(3S,E)-3-(tert-butoxycarbonylamino)-4-phenyl-1-phenylsulfonyl-1-butene | 799560-42-2

• 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: (3S,E)-3-(tert-butoxycarbonylamino)-4-phenyl-1-phenylsulfonyl-1-butene
• 英文别名: tert-butyl (S,E)-(1-phenyl-4-(phenylsulfonyl)but-3-en-2-yl)carbamate；tert-butyl N-[(E,2S)-4-(benzenesulfonyl)-1-phenylbut-3-en-2-yl]carbamate
• CAS: 799560-42-2
• 化学式: C₂₁H₂₅NO₄S
• 分子量: 387.5
• InChiKey: IUUMZWSXOGEILR-LGHUBQEGSA-N

物化性质

• 熔点：
  139-140.5 °C
• 沸点：
  585.8±50.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,E)-3-(tert-butoxycarbonylamino)-4-phenyl-1-phenylsulfonyl-1-butene 在 N-甲基吗啉 、 盐酸 、 氯甲酸异丁酯 作用下， 以 乙酸乙酯 为溶剂， 生成 phenyl (3S)-3-(N-carbobenzyloxyleucyl)amino-4-phenylbut-1-enyl sulfone
  参考文献：
  名称：

  肽基烯丙基砜：一类新型的CA家族半胱氨酸蛋白酶抑制剂。

  摘要：

  在尝试使用碱性氧化条件从乙烯基砜合成环氧砜抑制剂时，发现了一系列新的肽基烯丙基砜抑制剂。用钙蛋白酶I，木瓜蛋白酶，组织蛋白酶B和L，克鲁萨因和罗氏蛋白酶对各种二肽基烯丙基砜进行了评估，发现它们是有效的抑制剂。与先前开发的一类乙烯基砜抑制剂相比，新型二肽基烯丙基砜比相应的二肽基乙烯基砜更有效。观察到乙烯基砜前体的立体化学在二肽基烯丙基砜抑制剂的效力中起作用。

  DOI：

  10.1016/j.bmc.2004.07.016
• 作为产物：
  描述：

  1-苄基-2,3-环氧正丙基-氨基甲酸叔丁酯 在 4-二甲氨基吡啶 、 甲基磺酰氯 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (3S,E)-3-(tert-butoxycarbonylamino)-4-phenyl-1-phenylsulfonyl-1-butene
  参考文献：
  名称：

  Enantiodivergent, Catalytic Asymmetric Synthesis of γ-Amino Vinyl Sulfones

  摘要：

  A set of diversely substituted N-Boc-gamma-amino vinyl sulfones has been prepared by a four-step procedure from readily available, highly enantiopure anti-N-Boc-3-amino-1,2-alkanediols. This new route, which does not depend on the accessibility of alpha-amino acids as starting materials, is noteworthy for its efficiency, for its generality, and for the fact that both enantiomers of a given gamma-amino vinyl sulfone can be obtained with equal ease.

  DOI：

  10.1021/jo0268456

文献信息

• Vinyl sulfone-based inhibitors of trypanosomal cysteine protease rhodesain with improved antitrypanosomal activities
  作者：Huaisheng Zhang、Jasmine Collins、Rogers Nyamwihura、Olamide Crown、Oluwatomi Ajayi、Ifedayo Victor Ogungbe

  DOI：10.1016/j.bmcl.2020.127217

  日期：2020.7

  antitrypanosomal agents, we found that partially saturated quinoline-based vinyl sulfone compounds selectively inhibit the growth of T. brucei but displayed relatively weak inhibitory activity towards T. brucei’s cysteine protease rhodesain. While two nitroaromatic analogues of the quinoline-based vinyl sulfone compounds displayed potent inhibition of T. brucei and rhodesain. The quinoline derivatives and

  在非洲撒哈拉以南地区，由运动型原生动物寄生虫布鲁氏锥虫引起的人类非洲锥虫病（HAT）病例数正在下降。从历史上看，这种下降通常是在发病率较高的时期之后进行的，而HAT的挥之不去的公共卫生挑战之一就是其药物开发渠道在历史上是稀疏的。作为我们对新型抗锥虫病药物的研究的继续，我们发现部分饱和的喹啉基乙烯基砜化合物选择性地抑制了布鲁氏菌的生长，但对布鲁氏菌的半胱氨酸蛋白酶罗氏蛋白酶的抑制活性相对较弱。喹啉基乙烯基砜化合物的两个硝基芳香族类似物显示出对布氏锥虫和rhodesain。在这项工作中发现的喹啉衍生物和基于硝基芳香族的化合物可以作为基于ADME的优化和临床前研究的线索。
• Vinyl Sulfone-Based Inhibitors of Nonstructural Protein 2 Block the Replication of Venezuelan Equine Encephalitis Virus
  作者：Huaisheng Zhang、Moeshia Harmon、Sheli R. Radoshitzky、Veronica Soloveva、Christopher D. Kane、Allen J. Duplantier、Ifedayo Victor Ogungbe

  DOI：10.1021/acsmedchemlett.0c00215

  日期：2020.11.12

  an acrylate and vinyl sulfone-based chemical series was investigated as promising starting scaffolds against VEEV and as inhibitors of the cysteine protease domain of VEEV’s nonstructural protein 2 (nsP2). Primary screen and dose response studies were performed to evaluate the potency and cytotoxicity of the compounds. The results provide structural insights into a new class of potent nonpeptidic covalent

  委内瑞拉马脑炎病毒 (VEEV) 等虫媒病毒引起的新发传染病对公共卫生系统构成严重威胁。制定针对新发传染病的医学对策至关重要。在这项工作中，基于丙烯酸酯和乙烯基砜的化学系列被研究为有前途的 VEEV 起始支架和作为 VEEV 非结构蛋白 2 (nsP2) 半胱氨酸蛋白酶结构域的抑制剂。进行初步筛选和剂量反应研究以评估化合物的效力和细胞毒性。结果提供了对由化合物11 (VEEV TrD, EC 50= 2.4 μM (HeLa), 1.6 μM (Vero E6))。这些结果可能有助于将化合物进化为选择性和广谱的抗甲病毒药物先导药物。
• Dipeptidyl α-fluorovinyl Michael acceptors: Synthesis and activity against cysteine proteases
  作者：Koen Steert、Ibrahim El-Sayed、Pieter Van der Veken、Alisa Krishtal、Christian Van Alsenoy、Gareth D. Westrop、Jeremy C. Mottram、Graham H. Coombs、Koen Augustyns、Achiel Haemers

  DOI：10.1016/j.bmcl.2007.09.075

  日期：2007.12

  The synthesis of novel dipeptidyl alpha-fluorovinyl sulfones using a Horner-Wadsworth-Emmons approach on N-Boc-L-phenylalaninal is described. Inhibitory assays against a Leishmania mexicana cysteine protease (CPB2.8 Delta CTE) revealed low biological activity. Relative rates of Michael additions of 2'-(phenethyl) thiol with vinyl sulfone and alpha-fluorovinyl sulfone were determined, and ab initio calculations on several Michael acceptor model structures were performed; both were in agreement with the biological testing results. (c) 2007 Elsevier Ltd. All rights reserved.
• Peptidyl allyl sulfones: a new class of inhibitors for clan CA cysteine proteases
  作者：Marion G. Götz、Conor R. Caffrey、Elizabeth Hansell、James H. McKerrow、James C. Powers

  DOI：10.1016/j.bmc.2004.07.016

  日期：2004.10

  series of peptidyl allyl sulfone inhibitors was discovered while trying to synthesize epoxy sulfone inhibitors from vinyl sulfones using basic oxidizing conditions. The various dipeptidyl allyl sulfones were evaluated with calpain I, papain, cathepsins B and L, cruzain and rhodesain and found to be potent inhibitors. In comparison to the previously developed class of vinyl sulfone inhibitors, the novel

  在尝试使用碱性氧化条件从乙烯基砜合成环氧砜抑制剂时，发现了一系列新的肽基烯丙基砜抑制剂。用钙蛋白酶I，木瓜蛋白酶，组织蛋白酶B和L，克鲁萨因和罗氏蛋白酶对各种二肽基烯丙基砜进行了评估，发现它们是有效的抑制剂。与先前开发的一类乙烯基砜抑制剂相比，新型二肽基烯丙基砜比相应的二肽基乙烯基砜更有效。观察到乙烯基砜前体的立体化学在二肽基烯丙基砜抑制剂的效力中起作用。
• Enantiodivergent, Catalytic Asymmetric Synthesis of γ-Amino Vinyl Sulfones
  作者：Anna Picó、Albert Moyano、Miquel A. Pericàs

  DOI：10.1021/jo0268456

  日期：2003.6.1

  A set of diversely substituted N-Boc-gamma-amino vinyl sulfones has been prepared by a four-step procedure from readily available, highly enantiopure anti-N-Boc-3-amino-1,2-alkanediols. This new route, which does not depend on the accessibility of alpha-amino acids as starting materials, is noteworthy for its efficiency, for its generality, and for the fact that both enantiomers of a given gamma-amino vinyl sulfone can be obtained with equal ease.