tert-butyl 21-{4-[({4-[(3-pyridinylamino)carbonyl]benzyl}amino)sulfonyl]phenyl}-3,6,9,12,15,18-hexaoxahenicos-1-ylcarbamate

• 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: tert-butyl 21-{4-[({4-[(3-pyridinylamino)carbonyl]benzyl}amino)sulfonyl]phenyl}-3,6,9,12,15,18-hexaoxahenicos-1-ylcarbamate
• 英文别名: tert-butyl21-{4-[({4-[(3-pyridinylamino)carbonyl]benzyl}amino)sulfonyl]phenyl}-3,6,9,12,15,18-hexaoxahenicos-1-ylcarbamate
• 化学式: C₃₉H₅₆N₄O₁₁S
• 分子量: 788.96
• InChiKey: HZAZUDYAJGLAIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  55.0
• 可旋转键数：
  28.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  181.87
• 氢给体数：
  3.0
• 氢受体数：
  12.0

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	tert-butyl 21-{4-[({4-[(3-pyridinylamino)carbonyl]benzyl}amino)sulfonyl]phenyl}-3,6,9,12,15,18-hexaoxahenicos-20-yn-1-ylcarbamate	——	C39H52N4O11S	784.928

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-[({[4-(21-amino-4,7,10,13,16,19-hexaoxahenicos-1-yl)phenyl]sulfonyl}amino)methyl]-N-(3-pyridinyl)benzamide	——	C34H48N4O9S	688.843

反应信息

• 作为反应物：
  描述：

  tert-butyl 21-{4-[({4-[(3-pyridinylamino)carbonyl]benzyl}amino)sulfonyl]phenyl}-3,6,9,12,15,18-hexaoxahenicos-1-ylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以71%的产率得到4-[({[4-(21-amino-4,7,10,13,16,19-hexaoxahenicos-1-yl)phenyl]sulfonyl}amino)methyl]-N-(3-pyridinyl)benzamide
  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
• 作为产物：
  描述：

  六甘醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium azide 、 palladium 10% on activated carbon 、 palladium on activated charcoal 、 氢气 、 sodium hydride 、 三乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 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 tert-butyl 21-{4-[({4-[(3-pyridinylamino)carbonyl]benzyl}amino)sulfonyl]phenyl}-3,6,9,12,15,18-hexaoxahenicos-1-ylcarbamate
  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

• HETEROARYL BENZAMIDES, COMPOSITIONS AND METHODS OF USE
  申请人：Sutphin Patrick D.

  公开号：US20120225862A1

  公开（公告）日：2012-09-06

  Provided are certain heteroaryl benzamides, compositions, and methods of their manufacture and use.

  提供了某些杂环芳酰苯胺、组成物及其制造和使用方法。
• 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.