(E)-N,N-dimethyl-2-phenylethene-1-sulfonamide | 56631-61-9

• 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: (E)-N,N-dimethyl-2-phenylethene-1-sulfonamide
• 英文别名: (E)-N,N-dimethyl-2-phenylethenesulfonamide
• CAS: 56631-61-9
• 化学式: C₁₀H₁₃NO₂S
• 分子量: 211.285
• InChiKey: NFNZBXXSRCGCIR-CMDGGOBGSA-N

物化性质

• 熔点：
  103.2-104 °C
• 沸点：
  332.8±35.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 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：

  (E)-N,N-dimethyl-2-phenylethene-1-sulfonamide 在 palladium on activated charcoal sodium hypophosphite 、 potassium tert-butylate 、 溴 作用下， 以 1,4-二氧六环 、 四氯化碳 、 乙醇 、 叔丁醇 为溶剂， 反应 22.5h， 生成 cis-N,N-dimethyl-2-phenylethenesulfonamide
  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
• 作为产物：
  描述：

  苯甲醛 、 N,N-二甲基-1-(三甲基甲硅烷基)甲烷磺酰胺 在 正丁基锂 、 二异丙胺 作用下， 生成 (E)-N,N-dimethyl-2-phenylethene-1-sulfonamide
  参考文献：
  名称：

  Mladenova, Margarita; Gaudemar-Bardone, Francoise, Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 62, # 14, p. 257 - 268

  摘要：

  DOI：

文献信息

• EIF4A-INHIBITING COMPOUNDS AND METHODS RELATED THERETO
  申请人：eFFECTOR Therapeutics, Inc.

  公开号：US20170145026A1

  公开（公告）日：2017-05-25

  The present invention provides synthesis, pharmaceutically acceptable formulations and uses of compounds in accordance with Formula I, or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof. For Formula I compounds X, Y, R 1 , R 2 , R 3a , R 3b , R 4a , R 4b and R 5 are as defined in the specification. The inventive Formula I compounds are inhibitors of eIF4A and find utility in any number of therapeutic applications, including but not limited to treatment of inflammation and various cancers.

  本发明提供了根据式I合成的化合物、药用可接受的配方和用途，或其立体异构体、互变异构体或药用可接受的盐。对于式I化合物X、Y、R1、R2、R3a、R3b、R4a、R4b和R5如规范中所定义。这些创新的式I化合物是eIF4A的抑制剂，在许多治疗应用中发挥作用，包括但不限于治疗炎症和各种癌症。
• Design of Development Candidate eFT226, a First in Class Inhibitor of Eukaryotic Initiation Factor 4A RNA Helicase
  作者：Justin T. Ernst、Peggy A. Thompson、Christian Nilewski、Paul A. Sprengeler、Samuel Sperry、Garrick Packard、Theodore Michels、Alan Xiang、Chinh Tran、Christopher J. Wegerski、Boreth Eam、Nathan P. Young、Sarah Fish、Joan Chen、Haleigh Howard、Jocelyn Staunton、Jolene Molter、Jeff Clarine、Andres Nevarez、Gary G. Chiang、Jim R. Appleman、Kevin R. Webster、Siegfried H. Reich

  DOI：10.1021/acs.jmedchem.0c00182

  日期：2020.6.11

  component of the eIF4F complex, which regulates cap-dependent protein synthesis. The flavagline class of natural products (i.e., rocaglamide A) has been shown to inhibit protein synthesis by stabilizing a translation–incompetent complex for select messenger RNAs (mRNAs) with eIF4A. Despite showing promising anticancer phenotypes, the development of flavagline derivatives as therapeutic agents has been hampered

  蛋白质翻译失调是许多癌症发病机理的关键驱动因素。真核生物起始因子4A（eIF4A）是ATP依赖的DEAD-box RNA解旋酶，是eIF4F复合体的重要组成部分，该复合体调节帽依赖性蛋白质的合成。天然产品的黄精油类（即，rocaglamide A）已被证明可以通过稳定带有eIF4A的特定信使RNA（mRNA）的翻译无能力复合物来抑制蛋白质合成。尽管显示出有希望的抗癌表型，但由于不良的类药物性质和合成复杂性，阻碍了黄酮衍生物作为治疗剂的开发。利用基于配体的设计策略进行了重点研究，以鉴定具有优化的理化性质的化学型。此外，进行了详细的机理研究，以进一步阐明mRNA序列的选择性，关键的调控靶基因以及相关的抗肿瘤表型。这项工作导致了eFT226的设计 （Zotatifin），具有出色的理化特性和显着的抗肿瘤活性的化合物，可支持临床发展。
• Synthesis and reactivity of the 1,1-dilithio derivatives of alkyl phenyl sulfones and N,N-dimethyl methanesulfonamide
  作者：A. Bongini、D. Savoia、A. Umani-Ronchi

  DOI：10.1016/s0022-328x(00)89360-2

  日期：1976.5

  Alkyl phenyl sulfones Ia,b and N,N-dimethyl methanesulfonamide (Ic) are rapidly converted into their 1,1-dilithio salts IIa–c on reaction with n-butyllithium in THF—hexane. The nature of these new organometallic species was confirmed by deuteration and condensation with benzaldehyde. The gem-dimetallo derivatives Va–c and VIa, obtained from IIa–c by lithium—magnesium and lithium—boron exchange respectively

  与正丁基锂在THF-己烷中反应后，烷基苯基砜Ia，b和N，N-二甲基甲磺酰胺（Ic）迅速转化为1,1-二硫代盐IIa-c。通过氘化和与苯甲醛缩合证实了这些新的有机金属物种的性质。分别通过锂-镁和锂-硼交换从IIa-c获得的宝石双金属衍生物Va-c和VIa与羰基化合物反应生成α，β-不饱和砜VIIa-c和相应的β-羟基砜VIIIa- C。
• EIF4A-inhibiting compounds and methods related thereto
  申请人：eFFECTOR Therapeutics, Inc.

  公开号：US10577378B2

  公开（公告）日：2020-03-03

  The present invention provides synthesis, pharmaceutically acceptable formulations and uses of compounds in accordance with Formula I, or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof. For Formula I compounds X, Y, R1, R2, R3a, R3b, R4a, R4b and R5 are as defined in the specification. The inventive Formula I compounds are inhibitors of eIF4A and find utility in any number of therapeutic applications, including but not limited to treatment of inflammation and various cancers.

  本发明提供了符合式 I 的化合物或其立体异构体、同分异构体或药学上可接受的盐的合成、药学上可接受的制剂和用途。 对于式 I 化合物，X、Y、R1、R2、R3a、R3b、R4a、R4b 和 R5 如说明书中所定义。本发明的式 I 化合物是 eIF4A 的抑制剂，可用于各种治疗领域，包括但不限于炎症和各种癌症的治疗。
• CARDILLO G.; SAVOIA D.; UMANI-RONCHI A., SYNTHESIS <SYNT-BF>, 1975, NO 7, 453-455
  作者：CARDILLO G.、 SAVOIA D.、 UMANI-RONCHI A.

  DOI：——

  日期：——