4-amino-N-(4-chlorobenzyl)benzenesulfonamide | 928001-88-1

• 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: 4-amino-N-(4-chlorobenzyl)benzenesulfonamide
• 英文别名: 4-amino-N-[(4-chlorophenyl)methyl]benzene-1-sulfonamide；4-amino-N-[(4-chlorophenyl)methyl]benzenesulfonamide
• CAS: 928001-88-1
• 化学式: C₁₃H₁₃ClN₂O₂S
• mdl: MFCD08164713
• 分子量: 296.777
• InChiKey: SWVGTNYFDHQAOW-UHFFFAOYSA-N

物化性质

• 熔点：
  122.9-123.6 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  495.5±55.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-N-(4-chlorobenzyl)benzenesulfonamide 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到N-(4-(N-(4-chlorobenzyl)sulfamoyl)phenyl)acrylamide
  参考文献：
  名称：

  发现次磺酰胺作为IDO1抑制剂在体内具有强大的抗肿瘤作用。

  摘要：

  吲哚胺2,3-二加氧酶1（IDO1）是色氨酸代谢的犬尿氨酸途径中的关键限速酶，在肿瘤免疫逃逸中起重要作用。本文中，合成了多种仲磺酰胺，并在基于HeLa细胞的IDO1 /犬尿氨酸测定中进行了评估，从而鉴定了新的IDO1抑制剂。其中，化合物5d，5l和8g显示出最强的抑制作用，并且与命中的化合物BS-1相比具有显着改善的活性。体外结果表明，这些化合物可恢复T细胞增殖并抑制幼稚CD4 + T细胞分化为高度免疫抑制的FoxP3 +调节性T（Treg）细胞，而不会影响HeLa细胞的活力和IDO1蛋白的表达。重要的，药效学分析表明，化合物5d在携带免疫功能小鼠的CT26和B16F1肿瘤中均具有有效的抗肿瘤作用，而在免疫缺陷小鼠中则没有。从功能上讲，后续实验表明化合物5d可有效抑制肿瘤细胞增殖，诱导细胞凋亡，上调IFN-γ和颗粒酶B的表达并抑制FoxP3 + Treg细胞分化，从而激活免疫系统。因此，化

  DOI：

  10.1080/14756366.2020.1765165
• 作为产物：
  描述：

  N-(4-(N-(4-chlorobenzyl)sulfamoyl)phenyl)acetamide 在 盐酸 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以95%的产率得到4-amino-N-(4-chlorobenzyl)benzenesulfonamide
  参考文献：
  名称：

  发现次磺酰胺作为IDO1抑制剂在体内具有强大的抗肿瘤作用。

  摘要：

  吲哚胺2,3-二加氧酶1（IDO1）是色氨酸代谢的犬尿氨酸途径中的关键限速酶，在肿瘤免疫逃逸中起重要作用。本文中，合成了多种仲磺酰胺，并在基于HeLa细胞的IDO1 /犬尿氨酸测定中进行了评估，从而鉴定了新的IDO1抑制剂。其中，化合物5d，5l和8g显示出最强的抑制作用，并且与命中的化合物BS-1相比具有显着改善的活性。体外结果表明，这些化合物可恢复T细胞增殖并抑制幼稚CD4 + T细胞分化为高度免疫抑制的FoxP3 +调节性T（Treg）细胞，而不会影响HeLa细胞的活力和IDO1蛋白的表达。重要的，药效学分析表明，化合物5d在携带免疫功能小鼠的CT26和B16F1肿瘤中均具有有效的抗肿瘤作用，而在免疫缺陷小鼠中则没有。从功能上讲，后续实验表明化合物5d可有效抑制肿瘤细胞增殖，诱导细胞凋亡，上调IFN-γ和颗粒酶B的表达并抑制FoxP3 + Treg细胞分化，从而激活免疫系统。因此，化

  DOI：

  10.1080/14756366.2020.1765165

文献信息

• Nitrogen-containing polyhydroxylated aromatics as HIV-1 integrase inhibitors: synthesis, structure-activity relationship analysis, and biological activity
  作者：Shenghui Yu、Linna Zhang、Shifeng Yan、Peng Wang、Tino Sanchez、Frauke Christ、Zeger Debyser、Nouri Neamati、Guisen Zhao

  DOI：10.3109/14756366.2011.604851

  日期：2012.10.1

  polyhydroxylated aromatics based on caffeic acid phenethyl ester were designed and synthesized as HIV-1 integrase (IN) inhibitors. Most of these compounds inhibited IN catalytic activities in low micromolar range. Among these new analogues, compounds 9e and 9f were the most potent IN inhibitors with IC(50) value of 0.7 μM against strand transfer reaction. Their key structure-activity relationships were also

  设计并合成了四种基于咖啡酸苯乙酯的四十五种含氮多羟基化芳烃作为HIV-1整合酶（IN）抑制剂。这些化合物大多数在低微摩尔范围内抑制IN催化活性。在这些新的类似物中，化合物9e和9f是最有效的IN抑制剂，针对链转移反应的IC（50）值为0.7μM。还讨论了它们的关键结构-活性关系。
• 一种合成氨基-(N-烷基)苯磺酰胺的方法
  申请人：南京理工大学

  公开号：CN106146358B

  公开（公告）日：2018-01-23

  本发明公开了一种合成氨基‑(N‑烷基)苯磺酰胺的方法。包括如下步骤：在反应容器中，加入氨基苯磺酰胺、铱络合物催化剂、碱、化合物醇、溶剂叔戊醇，反应混合物在120‑150 oC下反应数小时后，冷却到室温，旋转蒸发除去溶剂，然后通过柱分离，得到目标化合物。本发明使用商品化的氨基苯磺酰胺和近于无毒的化合物醇为起始原料；反应只生成水为副产物，无环境危害；反应原子经济性高。
• Design and synthesis of novel nitrogen-containing polyhydroxylated aromatics as HIV-1 integrase inhibitors from caffeic acid phenethyl ester
  作者：Peng Wang、Chuan Liu、Tino Sanches、Yuan Zhong、Bo Liu、Junlong Xiong、Nouri Neamati、Guisen Zhao

  DOI：10.1016/j.bmcl.2009.06.100

  日期：2009.8

  A series of nitrogen-containing polyhydroxylated aromatics from caffeic acid phenethyl ester were designed and synthesized as HIV-1 integrase inhibitors. Most of these compounds exhibited potent inhibitory activities at micromolar concentrations against HIV-1 integrase in the 3'-end processing and the strand transfer. Their key structure-activity relationship was also discussed. (C) 2009 Elsevier Ltd. All rights reserved.
• Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1
  作者：Elisabeth-Maria Bissinger、Ralf Heinke、Astrid Spannhoff、Adrien Eberlin、Eric Metzger、Vincent Cura、Pierre Hassenboehler、Jean Cavarelli、Roland Schüle、Mark T. Bedford、Wolfgang Sippl、Manfred Jung

  DOI：10.1016/j.bmc.2011.02.032

  日期：2011.6

  Arginine methylation is an epigenetic modification that receives increasing interest as it plays an important role in several diseases. This is especially true for hormone-dependent cancer, seeing that histone methylation by arginine methyltransferase I (PRMT1) is involved in the activation of sexual hormone receptors. Therefore, PRMT inhibitors are potential drugs and interesting tools for cell biology. A dapsone derivative called allantodapsone previously identified by our group served as a lead structure for inhibitor synthesis. Acylated derivatives of p-aminobenzenesulfonamides and the antilepra drug dapsone were identified as new inhibitors of PRMT1 by in vitro testing. The bis-chloroacetyl amide of dapsone selectively inhibited human PRMT1 in the low micromolar region and was selective for PRMT1 as compared to the arginine methyltransferase CARM1 and the lysine methyltransferase Set7/9. It showed anticancer activity on MCF7a and LNCaP cells and blocked androgen dependent transcription specifically in a reporter gene system. Likewise, a transcriptional block was also demonstrated in LNCaP cells using quantitative RT-PCR on the mRNA of androgen dependent genes. (C) 2011 Elsevier Ltd. All rights reserved.
• Effective Recognition of Different Types of Amino Groups: From Aminobenzenesulfonamides to Amino-(<i>N</i>-alkyl)benzenesulfonamides via Iridium-Catalyzed <i>N</i>-Alkylation with Alcohols
  作者：Lei Lu、Juan Ma、Panpan Qu、Feng Li

  DOI：10.1021/acs.orglett.5b00824

  日期：2015.5.15

  A simple, highly efficient, and general strategy for the direct synthesis of amino-(N-alkyl)benzenesulfonamides has been accomplished via direct N-alkylation of aminobenzenesulfonamides bearing both different types of amino groups with alcohols as alkylating agents. Notably, this research exhibited the potential for the recognition of different types of amino groups in the N-alkylation of complex molecules with alcohols, facilitating the progress of the transition-metal-catalyzed "hydrogen autotransfer (or hydrogen-borrowing) process.