N-(6-硝基苯并[d]噻唑-2-基)-4-(三氟甲基)苯甲酰胺 | 1048025-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(6-硝基苯并[d]噻唑-2-基)-4-(三氟甲基)苯甲酰胺
• 英文名称: N-(6-nitrobenzo[d]thiazol-2-yl)-4-(trifluoromethyl)benzamide
• 英文别名: N-(6-nitro-1,3-benzothiazol-2-yl)-4-(trifluoromethyl)benzamide
• CAS: 1048025-74-6
• 化学式: C₁₅H₈F₃N₃O₃S
• 分子量: 367.308
• InChiKey: LAHBEYJYTGNIGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(6-硝基苯并[d]噻唑-2-基)-4-(三氟甲基)苯甲酰胺 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 N-(6-(2-(cyclohexylthio)acetamido)benzo[d]thiazol-2-yl)-4-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Discovery of benzothiazole derivatives as novel non-sulfamide NEDD8 activating enzyme inhibitors by target-based virtual screening

  摘要：

  NEDD8 activating enzyme (NAE) plays a critical role in various cellular functions in cancers. In this study, a target-based virtual screening was applied to discover benzothiazoles to be potent non-covalent NAE inhibitors. Further two round optimizations concluded a preliminary structure-activity relationship (SAR) of their derivatives. Three compounds (6k, 7b, ZM223) exhibited antitumor activities in nanomolar range. ZM223 showed excellent anticancer activity against HCT116 colon cancer cells with an IC50 value of 100 nM. Mechanistically, compounds 6k, 7b, and ZM223 caused a dose-response decrease in the level of NEDD8 and an increase in the downstream UBC12 protein. This scaffold represents a promising lead for developing non-sulfamide NAE inhibitors. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.076
• 作为产物：
  描述：

  4-三氟甲基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 N-(6-硝基苯并[d]噻唑-2-基)-4-(三氟甲基)苯甲酰胺
  参考文献：
  名称：

  Synthesis and Antifungal Activity of Cuminic Acid Derivatives

  摘要：

  一系列苯甲酰胺衍生物（化合物1-29）是基于前导化合物枯酸合成得到的。化合物11的晶体结构通过单晶X射线衍射进行了表征。合成的化合物对七种植物病原真菌，即立枯丝核菌、玉蜀黍赤霉、玉蜀黍蠕孢、核盘菌、灰葡萄孢、双孢脐腐菌和葫芦脐腐菌，进行了抗真菌活性测定。初步结果表明，大多数化合物显示出显著的抗真菌活性。其中，化合物22表现出最强的活性，并且对H. maydis、S. sclerotiorum和B. cinerea的抗真菌活性优于多菌灵。

  DOI：

  10.1007/s10600-017-2212-z

文献信息

• USE OF BENZO-HETEROCYCLE DERIVATIVES FOR PREVENTING AND TREATING CANCER OR FOR INHIBITING CANCER METASTASIS
  申请人：SNU R&DB Foundation

  公开号：EP2497471A2

  公开（公告）日：2012-09-12

  This application relates to a novel benzo-heterocycle derivative and more particularly, it relates a composition for preventing and treating cancer or for inhibiting metastasis comprising benzo-heterocycle derivative or pharmaceutically acceptable salts thereof as an active ingredient. The present inventors confirmed that KRS has an effect on cancer metastasis by facilitating cancer (or tumor) cell migration through interaction with 67LR, and also found that a substance inhibiting the interaction between KRS and 67LR can prevent and treat cancer by inhibiting cancer cell metastasis. Accordingly, the composition of the present invention can inhibit cancer metastasis, and thus provide a novel means for prevention and treatment of cancer.

  本申请涉及一种新型苯并异环衍生物，更具体地说，它涉及一种用于预防和治疗癌症或抑制转移的组合物，其活性成分包括苯并异环衍生物或其药学上可接受的盐。本发明者证实，KRS 通过与 67LR 相互作用促进癌（或肿瘤）细胞迁移，从而对癌症转移产生影响，还发现抑制 KRS 与 67LR 相互作用的物质可以通过抑制癌细胞转移来预防和治疗癌症。因此，本发明的组合物可以抑制癌症转移，从而为癌症的预防和治疗提供了一种新的手段。
• Use of benzo-heterocycle derivatives for preventing and treating cancer or for inhibiting cancer metastasis
  申请人：Kim Sunghoon

  公开号：US10130611B2

  公开（公告）日：2018-11-20

  This application relates to a novel benzo-heterocycle derivative and more particularly, it relates a composition for preventing and treating cancer or for inhibiting metastasis comprising benzo-heterocycle derivative or pharmaceutically acceptable salts thereof as an active ingredient. The present inventors confirmed that KRS has an effect on cancer metastasis by facilitating cancer (or tumor) cell migration through interaction with 67LR, and also found that a substance inhibiting the interaction between KRS and 67LR can prevent and treat cancer by inhibiting cancer cell metastasis. Accordingly, the composition of the present invention can inhibit cancer metastasis, and thus provide a novel means for prevention and treatment of cancer.

  本申请涉及一种新型苯并异环衍生物，更具体地说，它涉及一种用于预防和治疗癌症或抑制转移的组合物，其活性成分包括苯并异环衍生物或其药学上可接受的盐。本发明者证实，KRS 通过与 67LR 相互作用促进癌（或肿瘤）细胞迁移，从而对癌症转移产生影响，还发现抑制 KRS 与 67LR 相互作用的物质可以通过抑制癌细胞转移来预防和治疗癌症。因此，本发明的组合物可以抑制癌症转移，从而为癌症的预防和治疗提供了一种新的手段。
• Synthesis of amide and urea derivatives of benzothiazole as Raf-1 inhibitor
  作者：Eun Young Song、Navneet Kaur、Mi-Young Park、Yinglan Jin、Kyeong Lee、Guncheol Kim、Ki Youn Lee、Jee Sun Yang、Jae Hong Shin、Ky-Youb Nam、Kyoung Tai No、Gyoonhee Han

  DOI：10.1016/j.ejmech.2007.10.008

  日期：2008.7

  A series of amide and urea derivatives of benzothiazole have been synthesized and evaluated for their antiproliferative profile in human SK-Hep-1 (liver), MDA-MB-231 (breast), and NUGC-3 (gastric) cell lines. Among them, compounds 1-2, 16-18, 23, and 25-26 had potent to moderate inhibitory activities. Further these compounds were investigated for their ability to inhibit Raf-1 activity. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Identification of novel benzothiazole derivatives as inhibitors of NEDDylation pathway to inhibit the progression of gastric cancer
  作者：Xuan Wang、Mei Zhao、Yuanyuan Chang、Sumeng Guan、Mengyu Li、Hua Yang、Moran Sun

  DOI：10.1016/j.bmcl.2024.129647

  日期：2024.3
• EP2497471B1
  申请人：——

  公开号：EP2497471B1

  公开（公告）日：2015-04-15