 0.082 and MMP-2, IC50 = 36.83 +/- 0.015, 19.57 +/- 0.005 (nM). In the enzyme kinetics study, lead molecule 46 showed noncompetitive inhibition of AChE with K-i = 7 nM and competitive inhibition of MMP-2 with K-i = 20 nM. Compounds 52 and 46 inhibited AChE-induced A beta aggregation at 20 mu M. The compounds also exhibited in-vitro antioxidant potential in DPPH assay. Further, compound 46 was found to be a promising neuroprotective agent in MC65 cells. Lead molecule 46 significantly enhanced working memory in scopolamine induced amnesia animal model at dose of 5 mg/kg dose. The mitochondrial membrane potential was restored in animals when treated with compounds 52 and 46. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.078
• 作为产物：
  描述：

  L-苯甘氨酸 、 4-溴苯磺酰氯 以 水 、 丙酮 为溶剂， 反应 24.0h， 生成 2-((4-bromophenyl)sulfonamido)-2-phenylacetic acid
  参考文献：
  名称：

  Development of Piperazinediones as dual inhibitor for treatment of Alzheimer's disease

  摘要：

  Novel multifunctional 3,6-Diphenyl-1,4-bis(phenylsulfonyl)piperazine-2,5-dione derivatives were designed and synthesized for the treatment of Alzheimer's disease (AD). The designed scaffold has blood brain barrier penetrating ability, acetylcholinesterase (AChE) and matrix metalloproteinase-2 (MMP-2) inhibition potential. Compounds 52 and 46 showed very significant inhibition against AChE, IC50 = 32.45 +/- 0.044, 28.65 +/- 0.029, BuChE, IC50 = 157.95 +/- 0.264, 160.58 +/- 0.082 and MMP-2, IC50 = 36.83 +/- 0.015, 19.57 +/- 0.005 (nM). In the enzyme kinetics study, lead molecule 46 showed noncompetitive inhibition of AChE with K-i = 7 nM and competitive inhibition of MMP-2 with K-i = 20 nM. Compounds 52 and 46 inhibited AChE-induced A beta aggregation at 20 mu M. The compounds also exhibited in-vitro antioxidant potential in DPPH assay. Further, compound 46 was found to be a promising neuroprotective agent in MC65 cells. Lead molecule 46 significantly enhanced working memory in scopolamine induced amnesia animal model at dose of 5 mg/kg dose. The mitochondrial membrane potential was restored in animals when treated with compounds 52 and 46. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.078

文献信息

• Development of Piperazinediones as dual inhibitor for treatment of Alzheimer's disease
  作者：Devendra Kumar、Sukesh K. Gupta、Ankit Ganeshpurkar、Gopichand Gutti、Sairam Krishnamurthy、Gyan Modi、Sushil K. Singh

  DOI：10.1016/j.ejmech.2018.02.078

  日期：2018.4

  Novel multifunctional 3,6-Diphenyl-1,4-bis(phenylsulfonyl)piperazine-2,5-dione derivatives were designed and synthesized for the treatment of Alzheimer's disease (AD). The designed scaffold has blood brain barrier penetrating ability, acetylcholinesterase (AChE) and matrix metalloproteinase-2 (MMP-2) inhibition potential. Compounds 52 and 46 showed very significant inhibition against AChE, IC50 = 32.45 +/- 0.044, 28.65 +/- 0.029, BuChE, IC50 = 157.95 +/- 0.264, 160.58 +/- 0.082 and MMP-2, IC50 = 36.83 +/- 0.015, 19.57 +/- 0.005 (nM). In the enzyme kinetics study, lead molecule 46 showed noncompetitive inhibition of AChE with K-i = 7 nM and competitive inhibition of MMP-2 with K-i = 20 nM. Compounds 52 and 46 inhibited AChE-induced A beta aggregation at 20 mu M. The compounds also exhibited in-vitro antioxidant potential in DPPH assay. Further, compound 46 was found to be a promising neuroprotective agent in MC65 cells. Lead molecule 46 significantly enhanced working memory in scopolamine induced amnesia animal model at dose of 5 mg/kg dose. The mitochondrial membrane potential was restored in animals when treated with compounds 52 and 46. (C) 2018 Elsevier Masson SAS. All rights reserved.