1-<(p-Nitrobenzyl)oxy>propan-3-ol

• 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: 1-<(p-Nitrobenzyl)oxy>propan-3-ol
• 英文别名: 3-[(4-nitrophenyl)methoxy]propan-1-ol；3-((4-nitrobenzyl)oxy)propan-1-ol
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: NPRCSUSBGLDESZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<(p-Nitrobenzyl)oxy>propan-3-ol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 1.58h， 以53%的产率得到3-((4-nitrobenzyl)oxy)propanoic acid
  参考文献：
  名称：

  Identification of the subtype-selective Sirt5 inhibitor balsalazide through systematic SAR analysis and rationalization via theoretical investigations

  摘要：

  We report here an extensive structure-activity relationship study of balsalazide, which was previously identified in a high-throughput screening as an inhibitor of Sirt5. To get a closer understanding why this compound is able to inhibit Sirt5, we initially performed docking experiments comparing the binding mode of a succinylated peptide as the natural substrate and balsalazide with Sirt5 in the presence of NAD(+). Based on the evidence gathered here, we designed and synthesized 13 analogues of balsalazide, in which single functional groups were either deleted or slightly altered to investigate which of them are mandatory for high inhibitory activity. Our study confirms that balsalazide with all its given functional groups is an inhibitor of Sirt5 in the low micromolar concentration range and structural modifications presented in this study did not increase potency. While changes on the N-aroyl-beta-alanine side chain eliminated potency, the introduction of a truncated salicylic acid part minimally altered potency. Calculations of the associated reaction paths showed that the inhibition potency is very likely dominated by the stability of the inhibitor-enzyme complex and not the type of inhibition (covalent vs. non-covalent). Further in-vitro characterization in a trypsin coupled assay determined that the tested inhibitors showed no competition towards NAD(+) or the synthetic substrate analogue ZKsA. In addition, investigations for subtype selectivity revealed that balsalazide is a subtype-selective Sirt5 inhibitor, and our initial SAR and docking studies pave the way for further optimization. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112676
• 作为产物：
  描述：

  2-(p-nitrophenyl)-1,3-dioxane 在 bismuth(lll) trifluoromethanesulfonate 、 1,1,3,3-四甲基二硅氧烷 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到1-<(p-Nitrobenzyl)oxy>propan-3-ol
  参考文献：
  名称：

  环保金属 三氟甲磺酸催化的C-O键的还原裂解 缩醛 到 醚

  摘要：

  描述了还原性裂解芳香族和脂肪族C-O键的方案 缩醛 到 醚 由...催化 铜（OTf）2 或者 铋（OTf）3 在室温下以优异的收率，而不会影响芳环， 硝基的， 腈， 酯 和 羟 团体。与以前的方法相比，该协议通过显着减少还原剂的用量，代表了原子经济性方面的改进。1,1,3,3-四甲基二硅氧烷 （TMDS），并使用少量 催化剂。

  DOI：

  10.1039/c1gc15636e

文献信息

• WO2020132658A5
  申请人：——

  公开号：WO2020132658A5

  公开（公告）日：2022-12-27
• A selectivity study of activated ketal reduction with borane dimethyl sulfide
  作者：Birgit Bartels、Roger Hunter

  DOI：10.1021/jo00076a041

  日期：1993.11

  A chemo- and regioselectivity study of the reagent combination BH3.SMe2/TMSOTf for ketal reduction has been undertaken. It has revealed that simple 1,3-dioxanes reduce cleanly at low temperature in CH2Cl2 while simple 1,3-dioxolanes may give complete ring cleavage and dimerization products. A study of reduction of 4-substituted 1,3-dioxolanes has revealed a solvent-directed regioselectivity which in THF favors the secondary protected derivative. A mechanism is postulated to account for the selectivities based on recent thinking on acetal substitution reactions.
• Synthesis and biological evaluation of new 4β-anilino-4′-O-demethyl-4-desoxypodophyllotoxin derivatives as potential antitumor agents
  作者：Li Wang、Fenyan Yang、Xiaochun Yang、Xianghong Guan、Chunqi Hu、Tao Liu、Qiaojun He、Bo Yang、Yongzhou Hu

  DOI：10.1016/j.ejmech.2010.11.016

  日期：2011.1

  A series of new 4 beta-anilino-4'-O-demethyl-4-desoxypodophyllotoxin derivatives were prepared and evaluated for their cytotoxicities against four human cancer cell lines including KB, KB/VCR, A549 and 95D. Most compounds showed better growth-inhibition activities against tested cell lines than that of etoposide (VP-16). Preliminary structure-activity relationships (SARs) were concluded and it indicated that the side chains substituted at 4 beta position of podophyllotoxin significantly influenced the cytotoxic activity, especially for the drug resistance profile. In vivo studies of compound 26c on highly metastatic human lung cancer xenograft in nude mice showed that it can significantly inhibit tumor growth with administrating by oral route. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Bartels Birgit, Hunter Roger, J. Org. Chem, 58 (1993) N 24, S 6756-6765
  作者：Bartels Birgit, Hunter Roger

  DOI：——

  日期：——
• TUBULYSINS AND PROTEIN-TUBULYSIN CONJUGATES
  申请人：REGENERON PHARMACEUTICALS, INC.

  公开号：EP3898651A2

  公开（公告）日：2021-10-27