2-chloro-N-(α,α-dimethylbenzyl)acetamide | 26095-78-3

• 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: 2-chloro-N-(α,α-dimethylbenzyl)acetamide
• 英文别名: 2-chloro-N-(1-methyl-1-phenylethyl)acetamide；2-Chlor-N-(α,α-dimethylbenzyl)-acetamid；N(α,α-Dimethylbenzyl)-chlor-acetamid；2-chloro-N-(alpha,alpha-dimethylbenzyl)-acetamide；2-chloro-N-(2-phenylpropan-2-yl)acetamide
• CAS: 26095-78-3
• 化学式: C₁₁H₁₄ClNO
• 分子量: 211.691
• InChiKey: AFUVGTCUGAVOPM-UHFFFAOYSA-N

物化性质

• 沸点：
  369.4±35.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-硝基-2-糠酸 、 2-chloro-N-(α,α-dimethylbenzyl)acetamide 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以43%的产率得到2-Oxo-2-[(2-phenylpropan-2-yl)amino]ethyl 5-nitrofuran-2-carboxylate
  参考文献：
  名称：

  Structural and biochemical study on the inhibitory activity of derivatives of 5-nitro-furan-2-carboxylic acid for RNase H function of HIV-1 reverse transcriptase

  摘要：

  Rapid emergence of drug-resistant variants is one of the most serious problems in chemotherapy for HIV-1 infectious diseases. Inhibitors acting on a target not addressed by approved drugs are of great importance to suppress drug-resistant viruses. HIV-1 reverse transcriptase has two enzymatic functions, DNA polymerase and RNase H activities. The RNase H activity is an attractive target for a new class of antiviral drugs. On the basis of the hit chemicals found in our previous screening with 20,000 small molecular-weight compounds, we synthesized derivatives of 5-nitro-furan-2-carboxylic acid. Inhibition of RNase H enzymatic activity was measured in a biochemical assay with real-time monitoring of florescence emission from the digested RNA substrate. Several derivatives showed higher inhibitory activities that those of the hit chemicals. Modulation of the 5-nitro-furan-2-carboxylic moiety resulted in a drastic decrease in inhibitory potency. In contrast, many derivatives with modulation of other parts retained inhibitory activities to varying degrees. These findings suggest the binding mode of active derivatives, in which three oxygen atoms aligned in a straight form at the nitro-furan moiety are coordinated to two divalent metal ions located at RNase H reaction site. Hence, the nitro-furan-carboxylic moiety is one of the critical scaffolds for RNase H inhibition. Of note, the RNase H inhibitory potency of a derivative was improved by 18-fold compared with that of the original hit compound, and no significant cytotoxicity was observed for most of the derivatives showing inhibitory activity. Since there is still much room for modification of the compounds at the part opposite the nitro-furan moiety, further chemical conversion will lead to improvement of compound potency and specificity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.011
• 作为产物：
  描述：

  氯乙酰氯 、 Alpha,Alpha-二甲基苄胺 在 polymer-bound diisopropylethylamine 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以87%的产率得到2-chloro-N-(α,α-dimethylbenzyl)acetamide
  参考文献：
  名称：

  WO2007/69986

  摘要：

  公开号：

文献信息

• Glycylglycine amide preparations and method of use antiarrhythmic
  申请人：Astra Lakemedel Aktiebolag

  公开号：US03976771A1

  公开（公告）日：1976-08-24

  A novel class of glycylglycine amides has been discovered having value as antiarrhythmic agents. The preferred compound of the present invention has the structural formula ##EQU1## Also included within the scope of this invention are compounds having C.sub.1 -C.sub.3 alkyl, alkoxy and halo substituents in the ortho, para or meta positions of the aromatic ring, compounds in which the phenyl group is replaced by benzyl or substituted benzyl and compounds in which the glycylglycine chain may be substituted with lower alkyl groups or may contain heterocyclic rings.

  一种新型的甘氨酸酰胺类化合物被发现具有抗心律失常药物的价值。本发明的首选化合物具有下列结构式：##EQU1## 本发明的范围还包括具有C.sub.1-C.sub.3烷基、烷氧基和卤素取代基的芳环的邻、对或间位，以苯基被苄基或取代苄基所替代的化合物，以及甘氨酸甘氨酰链可能被低烷基取代或含有杂环的化合物。
• WO2007/69986
  申请人：——

  公开号：——

  公开（公告）日：——
• Structural and biochemical study on the inhibitory activity of derivatives of 5-nitro-furan-2-carboxylic acid for RNase H function of HIV-1 reverse transcriptase
  作者：Hiroshi Yanagita、Emiko Urano、Kishow Matsumoto、Reiko Ichikawa、Yoshihisa Takaesu、Masakazu Ogata、Tsutomu Murakami、Hongui Wu、Joe Chiba、Jun Komano、Tyuji Hoshino

  DOI：10.1016/j.bmc.2010.12.011

  日期：2011.1

  Rapid emergence of drug-resistant variants is one of the most serious problems in chemotherapy for HIV-1 infectious diseases. Inhibitors acting on a target not addressed by approved drugs are of great importance to suppress drug-resistant viruses. HIV-1 reverse transcriptase has two enzymatic functions, DNA polymerase and RNase H activities. The RNase H activity is an attractive target for a new class of antiviral drugs. On the basis of the hit chemicals found in our previous screening with 20,000 small molecular-weight compounds, we synthesized derivatives of 5-nitro-furan-2-carboxylic acid. Inhibition of RNase H enzymatic activity was measured in a biochemical assay with real-time monitoring of florescence emission from the digested RNA substrate. Several derivatives showed higher inhibitory activities that those of the hit chemicals. Modulation of the 5-nitro-furan-2-carboxylic moiety resulted in a drastic decrease in inhibitory potency. In contrast, many derivatives with modulation of other parts retained inhibitory activities to varying degrees. These findings suggest the binding mode of active derivatives, in which three oxygen atoms aligned in a straight form at the nitro-furan moiety are coordinated to two divalent metal ions located at RNase H reaction site. Hence, the nitro-furan-carboxylic moiety is one of the critical scaffolds for RNase H inhibition. Of note, the RNase H inhibitory potency of a derivative was improved by 18-fold compared with that of the original hit compound, and no significant cytotoxicity was observed for most of the derivatives showing inhibitory activity. Since there is still much room for modification of the compounds at the part opposite the nitro-furan moiety, further chemical conversion will lead to improvement of compound potency and specificity. (C) 2010 Elsevier Ltd. All rights reserved.