3-(4-formyl-2-methoxy-5-nitrophenoxy)propionic acid | 550356-12-2

• 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: 3-(4-formyl-2-methoxy-5-nitrophenoxy)propionic acid
• 英文别名: 3-(4-Formyl-2-methoxy-5-nitrophenoxy)propanoic acid
• CAS: 550356-12-2
• 化学式: C₁₁H₁₁NO₇
• mdl: MFCD12665350
• 分子量: 269.211
• InChiKey: NWFIYJFJOFTMHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(4-formyl-2-methoxy-5-nitrophenoxy)propionic acid 在 palladium on activated charcoal 吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 草酰氯 、 氢气 、 双氧水 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， -40.0~20.0 ℃ 、344.74 kPa 条件下， 反应 40.34h， 生成 2,2,2-trichloroethyl 3-(5-amino-4-{[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-2-methoxyphenoxy)propionate
  参考文献：
  名称：

  Unsymmetrical DNA Cross-Linking Agents:  Combination of the CBI and PBD Pharmacophores

  摘要：

  A set of 10 compounds, each combining the seco-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (seco-CBI) and pyrrolo[2,1-c][1,4]benzodiazepine (PBD) pharmacophores, was designed and prepared. These compounds were anticipated to cross-link between N3 of adenine and N2 of guanine in the minor groove of DNA. The compounds, which differ in the chain length separating the two alkylation subunits, and the configuration of the CBI portion, showed great variation in cellular toxicity (over 4 orders of magnitude in a cell line panel) with the most potent example exhibiting IC50S in the pM range. Cytotoxicity correlated with the ability of the compounds to cross-link naked DNA. Cross-linking was also observed in living cells, at much lower concentrations than for a related symmetrical PBD dimer. A thermal cleavage assay was used to assess sequence selectivity, demonstrating that the CBI portion controlled the alkylation sites, while the PBD substituent increased the overall efficiency of alkylation. Several compounds were tested for in vivo activity using a tumor growth delay assay against WiDr human colon carcinoma xenografts, with one compound (the most cytotoxic and most efficient cross-linker) showing a statistically significant increase in survival time following a single iv dose.

  DOI：

  10.1021/jm020526p
• 作为产物：
  描述：

  3-甲氧基-4-(3-羟基丙氧基)苯甲醛 在 硝酸 作用下， 反应 0.33h， 以48%的产率得到3-(4-formyl-2-methoxy-5-nitrophenoxy)propionic acid
  参考文献：
  名称：

  Unsymmetrical DNA Cross-Linking Agents:  Combination of the CBI and PBD Pharmacophores

  摘要：

  A set of 10 compounds, each combining the seco-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (seco-CBI) and pyrrolo[2,1-c][1,4]benzodiazepine (PBD) pharmacophores, was designed and prepared. These compounds were anticipated to cross-link between N3 of adenine and N2 of guanine in the minor groove of DNA. The compounds, which differ in the chain length separating the two alkylation subunits, and the configuration of the CBI portion, showed great variation in cellular toxicity (over 4 orders of magnitude in a cell line panel) with the most potent example exhibiting IC50S in the pM range. Cytotoxicity correlated with the ability of the compounds to cross-link naked DNA. Cross-linking was also observed in living cells, at much lower concentrations than for a related symmetrical PBD dimer. A thermal cleavage assay was used to assess sequence selectivity, demonstrating that the CBI portion controlled the alkylation sites, while the PBD substituent increased the overall efficiency of alkylation. Several compounds were tested for in vivo activity using a tumor growth delay assay against WiDr human colon carcinoma xenografts, with one compound (the most cytotoxic and most efficient cross-linker) showing a statistically significant increase in survival time following a single iv dose.

  DOI：

  10.1021/jm020526p

文献信息

• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• BI-FUNCTIONAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES
  申请人：Nuevolution A/S

  公开号：EP2558577A1

  公开（公告）日：2013-02-20
• BI-FUNCTINAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES
  申请人：Gouliaev Alex Haahr

  公开号：US20130281324A1

  公开（公告）日：2013-10-24

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.
• [EN] BI-FUNCTIONAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES<br/>[FR] COMPLEXES BIFONCTIONNELS ET PROCÉDÉS DE FABRICATION ET D'UTILISATION DE TELS COMPLEXES
  申请人：NUEVOLUTION AS

  公开号：WO2011127933A1

  公开（公告）日：2011-10-20

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.