3-(丁基氨磺酰基)苯甲酸 | 7385-16-2

• 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: 3-(丁基氨磺酰基)苯甲酸
• 英文名称: m-butylaminosulfonyl-benzoic acid
• 英文别名: 3-Carboxy-benzolsulfonsaeure-；3-(Butylsulfamoyl)benzoic acid
• CAS: 7385-16-2
• 化学式: C₁₁H₁₅NO₄S
• mdl: MFCD09041593
• 分子量: 257.31
• InChiKey: QQZLEFLDGXHDDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  3-(丁基氨磺酰基)苯甲酸 在 硫酸 、 肼 作用下， 以 甲醇 为溶剂， 反应 12.5h， 生成 N-butyl-3-(hydrazinecarbonyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and biological evaluation of novel (E)-N′-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides as potent LSD1 inhibitors

  摘要：

  Lysine specific demethylase 1 (LSD1) plays an important role in regulating histone lysine methylation at residues K4 and K9 on histone H3 and is recognized as an attractive therapeutic target in multiple malignancies. In this study, a series of novel (E)-N'-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides were synthesized and biologically evaluated for their potential LSD1 inhibitory effect. Among them, compounds 5a and 5n showed the most potent LSD1 inhibitory activity with IC50 values of 1.4 and 1.7 nM, respectively, which were about 10 times more potent compared with (E)-N-(1-(5-chloro-2-hydroxyphenyl) ethylidene)-3-(morpholinosulf-only) benzohydrazide (J. Med. Chem. 2013, 56, 9496-9508; as reference compound). Compounds 5a and 5n also exhibited marked anti-proliferation activities against cancer cell lines that highly expressed LSD1. These results suggest that these optimized compounds might be served as promising LSD1 inhibitors against cancer, which merit further study. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2015.06.054
• 作为产物：
  描述：

  苯甲酸 在 氯磺酸 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 3-(丁基氨磺酰基)苯甲酸
  参考文献：
  名称：

  苯乙酸和三氟甲基苯基取代的苯甲酰胺衍生物作为潜在的PPARδ激动剂的合成，对接和评价

  摘要：

  背景：过氧化物酶体增殖物激活受体（PPAR）δ是一种类固醇，属于类固醇或核激素受体超家族。PPARδ的活化导致脂肪代谢，而不是人体能量代谢所需的葡萄糖。PPARδ代表用于治疗代谢综合征（MS）的新兴药理学靶标。已经合成了许多选择性和有效的PPARδ激动剂，在治疗与MS相关的各种疾病（包括2型糖尿病和炎症）方面具有潜在作用。 目的：本工作旨在合成和评估一些新型的苯乙酸和三氟甲基苯基取代的苯甲酰胺衍生物作为潜在的PPARδ激动剂的抗糖尿病和抗炎活性。 方法：这项工作涉及合成新的氨磺酰基苯甲酰胺衍生物，并通过分子对接研究对其进行评估，以确定在PPARδ蛋白结合位点最合适的构象的结合相互作用。根据计算机研究的结果，测试了所选化合物在动物模型中的抗糖尿病和抗炎活性。 结果：在合成的分子中，化合物7具有较高的抗糖尿病活性，化合物19具有较高的抗炎活性。发现实验结果与计算机模拟结果一致。如Lipinsk

  DOI：

  10.2174/1570180814666170327164443

文献信息

• Synthesis, Docking and Antidiabetic Activity of Some Newer Benzamide Derivatives as Potential Glucokinase Activators
  作者：Rohit Singh、Viney Lather、Deepti Pandita、Vikramjeet Judge、Karthikeyan Arumugam、Ajmer Grewal

  DOI：10.2174/1570180813666160819125342

  日期：2017.4.6

  Glucokinase activators (GKAs) are the new class of candidate drugs which act on glucokinase (GK) enzyme and show their hypoglycaemic activity. Objective: The present work was planned to synthesize and evaluate the antidiabetic activity of a series of newer benzamide derivatives as potential GKAs. Method: This work involved synthesis of newer benzamide derivatives from benzoic acid and their evaluation

  背景：葡萄糖激酶激活剂（GKA）是新型的候选药物，可作用于葡萄糖激酶（GK）酶并显示其降血糖活性。 目的：目前的工作计划是合成和评估一系列新型苯甲酰胺衍生物作为潜在的GKA的抗糖尿病活性。 方法：这项工作涉及从苯甲酸合成新的苯甲酰胺衍生物，并通过对接研究进行评估，以确定在GK酶结合位点最合适的构象的结合相互作用。根据对接研究的结果，测试所选分子在动物模型中的抗糖尿病活性。 结果：在合成的分子中，酰胺氮上具有苯基取代的噻唑部分的化合物14和20在体内表现出最高的活性。发现体内抗糖尿病研究的结果与对接研究的结果一致。 结论：因此，这些新合成的分子可以作为开发新型，安全，有效和口服生物利用型GKAs作为治疗糖尿病疾病的治疗剂的初步方法。
• Synthesis, Docking and Evaluation of Phenylacetic Acid and Trifluoro-methylphenyl Substituted Benzamide Derivatives as Potential PPARδ Agonists
  作者：Ajmer Singh Grewal、Viney Lather、Deepti Pandita、Garima Bhayana

  DOI：10.2174/1570180814666170327164443

  日期：2017.10.3

  PPARδ agonists had been synthesized with a potential role in the treatment of various disorders associated with MS including type 2 diabetes and inflammation. Objective: The present work was designed to synthesize and evaluate the antidiabetic and anti-inflammatory activity of some newer phenylacetic acid and trifluoromethylphenyl substituted benzamide derivatives as potential PPARδ agonists. Methods:

  背景：过氧化物酶体增殖物激活受体（PPAR）δ是一种类固醇，属于类固醇或核激素受体超家族。PPARδ的活化导致脂肪代谢，而不是人体能量代谢所需的葡萄糖。PPARδ代表用于治疗代谢综合征（MS）的新兴药理学靶标。已经合成了许多选择性和有效的PPARδ激动剂，在治疗与MS相关的各种疾病（包括2型糖尿病和炎症）方面具有潜在作用。 目的：本工作旨在合成和评估一些新型的苯乙酸和三氟甲基苯基取代的苯甲酰胺衍生物作为潜在的PPARδ激动剂的抗糖尿病和抗炎活性。 方法：这项工作涉及合成新的氨磺酰基苯甲酰胺衍生物，并通过分子对接研究对其进行评估，以确定在PPARδ蛋白结合位点最合适的构象的结合相互作用。根据计算机研究的结果，测试了所选化合物在动物模型中的抗糖尿病和抗炎活性。 结果：在合成的分子中，化合物7具有较高的抗糖尿病活性，化合物19具有较高的抗炎活性。发现实验结果与计算机模拟结果一致。如Lipinsk
• Urea-tetrahydrobenzoxanthene receptors for carboxylic acids
  作者：Ana I Oliva、Luis Simón、Francisco M Muñiz、Francisca Sanz、Joaquı́n R Morán

  DOI：10.1016/j.tet.2004.03.015

  日期：2004.4

  Hydrogen-bonding receptors for carboxylic acids have been prepared based on a cis tetrahydrobenzoxanthene skeleton. X-ray diffraction study of one of these compounds revealed that the cleft is suitable for establishing strong linear hydrogen bonds with the oxygen of a water molecule. Complexes that set only three H-bonds with the guests showed no chiral recognition with amino acid derivatives. However, suitable

  已经基于顺式四氢苯并氧杂蒽骨架制备了羧酸的氢键受体。这些化合物之一的X射线衍射研究表明，该裂口适合与水分子的氧建立牢固的线性氢键。与客体仅设置三个H键的复合物没有显示出与氨基酸衍生物的手性识别。然而，受体的适当官能化提供了与某些氨基酸衍生物的第四H键，在这种情况下导致显着的对映选择性络合。
• Synthesis and biological evaluation of novel (E)-N′-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides as potent LSD1 inhibitors
  作者：Yang Zhou、Yan Li、Wen-Jing Wang、Pu Xiang、Xin-Mei Luo、Li Yang、Sheng-Yong Yang、Ying-Lan Zhao

  DOI：10.1016/j.bmcl.2015.06.054

  日期：2016.9

  Lysine specific demethylase 1 (LSD1) plays an important role in regulating histone lysine methylation at residues K4 and K9 on histone H3 and is recognized as an attractive therapeutic target in multiple malignancies. In this study, a series of novel (E)-N'-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides were synthesized and biologically evaluated for their potential LSD1 inhibitory effect. Among them, compounds 5a and 5n showed the most potent LSD1 inhibitory activity with IC50 values of 1.4 and 1.7 nM, respectively, which were about 10 times more potent compared with (E)-N-(1-(5-chloro-2-hydroxyphenyl) ethylidene)-3-(morpholinosulf-only) benzohydrazide (J. Med. Chem. 2013, 56, 9496-9508; as reference compound). Compounds 5a and 5n also exhibited marked anti-proliferation activities against cancer cell lines that highly expressed LSD1. These results suggest that these optimized compounds might be served as promising LSD1 inhibitors against cancer, which merit further study. (C) 2016 Published by Elsevier Ltd.
• Design and synthesis of newer N-benzimidazol-2yl benzamide analogues as allosteric activators of human glucokinase
  作者：Sukhbir Singh、Sandeep Arora、Ervon Dhalio、Neelam Sharma、Kunal Arora、Ajmer Singh Grewal

  DOI：10.1007/s00044-020-02697-z

  日期：2021.3