N-(4-(2-aminoethoxy)phenyl)methanesulfonamide | 685087-23-4

• 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-(4-(2-aminoethoxy)phenyl)methanesulfonamide
• 英文别名: N-[4-(2-aminoethoxy)phenyl]methanesulfonamide
• CAS: 685087-23-4
• 化学式: C₉H₁₄N₂O₃S
• mdl: MFCD10025161
• 分子量: 230.288
• InChiKey: SUFYLBOHWWHCCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 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：

  N-(4-(2-aminoethoxy)phenyl)methanesulfonamide 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 16.0h， 生成 N-(3,4-dichlorophenyl)-2-(2-(4-(methylsulfonamido)-phenoxy)ethylamino) acetamide hydrochloride
  参考文献：
  名称：

  Synthesis, structural activity-relationships, and biological evaluation of novel amide-based allosteric binding site antagonists in NR1A/NR2B N-methyl-d-aspartate receptors☆

  摘要：

  The synthesis and structure-activity relationship analysis of a novel class of amide-based biaryl NR2B-selective NMDA receptor antagonists are presented. Some of the studied compounds are potent, selective, non-competitive, and voltage-independent antagonists of NR2B-containing NMDA receptors. Like the founding member of this class of antagonists (ifenprodil), several interesting compounds of the series bind to the amino terminal domain of the NR2B subunit to inhibit function. Analogue potency is modulated by linker length, flexibility, and hydrogen bonding opportunities. However, unlike previously described classes of NR2B-selective NMDA antagonists that exhibit off-target activity at a variety of monoamine receptors, the compounds described herein show much diminished effects against the hERG channel and alpha(1)-adrenergic receptors. Selections of the compounds discussed have acceptable half-lives in vivo and are predicted to permeate the blood-brain barrier. These data together suggest that masking charged atoms on the linker region of NR2B-selective antagonists can decrease undesirable side effects while still maintaining on-target potency. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.05.085
• 作为产物：
  描述：

  2-(4-氨基苯氧基)乙基氨基甲酸叔丁酯 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 N-(4-(2-aminoethoxy)phenyl)methanesulfonamide
  参考文献：
  名称：

  Synthesis, structural activity-relationships, and biological evaluation of novel amide-based allosteric binding site antagonists in NR1A/NR2B N-methyl-d-aspartate receptors☆

  摘要：

  The synthesis and structure-activity relationship analysis of a novel class of amide-based biaryl NR2B-selective NMDA receptor antagonists are presented. Some of the studied compounds are potent, selective, non-competitive, and voltage-independent antagonists of NR2B-containing NMDA receptors. Like the founding member of this class of antagonists (ifenprodil), several interesting compounds of the series bind to the amino terminal domain of the NR2B subunit to inhibit function. Analogue potency is modulated by linker length, flexibility, and hydrogen bonding opportunities. However, unlike previously described classes of NR2B-selective NMDA antagonists that exhibit off-target activity at a variety of monoamine receptors, the compounds described herein show much diminished effects against the hERG channel and alpha(1)-adrenergic receptors. Selections of the compounds discussed have acceptable half-lives in vivo and are predicted to permeate the blood-brain barrier. These data together suggest that masking charged atoms on the linker region of NR2B-selective antagonists can decrease undesirable side effects while still maintaining on-target potency. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.05.085

文献信息

• [EN] CATALYTIC HYDROGENATION OF NITRILES TO PRODUCE CAPSAICINOID DERIVATIVES AND AMINE COMPOUNDS, AND METHODS FOR PURIFIYING AND OBTAINING THE POLYMORPHS THEREOF<br/>[FR] HYDROGENATION CATALYTIQUE DE NITRILES POUR PRODUIRE DES DERIVES CAPSAICINOIDES ET DES COMPOSES D'AMINES, ET PROCEDES DE PURIFICATION ET D'OBTENTION DE LEURS POLYMORPHES
  申请人：STIEFEL LABORATORIES

  公开号：WO2005068414A1

  公开（公告）日：2005-07-28

  Processes for preparing an amine compound by catalytically hydrogenating a precursor nitrile compound. In a particular aspect, the present hydrogenation process occurs in a dipolar organic solvent in the presence of a palladium/carbon catalyst and a strong anhydrous protic acid. In a further aspect, the preferred embodiment relates to a process for deprotecting a compound to produce an amine compound. In yet a further aspect, the preferred embodiment relates to amine products produced by the present processes. These amine products may be used for a variety of purposes.

  通过在存在钯/碳催化剂和强无水质子酸的情况下，在偶极有机溶剂中催化氢化前体腈化合物的过程。在一个特定方面，目前的氢化过程发生在一个偶极有机溶剂中，在钯/碳催化剂和强无水质子酸的存在下。在另一个方面，首选实施例涉及一种去保护化合物以产生胺化合物的过程。在另一个方面，首选实施例涉及通过目前的过程产生的胺产品。这些胺产品可以用于各种目的。
• Catalytic hydrogenation of nitriles to produce capsaicinoid derivatives and amine compounds, and methods for purifying and obtaining the polymorphs thereof
  申请人：Meckler Harold

  公开号：US20060047171A1

  公开（公告）日：2006-03-02

  Processes for preparing an amine compound by catalytically hydrogenating a precursor nitrile compound. In a particular aspect, the present hydrogenation process occurs in a dipolar organic solvent in the presence of a palladium/carbon catalyst and a strong anhydrous protic acid. In a further aspect, the preferred embodiment relates to a process for deprotecting a compound to produce an amine compound. In yet a further aspect, the preferred embodiment relates to amine products produced by the present processes. These amine products may be used for a variety of purposes.

  通过催化氢化前体腈化合物制备胺化合物的过程。在特定方面，本氢化过程发生在极性有机溶剂中，在钯/碳催化剂和强无水质子酸的存在下。在进一步方面，首选实施例涉及去保护化合物以产生胺化合物的过程。在另一个进一步方面，首选实施例涉及由本过程产生的胺产品。这些胺产品可用于各种用途。
• Discovery of a Potent and Highly Selective Dipeptidyl Peptidase IV and Carbonic Anhydrase Inhibitor as “Antidiabesity” Agents Based on Repurposing and Morphing of WB-4101
  作者：Angelica Artasensi、Andrea Angeli、Carmen Lammi、Carlotta Bollati、Silvia Gervasoni、Giovanna Baron、Rosanna Matucci、Claudiu T. Supuran、Giulio Vistoli、Laura Fumagalli

  DOI：10.1021/acs.jmedchem.2c01192

  日期：2022.10.27

  multidrug therapies and the relevance of dipeptidyl peptidase IV (DPP IV) and carbonic anhydrases (CAs II and V) in T2DM and in the weight loss, we report a new class of multitarget ligands targeting the mentioned enzymes. We started from the known α1-AR inhibitor WB-4101, which was progressively modified through a tailored morphing strategy to optimize the potency of DPP IV and CAs while losing the adrenergic

  2 型糖尿病 (T2DM) 患者的管理正在从以心脏为中心转变为以体重为中心，或者更好的是，以脂肪为中心的治疗。考虑到多药治疗的缺点以及二肽基肽酶 IV (DPP IV) 和碳酸酐酶 (CAs II 和 V) 在 T2DM 和体重减轻中的相关性，我们报告了一类新的多靶点配体靶向上述酶。我们从已知的 α 1 -AR 抑制剂 WB-4101 开始，通过定制的变形策略对其进行逐步修改，以优化 DPP IV 和 CA 的效力，同时失去肾上腺素能活性。获得的化合物12显示出令人满意的 DPP IV 抑制作用，具有良好的选择性 CA 特征（DPP IV IC 50：0.0490 μM；CA II Ki 0.2615 μM；CA VA K i 0.0941 μM；CA VB K i 0.0428 μM）。此外，其在 Caco-2 中的 DPP IV 抑制活性及其可接受的前 ADME/Tox 特征表明它是此类新型多靶点配体中的先导化合物。
• CATALYTIC HYDROGENATION OF NITRILES TO PRODUCE CAPSAICINOID DERIVATIVES AND AMINE COMPOUNDS, AND METHODS FOR PURIFIYING AND OBTAINING THE POLYMORPHS THEREOF
  申请人：STIEFEL LABORATORIES, INC.

  公开号：EP1697303A1

  公开（公告）日：2006-09-06
• EP1697303A4
  申请人：——

  公开号：EP1697303A4

  公开（公告）日：2007-07-04