2-(2-chloroacetamido)-5-nitrobenzoic acid | 135590-27-1

• 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-(2-chloroacetamido)-5-nitrobenzoic acid
• 英文别名: 2-[(2-Chloroacetyl)amino]-5-nitrobenzoic acid
• CAS: 135590-27-1
• 化学式: C₉H₇ClN₂O₅
• 分子量: 258.618
• InChiKey: MWYDCFDDIWTPGE-UHFFFAOYSA-N

物化性质

• 沸点：
  528.3±50.0 °C(Predicted)
• 密度：
  1.634±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-chloroacetamido)-5-nitrobenzoic acid 在 乙酸酐 作用下， 反应 0.67h， 以88%的产率得到2-(chloromethyl)-6-nitro-4H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  The synthesis of some 3-amino-2-halomethyl-, 2-halomethyl-3-(subst.amino)- and 2-halomethyl-3-hetarylquinazolin-4(3)-ones as potential plant protecting agents

  摘要：

  A series of N(2)-(2-halomethyl-4-oxo-3,4-dihydroquin-azolin-3-yl) carbazates 4 and 5 and 2-halomethyl-3-hetarylquinazolin--4-(3H)-ones 8 and 9 were obtained by reacting 2-halomethyl-4H-3,1-benzoaxin-4-ones (12) with alkyl carbazates and hetarylamines, respectively. Some of the carbazates 4 and 5 were obtained alternatively, by treatment of N-(2)-(2-aminobenzoyl)carbazate 15 with haloacetyl halides. The t-butyl carbazates 5 were converted into 3-amino-2-halomethylquin-azolin-4(3H)-ones (6), some of which were further converted into 3-(2,5-dimethylpyrrol-1-yl)-2-halomethylquinazolin-4(3H)-ones (7). 3-Amino-2-bromomethylquinazolin-4(3H)-one (6b) was also obtained by brominating its 2-methyl analogue 1 with cyanogen bromide.

  DOI：

  10.1016/s0040-4020(01)80886-3
• 作为产物：
  描述：

  2-chloroacetamidobenzoic acid 在 硝酸 作用下， 反应 0.5h， 以92%的产率得到2-(2-chloroacetamido)-5-nitrobenzoic acid
  参考文献：
  名称：

  The synthesis of some 3-amino-2-halomethyl-, 2-halomethyl-3-(subst.amino)- and 2-halomethyl-3-hetarylquinazolin-4(3)-ones as potential plant protecting agents

  摘要：

  A series of N(2)-(2-halomethyl-4-oxo-3,4-dihydroquin-azolin-3-yl) carbazates 4 and 5 and 2-halomethyl-3-hetarylquinazolin--4-(3H)-ones 8 and 9 were obtained by reacting 2-halomethyl-4H-3,1-benzoaxin-4-ones (12) with alkyl carbazates and hetarylamines, respectively. Some of the carbazates 4 and 5 were obtained alternatively, by treatment of N-(2)-(2-aminobenzoyl)carbazate 15 with haloacetyl halides. The t-butyl carbazates 5 were converted into 3-amino-2-halomethylquin-azolin-4(3H)-ones (6), some of which were further converted into 3-(2,5-dimethylpyrrol-1-yl)-2-halomethylquinazolin-4(3H)-ones (7). 3-Amino-2-bromomethylquinazolin-4(3H)-one (6b) was also obtained by brominating its 2-methyl analogue 1 with cyanogen bromide.

  DOI：

  10.1016/s0040-4020(01)80886-3

文献信息

• Development of (<i>E</i>)-2-((1,4-Dimethylpiperazin-2-ylidene)amino)-5-nitro-<i>N</i>-phenylbenzamide, ML336: Novel 2-Amidinophenylbenzamides as Potent Inhibitors of Venezuelan Equine Encephalitis Virus
  作者：Chad E. Schroeder、Tuanli Yao、Julie Sotsky、Robert A. Smith、Sudeshna Roy、Yong-Kyu Chu、Haixun Guo、Nichole A. Tower、James W. Noah、Sara McKellip、Melinda Sosa、Lynn Rasmussen、Layton H. Smith、E. Lucile White、Jeffrey Aubé、Colleen B. Jonsson、Donghoon Chung、Jennifer E. Golden

  DOI：10.1021/jm501203v

  日期：2014.10.23

  Venezuelan equine encephalitis virus (VEEV) is an emerging pathogenic alphavirus that can cause significant disease in humans. Given the absence of therapeutic options available and the significance of VEEV as a weaponized agent, an optimization effort was initiated around a quinazolinone screening hit 1 with promising cellular antiviral activity (EC50 = 0.8 mu M), limited cytotoxic liability (CC50 > 50 mu M), and modest in vitro efficacy in reducing viral progeny (63-fold at 5 mu M). Scaffold optimization revealed a novel rearrangement affording amidines, specifically compound 45, which was found to potently inhibit several VEEV strains in the low nanomolar range without cytotoxicity (EC50 = 0.02-0.04 mu M, CC50 > 50 mu M) while limiting in vitro viral replication (EC90 = 0.17 mu M). Brain exposure was observed in mice with 45. Significant protection was observed in VEEV-infected mice at 5 mg kg(-1) day(-1) and viral replication appeared to be inhibited through interference of viral nonstructural proteins.
• The synthesis of some 3-amino-2-halomethyl-, 2-halomethyl-3-(subst.amino)- and 2-halomethyl-3-hetarylquinazolin-4(3)-ones as potential plant protecting agents
  作者：Józset Fetter、Tibor Czuppon、Gyula Hornyák、Antal Feller

  DOI：10.1016/s0040-4020(01)80886-3

  日期：1991.11

  A series of N(2)-(2-halomethyl-4-oxo-3,4-dihydroquin-azolin-3-yl) carbazates 4 and 5 and 2-halomethyl-3-hetarylquinazolin--4-(3H)-ones 8 and 9 were obtained by reacting 2-halomethyl-4H-3,1-benzoaxin-4-ones (12) with alkyl carbazates and hetarylamines, respectively. Some of the carbazates 4 and 5 were obtained alternatively, by treatment of N-(2)-(2-aminobenzoyl)carbazate 15 with haloacetyl halides. The t-butyl carbazates 5 were converted into 3-amino-2-halomethylquin-azolin-4(3H)-ones (6), some of which were further converted into 3-(2,5-dimethylpyrrol-1-yl)-2-halomethylquinazolin-4(3H)-ones (7). 3-Amino-2-bromomethylquinazolin-4(3H)-one (6b) was also obtained by brominating its 2-methyl analogue 1 with cyanogen bromide.