Phenyl-ethynesulfonic acid dimethylamide | 110381-00-5

• 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: Phenyl-ethynesulfonic acid dimethylamide
• 英文别名: N,N-dimethyl-2-phenylethynesulfonamide
• CAS: 110381-00-5
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: URBPMQRELBXDMF-UHFFFAOYSA-N

物化性质

• 熔点：
  94 °C(Solv: methanol (67-56-1))
• 沸点：
  323.5±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Phenyl-ethynesulfonic acid dimethylamide 以40%的产率得到
  参考文献：
  名称：

  BRIENE, MARIE-JOSEPHE;VARECH, DANIEL;LECLERCQ, MARTINE;JACQUES, JEAN;BADE+, J. MED. CHEM., 30,(1987) N 12, 2232-2239

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-N,N-dimethyl-2-phenylethene-1-sulfonamide 在 potassium tert-butylate 、 溴 作用下， 以 1,4-二氧六环 、 四氯化碳 、 叔丁醇 为溶剂， 反应 5.5h， 生成 Phenyl-ethynesulfonic acid dimethylamide
  参考文献：
  名称：

  New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides

  摘要：

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.

  DOI：

  10.1021/jm00395a010

文献信息

• Risk of Late-Onset Alzheimer's Disease by Plasma Cholesterol: Rational<i>In Silico</i>Drug Investigation of Pyrrole-Based HMG-CoA Reductase Inhibitors
  作者：Sajad Shahbazi、Jagdeep Kaur、Ananya Kuanar、Dattatreya Kar、Shikha Singh、Ranbir Chander Sobti

  DOI：10.1089/adt.2017.804

  日期：2017.11

  blood cholesterol. Selective HMGCR inhibitor drugs such as statins, which increase the catabolism of plasma LDL and reduce the plasma concentration of cholesterol, have been investigated as a possible treatment for AD. In the present study, we have identified the binding modes of 22 various derivatives of 3-sulfamoylpyrroles 16, prepared via a [3 + 2] cycloaddition of a münchnone with a sulfonamide-substituted

  阿尔茨海默氏病（AD）是享誉全球的进行性神经退行性疾病，是痴呆症的最常见病因。胆固醇代谢在AD发病机理中的重要作用已有几项研究，表明高浓度的血清胆固醇会增加AD的风险。3-羟-3-甲基戊二酰辅酶A还原酶（HMGCR）通过甲羟戊酸途径中的HMG-CoA转化为甲羟戊酸来催化血浆胆固醇和其他类异戊二烯的生物合成。通常，血浆LDL降解会导致HGMCR抑制而使血浆胆固醇水平下调，但在异常情况下（例如，高血糖），HMGCR过度活化会导致血液胆固醇失控。选择性HMGCR抑制剂药物，例如他汀类药物，已经研究了增加血浆LDL分解代谢并降低血浆胆固醇浓度的药物，可以作为AD的治疗方法。在本研究中，我们已经确定了22种3-氨磺酰基吡咯16衍生物的结合模式，这是通过使用有效的生物计算工具，通过将Münchnone与磺酰胺取代的炔烃进行[3 + 2]环加成而制备的。在22种配体中，代号为5b，5c，5d，5i和5j
• 10.1055/a-2348-5631
  作者：Maguire, Anita R、Judge, Evan、O'Shaughnessy, Keith A、Lawrence, Simon E.、Collins, Stuart G.

  DOI：10.1055/a-2348-5631

  日期：——

  Copper-mediated reactions of α-diazo-β-keto sulfonamides led to a range of products, including alkynesulfonamides, enamines, and α-halosulfonamides, with no evidence for intramolecular C–H insertion in any of the reactions, in contrast to the reactivity of the comparable α-diazo-β-oxo sulfones. Use of copper(II) triflate (5 mol%) led to the isolation of a series of alkynesulfonamides (up to 12% yield)

  α-重氮-β-酮磺酰胺的铜介导反应产生了一系列产物，包括炔磺酰胺、烯胺和 α-卤代磺酰胺，与反应性相反，没有证据表明任何反应中存在分子内 C-H 插入类似的α-重氮-β-氧代砜。使用三氟甲磺酸铜(II) (5 mol%) 可以分离出一系列炔磺酰胺（产率高达 12%）和烯胺（产率高达 64%）。使用氯化铜(II) (5 mol%)还导致形成α-卤代磺酰胺；使用化学计量的氯化铜(II)/溴化铜(II)可以轻松地将β-酮磺酰胺卤化形成α-卤代磺酰胺（产率高达63%）。
• Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors
  作者：William K.C. Park、Robert M. Kennedy、Scott D. Larsen、Steve Miller、Bruce D. Roth、Yuntao Song、Bruce A. Steinbaugh、Kevin Sun、Bradley D. Tait、Mark C. Kowala、Bharat K. Trivedi、Bruce Auerbach、Valerie Askew、Lisa Dillon、Jeffrey C. Hanselman、Zhiwu Lin、Gina H. Lu、Andrew Robertson、Catherine Sekerke

  DOI：10.1016/j.bmcl.2007.11.124

  日期：2008.2

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.
• BRIENE, MARIE-JOSEPHE;VARECH, DANIEL;LECLERCQ, MARTINE;JACQUES, JEAN;BADE+, J. MED. CHEM., 30,(1987) N 12, 2232-2239
  作者：BRIENE, MARIE-JOSEPHE、VARECH, DANIEL、LECLERCQ, MARTINE、JACQUES, JEAN、BADE+

  DOI：——

  日期：——
• New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides
  作者：Marie Josephe Brienne、Daniel Varech、Martine Leclercq、Jean Jacques、Nathalie Radembino、Christine Dessalles、Georges Mahuzier、Chantal Gueyouche、Christian Bories

  DOI：10.1021/jm00395a010

  日期：1987.12

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.