3-乙炔基苯磺酰胺 | 1310456-99-5

• 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-乙炔基苯磺酰胺
• 英文名称: 3-ethynylbenzenesulfonamide
• CAS: 1310456-99-5
• 化学式: C₈H₇NO₂S
• 分子量: 181.215
• InChiKey: WGEWFHNQCHZZMF-UHFFFAOYSA-N

物化性质

• 沸点：
  367.4±44.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-乙炔基苯磺酰胺 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以80%的产率得到4-[3-(aminosulfonyl)phenyl]-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  A Prodrug Approach Toward Cancer-Related Carbonic Anhydrase Inhibition

  摘要：

  The selective inhibition of cancer-associated human carbonic anhydrase (CA) enzymes, specifically CA IX and XII, has been validated as a mechanistically novel approach toward personalized cancer management. Herein we report the design and synthesis of a panel of 24 novel glycoconjugate primary sulfonamides that bind to the extracellular catalytic domain of CA IX and XII. These compounds were synthesized from variably acylated glycopyranosyl azides and either 3- or 4-ethynyl benzene sulfonamide using Cu(I)-catalyzed azide alkyne cycloaddition (CuAAC). The CA enzyme inhibition profile for all compounds was determined, while in vitro metabolic stability, plasma stability, and plasma protein binding for a representative set of compounds was measured. Our findings demonstrate the influence of the differing acyl groups on these key biopharmaceutical properties, confirming that acyl group protected carbohydrate-based sulfonamides have potential as prodrugs for selectively targeting the extracellular cancer-associated CA enzymes.

  DOI：

  10.1021/jm401163e
• 作为产物：
  描述：

  3-[(三甲基甲硅烷基)乙炔基]苯磺酰胺 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到3-乙炔基苯磺酰胺
  参考文献：
  名称：

  碳酸酐酶II中的立体和区域选择性叠氮化物/炔烃环加成反应，通过束缚，通过晶体学和质谱法进行监测

  摘要：

  制备了碳酸酐酶II突变体His64Cys，并将其用于拴系的炔烃/叠氮化物环加成反应。叠氮化物组分可以通过二硫键连接到酶的表面，而炔烃组分则通过磺酰胺锚与酶的原始催化中心的锌离子可逆地配位。通过结晶学表征反应物在结合位点和形成的三唑产物的初始取向。反应进程可通过HPLC-MS分析进行监控。

  DOI：

  10.1002/chem.201002437

文献信息

• Cyclic Secondary Sulfonamides: Unusually Good Inhibitors of Cancer-Related Carbonic Anhydrase Enzymes
  作者：Janina Moeker、Thomas S. Peat、Laurent F. Bornaghi、Daniela Vullo、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm500255y

  日期：2014.4.24

  IX selective ligands is imperative for the development of these agents. Primary sulfonamides are broad specificity inhibitors of CA enzymes, while secondary sulfonamides are generally poor CA inhibitors. However, saccharin, a cyclic secondary sulfonamide, has unusually good inhibition of CA IX (Ki = 103 nM). In this study, we demonstrate that the affinity and selectivity of saccharin for CA IX can

  碳酸酐酶IX（CA IX）是低氧癌症治疗的目标，而CA IX选择性配体的发现对于这些药物的开发至关重要。一级磺酰胺是CA酶的广泛特异性抑制剂，而二级磺酰胺通常是较差的CA抑制剂。但是，糖精（一种环状仲磺酰胺）对CA IX的抑制作用非常好（K i = 103 nM）。在这项研究中，我们证明了糖精对CA IX的亲和力和选择性在与疏水或亲水取代基连接时可以得到进一步调节。亲水性糖缀合物衍生物（12）对CA IX的抑制作用得到改善（K i = 49.5 nM），对主要脱靶CAs的抑制作用非常差（K i > 50 000 nM）与糖精相比。对于CA IX的脱靶CA选择性> 1000倍，对于经典的伯磺酰胺CA抑制剂来说是前所未有的。我们的研究强调了环状仲磺酰胺被用于发现有效的，对癌症有选择性的CA抑制剂的潜力。
• HETEROARYL-PYRAZOLE DERIVATIVE
  申请人：Nakamura Toshio

  公开号：US20130137865A1

  公开（公告）日：2013-05-30

  A compound represented by formula [I] and a pharmaceutically accepted salt of said compound are a novel compound and a pharmaceutically accepted salt thereof which exert antagonistic activity against group II metabotropic glutamate (mGlu) receptors, and are effective as a novel preventive or therapeutic agent for disorders such as mood disorders (depressive disorder, bipolar disorder, etc.), anxiety disorders (generalized anxiety disorder, panic disorder, obsessive-compulsive disorder, social anxiety disorder, posttraumatic stress disorder, a specific phobic disorder, acute stress disorder, etc.), schizophrenia, Alzheimer's disease, cognitive impairment, dementia, drug dependence, convulsions, shivering, pain, sleep disorders, and the like.

  公式[I]所代表的化合物及其药学上可接受的盐是一种新颖的化合物及其药学上可接受的盐，对II类代谢型谷氨酸（mGlu）受体具有拮抗活性，并且作为一种新型预防或治疗剂对情绪障碍（抑郁症、双相情感障碍等）、焦虑障碍（广泛性焦虑障碍、恐慌障碍、强迫症、社交焦虑障碍、创伤后应激障碍、特定恐惧障碍、急性应激障碍等）、精神分裂症、阿尔茨海默病、认知障碍、痴呆、药物依赖、抽搐、颤抖、疼痛、睡眠障碍等疾病具有有效性。
• ETHINYL-PYRAZOLE DERIVATIVE
  申请人：Nakamura Toshio

  公开号：US20130123500A1

  公开（公告）日：2013-05-16

  Provided is a novel compound represented by formula [I] or a pharmaceutically acceptable salt thereof having antagonistic activity against group II metabolism-type glutamic acid (m-Glu) receptors. The compound or pharmaceutically acceptable salt thereof is useful as a prophylactic or therapeutic agent for diseases such as new mood disorders (depressive and bipolar disorders), anxiety disorders (generalized anxiety disorder, panic disorder, obsessive-compulsive disorder, social anxiety disorder, post-traumatic stress disorder, specific phobias, and acute stress disorder), schizophrenia, Alzheimer's disease, cognitive dysfunction, dementia, drug dependence, convulsions, tremors, pain, sleep disorders, and the like.

  提供的是一种由化学式[I]表示的新化合物，或者其在药学上可接受的盐，具有对抗第二组代谢型谷氨酸（m-Glu）受体的拮抗活性。该化合物或其药学上可接受的盐可用作预防或治疗剂，用于诸如新的情绪障碍（抑郁和双相障碍）、焦虑障碍（广泛性焦虑障碍、恐慌障碍、强迫症、社交焦虑障碍、创伤后应激障碍、特定恐惧症和急性应激障碍）、精神分裂症、阿尔茨海默病、认知功能障碍、痴呆、药物依赖、癫痫、震颤、疼痛、睡眠障碍等疾病。
• Stereo- and Regioselective Azide/Alkyne Cycloadditions in Carbonic Anhydrase II via Tethering, Monitored by Crystallography and Mass Spectrometry
  作者：Johannes Schulze Wischeler、Dong Sun、Nicola U. Sandner、Uwe Linne、Andreas Heine、Ulrich Koert、Gerhard Klebe

  DOI：10.1002/chem.201002437

  日期：2011.5.16

  The carbonic anhydrase II mutant His64Cys was prepared and applied to tethered alkyne/azide cycloaddition reactions. The azide component could be tethered to the enzyme surface through a disulfide bridge, while the alkyne component was reversibly coordinated through a sulfonamide anchor to the zinc ion in the original catalytic center of the enzyme. The incipient orientation of the reactants in the

  制备了碳酸酐酶II突变体His64Cys，并将其用于拴系的炔烃/叠氮化物环加成反应。叠氮化物组分可以通过二硫键连接到酶的表面，而炔烃组分则通过磺酰胺锚与酶的原始催化中心的锌离子可逆地配位。通过结晶学表征反应物在结合位点和形成的三唑产物的初始取向。反应进程可通过HPLC-MS分析进行监控。
• Ethinyl-pyrazole derivative
  申请人：Nakamura Toshio

  公开号：US08642626B2

  公开（公告）日：2014-02-04

  Provided is a novel compound represented by formula [I] or a pharmaceutically acceptable salt thereof having antagonistic activity against group II metabolism-type glutamic acid (m-Glu) receptors. The compound or pharmaceutically acceptable salt thereof is useful as a prophylactic or therapeutic agent for diseases such as new mood disorders (depressive and bipolar disorders), anxiety disorders (generalized anxiety disorder, panic disorder, obsessive-compulsive disorder, social anxiety disorder, post-traumatic stress disorder, specific phobias, and acute stress disorder), schizophrenia, Alzheimer's disease, cognitive dysfunction, dementia, drug dependence, convulsions, tremors, pain, sleep disorders, and the like.

  提供的是一种由式[I]所表示的新化合物，或其药学上可接受的盐，该化合物具有对群体II代谢型谷氨酸（m-Glu）受体的拮抗活性。该化合物或其药学上可接受的盐可用作预防或治疗新的情绪障碍（抑郁症和双相障碍）、焦虑症（广泛性焦虑症、恐慌症、强迫症、社交焦虑症、创伤后应激障碍、特定恐惧症和急性应激障碍）、精神分裂症、阿尔茨海默病、认知功能障碍、痴呆、药物依赖、惊厥、震颤、疼痛、睡眠障碍等疾病的预防或治疗剂。