tert-butyl (6-(4-sulfamoylphenoxy)hexyl)carbamate | 1446011-69-3

• 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 (6-(4-sulfamoylphenoxy)hexyl)carbamate
• 英文别名: tert-butyl 6-(4-sulfamoylphenoxy)hexylcarbamate；Tert-butyl (6-(4-sulfamoylphenoxy)hexyl)carbamate；tert-butyl N-[6-(4-sulfamoylphenoxy)hexyl]carbamate
• CAS: 1446011-69-3
• 化学式: C₁₇H₂₈N₂O₅S
• 分子量: 372.486
• InChiKey: BRGLSNPXZWXVDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (6-(4-sulfamoylphenoxy)hexyl)carbamate 在 氮气 、 水 作用下， 以 三氟乙酸 、 二氯甲烷 为溶剂， 反应 16.0h， 以to afford 4-((6-aminohexyl)oxy)benzenesulfonamide (1.664 g)的产率得到4-((6-aminohexyl)oxy)benzenesulfonamide
  参考文献：
  名称：

  Metal complexes of poly(carboxyl)amine-containing ligands having an affinity for carbonic anhydrase IX

  摘要：

  一种配体，一种药学上可接受的盐，互变异构体或酯可以表示为：在公式中，X是从群组中选择的，该群组包括—（CH2）n—，—（CH2）n—O—，—（CH2）n—N（Rg）—，—（CH2）n—N（Rg）—C（O）—和—O—；Rg是氢或（C1-C6）烷基；G是—（CH（Rm））n—Rh—，或—（CH2）p—C（O）—Rh；G'是—（CH（Rm））n—Rh—，或—（CH2）p—C（O）—Rh；Rh是—H，—OH，NRaRb或—CO2H；Rm是—H，—COOH或取代或未取代的—COO（C1-C6）烷基；Ra和Rb各自独立地为H，取代或未取代的（C1-C8）烷基，或取代或未取代的羧基（C1-C8）烷基；m为0、1、2、3、4、5、6、7、8、9或10；n为0、1、2、3、4、5、6、7、8、9或10；p为0、1、2、3、4、5、6、7、8、9或10。

  公开号：

  US09422251B2
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 偶氮二甲酸二异丙酯 、 N,N-二异丙基乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 tert-butyl (6-(4-sulfamoylphenoxy)hexyl)carbamate
  参考文献：
  名称：

  A Class of 4-Sulfamoylphenyl-ω-aminoalkyl Ethers with Effective Carbonic Anhydrase Inhibitory Action and Antiglaucoma Effects

  摘要：

  We report a series of 4-sulfamoylphenyl-omega-aminoalkyl ethers as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. The structureactivity relationship was drawn for the inhibition of four physiologically relevant isoforms: hCA I, II, IX, and XII. Many of these compounds were highly effective, low nanomolar inhibitors of all CA isoforms, whereas several isoform-selective were also identified. X-ray crystal structures of two new sulfonamides bound to the physiologically dominant CA II isoform showed the tails of these derivatives bound within the hydrophobic half of the enzyme active site through van der Waals contacts with Val135, Leu198, Leu204, Trp209, Pro201, and Pro202 amino acids. One of the highly water-soluble compound (as trifluoroacetate salt) showed effective IOP lowering properties in an animal model of glaucoma. Several fluorescent sulfonamides incorporating either the fluorescein-thiourea (7a-c) or tetramethylrhodamine-thiourea (9a,b) moieties were also obtained and showed interesting CA inhibitory properties for the tumor-associated isoforms CA IX and XII.

  DOI：

  10.1021/jm501497m

文献信息

• [EN] METAL COMPLEXES OF POLY(CARBOXYL)AMINE-CONTAINING LIGANDS HAVING AN AFFINITY FOR CARBONIC ANHYDRASE IX<br/>[FR] COMPLEXE MÉTALLIQUES DE POLY (CARBOXYL) AMINE CONTENANT DES LIGANDS AYANT UNE AFFINITÉ POUR L'ANHYDRASE CARBONIQUE IX
  申请人：MOLECULAR INSIGHT PHARM INC

  公开号：WO2013103813A1

  公开（公告）日：2013-07-11

  The present invention is directed to CA I X inhibitors that conform to Formula 1 where the substituents X, A, B, D, E, E' and G are as defined above. Also described are Pt, 64Cu, 186Re, 188Re and 99mTc metal complexes of Formula 1 compounds which find use as candidate agents for imaging tumors.

  本发明涉及符合式1的CA IX抑制剂，其中取代基X、A、B、D、E、E'和G如上所定义。还描述了符合式1化合物的Pt、64Cu、186Re、188Re和99mTc金属配合物，这些配合物可用作肿瘤成像候选药物。
• Metal complexes of poly(carboxyl)amine-containing ligands having an affinity for carbonic anhydrase IX
  申请人：Molecular Insight Pharmaceuticals

  公开号：US09120837B2

  公开（公告）日：2015-09-01

  The present invention is directed to CA IX inhibitors that conform to Formula I where the substituents X, A, B, D, E, E′ and G are as defined above. Also described are Pt, 64Cu, 186Re, 188Re and 99mTc metal complexes of Formula I compounds which find use as candidate agents for imaging tumors.

  本发明涉及符合公式I的CA IX抑制剂，其中取代基X、A、B、D、E、E'和G的定义如上所述。还描述了公式I化合物的Pt、64Cu、186Re、188Re和99mTc金属配合物，这些配合物可用作肿瘤成像候选药物。
• US9120837B2
  申请人：——

  公开号：US9120837B2

  公开（公告）日：2015-09-01
• US9422251B2
  申请人：——

  公开号：US9422251B2

  公开（公告）日：2016-08-23
• A Class of 4-Sulfamoylphenyl-ω-aminoalkyl Ethers with Effective Carbonic Anhydrase Inhibitory Action and Antiglaucoma Effects
  作者：Murat Bozdag、Melissa Pinard、Fabrizio Carta、Emanuela Masini、Andrea Scozzafava、Robert McKenna、Claudiu T. Supuran

  DOI：10.1021/jm501497m

  日期：2014.11.26

  We report a series of 4-sulfamoylphenyl-omega-aminoalkyl ethers as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. The structureactivity relationship was drawn for the inhibition of four physiologically relevant isoforms: hCA I, II, IX, and XII. Many of these compounds were highly effective, low nanomolar inhibitors of all CA isoforms, whereas several isoform-selective were also identified. X-ray crystal structures of two new sulfonamides bound to the physiologically dominant CA II isoform showed the tails of these derivatives bound within the hydrophobic half of the enzyme active site through van der Waals contacts with Val135, Leu198, Leu204, Trp209, Pro201, and Pro202 amino acids. One of the highly water-soluble compound (as trifluoroacetate salt) showed effective IOP lowering properties in an animal model of glaucoma. Several fluorescent sulfonamides incorporating either the fluorescein-thiourea (7a-c) or tetramethylrhodamine-thiourea (9a,b) moieties were also obtained and showed interesting CA inhibitory properties for the tumor-associated isoforms CA IX and XII.