N-[3-(4-chlorophenyl)sulfonyl-2-thienyl]-2,2,3,3,4,4,4-heptafluoro-butanamide

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: N-[3-(4-chlorophenyl)sulfonyl-2-thienyl]-2,2,3,3,4,4,4-heptafluoro-butanamide
• 英文别名: N-[3-(4-chlorophenyl)sulfonylthiophen-2-yl]-2,2,3,3,4,4,4-heptafluorobutanamide
• 化学式: C₁₄H₇ClF₇NO₃S₂
• 分子量: 469.788
• InChiKey: BHTQXQHFHOLQEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  99.9
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (4-氯苯磺酰)乙腈 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 34.0h， 生成 N-[3-(4-chlorophenyl)sulfonyl-2-thienyl]-2,2,3,3,4,4,4-heptafluoro-butanamide
  参考文献：
  名称：

  Synthesis and antiviral/antitumor evaluation of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes and related compounds as a new class of diarylsulfones

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(00)00333-3