2,5-dioxopyrrolidin-1-yl 5-chloro-2-hydroxybenzoate | 1072896-51-5

• 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: 2,5-dioxopyrrolidin-1-yl 5-chloro-2-hydroxybenzoate
• CAS: 1072896-51-5
• 化学式: C₁₁H₈ClNO₅
• 分子量: 269.641
• InChiKey: PZKRQYVTJNOJKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,5-dioxopyrrolidin-1-yl 5-chloro-2-hydroxybenzoate 、 p-methoxyphenyl (9-amino-3,5,9-trideoxy-5-glycolamido-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside 在 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以70%的产率得到p-methoxyphenyl (9-(5-chloro-2-hydroxybenzamido)-3,5,9-trideoxy-5-glycolamido-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside
  参考文献：
  名称：

  Design, Synthesis, and Structure−Affinity Relationships of Novel Series of Sialosides as CD22-Specific Inhibitors

  摘要：

  Sialosides incorporating substituted amides or amines at 9-position of sialic acid moiety have been synthesized and evaluated as CD22 inhibitors. Several derivatives exhibited inhibitory potency in sub- to low micromolar range (e. g., 8o, 9d, 9g, and 9k showed IC50 values 0.40, 0.47, 0.24, and 0.23 mu M, respectively, for hCD22, while 8p. 8q, and 9f, showed IC50 values 1.70, 2.90, and 4.10 mu M, respectively, for mCD22). The most significant result was the strongly enhanced affinity of 9g and 9k containing 9-(2' or 4'-hydroxy-4-biphenyl) methylamino substituents (600-fold more potent for hCD22 than the corresponding 9-hydroxy derivative; 7a). Molecular modeling study was carried out to get some insights into the molecular basis of CD22 inhibition. To the best of our knowledge, this is the first systematic structure-affinity relationship study on inhibition of CD22.

  DOI：

  10.1021/jm8000696
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 5-氯代水杨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2,5-dioxopyrrolidin-1-yl 5-chloro-2-hydroxybenzoate
  参考文献：
  名称：

  Effect of the mimic structure on the molecular recognition properties of molecularly imprinted polymers for ochratoxin A prepared by a fragmental approach

  摘要：

  In this work the fragmental approach was used to prepare several molecularly imprinted ethylene dimethacrylate-co-methacrylic acid polymers with molecular recognition towards the mycotoxin ochratoxin A, with the aim of searching for simpler mimic templates than the well-known N-(4-chloro-1-hydroxy-2-naphthoylamido)-(L)-phenylalanine. The screening for binding of two different kinds of ochratoxin-related molecules was performed by HPLC analysis. Ochratoxin A and the mimic templates were eluted in acetonitrile-acetic acid (0.1% v/v) and the imprinting factor was measured for all the ligands on all the columns packed with the imprinted polymers. The experimental results show that changes to the amino acidic sub-structure or the presence/absence of a chlorine atom in position 4 on the naphthalene ring system does not affect the molecular recognition of ochratoxin A by the resulting imprinted polymer. On the contrary, the presence of the bulky naphthalene ring system in the mimic template seems to be necessary to preserve the molecular recognition of ochratoxin. This binding behavior was found to be compatible with in silico simulations of the complexation between some of the mimic templates and molecules of methacrylic acid. The use of the mimic template N-(1-hydroxy-2-naphthoylamido)-(L)-phenylalanine seems to represent a synthetically simple approach to the preparation of imprinted polymers with molecular recognition properties towards ochratoxin A. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.reactfunctpolym.2013.03.018

文献信息

• Identification of novel triazole inhibitors of Wnt/β-catenin signaling based on the Niclosamide chemotype
  作者：Robert A. Mook、Jiangbo Wang、Xiu-Rong Ren、Hailan Piao、H. Kim Lyerly、Wei Chen

  DOI：10.1016/j.bmcl.2018.11.022

  日期：2019.1

  that expanded the chemotype structural diversity. Here, we asked a specific SAR question unresolved in previous SAR studies of Niclosamide's inhibition of Wnt/β-catenin signaling to identify a new structural class of Wnt/β-catenin signaling inhibitors based on a triazole motif. Similar to Niclosamide, we found that the new triazole derivatives internalized Frizzled-1 GFP receptors, inhibited Wnt/β-catenin

  Wnt信号通路的失调是多种疾病（尤其是癌症）的潜在机制。直到最近，鉴定靶向该途径的药物一直很困难，结果，尚不存在专门针对该途径的已批准药物。我们以前曾报道过，驱虫药NicloSAmide抑制Wnt /β-catenin信号通路并在体外和体内抑制结直肠癌细胞的生长。在此基础上，我们努力寻找新的Wnt /β-catenin抑制剂，以扩大化学型的结构多样性。在这里，我们问了一个具体的SAR问题，在以前的SAR研究中，氯硝酰胺对Wnt /β-catenin信号传导的抑制作用尚未得到解决，以基于三唑基序识别Wnt /β-catenin信号传导抑制剂的新结构类型。与尼氯胺类似，我们发现，新的三唑衍生物内化了Frizzled-1 GFP受体，在TOPflash分析中抑制了Wnt /β-catenin信号传导，并降低了Wnt途径中突变的CRC细胞的Wnt /β-catenin靶基因水平。此外，在先导性SA