tert-butyl 6-(4-{4-[2-(3-toluidino)-1,3-thiazol-4-yl]-2-pyridinyl}-1H-1,2,3-triazol-1-yl)hexylcarbamate | 1542733-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl 6-(4-{4-[2-(3-toluidino)-1,3-thiazol-4-yl]-2-pyridinyl}-1H-1,2,3-triazol-1-yl)hexylcarbamate
• CAS: 1542733-85-6
• 化学式: C₂₈H₃₅N₇O₂S
• 分子量: 533.698
• InChiKey: IZFZNMZJEAYXMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  106.85
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 6-(4-{4-[2-(3-toluidino)-1,3-thiazol-4-yl]-2-pyridinyl}-1H-1,2,3-triazol-1-yl)hexylcarbamate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到6-(4-{4-[2-(3-methylphenylamino)-1,3-thiazol-4-yl]-2-pyridinyl}-1H-1,2,3-triazol-1-yl)-1-hexanammonium trifluoroacetate
  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：

  4-(2-bromo-4-pyridinyl)-N-(3-methylphenyl)-1,3-thiazol-2-amine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 tert-butyl 6-(4-{4-[2-(3-toluidino)-1,3-thiazol-4-yl]-2-pyridinyl}-1H-1,2,3-triazol-1-yl)hexylcarbamate
  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