O-2-formyl-4-nitro-6-methoxyphenyl-N,N-dimethylcarbamothioate | 101851-43-8

• 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: O-2-formyl-4-nitro-6-methoxyphenyl-N,N-dimethylcarbamothioate
• 英文别名: O-2-formyl-6-methoxy-4-nitrophenyl N,N-dimethylcarbamothioate；O-(2-formyl-6-methoxy-4-nitrophenyl) N,N-dimethylcarbamothioate
• CAS: 101851-43-8
• 化学式: C₁₁H₁₂N₂O₅S
• 分子量: 284.293
• InChiKey: LSCYKXGXHLBHPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-2-formyl-4-nitro-6-methoxyphenyl-N,N-dimethylcarbamothioate 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 35.0h， 生成 (7-methoxy-5-nitrobenzo[b]thiophen-2-yl)(4-methoxyphenyl)methanone
  参考文献：
  名称：

  Concise Synthesis and Biological Evaluation of 2-Aroyl-5-Amino Benzo[b]thiophene Derivatives As a Novel Class of Potent Antimitotic Agents

  摘要：

  The biological importance of microtubules make them an interesting target for the synthesis of antitumor agents. The 2(3',4',5'-trimethoxybenzoyl)-5-aminobenzo[b]thiophene moiety was identified as a novel scaffold for the preparation of potent inhibitors of microtubule polymerization acting through the colchicine site of tubulin. The position of the methoxy group on the benzo[b]thiophene was important for maximal antiproliferative activity. Structure-activity relationship analysis established that the best activities were obtained with amino and methoxy groups placed at the C-5 and C-7 positions, respectively. Compounds 3c-e showed more potent inhibition of tubulin polymerization than combretastatin A-4 and strong binding to the colchicine site. These compounds also demonstrated substantial antiproliferative activity, with IC50 values ranging from 2.6 to 18 nM in a variety of cancer cell lines. Importantly, compound 3c (50 mg/kg), significantly inhibited the growth of the human osteosarcoma MNNG/HOS xenograft in nude mice.

  DOI：

  10.1021/jm4013938
• 作为产物：
  描述：

  2-羟基-3-甲氧基-5-硝基苯甲醛 、 二甲氨基硫代甲酰氯 在 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到O-2-formyl-4-nitro-6-methoxyphenyl-N,N-dimethylcarbamothioate
  参考文献：
  名称：

  Duocarmycin SA硫代类似物的合成与评价

  摘要：

  1,2,8,8a-四氢环丙[ c ]噻吩并[3,2 - e ] indol- 4-one-6-carboxylate (CTI)衍生物的设计、合成和初步评估详细说明了单原子变化(N 到 S) 嵌入 duocarmycin SA 烷基化亚基中。

  DOI：

  10.1016/j.bmcl.2009.10.063

文献信息

• PHOTOCHROMISM. SYNTHESIS AND PROPERTIES OF INDOLINOSPIROBENZOTHIOPYRANS
  作者：Sei’ichi Arakawa、Hirofumi Kondo、Jun’etsu Seto

  DOI：10.1246/cl.1985.1805

  日期：1985.12.5

  Novel photochromic compounds, indolinospirobenzothiopyrans, were prepared and their properties in polymer films were examined. The absorption bands of the colored form lie around 100 nm deeper in the long-wave region of the spectrum than are the case with the common spiropyrans.

  新型光变色化合物，吲哚氮杂双噁烯，已制备并对其在聚合物薄膜中的性质进行了研究。其着色形式的吸收带在光谱的长波区域比常见的螺吡喃低约100纳米。