3-hydroxymethyl-4-nitrobenzoic acid ethyl ester | 412317-99-8

• 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: 3-hydroxymethyl-4-nitrobenzoic acid ethyl ester
• 英文别名: ethyl 3-(hydroxymethyl)-4-nitrobenzoate；Ethyl 3-(hydroxymethyl)-4-nitrobenzoate
• CAS: 412317-99-8
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: FUWBIXKMLYIVJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxymethyl-4-nitrobenzoic acid ethyl ester 在 吡啶 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 66.0h， 生成 2-nitro-5-(allyloxycarbonyl)benzyl 4-nitrophenyl carbonate
  参考文献：
  名称：

  设计用于低氧肿瘤组织中生物还原活化的新型紫杉醇前药的合成。

  摘要：

  描述了第一种潜在的生物还原性紫杉醇前药的合成和初步评估。通过针对缺氧肿瘤组织，这些前药被设计为更选择性化疗的潜在候选药物。芳香硝基和叠氮化物基团被用作生物还原触发物。紫杉醇的生成发生在还原和随后的1,6-消除或1,8-消除之后。所有前药在缓冲液中都是稳定的，并且在化学还原芳香族硝基或叠氮化物官能度后，的确会产生紫杉醇。在有氧细胞毒性测定中，几种前药表现出减弱的细胞毒性。这些化合物是用于进一步生物学评估的有趣候选物。

  DOI：

  10.1016/s0968-0896(01)00235-8
• 作为产物：
  描述：

  3-(溴甲基)-4-硝基苯甲酸乙酯 在 硫酸 作用下， 以 水 为溶剂， 以89%的产率得到3-hydroxymethyl-4-nitrobenzoic acid ethyl ester
  参考文献：
  名称：

  设计用于低氧肿瘤组织中生物还原活化的新型紫杉醇前药的合成。

  摘要：

  描述了第一种潜在的生物还原性紫杉醇前药的合成和初步评估。通过针对缺氧肿瘤组织，这些前药被设计为更选择性化疗的潜在候选药物。芳香硝基和叠氮化物基团被用作生物还原触发物。紫杉醇的生成发生在还原和随后的1,6-消除或1,8-消除之后。所有前药在缓冲液中都是稳定的，并且在化学还原芳香族硝基或叠氮化物官能度后，的确会产生紫杉醇。在有氧细胞毒性测定中，几种前药表现出减弱的细胞毒性。这些化合物是用于进一步生物学评估的有趣候选物。

  DOI：

  10.1016/s0968-0896(01)00235-8

文献信息

• Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials
  作者：Yazmin M. Osornio、Peter Uebelhart、Silvan Bosshard、Fabian Konrad、Jay S. Siegel、Ehud M. Landau

  DOI：10.1021/jo301659c

  日期：2012.12.7

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.
• [EN] LIPIDIC BIOMATERIALS FOR ENCAPSULATION AND TRIGGERED RELEASE<br/>[FR] BIOMATÉRIAUX LIPIDIQUES POUR L'ENCAPSULATION ET LA LIBÉRATION DÉCLENCHÉE
  申请人：UNIV ZUERICH

  公开号：WO2014056939A1

  公开（公告）日：2014-04-17

  The present invention relates to novel compounds, particularly for use as additives in a lipidic cubic phase material, and to novel lipidic cubic phase materials. These materials are biocompatible, stable and transparent and can encapsulate active compounds such as drugs and release them at will by chemical and/or photochemical triggering. A method of controlled release of a predetermined active compound, comprises the steps of: forming a lipidic cubic phase material by mixing a lipophilic component and a hydrophilic component comprising an aqueous solution containing the active compound; placing the lipidic cubic phase material in a region of interest; releasing the active compound by subjecting the lipidic cubic phase material to a chemical or photochemical stimulus.
• Synthesis of novel paclitaxel prodrugs designed for bioreductive activation in hypoxic tumour tissue
  作者：Eric W.P. Damen、Tapio J. Nevalainen、Toine J.M. van den Bergh、Franciscus M.H. de Groot、Hans W. Scheeren

  DOI：10.1016/s0968-0896(01)00235-8

  日期：2002.1

  bioreductive paclitaxel prodrugs are described. These prodrugs were designed as potential candidates in more selective chemotherapy by targeting hypoxic tumour tissue. Aromatic nitro and azide groups were used as the bioreductive trigger. Generation of paclitaxel occurs after reduction and subsequent 1,6-elimination or 1,8-elimination. All prodrugs are stable in buffer and indeed give paclitaxel after chemical

  描述了第一种潜在的生物还原性紫杉醇前药的合成和初步评估。通过针对缺氧肿瘤组织，这些前药被设计为更选择性化疗的潜在候选药物。芳香硝基和叠氮化物基团被用作生物还原触发物。紫杉醇的生成发生在还原和随后的1,6-消除或1,8-消除之后。所有前药在缓冲液中都是稳定的，并且在化学还原芳香族硝基或叠氮化物官能度后，的确会产生紫杉醇。在有氧细胞毒性测定中，几种前药表现出减弱的细胞毒性。这些化合物是用于进一步生物学评估的有趣候选物。
• 2,4-Bis(hydroxymethyl)aniline as a Building Block for Oligomers with Self-Eliminating and Multiple Release Properties
  作者：André Warnecke、Felix Kratz

  DOI：10.1021/jo702484z

  日期：2008.2.1

  Linear self-eliminating (LSE) systems are oligomers of branched self-eliminating linkers that disassemble upon a single triggering event under complete degradation of the linear backbone, accompanied by the release of side-chain bound effector molecules. Enabling a controlled and almost simultaneous release of different effectors (drugs) in defined ratios, LSE systems may gain importance for the development of novel combination therapeutics. On the basis of the well-known self-eliminating p-aminobenzyloxycarbonyl (PABC) linker, 2 4-bis(hydroxymethyl)aniline was considered a suitable branched linker for building LSE systems that degrade by 1,6- and 1,4-benzyl elimination reactions. A first LSE model system based on this linker was prepared in a simple procedure and was shown to release its effector payload efficiently after activation. In addition, elimination model compounds were synthesized to study the release behavior of LSE systems based on 2,4-bis(hydroxymethyl)aniline. It was found that chain degrading 1,6-benzyl elimination occurs much faster than the effector releasing 1,4-elimination.