乙酰腈,[(2-硝基苯基)磺酰]- | 100559-85-1

• 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: 乙酰腈,[(2-硝基苯基)磺酰]-
• 英文名称: 1-(cyanomethyl)sulfonyl-2-nitrobenzene
• 英文别名: (2-nitrophenylsulfonyl)acetonitrile；o-Nitrophenyl-sulphonyl-acetonitril；[(2-Nitrophenyl)sulfonyl]acetonitrile；2-(2-nitrophenyl)sulfonylacetonitrile
• CAS: 100559-85-1
• 化学式: C₈H₆N₂O₄S
• 分子量: 226.213
• InChiKey: GHPMKTYAHVZTBO-UHFFFAOYSA-N

物化性质

• 沸点：
  494.8±45.0 °C(Predicted)
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酰腈,[(2-硝基苯基)磺酰]- 在 palladium on activated charcoal ammonium acetate 、 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-cyano-3-(4-cyanophenyl)-3,4-dihydrobenzo[b]-1,4-thiazine 1,1-dioxide
  参考文献：
  名称：

  [EN] ARYLSULFONE DERIVATIVES WITH ACTIVITY AGAINST HUMAN BETAHERPESVIRUSES
  [FR] DÉRIVÉS D'ARYLSULFONE AGISSANT CONTRE LES VIRUS DE BÉTA-HERPÈS HUMAINS

  摘要：

  本发明涉及具有抗病毒活性的化合物和组合物，特别是抗疱疹活性，更具体地说是抗β-疱疹活性。本发明的化合物为式(I)的化合物，或其互变异构体，或其药学上可接受的盐或溶剂，其中R1、R2、R3、R4、R5和R6具有定义的含义。

  公开号：

  WO2012113920A1
• 作为产物：
  描述：

  (2-nitrophenylthio)acetonitrile 在 双氧水 、 溶剂黄146 作用下， 反应 6.0h， 以89%的产率得到乙酰腈,[(2-硝基苯基)磺酰]-
  参考文献：
  名称：

  由3-烷氧基-2-芳基（或甲基）-磺酰基丙烯腈合成3-氨基-4-芳基（或甲基）磺酰基-2-噻吩羧酸甲酯

  摘要：

  描述了在三乙胺存在下，通过3-烷氧基-2-芳基（或甲基）磺酰基丙烯腈与硫代乙醇酸甲酯的反应，合成一系列3-氨基-4-芳基（或甲基）磺酰基噻吩-2-羧酸甲酯。酯在2-位的水解/脱羧和所得胺的酰化代表了形成4-芳基磺酰基-3-羧酰胺基噻吩的便利途径。在标准条件下尝试酰化标题氨基噻吩未成功。

  DOI：

  10.1002/jhet.5570360314

文献信息

• Synthesis of 4<i>H</i>-3-aryl-2-cyano-1,4-benzothiazine 1,1-dioxides for antiviral studies
  作者：Phillip D. Wilkerson、Andrew C. Bean、Chad E. Stephens

  DOI：10.1515/hc-2017-0028

  日期：2017.4.1

  Abstract 2-Cyano-substituted 1,4-benzothiazine 1,1-dioxides, required for antiviral studies, were prepared by a reductive cyclodehydration of an ortho-nitro sulfone precursor containing a pendant aryl ketone group. The ring-forming reaction also furnishes a non-cyclized benzamide as a major byproduct via an unexpected acyl transfer reaction.

  摘要 抗病毒研究所需的 2-氰基取代的 1,4-苯并噻嗪 1,1-二氧化物是通过含有芳基酮侧基的邻硝基砜前体的还原环脱水​​制备的。环形成反应还通过意想不到的酰基转移反应提供非环化苯甲酰胺作为主要副产物。
• Synthesis and antiviral/antitumor evaluation of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes and related compounds as a new class of diarylsulfones
  作者：C Stephens

  DOI：10.1016/s0968-0896(00)00333-3

  日期：2001.5

  Based on general SARs previously described for anti-HIV-l diarylsulfone derivatives, a series of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes has been prepared and evaluated as potential antiviral and antitumor agents. In cell culture, some of the 2-aminothiophenes exhibited moderate and selective activity against HIV-1, with 2-amino-3-(2-nitrophenylsulfonyl)thiophene (7e) being most attractive (EC50 = 3.8 mug/mL: CC50 = > 100 mug/mL). In broad-spectrum antiviral assays, the 3-arylsulfonyl-2-(trifluoroacetamido)thio (8c-g) and 2-acetamido-3-arylsulfonyl-5-nitrothiophenes (9f-g) proved considerably active (IC50 = 0.1-10 mug/mL) against human cytomegalovirus (CMV) and/or varicella tester virus (VZV). Based on the activity of the trifluoroacetamides, ring-modified furan, N-(substituted)pyrrole, phenyl, and 3,4-thiophene analogues were prepared, and these compounds were also active against CMV and/or VZV, with the notable exception of the 3,4-thiophene derivative. In contrast to other amines, the 2-aminopyrrole precursors (13a-d) also exhibited potent activity against CMV. Unfortunately, most of these compounds displayed significant cytotoxicity against human fibroblasts, the cells supporting CMV and VZV replication, and thus selectivity indices were low. The most notable exception to this was the naphthyl-substituted aminopyrrole 13d, which exhibited both potent (IC50 = 0.3 mug/mL) and selective (CC50 = > 50 mug/mL) activity against CMV. Finally, thiophene aryl amides 8i-k displayed moderate in vitro activity against certain leukemia, breast, and colon cancer cell lines. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Baliah,V.; Ananthapadmanabhan,S., Indian Journal of Chemistry, 1972, vol. 10, p. 917 - 918
  作者：Baliah,V.、Ananthapadmanabhan,S.

  DOI：——

  日期：——
• MATSCHINER, H.;BIERING, H.;SCHILLING, H.;TANNEBERG, H.;TRAUTNER, K.;MASCH+
  作者：MATSCHINER, H.、BIERING, H.、SCHILLING, H.、TANNEBERG, H.、TRAUTNER, K.、MASCH+

  DOI：——

  日期：——
• US5348838A
  申请人：——

  公开号：US5348838A

  公开（公告）日：1994-09-20