N-[4-(methylsulfonyl)-2-nitrophenyl]-1,3-benzodioxol-5-amine | 852702-51-3

• 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: N-[4-(methylsulfonyl)-2-nitrophenyl]-1,3-benzodioxol-5-amine
• 英文别名: (N-(4-methanesulfonyl-2-nitrophenyl)-2H-1,3-benzodioxol-5-amine)；MSNBA；N-(4-methanesulfonyl-2-nitrophenyl)-2H-1,3-benzodioxol-5-amine；N-(4-methylsulfonyl-2-nitrophenyl)-1,3-benzodioxol-5-amine
• CAS: 852702-51-3
• 化学式: C₁₄H₁₂N₂O₆S
• 分子量: 336.325
• InChiKey: FUVYUOPHDIDJOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为产物：
  描述：

  2-氟-5-甲基磺酰硝基苯 、 3,4-亚甲二氧基苯胺 以 水 为溶剂， 反应 0.67h， 以64.7%的产率得到N-[4-(methylsulfonyl)-2-nitrophenyl]-1,3-benzodioxol-5-amine
  参考文献：
  名称：

  乳腺癌中GLUT1和GLUT5的分子成像：小鼠多示踪正电子发射断层成像成像研究。

  摘要：

  [18F] FDG-正电子发射断层扫描（PET）在临床乳腺癌（BC）成像中的使用受到限制，主要是在多达50％的患者中，促进葡萄糖转运蛋白（GLUT）1的表达水平不足。果糖特异性促进性己糖转运蛋白GLUT5代表了BC中己糖代谢的PET成像的替代生物标志物。本研究的目的是比较在小鼠BC模型EMT6中选定的基于己糖的PET放射性示踪剂的吸收特性。摄取1-脱氧-1- [18F]氟-d-果糖（1- [18F] FDF），6-脱氧-6- [18F]氟-d-果糖（6- [18F] FDF），1-脱氧-1- [18F]氟-2,5-脱水甘露醇（1- [18F] FDAM），2-脱氧-2- [18F]氟-d-葡萄糖（2- [18F] FDG）和6在EMT6细胞，肿瘤和肌肉中研究了-deoxy-6- [18F]氟-d-葡萄糖（6- [18F] FDG），并与GLUT1和GLUT5表达水平相关。与结构类似物1- [18F]

  DOI：

  10.1124/mol.117.110007

文献信息

• Human GLUT5 specific inhibitors and methods of treatment
  申请人：UNM RAINFOREST INNOVATIONS

  公开号：US10822325B2

  公开（公告）日：2020-11-03

  The present invention relates to compounds which have been discovered to be potent ligands (inhibitors) of human GLUT5 (glucose transporter type 5), a facilitative glucose transporter that transports fructose, and their use as ligands assays which can uncover additional ligands of GLUT5, having the potential for being used as drugs. In addition, the present invention is directed to compounds, chemical compositions and methods for treating disease states and conditions which are mediated through GLUT5, including such disease states and conditions as GLUT5 deficiency syndrome, diabetes (type I and II), cancer, metabolic diseases including metabolic syndrome and fatty liver disease, among others.

  本发明涉及已被发现是人类 GLUT5（5 型葡萄糖转运体）（一种转运果糖的促进性葡萄糖转运体）的强效配体（抑制剂）的化合物，以及将其用作配体测定的方法，该方法可发现 GLUT5 的其他配体，具有用作药物的潜力。此外，本发明还涉及用于治疗通过 GLUT5 介导的疾病状态和病症的化合物、化学组合物和方法，包括 GLUT5 缺乏综合征、糖尿病（I 型和 II 型）、癌症、代谢性疾病（包括代谢综合征和脂肪肝）等疾病状态和病症。
• HUMAN GLUT5 SPECIFIC INHIBITORS AND METHODS OF TREATMENT
  申请人：STC.UNM

  公开号：US20180170897A1

  公开（公告）日：2018-06-21

  The present invention relates to compounds which have been discovered to be potent ligands (inhibitors) of human GLUT5 (glucose transporter type 5), a facilitative glucose transporter that transports fructose, and their use as ligands assays which can uncover additional ligands of GLUT5, having the potential for being used as drugs. In addition, the present invention is directed to compounds, chemical compositions and methods for treating disease states and conditions which are mediated through GLUT5, including such disease states and conditions as GLUT5 deficiency syndrome, diabetes (type I and II), cancer, metabolic diseases including metabolic syndrome and fatty liver disease, among others.
• COMPOSITIONS AND METHODS FOR TARGETING FRUCTOSE ENZYMES AND TRANSPORTERS FOR THE TREATMENT OF CANCER
  申请人：Duke University

  公开号：US20190231761A1

  公开（公告）日：2019-08-01

  The disclosure relates to compositions and methods of treating cancer in a subject in need thereof, the method comprising administering to the subject an effective amount of a therapeutic agent capable of down-regulating and/or inhibiting a fructose enzyme or fructose transporter in a cell of the subject such that the cancer growth is suppressed.
• ANTI-FRUCTOSE THERAPY FOR COLORECTAL AND SMALL INTESTINE CANCERS
  申请人：Cornell University

  公开号：US20220400732A1

  公开（公告）日：2022-12-22

  As described herein ingestion of high amounts of sugar, especially fructose, can increase the growth of intestinal tumors. Such cancer growth can be inhibited or prevented by limiting the amounts of sugar and amino acids ingested, by inhibiting ketohexokinase (KHK), fructose transport (via GLUT5), fatty acid synthesis (via FASN), phosphoinositide 3-kinases (PI3K), or by limiting amounts of sugar and amino acids ingested while also receiving KHK inhibitors, GLUT5 inhibitors, FASN inhibitors, PI3K inhibitors, or a combination of such inhibitors.
• [EN] HUMAN GLUT5 SPECIFIC INHIBITORS AND METHODS OF TREATMENT<br/>[FR] INHIBITEURS SPÉCIFIQUES DE GLUT5 HUMAINE ET PROCÉDÉS DE TRAITEMENT
  申请人：STC UNM

  公开号：WO2016201214A1

  公开（公告）日：2016-12-15

  The present invention relates to compounds which have been discovered to be potent ligands (inhibitors) of human GLUT5 (glucose transporter type 5), a facilitative glucose transporter that transports fructose, and their use as ligands assays which can uncover additional ligands of GLUT5, having the potential for being used as drugs. In addition, the present invention is directed to compounds, chemical compositions and methods for treating disease states and conditions which are mediated through GLUT5, including such disease states and conditions as GLUT5 deficiency syndrome, diabetes (type I and II), cancer, metabolic diseases including metabolic syndrome and fatty liver disease, among others.