N-(4-(((4-chlorophenyl)sulfonamido)methyl)benzyl)-2-methylbenzamide

• 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-(((4-chlorophenyl)sulfonamido)methyl)benzyl)-2-methylbenzamide
• 英文别名: N-[[4-[[(4-chlorophenyl)sulfonylamino]methyl]phenyl]methyl]-2-methylbenzamide
• 化学式: C₂₂H₂₁ClN₂O₃S
• 分子量: 428.939
• InChiKey: AECCHBREIDXZPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(N-Boc-氨基甲基)-4-(氨基甲基)苯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 N-(4-(((4-chlorophenyl)sulfonamido)methyl)benzyl)-2-methylbenzamide
  参考文献：
  名称：

  Amide-sulfamide modulators as effective anti-tumor metastatic agents targeting CXCR4/CXCL12 axis

  摘要：

  Breast cancer is the most frequently diagnosed malignancy and the second common cause of death in women worldwide. High mortality in breast cancer is frequently associated with metastatic progression rather than the primary tumor itself. It has been recently identified that the CXCR4/CXCL12 axis plays a pivotal role in breast cancer metastasis, especially in directing metastatic cancer cells to CXCL12-riched organs and tissues. Herein, taking the amide-sulfamide as the lead structure, the second-round structural modifications to the sulfamide structure were performed to obtain more active CXCR4 modulators against tumor metastasis. Both in vivo and in vitro experiments illustrated that compound he possessed potent CXCR4 binding affinity, excellent anti-metastatic and anti-angiogenetic activity against breast cancer. More importantly, in a mouse breast cancer lung metastasis model, compound Me exerted a significant inhibitory effect on breast cancer metastasis. Taken together, all these positive results demonstrated that developing of CXCR4 modulators is a promising strategy to mediate breast cancer metastasis. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111823

文献信息

• Amide-sulfamide modulators as effective anti-tumor metastatic agents targeting CXCR4/CXCL12 axis
  作者：Rui Wu、Wenyan Yu、Chuansheng Yao、Zhongxing Liang、Younghyoun Yoon、Yuanyuan Xie、Hyunsuk Shim、Renren Bai

  DOI：10.1016/j.ejmech.2019.111823

  日期：2020.1

  Breast cancer is the most frequently diagnosed malignancy and the second common cause of death in women worldwide. High mortality in breast cancer is frequently associated with metastatic progression rather than the primary tumor itself. It has been recently identified that the CXCR4/CXCL12 axis plays a pivotal role in breast cancer metastasis, especially in directing metastatic cancer cells to CXCL12-riched organs and tissues. Herein, taking the amide-sulfamide as the lead structure, the second-round structural modifications to the sulfamide structure were performed to obtain more active CXCR4 modulators against tumor metastasis. Both in vivo and in vitro experiments illustrated that compound he possessed potent CXCR4 binding affinity, excellent anti-metastatic and anti-angiogenetic activity against breast cancer. More importantly, in a mouse breast cancer lung metastasis model, compound Me exerted a significant inhibitory effect on breast cancer metastasis. Taken together, all these positive results demonstrated that developing of CXCR4 modulators is a promising strategy to mediate breast cancer metastasis. (C) 2019 Elsevier Masson SAS. All rights reserved.