4-丙烯氧基苯甲醛 | 50262-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 4-丙烯氧基苯甲醛
• 中文别名: 4-丙酰氧基苯甲醛
• 英文名称: 4-formylphenyl propionate
• 英文别名: (4-formylphenyl) propanoate
• CAS: 50262-48-1
• 化学式: C₁₀H₁₀O₃
• mdl: MFCD00043522
• 分子量: 178.188
• InChiKey: NKXPJXVTMWLHBC-UHFFFAOYSA-N

物化性质

• 沸点：
  132-136°C 0,5mm
• 密度：
  1.147±0.06 g/cm3(Predicted)
• 闪点：
  132-136°C/0.5mm
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，未有已知危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2915509000
• 安全说明：
  S24/25

反应信息

• 作为反应物：
  描述：

  4-丙烯氧基苯甲醛 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以61%的产率得到4-(羟基甲基)苯基丙酸酯
  参考文献：
  名称：

  Formulating a new basis for the treatment against botulinum neurotoxin intoxication: 3,4-Diaminopyridine prodrug design and characterization

  摘要：

  Botulism is a disease characterized by neuromuscular paralysis and is produced from botulinum neurotoxins (BoNTs) found within the Gram positive bacterium Clostridium botulinum. This bacteria produces the most deadliest toxin known, with lethal doses as low as 1 ng/kg. Due to the relative ease of production and transport, the use of these agents as potential bioterrorist weapons has become of utmost concern. No small molecule therapies against BoNT intoxication have been approved to date. However, 3,4-diaminopyridine (3,4-DAP), a potent reversible inhibitor of voltage-gated potassium channels, is an effective cholinergic agonist used in the treatment of neuromuscular degenerative disorders that require cholinergic enhancement. 3,4-DAP has also been shown to facilitate recovery of neuromuscular action potential post botulinum intoxication by blocking K(+) channels. Unfortunately, 3,4-DAP displays toxicity largely due to blood-brain-barrier (BBB) penetration. As a dual-action prodrug approach to cholinergic enhancement we have designed carbamate and amide conjugates of 3,4-DAP. The carbamate prodrug is intended to be a slowly reversible inhibitor of acetylcholinesterase (AChE) along the lines of the stigmines thereby allowing increased persistence of released acetylcholine within the synaptic cleft. As a secondary activity, cleavage of the carbamate prodrug by AChE will afford the localized release of 3,4-DAP, which in turn, will enhance the pre-synaptic release of additional acetylcholine. Being a competitive inhibitor with respect to acetylcholine, the activity of the prodrug will be greatest at the synaptic junctions most depleted of acetylcholine. Here we report upon the synthesis and biochemical characterization of three new classes of prodrugs intended to limit previously reported stability and toxicity issues. Of the prodrugs examined, compound 32, demonstrated the most clinically relevant half-life of 2.76 h, while selectively inhibiting AChE over butyrylcholinesterase-a plasma-based high activity esterase. Future in vivo studies could provide validation of prodrug 32 as a potential treatment against BoNT intoxication as well as other neuromuscular disorders. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.019
• 作为产物：
  描述：

  丙酰氯 、 对羟基苯甲醛 在 三乙胺 作用下， 生成 4-丙烯氧基苯甲醛
  参考文献：
  名称：

  新型喹唑啉酮衍生物：用于治疗青光眼、阿尔茨海默病和糖尿病的潜在合成类似物

  摘要：

  喹唑啉酮类化合物是含氮六元杂环化合物的重要组成部分，由于其广泛的生物活性特性而经常用于药物设计。因此，通过 4-羟基苯甲醛的酰化衍生物与 3-氨基-2-烷基喹唑啉-4( 3H )-酮的反应合成了新型喹唑啉酮，收率良好 (85–94 %)，并使用傅里叶-红外光谱对其结构进行了表征。变换红外 (FT-IR)、核磁共振（1 H-NMR、13 C-NMR）和高分辨率质谱 (HR-MS)。作为合成化合物的应用，研究了合成化合物对α-葡萄糖苷酶（α-Glu）、乙酰胆碱酯酶（AChE）、丁酰胆碱酯酶（BChE）和碳酸酐酶I-II（hCA I-II）代谢酶的抑制特性。调查了。所有化合物均表现出纳摩尔水平的抑制作用，AChE 的 K i值范围为 12.73±1.26–93.42±9.44 nM，BChE 的 K i 值范围为 8.48±0.92–25.84±2.59 nM，α-Glu 的 K i 值范围为 66

  DOI：

  10.1002/cbdv.202301134

文献信息

• Stereoselective Synthesis of Z Fluoroalkenes through Copper-Catalyzed Hydrodefluorination of <i>gem</i> -Difluoroalkenes with Water
  作者：Jiefeng Hu、Xiaowei Han、Yu Yuan、Zhuangzhi Shi

  DOI：10.1002/anie.201708224

  日期：2017.10.16

  A copper catalytic system was established for the stereoselective hydrodefluorination of gem‐difluoroalkenes through C−F activation to synthesize various Z fluoroalkenes. H2O is used as the hydrogen source for the fluorine acceptor moiety. This mild catalytic system shows good‐functional group compatibility, accepting a range of carbonyls as precursors to the gem‐difluoroalkenes, including aliphatic

  建立了铜催化体系，用于通过C-F活化来合成各种Z 氟烯烃，以进行宝石二氟烯烃的立体选择性加氢脱氟。H 2 O用作氟受体部分的氢源。这种温和的催化体系显示出良好的官能团相容性，可以接受多种羰基化合物作为双二氟烯烃的前体，包括脂族，芳族和α，β-不饱和醛，甚至酮。它是复杂化合物后期修饰的有力合成方法。
• Photodynamic activity attained through the ruptured π-conjugation of pyridyl groups with a porphyrin macrocycle: synthesis and the photophysical and photobiological evaluation of 5-mono-(4-nitrophenyl)-10,15,20-tris-[4-(phenoxymethyl)pyridine]-porphyrin and its Zn(ii) complex
  作者：Zeaul H. Mazumder、Debdulal Sharma、Devashish Sengupta、Avinaba Mukherjee、Jayanta Sarmah Boruah、Samita Basu、Pradeep Kumar Shukla、Tarun Jha

  DOI：10.1039/d0pp00319k

  日期：2020.12

  with three distal pyridyl groups. Both P3N and P3NZn experience ruptured π-conjugation with the porphyrin macrocycle and attain hydrophilicity, as indicated via density functional theory (DFT) calculations, becoming photobiologically active under in vitro conditions. The non-invasive photodynamic activity (PDA) predominantly shown by the zinc-complex P3NZn (with higher hydrophilicity) towards KRAS-mutated

  本文比较了报道的带有单个内消旋-4-硝基苯基和三个内消旋吡啶基（A 3 B型）的疏水性和光生物学惰性的卟啉合成子（NPh） TPyP与一种新的无光生物学活性的金属卟啉P 3 N及其锌络合物P 3 NZn，它带有一个内消旋-4-硝基苯基和三个远端吡啶基。两个P 3 Ñ和P 3 NZN经验破裂π共轭与卟啉大环化合物和达到亲水性，如所指示经由密度泛函理论（DFT）计算，在体外条件下具有光生物学活性。研究了锌复合物P 3 NZn（具有更高的亲水性）对KRAS突变的人肺癌细胞（A549）的无创光动力活性（PDA）。结果表明存在细胞内单线态氧引起的抗癌PDA，这通过细胞内活性氧（ROS）的上调和细胞内超氧化物歧化酶（SOD）和细胞内还原型谷胱甘肽（GSH）含量的下调来体现。来自SOD和GSH测定获得的趋势是对氧化应激的治疗防御的指标通过 中和超氧阴离子（SOA）。
• [2+2] Photodimerization of Stilbazoles Promoted by Oxalic Acid in Suspension
  作者：Thanh Binh Nguyen、Tuan Minh Nguyen、Pascal Retailleau

  DOI：10.1002/chem.201905597

  日期：2020.4.9

  waxy or even insoluble stilbazoles. Moreover, the oxalic acid loading could be lowered to sub-stoichiometric amounts. When further optimizations were needed, our strategy was found to be highly flexible to identify other oligocarboxylic acids as alternative additive to improve or even overturn regioselectivity. Oxalic acid and other oligocarboxylic acids were found to be capable of orienting more than

  在这项研究中，我们报道了一种非常简单的技术，可以有效地对某些乙烯基吡啶进行光二聚化。通过用几种苯乙烯基唑与分散在非极性（例如环己烷）或中等极性（苯，二氯甲烷，二恶烷）溶剂中的固体草酸二水合物的搅拌混合物进行辐照，可以高收率获得相应的二聚环丁烷加合物，具有极好的区域选择性。和立体选择性。该策略也可以成功地应用于油性，蜡质或什至不溶性斯蒂巴唑。此外，草酸负载量可降低至亚化学计量量。当需要进一步优化时，我们的策略非常灵活，可以确定其他低聚羧酸作为替代添加剂，从而改善甚至推翻区域选择性。
• Synthesis, biological evaluation, QSAR and molecular dynamics simulation studies of potential fibroblast growth factor receptor 1 inhibitors for the treatment of gastric cancer
  作者：Shilong Ying、Xiaojing Du、Weitao Fu、Di Yun、Liping Chen、Yuepiao Cai、Qing Xu、Jianzhang Wu、Wulan Li、Guang Liang

  DOI：10.1016/j.ejmech.2016.10.066

  日期：2017.2

  evidence suggests that fibroblast growth factor receptor 1 (FGFR1) is an attractive target in gastric cancer therapy. Based on our previous discovery of two non-ATP competitive FGFR1 inhibitors, A114 and A117, we designed and screened a series of compounds with the framework of bisaryl-1,4-dien-3-one. Among them, D12 and D15 exhibited the most potent FGFR1 inhibitory activity, which was ATP-independent

  越来越多的证据表明，成纤维细胞生长因子受体1（FGFR1）是胃癌治疗中有吸引力的靶标。基于我们先前发现的两种非ATP竞争性FGFR1抑制剂A114和A117，我们设计并筛选了具有bisaryl-1,4-dien-3-one构架的一系列化合物。其中，D12和D15表现出最强的FGFR1抑制活性，这是与ATP无关的。此外，对41种类似物的定量构效关系分析表明，特定的结构取代会改变其生物活性。分子对接和动力学模拟分析表明，在FGFR1-D12 / D15相互作用中疏水相互作用是主要的。对D12和D15的抗胃癌功效的评估表明有效抑制了细胞增殖，凋亡诱导和细胞周期停滞。因此，这两种FGFR1抑制剂在胃癌的治疗中具有治疗潜力，这项研究将为新型非ATP竞争性FGFR1抑制剂的合理设计做出贡献。
• Circular Dichroism of Neutral Zinc Porphyrin–Oligonucleotide Conjugates Modified with Flexible Linker
  作者：Akira Onoda、Masahiro Igarashi、Satoshi Naganawa、Kiyomi Sasaki、Shinya Ariyasu、Takeshi Yamamura

  DOI：10.1246/bcsj.82.1280

  日期：2009.10.15

  Neutral zinc porphyrin containing flexible alkyl linker, 5-[4-(5-hydroxypentyloxy)phenyl]-10,15,20-tri-p-tolylporphyrinatozinc, was attached to the 5′ ends of 20- and 30-bp oligodeoxynucleotides (ODN) by solid-phase synthesis. Zinc porphyrin-modified double-stranded DNA (dsDNAs), which included dsDNAs with porphyrin moieties on one end and on both ends (ZnPor–ds20, ds20–ZnPor, ZnPor–ds20–ZnPor, ZnPor–ds30, ds30–ZnPor, and ZnPor–ds30–ZnPor), were successfully prepared and were analyzed by variable-temperature UV–vis spectroscopy and CD measurements to elucidate the interaction behavior of the porphyrin ring. Detailed investigation revealed that the zinc porphyrin–DNA conjugates exhibited intra-duplex porphyrin–ODN interaction in a low-salt condition and inter-duplex porphyrin–porphyrin interaction in a high-salt condition.

  含有柔性烷基接头 5-[4-(5-羟基戊氧基)苯基]-10,15,20-三对甲苯基卟啉锌的中性锌卟啉连接到 20-和 30-bp 寡脱氧核苷酸 (ODN) 的 5' 末端）通过固相合成。锌卟啉修饰的双链 DNA (dsDNA)，包括一端和两端均带有卟啉部分的 dsDNA（ZnPor–ds20、ds20–ZnPor、ZnPor–ds20–ZnPor、ZnPor–ds30、ds30–ZnPor 和 ZnPor –ds30–ZnPor）已成功制备，并通过变温紫外可见光谱和圆二色测量进行分析，以阐明卟啉环的相互作用行为。详细研究表明，锌卟啉-DNA 缀合物在低盐条件下表现出双链体内卟啉-ODN 相互作用，在高盐条件下表现出双链体间卟啉-卟啉相互作用。

表征谱图