N-(2-phenylethyl)-4-bromobenzenesulfonamide | 3609-88-9

• 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-(2-phenylethyl)-4-bromobenzenesulfonamide
• 英文别名: 4-bromo-benzenesulfonic acid phenethylamide；4-Brom-benzol-sulfonsaeure-(1)-β-phenaethylamid；4-Brom-benzolsulfonsaeure-phenaethylamid；4-bromo-N-(2-phenylethyl)benzenesulfonamide
• CAS: 3609-88-9
• 化学式: C₁₄H₁₄BrNO₂S
• mdl: MFCD01215105
• 分子量: 340.241
• InChiKey: VFOBSMYKUKRMRR-UHFFFAOYSA-N

物化性质

• 熔点：
  88.5-89.5 °C
• 沸点：
  459.4±55.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)
• 溶解度：
  3.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-phenylethyl)-4-bromobenzenesulfonamide 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-(2-phenylethyl)-N-[(4-bromophenyl)sulfonyl]glycine
  参考文献：
  名称：

  Progresses in the pursuit of aldose reductase inhibitors: The structure-based lead optimization step

  摘要：

  Aldose reductase (ALR2) is a crucial enzyme in the development of the major complications of diabetes mellitus. Very recently it has been demonstrated that the ARL2 inhibitor, fidarestat, significantly prevents inflammatory signals (TNF-alpha, LPS) that cause cancer (colon, breast, prostate and lung), metastasis, asthma, and other inflammatory diseases. Currently, fidarestat is in phase Ill clinical trial for diabetic neuropathy and was found to be safe. Thus the finding of novel, potent ARL2 inhibitors is today more than in the past in great demand as they can pave the way for a novel therapeutic approach for a number of diseases besides the diabetes. Herein, starting from the virtual screening-derived ALR2 inhibitor S12728 (1), a rational receptor-based lead optimization has been undertaken. The design and synthetic efforts here reported led to the discovery of several new compounds endowed with low micromolar/submicromolar activities. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.045
• 作为产物：
  描述：

  2-苯乙胺 、 4-溴苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到N-(2-phenylethyl)-4-bromobenzenesulfonamide
  参考文献：
  名称：

  Progresses in the pursuit of aldose reductase inhibitors: The structure-based lead optimization step

  摘要：

  Aldose reductase (ALR2) is a crucial enzyme in the development of the major complications of diabetes mellitus. Very recently it has been demonstrated that the ARL2 inhibitor, fidarestat, significantly prevents inflammatory signals (TNF-alpha, LPS) that cause cancer (colon, breast, prostate and lung), metastasis, asthma, and other inflammatory diseases. Currently, fidarestat is in phase Ill clinical trial for diabetic neuropathy and was found to be safe. Thus the finding of novel, potent ARL2 inhibitors is today more than in the past in great demand as they can pave the way for a novel therapeutic approach for a number of diseases besides the diabetes. Herein, starting from the virtual screening-derived ALR2 inhibitor S12728 (1), a rational receptor-based lead optimization has been undertaken. The design and synthetic efforts here reported led to the discovery of several new compounds endowed with low micromolar/submicromolar activities. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.045

文献信息

• Stereoselective Addition of Alkynes to Ketenimines: Copper/Amine Catalyzed Sulfonyl Azide–Alkyne Cycloaddition Reactions for the Synthesis of (<i>Z</i>)-1,3-Enynes
  作者：Rajagopal Pothikumar、Chandrasekaran Sivaraj、Kayambu Giridharan、Mahesh Kumar Ravva、Kayambu Namitharan

  DOI：10.1021/acs.orglett.2c01180

  日期：2022.6.24

  Herein, we report a copper/amine catalyzed stereoselective addition of alkynes to ketenimine intermediates generated in situ from the sulfonyl azide–alkyne cycloaddition cascade for the stereoselective synthesis of (Z)-1,3-enynes. Significantly, for the first-time, enamine intermediates generated in the copper-catalyzed sulfonyl azide–alkyne cycloaddition reactions have been successfully trapped and

  在此，我们报道了一种铜/胺催化的炔烃对由磺酰叠氮化物-炔烃环加成级联原位生成的酮亚胺中间体的立体选择性加成，用于立体选择性合成 ( Z )-1,3-烯炔。值得注意的是，铜催化的磺酰叠氮化物-炔烃环加成反应中产生的烯胺中间体首次被成功捕获并分离为产物。还进行了密度泛函理论计算，发现与观察到的实验立体选择性一致。
• Carothers; Jones, Journal of the American Chemical Society, 1925, vol. 47, p. 3056
  作者：Carothers、Jones

  DOI：——

  日期：——
• MODULATORS OF THE HISTAMINE H3-RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO
  申请人：Arena Pharmaceuticals, Inc.

  公开号：EP2035372A1

  公开（公告）日：2009-03-18
• [EN] MODULATORS OF THE HISTAMINE H3-RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO<br/>[FR] MODULATEURS DU RÉCEPTEUR H3 DE L'HISTAMINE UTILES DANS LE TRAITEMENT DE TROUBLES LIÉS AUDIT RÉCEPTEUR
  申请人：ARENA PHARM INC

  公开号：WO2008005338A1

  公开（公告）日：2008-01-10

  [EN] The present invention relates to certain biphenyl sulfonamide derivatives of Formula (Ia) and pharmaceutical compositions thereof that modulate the activity of the histamine H3-receptor. Compounds and pharmaceutical compositions thereof are directed to methods useful in the treatment of histamine H3-receptor associated disorders, such as, cognitive disorders, epilepsy, brain trauma, depression, obesity, disorders of sleep and wakefulness such as narcolepsy, hypersomnia, somnolence syndrome, jet lag, sleep apnea and the like, attention deficit hyperactivity disorder (ADHD), schizophrenia, allergies, allergic responses in the upper airway, allergic rhinitis, nasal congestion, dementia, Alzheimer's disease and the like.
  [FR] La présente invention concerne certains dérivés biphényl-sulfonamides selon la formule (Ia) et leurs compositions pharmaceutiques qui modulent l'activité du récepteur H3 de l'histamine. Les composés et les compositions pharmaceutiques les contenant sont destinés à des procédés utiles dans le traitement de troubles associés au récepteur H3 de l'histamine, tels que les troubles cognitifs, l'épilepsie, les traumatismes crâniens, la dépression, l'obésité, les troubles de la veille et du sommeil tels que la narcolepsie, l'hypersomnie, le syndrome de somnolence, le syndrome de décalage horaire, l'apnée du sommeil et similaires, l'hyperactivité avec déficit de l'attention (ADHD), la schizophrénie, les allergies, les réactions allergiques au niveau des voies respiratoires supérieures, la rhinite allergique, la congestion nasale, la démence, la maladie d'Alzheimer et similaires.
• Progresses in the pursuit of aldose reductase inhibitors: The structure-based lead optimization step
  作者：Anna Ramunno、Sandro Cosconati、Stefania Sartini、Vita Maglio、Sara Angiuoli、Valeria La Pietra、Salvatore Di Maro、Mariateresa Giustiniano、Concettina La Motta、Federico Da Settimo、Luciana Marinelli、Ettore Novellino

  DOI：10.1016/j.ejmech.2012.02.045

  日期：2012.5

  Aldose reductase (ALR2) is a crucial enzyme in the development of the major complications of diabetes mellitus. Very recently it has been demonstrated that the ARL2 inhibitor, fidarestat, significantly prevents inflammatory signals (TNF-alpha, LPS) that cause cancer (colon, breast, prostate and lung), metastasis, asthma, and other inflammatory diseases. Currently, fidarestat is in phase Ill clinical trial for diabetic neuropathy and was found to be safe. Thus the finding of novel, potent ARL2 inhibitors is today more than in the past in great demand as they can pave the way for a novel therapeutic approach for a number of diseases besides the diabetes. Herein, starting from the virtual screening-derived ALR2 inhibitor S12728 (1), a rational receptor-based lead optimization has been undertaken. The design and synthetic efforts here reported led to the discovery of several new compounds endowed with low micromolar/submicromolar activities. (C) 2012 Elsevier Masson SAS. All rights reserved.