四甲基若丹明B异氰酸酯 | 6749-36-6

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 四甲基若丹明B异氰酸酯
• 英文名称: [9-(2-carboxy-4-isothiocyanatophenyl)-6-dimethylaminoxanthen-3-ylidene]dimethylammonium chloride
• 英文别名: tetramethylrhodamine-5-isothiocyanate；2-[3,6-Bis(dimethylamino)xanthen-10-ium-9-yl]-5-isothiocyanatobenzoate--hydrogen chloride (1/1)；2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]-5-isothiocyanatobenzoate;hydrochloride
• CAS: 6749-36-6
• 化学式: C₂₅H₂₂N₃O₃S*Cl
• 分子量: 479.987
• InChiKey: ZIDZWKOOWSJOJR-UHFFFAOYSA-N

物化性质

• 密度：
  1.1871 (rough estimate)
• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  97.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  四甲基若丹明B异氰酸酯 、 3-(4-aminomethyl[1,2,3]triazol-1-yl)benzenesulfonamide hydrochloride 在 三乙胺 作用下， 以18%的产率得到[9-(2-carboxy-4-{3-[(1-(3-sulfamoylphenyl)-1H-[1,2,3]triazol-4-yl)methyl]thioureido}phenyl)-6-dimethylaminoxanthen-3-ylidene]dimethylammonium chloride
  参考文献：
  名称：

  Fluorescent sulfonamide carbonic anhydrase inhibitors incorporating 1,2,3-triazole moieties: Kinetic and X-ray crystallographic studies

  摘要：

  Fluorescent sulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitors (CAIs) were essential for demonstrating the role played by the tumor-associated isoform CA IX in acidification of tumors, cancer progression towards metastasis and for the development of imaging and therapeutic strategies for the management of hypoxic tumors which overexpress CA IX. However, the presently available such compounds are poorly water soluble which limits their use. Here we report new fluorescent sulfonamides 7, 8 and 10 with increased water solubility. The new derivatives showed poor hCA I inhibitory properties, but were effective inhibitors against the hCA II (K(I)s of 366-127 nM), CA IX (K(I)s of 8.1-36.9 nM), CA XII (K(I)s of 4.1-20.5 nM) and CA XIV (K(I)s of 12.8-53.6 nM). A high resolution X-ray crystal structure of one of these compounds bound to hCA II revealed the factors associated with the good inhibitory properties. Furthermore, this compound showed a three-fold increase of water solubility compared to a similar derivative devoid of the triazole moiety, making it an interesting candidate for ex vivo/in vivo studies. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.031

文献信息

• 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.