N-(5-(N-benzylsulfamoyl)naphthalen-1-yl)acetamide | 648899-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(5-(N-benzylsulfamoyl)naphthalen-1-yl)acetamide
• 英文别名: N-[5-(Benzylsulfamoyl)naphthalen-1-yl]acetamide；N-[5-(benzylsulfamoyl)naphthalen-1-yl]acetamide
• CAS: 648899-28-9
• 化学式: C₁₉H₁₈N₂O₃S
• 分子量: 354.43
• InChiKey: IQBDHHCWSGKAQY-UHFFFAOYSA-N

物化性质

• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(5-(N-benzylsulfamoyl)naphthalen-1-yl)acetamide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 5-amino-N-benzylnaphthalene-1-sulfonamide
  参考文献：
  名称：

  Caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors

  摘要：

  HIV-1 integrase (IN) is an essential enzyme for retroviral replication and a rational target for the design of anti-AIDS drugs. In the present study, we have designed, synthesized and tested a series of caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors. Among these compounds, we found that HIV integrase inhibitory activities of compounds III-3 and III-4 were more potent than L-chicoric acid (IC50 = 11.8 mug/mL) and others were comparable to L-chicoric acid. Furthermore, the structure-activity relationships of these compounds were studied. The information gathered from this paper will be useful in the development and design of HIV-1 integrase inhibitors in the future. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00372-9
• 作为产物：
  描述：

  5-acetamidonaphthalene-1-sulfonic acid 在 五氯化磷 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 9.0h， 生成 N-(5-(N-benzylsulfamoyl)naphthalen-1-yl)acetamide
  参考文献：
  名称：

  5-氨基萘衍生物作为选择性非核苷核受体结合 SET 结构域蛋白 2 (NSD2) 抑制剂，用于治疗多发性骨髓瘤

  摘要：

  大约 20% 的多发性骨髓瘤 (MM) 是由染色体易位 t (4;14) 引起的，该易位导致核受体结合 SET 结构域蛋白 2 (NSD2) 组蛋白甲基转移酶的过度表达。NSD2 催化组蛋白 H3 (H3K36me2) 上赖氨酸 36 的甲基化，并与转录活性区域相关。使用高通量筛选 (HTS) 和生物学分析，设计并合成了一系列 5-氨基萘衍生物作为新型 NSD2 抑制剂。在所有制备的化合物中，9c显示出良好的 NSD2 抑制活性 (IC 50 = 2.7 μM) 和对含 SET 域和不含 SET 域的甲基转移酶的选择性。初步研究表明化合物9c的抑制机制通过显着抑制 H3K36me2 的甲基化。化合物9c通过诱导细胞周期停滞和细胞凋亡而特异性抑制人 B 细胞前体白血病细胞系 RS4:11 和人骨髓瘤细胞系 KMS11 的增殖，而细胞毒性很小。据报道，化合物9c的抗癌作用部分是通过完全抑制NSD2靶向基因的转录激活来实现的。当以

  DOI：

  10.1016/j.ejmech.2021.113592

文献信息

• Evaluation of fluorogenic aminonaphthalenesulfonamides and 6-hydrazinobenz[de]isoquinoline-1,3-diones for the detection of bacteria
  作者：Jia Lin Luo、Terry Jin、Linda Váradi、John D. Perry、David E. Hibbs、Paul W. Groundwater

  DOI：10.1016/j.dyepig.2015.09.031

  日期：2016.2

  New fluorogenic enzyme substrates were synthesized by the coupling of aminonaphthalenesulfonamides or 6-hydrazinobenz[de]isoquinoline-1,3-diones with beta-alanine. The 6-hydrazinobenz[de]isoquinoline-1,3-diones were also condensed with a range of aryl aldehydes to give the corresponding hydrazones. The photophysical properties of the synthesized amines and hydrazines and their amide, hydrazide and hydrazone derivatives, were examined and they were also incorporated into Columbia agar in order to determine their potential for the detection of pathogenic bacteria. (C) 2015 Elsevier Ltd. All rights reserved.
• 5-Aminonaphthalene derivatives as selective nonnucleoside nuclear receptor binding SET domain-protein 2 (NSD2) inhibitors for the treatment of multiple myeloma
  作者：Shuni Wang、Hong Yang、Mingbo Su、Fulin Lian、Zhanqing Cong、Rongrui Wei、Yubo Zhou、Xingjun Li、Xingling Zheng、Chunpu Li、Xuhong Fu、Xu Han、Qiongyu Shi、Cong Li、Naixia Zhang、Meiyu Geng、Hong Liu、Jia Li、Xun Huang、Jiang Wang

  DOI：10.1016/j.ejmech.2021.113592

  日期：2021.10

  leads to the overexpression of the nuclear receptor binding SET domain-protein 2 (NSD2) histone methyltransferase. NSD2 catalyzes the methylation of lysine 36 on histone H3 (H3K36me2) and is associated with transcriptionally active regions. Using high-throughput screening (HTS) with biological analyses, a series of 5-aminonaphthalene derivatives were designed and synthesized as novel NSD2 inhibitors

  大约 20% 的多发性骨髓瘤 (MM) 是由染色体易位 t (4;14) 引起的，该易位导致核受体结合 SET 结构域蛋白 2 (NSD2) 组蛋白甲基转移酶的过度表达。NSD2 催化组蛋白 H3 (H3K36me2) 上赖氨酸 36 的甲基化，并与转录活性区域相关。使用高通量筛选 (HTS) 和生物学分析，设计并合成了一系列 5-氨基萘衍生物作为新型 NSD2 抑制剂。在所有制备的化合物中，9c显示出良好的 NSD2 抑制活性 (IC 50 = 2.7 μM) 和对含 SET 域和不含 SET 域的甲基转移酶的选择性。初步研究表明化合物9c的抑制机制通过显着抑制 H3K36me2 的甲基化。化合物9c通过诱导细胞周期停滞和细胞凋亡而特异性抑制人 B 细胞前体白血病细胞系 RS4:11 和人骨髓瘤细胞系 KMS11 的增殖，而细胞毒性很小。据报道，化合物9c的抗癌作用部分是通过完全抑制NSD2靶向基因的转录激活来实现的。当以
• Caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors
  作者：Yu-Wen Xu、Gui-Sen Zhao、Cha-Gyun Shin、Heng-Chang Zang、Chong-Kyo Lee、Yong Sup Lee

  DOI：10.1016/s0968-0896(03)00372-9

  日期：2003.8

  HIV-1 integrase (IN) is an essential enzyme for retroviral replication and a rational target for the design of anti-AIDS drugs. In the present study, we have designed, synthesized and tested a series of caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors. Among these compounds, we found that HIV integrase inhibitory activities of compounds III-3 and III-4 were more potent than L-chicoric acid (IC50 = 11.8 mug/mL) and others were comparable to L-chicoric acid. Furthermore, the structure-activity relationships of these compounds were studied. The information gathered from this paper will be useful in the development and design of HIV-1 integrase inhibitors in the future. (C) 2003 Elsevier Ltd. All rights reserved.