N-(3-aminophenyl)-4-methoxybenzenesulfonamide | 1152500-78-1

• 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: N-(3-aminophenyl)-4-methoxybenzenesulfonamide
• CAS: 1152500-78-1
• 化学式: C₁₃H₁₄N₂O₃S
• 分子量: 278.332
• InChiKey: LDSJOODXMKSEKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对羟基苯丙酸 、 N-(3-aminophenyl)-4-methoxybenzenesulfonamide 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.36h， 生成 3-(4-hydroxyphenyl)-N-(3-((4-methoxyphenyl)sulfonamido)phenyl)propanamide
  参考文献：
  名称：

  Design, synthesis and biological activity of N-(3-substituted-phenyl)benzenesulfonamides as selective and reversible LSD1 inhibitors

  摘要：

  Lysine specific demethylase 1 plays a crucial role in regulating histone methylation at residues K4 and K9 on histone H3 and over-expresses in a variety of cancers. Here we designed, synthesized and evaluated a series of N-(3-substituted-phenyl)benzenesulfonamides as reversible lysine specific demethylase 1 inhibitors. All the compounds exhibited lysine specific demethylase 1 inhibition with the half maximal inhibitory concentration (IC50) values between 7.5 and 68 mu M. Three most active compounds 2a, 2c and 2i displayed only modest effect on flavin adenine dinucleotide-dependent enzymes mono-amine oxidases A and B, and their reversibilities of lysine specific demethylase 1 inhibition were confirmed. Molecular docking was also carried out to predict the binding mode of 2a into the active site of lysine specific demethylase 1. Taken together, N-(3-substituted-phenyl)benzenesulfonamides including 2a represent a new class of selective and reversible lysine specific demethylase 1 inhibitors with pharmaceutical research.

  DOI：

  10.1007/s00044-016-1706-8
• 作为产物：
  描述：

  N-Boc-间苯二胺 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 N-(3-aminophenyl)-4-methoxybenzenesulfonamide
  参考文献：
  名称：

  [EN] CHEMICAL COMPOUNDS
  [FR] COMPOSÉS CHIMIQUES

  摘要：

  该发明涉及取代喹啉衍生物。具体而言，该发明涉及符合以下式（I）的化合物：其中R1、R2、R3；R4；和R5在此处被定义。该发明的化合物是乳酸脱氢酶A的抑制剂，可用于治疗癌症和与肿瘤细胞代谢相关的疾病，如乳腺癌、结肠癌、前列腺癌和肺癌等。因此，该发明进一步涉及包含该发明化合物的药物组合物。该发明还进一步涉及使用该发明化合物或包含该发明化合物的药物组合物来抑制乳酸脱氢酶A活性和治疗相关疾病的方法。

  公开号：

  WO2013096151A1

文献信息

• Synthesis and characterization of SiO2-supported ruthenium complexes containing aromatic sulfonamides: as catalysts for transfer hydrogenation of acetophenone
  作者：Serkan Dayan、Nilgün Özpozan Kalaycıoğlu、Osman Dayan、Namık Özdemir、Muharrem Dinçer、Orhan Büyükgüngör

  DOI：10.1039/c3dt32876g

  日期：——

  X-ray diffraction. 4–9 were used as catalysts for the transfer hydrogenation of acetophenone. 4–9 showed good catalytic activity and so the effects of the different groups were also examined. For the transfer hydrogenation of acetophenone, 7–9 had similar activity to 4–6. However, the longer lifetime of 7–9 makes them more advantageous than the non-supported catalysts (4–6) in terms of catalytic cycle

  通过下列反应成功地合成了3-氨基-N-芳基-苯磺酰胺（1-3）。间苯二胺以及各种苯磺酰氯。然后，由[RuCl 2（p- cymene）] 2和1-3的反应制备了一系列钌配合物（4–6）。最后，通过浸渍法制备了SiO 2负载的Ru（II）配合物（7-9）。合成的化合物和材料通过不同的方法进行了表征，例如NMR，FT-IR，TG / DTA，氮吸附-解吸（BET），SEM和EDX。同样，通过单晶X射线衍射确定4–6的固态结构。4–9被用作催化剂的转移加氢苯乙酮。4-9表现出良好的催化活性，因此还检查了不同组的作用。用于转移氢化苯乙酮，7–9具有与4–6类似的活动。但是，在催化循环方面，7–9的较长使用寿命使其比非负载型催化剂（4–6）更具优势。因此，研究了SiO 2作为催化剂的效果，结果表明，过量的氧化硅（IV）是氢化加氢的令人惊讶的活性催化剂。苯乙酮 在这些条件下。
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2013096151A1

  公开（公告）日：2013-06-27

  The invention is directed to substituted quinoline derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R1, R2, R3; R4; and R5 are defined herein. The compounds of the invention are inhibitors of lactate dehydrogenase A and can be useful in the treatment of cancer and diseases associated with tumor cell metabolism, such as cancer, and more specifically cancers of the breast, colon, prostate and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting lactate dehydrogenase A activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  该发明涉及取代喹啉衍生物。具体而言，该发明涉及符合以下式（I）的化合物：其中R1、R2、R3；R4；和R5在此处被定义。该发明的化合物是乳酸脱氢酶A的抑制剂，可用于治疗癌症和与肿瘤细胞代谢相关的疾病，如乳腺癌、结肠癌、前列腺癌和肺癌等。因此，该发明进一步涉及包含该发明化合物的药物组合物。该发明还进一步涉及使用该发明化合物或包含该发明化合物的药物组合物来抑制乳酸脱氢酶A活性和治疗相关疾病的方法。
• Design, synthesis and biological activity of N-(3-substituted-phenyl)benzenesulfonamides as selective and reversible LSD1 inhibitors
  作者：Xiaoming Zha、Liming Wu、Siyuan Xu、Fangxia Zou、Jiayue Xi、Tianfang Ma、Rongfeng Liu、Yu-Chih Liu、Dawei Deng、Yueqing Gu、Jinpei Zhou、Fei Lan

  DOI：10.1007/s00044-016-1706-8

  日期：2016.12

  Lysine specific demethylase 1 plays a crucial role in regulating histone methylation at residues K4 and K9 on histone H3 and over-expresses in a variety of cancers. Here we designed, synthesized and evaluated a series of N-(3-substituted-phenyl)benzenesulfonamides as reversible lysine specific demethylase 1 inhibitors. All the compounds exhibited lysine specific demethylase 1 inhibition with the half maximal inhibitory concentration (IC50) values between 7.5 and 68 mu M. Three most active compounds 2a, 2c and 2i displayed only modest effect on flavin adenine dinucleotide-dependent enzymes mono-amine oxidases A and B, and their reversibilities of lysine specific demethylase 1 inhibition were confirmed. Molecular docking was also carried out to predict the binding mode of 2a into the active site of lysine specific demethylase 1. Taken together, N-(3-substituted-phenyl)benzenesulfonamides including 2a represent a new class of selective and reversible lysine specific demethylase 1 inhibitors with pharmaceutical research.