3-bromo-N-(3-nitrophenyl)benzamide | 69754-49-0

• 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: 3-bromo-N-(3-nitrophenyl)benzamide
• 英文别名: Benzamide, N-(3-nitrophenyl)-3-bromo-
• CAS: 69754-49-0
• 化学式: C₁₃H₉BrN₂O₃
• 分子量: 321.13
• InChiKey: OPNCEGSGOXTCMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-N-(3-nitrophenyl)benzamide 在 tin(II) chloride dihdyrate 、 碳酸氢钠 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 3-bromo-N-(3-(4-methoxybenzamido)phenyl)benzamide
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship studies of novel sirtuin 2 (SIRT2) inhibitors with a benzamide skeleton

  摘要：

  Human sirtuin 2 (SIRT2) is an attractive target molecule for development of drugs to treat neurodegenerative diseases and cancer, because SIRT2 inhibitors have a protective effect against neurodegeneration and an anti-proliferative effect on cancer stem cells. We designed and synthesized a series of benzamide derivatives as SIRT2 inhibitor candidates. Among them, compound 17k showed the most potent SIRT2-inhibitory activity (IC50 = 0.60 mu M), with more than 150-fold selectivity over SIRT1 and SIRT3 isoforms (IC50 > 100 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.027
• 作为产物：
  描述：

  间溴苯甲酸 在 草酰氯 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 3-bromo-N-(3-nitrophenyl)benzamide
  参考文献：
  名称：

  新型分枝杆菌F-ATP合酶抑制剂的发现及其与二芳基喹啉联用的潜力。

  摘要：

  F 1 F O -ATP合酶是结核分枝杆菌生长和生存力所必需的并且是经过验证的临床目标。酶旋转γ亚基的分枝杆菌特异性环在酶复合物中ATP合成的偶联中起作用。我们报告发现了针对这种γ亚基环的新型抗分枝杆菌GaMF1的发现。生化和NMR研究表明，GaMF1通过与环结合来抑制ATP合酶活性。GaMF1具有杀菌作用，对多药耐药和苯达喹啉耐药菌株具有活性。在支架上的化学努力揭示了动态结构活性关系，并提供了具有纳摩尔浓度的类似物。GaMF1与苯达喹啉或新型二芳基喹啉类似物的结合在人胚胎干细胞报告基因分析中显示出增强作用，而不会引起基因毒性或表型变化。

  DOI：

  10.1002/anie.202002546

文献信息

• [EN] DI(HETERO)ARYLAMIDES AND SULFONAMIDES, METHODS FOR THEIR PREPARATION AND THERAPEUTIC USES THEREOF<br/>[FR] DI(HÉTÉRO)ARYLAMIDES ET SULFONAMIDES, PROCÉDÉS PERMETTANT LEUR PRÉPARATION ET UTILISATIONS THÉRAPEUTIQUES DE CEUX-CI
  申请人：MINORYX THERAPEUTICS S L

  公开号：WO2015014900A1

  公开（公告）日：2015-02-05

  The present invention refers to compounds of formula (I): as well as to a method for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or prevention of conditions associated with the alteration of the activity of β-galactosidase, specially galactosidase beta-1 or GLB1, including GM1 gangliosidoses and Morquio syndrome, type B.

  本发明涉及公式（I）的化合物，以及它们的制备方法，包含这些化合物的药物组合物，以及用于治疗和/或预防与β-半乳糖苷酶活性改变相关的疾病的用途，特别是β-半乳糖苷酶或GLB1的变异，包括GM1神经节苷脂病和莫奎奥综合征B型。
• N-Phenylbenzamide derivatives as alternative oxidase inhibitors: Synthesis, molecular properties, 1H-STD NMR, and QSAR
  作者：Paulo C.S. Costa、Mario R.O. Barsottini、Maria L.L. Vieira、Bárbara A. Pires、Joel S. Evangelista、Ana C.M. Zeri、Andrey F.Z. Nascimento、Jaqueline S. Silva、Marcelo F. Carazzolle、Gonçalo A.G. Pereira、Maurício L. Sforça、Paulo C.M.L. Miranda、Silvana A. Rocco

  DOI：10.1016/j.molstruc.2020.127903

  日期：2020.5

  DRX and 1H-NMR-STD. Single crystal X-ray diffraction showed intra- and intermolecular interactions of 3FH in solid-state and elucidated its 3D structural configuration. 1H-NMR-STD allowed us to derive protein-ligand interactions in a membrane-mimetic system and evidenced an outstanding interaction of 3FH with this enzyme. Results of both biological assays were used as input to Quantitative Structure-Activity

  摘要 在目前的工作中，制备了 117 种 N-苯基苯甲酰胺 (NPD)，并针对来自真菌病原体 Moniliophthora perniciosa 的重组 AOX 进行了评估。1H、13C NMR、FTIR 和质谱提供了 NPD 的结构信息。使用模型酵母毕赤酵母在两种不同的测定中测试文库化合物作为替代氧化酶抑制剂：细胞生长和耗氧量测定。活性最强的化合物 3FH 通过 DRX 和 1H-NMR-STD 进一步表征。单晶 X 射线衍射显示固态 3FH 的分子内和分子间相互作用，并阐明了其 3D 结构构型。1H-NMR-STD 使我们能够在膜模拟系统中推导出蛋白质-配体相互作用，并证明了 3FH 与这种酶的显着相互作用。
• DI(HETERO)ARYLAMIDES AND SULFONAMIDES, METHODS FOR THEIR PREPARATION AND THERAPEUTIC USES THEREOF
  申请人：MINORYX THERAPEUTICS S.L.

  公开号：US20160168132A1

  公开（公告）日：2016-06-16

  The present invention refers to compounds of formula (I): as well as to a method for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or prevention of conditions associated with the alteration of the activity of β-galactosidase, specially galactosidase beta-1 or GLB1, including GM1 gangliosidoses and Morquio syndrome, type B.

  本发明涉及公式（I）的化合物，以及它们的制备方法、包含它们的药物组合物，以及将其用于治疗和/或预防与β-半乳糖苷酶活性改变相关的疾病的用途，特别是β-半乳糖苷酶或GLB1，包括GM1神经节病和莫尔基奥综合症B型。
• Discovery of a Novel Mycobacterial F‐ATP Synthase Inhibitor and its Potency in Combination with Diarylquinolines
  作者：Adam Hotra、Priya Ragunathan、Pearly Shuyi Ng、Pattarakiat Seankongsuk、Amaravadhi Harikishore、Jickky Palmae Sarathy、Wuan‐Geok Saw、Umayal Lakshmanan、Patcharaporn Sae‐Lao、Nitin Pal Kalia、Joon Shin、Revathy Kalyanasundaram、Sivaraj Anbarasu、Krupakar Parthasarathy、Chaudhari Namrata Pradeep、Harshyaa Makhija、Peter Dröge、Anders Poulsen、Jocelyn Hui Ling Tan、Kevin Pethe、Thomas Dick、Roderick W. Bates、Gerhard Grüber

  DOI：10.1002/anie.202002546

  日期：2020.8.3

  that GaMF1 inhibits ATP synthase activity by binding to the loop. GaMF1 is bactericidal and is active against multidrug‐ as well as bedaquiline‐resistant strains. Chemistry efforts on the scaffold revealed a dynamic structure activity relationship and delivered analogues with nanomolar potencies. Combining GaMF1 with bedaquiline or novel diarylquinoline analogues showed potentiation without inducing genotoxicity

  F 1 F O -ATP合酶是结核分枝杆菌生长和生存力所必需的并且是经过验证的临床目标。酶旋转γ亚基的分枝杆菌特异性环在酶复合物中ATP合成的偶联中起作用。我们报告发现了针对这种γ亚基环的新型抗分枝杆菌GaMF1的发现。生化和NMR研究表明，GaMF1通过与环结合来抑制ATP合酶活性。GaMF1具有杀菌作用，对多药耐药和苯达喹啉耐药菌株具有活性。在支架上的化学努力揭示了动态结构活性关系，并提供了具有纳摩尔浓度的类似物。GaMF1与苯达喹啉或新型二芳基喹啉类似物的结合在人胚胎干细胞报告基因分析中显示出增强作用，而不会引起基因毒性或表型变化。
• Design, synthesis and structure–activity relationship studies of novel sirtuin 2 (SIRT2) inhibitors with a benzamide skeleton
  作者：Taki Sakai、Yotaro Matsumoto、Minoru Ishikawa、Kazuyuki Sugita、Yuichi Hashimoto、Nobuhiko Wakai、Akio Kitao、Era Morishita、Chikashi Toyoshima、Tomoatsu Hayashi、Tetsu Akiyama

  DOI：10.1016/j.bmc.2014.11.027

  日期：2015.1

  Human sirtuin 2 (SIRT2) is an attractive target molecule for development of drugs to treat neurodegenerative diseases and cancer, because SIRT2 inhibitors have a protective effect against neurodegeneration and an anti-proliferative effect on cancer stem cells. We designed and synthesized a series of benzamide derivatives as SIRT2 inhibitor candidates. Among them, compound 17k showed the most potent SIRT2-inhibitory activity (IC50 = 0.60 mu M), with more than 150-fold selectivity over SIRT1 and SIRT3 isoforms (IC50 > 100 mu M). (C) 2014 Elsevier Ltd. All rights reserved.