(E)-4-<(2-phenylethynyl)sulfonyl>morpholine | 17299-32-0

• 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)-4-<(2-phenylethynyl)sulfonyl>morpholine
• 英文别名: (E)-4-(styrylsulfonyl)morpholine；trans-2-Phenyl-ethylensulfonmorpholid；4-(2-phenyl-ethenesulfonyl)-morpholine；4-[(E)-2-phenylethenyl]sulfonylmorpholine
• CAS: 17299-32-0
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: RDTYOSMNVSOCAV-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-<(2-phenylethynyl)sulfonyl>morpholine 在 氢氧化钾 、 potassium hypochlorite 、 potassium chloride 、 四丁基硫酸氢铵 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 14.0h， 以40%的产率得到4-(trans-3-phenyl-oxiranesulfonyl)-morpholine
  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：

  4-<(phenylethynyl)sulfinyl>morpholine 在 lithium aluminium tetrahydride 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 (E)-4-<(2-phenylethynyl)sulfonyl>morpholine
  参考文献：
  名称：

  Baudin, Jean-Bernard; Julia, Sylvestre A.; Wang, Yuan, Bulletin de la Societe Chimique de France, 1995, vol. 132, p. 952 - 962

  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。
• Effect of Chiral Diene Ligands in Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to α,β-Unsaturated Sulfonyl Compounds
  作者：Takahiro Nishimura、Yuka Takiguchi、Tamio Hayashi

  DOI：10.1021/ja303109q

  日期：2012.6.6

  Asymmetric addition of arylboronic acids to α,β-unsaturated sulfonyl compounds proceeded in the presence of a rhodium catalyst coordinated with a chiral diene ligand to give high yields of the addition products with high enantioselectivity (96->99.5% ee). The diene ligand was proved to be essential for the formation of the addition products, while the use of a bisphosphine ligand mainly gave the cine-substitution

  在与手性二烯配体配位的铑催化剂存在下，芳基硼酸与 α,β-不饱和磺酰基化合物的不对称加成反应以高对映选择性 (96->99.5% ee) 得到高收率的加成产物。证明二烯配体对于加成产物的形成是必不可少的，而双膦配体的使用主要产生电影取代产物。
• 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。
• [EN] COMPOUND FOR REGULATING GENE EDITING EFFICIENCY AND APPLICATION THEREOF<br/>[FR] COMPOSÉ DESTINÉ À RÉGULER L'EFFICACITÉ D'ÉDITION DE GÈNE ET SON APPLICATION<br/>[ZH] 用于调控基因编辑效率的化合物及其应用
  申请人：SHANGHAI INST ORGANIC CHEMISTRY CAS

  公开号：WO2019238091A1

  公开（公告）日：2019-12-19

  一种用于提高基因编辑特异性的化合物及其应用。具体地公开了一种式I所示的化合物、或其药学上可接受的盐的用途，它们被用于制备抑制基因编辑和/或提高基因编辑特异性的抑制剂、组合物或制剂，其中式I结构如说明书中所述。化合物可显著提高CRISPR基因编辑的准确率，从而为精准的基因编辑提供了一种简单而又高效的策略。
• Cyclopropanesulfonic acid esters and amides
  作者：William E. Truce、Christian T. Goralski

  DOI：10.1021/jo01274a034

  日期：1968.10