(4-chloro-N-(naphthalen-1-ylmethyl)-5-(3-(piperazin-1-yl) phenoxy)thiophene-2-sulfonamide) | 1261576-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (4-chloro-N-(naphthalen-1-ylmethyl)-5-(3-(piperazin-1-yl) phenoxy)thiophene-2-sulfonamide)
• 英文别名: B355252；4-Chloro-N-(naphthalen-1-ylmethyl)-5-(3-(piperazin-1-yl)phenoxy)thiophene-2-sulfonamide；4-chloro-N-(naphthalen-1-ylmethyl)-5-(3-piperazin-1-ylphenoxy)thiophene-2-sulfonamide
• CAS: 1261576-81-1
• 化学式: C₂₅H₂₄ClN₃O₃S₂
• 分子量: 514.069
• InChiKey: YAAVQYDOVJQDFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-萘甲基胺 在 sodium hydride 、 caesium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.75h， 生成 (4-chloro-N-(naphthalen-1-ylmethyl)-5-(3-(piperazin-1-yl) phenoxy)thiophene-2-sulfonamide)
  参考文献：
  名称：

  [EN] PHENOXY THIOPHENE SULFONAMIDES AND THEIR USE AS INHIBITORS OF GLUCURONIDASE
  [FR] PHÉNOXYTHIOPHÈNESULFAMIDES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA GLUCURONIDASE

  摘要：

  本发明涉及一般与葡萄糖醛酸酶抑制剂有关的化合物。所描述的葡萄糖醛酸酶抑制剂包括苯氧基噻吩磺酰胺。其他化合物，例如吡啶磺酰基、苯磺酰基、噻吩磺酰基、噻唑磺酰基、噻吩羰基和噻唑羰基也被考虑在内。还考虑包括一种或多种此类化合物的组合物，用于抑制葡萄糖醛酸酶，并使用一种或多种此类化合物作为联合用药，与抗癌药物CPT-11一起使用的辅助药物。

  公开号：

  WO2011112858A1

文献信息

• [EN] PHENOXY THIOPHENE SULFONAMIDES AND THEIR USE AS INHIBITORS OF GLUCURONIDASE<br/>[FR] PHÉNOXYTHIOPHÈNESULFAMIDES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA GLUCURONIDASE
  申请人：UNIV NORTH CAROLINA

  公开号：WO2011112858A1

  公开（公告）日：2011-09-15

  This invention relates generally to compounds that are glucuronidase inhibitors. Glucuronidase inhibitors described include phenoxy thiophene sulfonamides. Other compounds, for instance pyridine sulfonyls, benzene sulfonyls, thiophene sulfonyls, thiazole sulfonyls, thiophene carbonyls, and thiazole carbonyls, are also contemplated. Also contemplated are compositions including one or more of such compounds for use inhibiting glucuronidase and methods of using one or more of such compounds as a co-drug to be used in combination with the anticancer drug CPT-11.

  本发明涉及一般与葡萄糖醛酸酶抑制剂有关的化合物。所描述的葡萄糖醛酸酶抑制剂包括苯氧基噻吩磺酰胺。其他化合物，例如吡啶磺酰基、苯磺酰基、噻吩磺酰基、噻唑磺酰基、噻吩羰基和噻唑羰基也被考虑在内。还考虑包括一种或多种此类化合物的组合物，用于抑制葡萄糖醛酸酶，并使用一种或多种此类化合物作为联合用药，与抗癌药物CPT-11一起使用的辅助药物。
• PHENOXY THIOPHENE SULFONAMIDES AND OTHER COMPOUNDS FOR USE AS INHIBITORS OF BACTERIAL GLUCURONIDASE
  申请人：NORTH CAROLINA CENTRAL UNIVERSITY

  公开号：US20160237058A1

  公开（公告）日：2016-08-18

  This invention relates generally to compounds that are glucuronidase inhibitors. The glucuronidase inhibitors include phenoxy thiophene sulfonamides, and other compounds such as pyridine sulfonyls, benzene sulfonyls, thiophene sulfonyls, thiazole sulfonyls, thiophene carbonyls, and thiazole carbonyls. These compounds include nialamide, isocarboxazid, phenelzine, amoxapine, loxapine and mefloquine. Also compositions including one or more of such compounds for use in inhibiting glucuronidase and methods of using one or more of such compounds for selective inhibition of bacterial β-glucoronidase. These compounds may be used as a co-drug in combination with the anticancer drug CPT-11. Also a method for screening compounds to determine their usefulness in reducing diarrhea associated with irinotecan chemotherapy.

  本发明涉及一般与葡萄糖醛酸酶抑制剂有关的化合物。这些葡萄糖醛酸酶抑制剂包括苯氧基噻吩磺酰胺和其他化合物，例如吡啶磺酰基、苯磺酰基、噻吩磺酰基、噻唑磺酰基、噻吩羰基和噻唑羰基。这些化合物包括尼氨胺、异卡泊嗪、苯妥英、阿莫西平、洛西平和美氟喹。此外，还包括含有一种或多种此类化合物的组合物，用于抑制葡萄糖醛酸酶，并使用一种或多种此类化合物进行细菌β-葡萄糖醛酸酶的选择性抑制的方法。这些化合物可作为联合抗癌药物CPT-11的辅助药物使用。还包括一种筛选化合物的方法，以确定它们在减少伊立替康化疗引起的腹泻方面的有用性。
• Microwave-assisted synthesis of 4-chloro-N-(naphthalen-1-ylmethyl)-5-(3-(piperazin-1-yl)phenoxy)thiophene-2-sulfonamide (B-355252): a new potentiator of nerve growth factor (NGF)-induced neurite outgrowth
  作者：Alfred L. Williams、Srinivasa R. Dandepally、Nailya Gilyazova、Sam M. Witherspoon、Gordon Ibeanu

  DOI：10.1016/j.tet.2010.09.028

  日期：2010.12

  The synthesis of 4-chloro-N-(naphthalen-1-ylmethyl)-5-(3-(piperazin-1 -y1)phenoxy)thiophene-2-sulfonamide (B-355252) using an MW-assisted nucleophilic aromatic substitution (SNAr) reaction will be discussed. Utilization of this method allowed for the rapid generation of B-355252 heteroaryl ether core structure in the presence of cesium carbonate in dimethylformamide or tripotassium phosphate in N-methyl-2-pyrrolidone in 94% yield. Evaluation of B-355252 enhancement of nerve growth factor's ability to stimulate neurite outgrowths was determined using NS-1 cells. (C) 2010 Elsevier Ltd. All rights reserved.
• PHENOXY THIOPHENE SULFONAMIDES AND THEIR USE AS INHIBITORS OF GLUCURONIDASE
  申请人：North Carolina Central University

  公开号：EP2544535B1

  公开（公告）日：2017-04-19
• US9617239B2
  申请人：——

  公开号：US9617239B2

  公开（公告）日：2017-04-11