4-[({[4-(21-amino-4,7,10,13,16,19-hexaoxahenicos-1-yn-1-yl)phenyl]sulfonyl}amino)methyl]-N-(3-pyridinyl)benzamide trifluoroacetate salt

• 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: 4-[({[4-(21-amino-4,7,10,13,16,19-hexaoxahenicos-1-yn-1-yl)phenyl]sulfonyl}amino)methyl]-N-(3-pyridinyl)benzamide trifluoroacetate salt
• 英文别名: 4-[[[4-[3-[2-[2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]prop-1-ynyl]phenyl]sulfonylamino]methyl]-N-pyridin-3-ylbenzamide;2,2,2-trifluoroacetic acid
• 化学式: (x)C₂HF₃O₂*C₃₄H₄₄N₄O₉S
• 分子量: 798.8
• InChiKey: QDXHHTMWIKHOHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  55.0
• 可旋转键数：
  24.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  206.86
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  六甘醇 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium azide 、 palladium on activated charcoal 、 氢气 、 sodium hydride 、 三乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 110.0 ℃ 、413.7 kPa 条件下， 反应 126.5h， 生成 4-[({[4-(21-amino-4,7,10,13,16,19-hexaoxahenicos-1-yn-1-yl)phenyl]sulfonyl}amino)methyl]-N-(3-pyridinyl)benzamide trifluoroacetate salt
  参考文献：
  名称：

  Identifying novel targets in renal cell carcinoma: Design and synthesis of affinity chromatography reagents

  摘要：

  Two novel scaffolds, 4-pyridylanilinothiazoles (PAT) and 3-pyridylphenylsulfonyl benzamides (PPB), previously identified as selective cytotoxins for von Hippel-Lindau-deficient Renal Carcinoma cells, were used as templates to prepare affinity chromatography reagents to aid the identification of the molecular targets of these two classes. Structure-activity data and computational models were used to predict possible points of attachment for linker chains. In the PAT class, Click coupling of long chain azides with 2- and 3-pyridylanilinothiazoleacetylenes gave triazole-linked pyridylanilinothiazoles which did not retain the VHL-dependent selectivity of parent analogues. For the PPB class, Sonagashira coupling of 4-iodo-(3-pyridylphenylsulfonyl) benzamide with a propargyl hexaethylene glycol carbamate gave an acetylene which was reduced to the corresponding alkyl 3-pyridylphenylsulfonylbenzamide. This reagent retained the VHL-dependent selectivity of the parent analogues and was successfully utilized as an affinity reagent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.028

文献信息

• JP5789603
  申请人：——

  公开号：——

  公开（公告）日：——
• Identifying novel targets in renal cell carcinoma: Design and synthesis of affinity chromatography reagents
  作者：Muriel Bonnet、Jack U. Flanagan、Denise A. Chan、Amato J. Giaccia、Michael P. Hay

  DOI：10.1016/j.bmc.2013.12.028

  日期：2014.1

  Two novel scaffolds, 4-pyridylanilinothiazoles (PAT) and 3-pyridylphenylsulfonyl benzamides (PPB), previously identified as selective cytotoxins for von Hippel-Lindau-deficient Renal Carcinoma cells, were used as templates to prepare affinity chromatography reagents to aid the identification of the molecular targets of these two classes. Structure-activity data and computational models were used to predict possible points of attachment for linker chains. In the PAT class, Click coupling of long chain azides with 2- and 3-pyridylanilinothiazoleacetylenes gave triazole-linked pyridylanilinothiazoles which did not retain the VHL-dependent selectivity of parent analogues. For the PPB class, Sonagashira coupling of 4-iodo-(3-pyridylphenylsulfonyl) benzamide with a propargyl hexaethylene glycol carbamate gave an acetylene which was reduced to the corresponding alkyl 3-pyridylphenylsulfonylbenzamide. This reagent retained the VHL-dependent selectivity of the parent analogues and was successfully utilized as an affinity reagent. (C) 2013 Elsevier Ltd. All rights reserved.