methyl 2,4-dimethyl-3-pyrrolepropionate | 54474-51-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2,4-dimethyl-3-pyrrolepropionate
• 英文别名: 3-(2-methoxycarbonylethyl)-2,4-dimethylpyrrole；3-(2,4-dimethyl-1H-pyrrol-3-yl)propionic acid methyl ester；methyl 2,4-dimethyl-1H-pyrrole-3-propanoate；2,4-dimethyl-1H-pyrrol-3-yl-3-propanoic acid methyl ester；methyl 3-(2,4-dimethyl-1H-pyrrol-3-yl) propanoate；3-(2,4-dimethyl-pyrrol-3-yl)-propionic acid methyl ester；3-(2,4-Dimethyl-pyrrol-3-yl)-propionsaeure-methylester；2,4-dimethyl-3-(2-methoxycarbonylethyl)pyrrole；methyl 3-(2,4-dimethyl-1H-pyrrol-3-yl)propanoate
• CAS: 54474-51-0
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: HEKYHUQPSNIMJD-UHFFFAOYSA-N

物化性质

• 熔点：
  35-37 °C
• 沸点：
  144-146 °C(Press: 9 Torr)
• 密度：
  1.068±0.06 g/cm3(Predicted)

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：
  0.5
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2,4-dimethyl-3-pyrrolepropionate 在 哌啶 、 sodium hydroxide 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 抗癌医药中间体
  参考文献：
  名称：

  Design, Synthesis, and Evaluations of Substituted 3-[(3- or 4-Carboxyethylpyrrol-2-yl)methylidenyl]indolin-2-ones as Inhibitors of VEGF, FGF, and PDGF Receptor Tyrosine Kinases

  摘要：

  Receptor tyrosine kinases (RTKs) have been implicated as therapeutic targets for the treatment of human diseases including cancers, inflammatory diseases, cardiovascular diseases including arterial restenosis, and fibrotic diseases of the lung, liver, and kidney. Three classes of 3-substituted indolin-2-ones containing propionic acid functionality attached to the pyrrole ring at the C-3 position of the core have been identified as catalytic inhibitors of the vascular endothelial growth factor (VEGF), fibroblast growth factor (FGF), and platelet-derived growth factor (PDGF) RTKs. Some of the compounds were found to inhibit the tyrosine kinase activity associated with isolated vascular endothelial growth factor receptor 2 (VEGF-R2) [fetal liver tyrosine kinase 1 (Flk-1)/kinase insert domain-containing receptor (KDR)], fibroblast growth factor receptor (FGF-R), and platelet-derived growth factor receptor (PDGF-R) tyrosine kinase with IC50 values at nanomolar level. Thus, compound 1 showed inhibition against VEGF-R2 (Flk-1/KDR) and FGF-R1 tyrosine kinase activity With IC50 values of 20 and 30 nM, respectively, while compound 16f inhibited the PDGF-R tyrosine kinase activity with IC50 value of 10 nM. Structural models and structure-activity relationship analysis of these compounds for the target receptors are discussed. The cellular activities of these compounds were profiled using cellular proliferation assays as measured by bromodeoxyuridine (BrdU) incorporation. Specific and potent inhibition of cell growth was observed for some of these compounds. These data provide evidence that these compounds can be used to inhibit the function of these target receptors.

  DOI：

  10.1021/jm9904295
• 作为产物：
  描述：

  butyl 4-(3-methoxy-3-oxopropyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate 在 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.67h， 以73%的产率得到methyl 2,4-dimethyl-3-pyrrolepropionate
  参考文献：
  名称：

  一锅合成不对称环状双吡咯

  摘要：

  活化的官能化吡咯与丙酮的缩合导致不对称的双（吡咯），其通过环环化形成。该方法在某种程度上是通用的，并且可以应用于各种酮，以及不与吡咯环直接相邻的不带有吸电子基团的一系列吡咯底物。

  DOI：

  10.1021/ol202457n

文献信息

• Indolinone compounds as kinase inhibitors
  申请人：Sugen, Inc.

  公开号：US06689806B1

  公开（公告）日：2004-02-10

  The invention relates to certain indolinone compounds, their method of synthesis, and a combinatorial library consisting of the indolinone compounds of the invention. The invention also relates to methods of modulating the function of protein kinases using indolinone compounds of the invention and methods of treating diseases by modulating the function of protein kinases and related signal transduction pathways.

  这项发明涉及某些吲哚酮化合物，它们的合成方法，以及由该发明的吲哚酮化合物组成的组合式文库。该发明还涉及使用该发明的吲哚酮化合物调节蛋白激酶功能的方法，以及通过调节蛋白激酶功能和相关信号转导途径治疗疾病的方法。
• Highly selective, red emitting BODIPY-based fluorescent indicators for intracellular Mg²⁺imaging
  作者：Qitian Lin、Daniela Buccella

  DOI：10.1039/c8tb01599f

  日期：——

  dependence in the physiologically relevant range. The choice of alkoxy groups decorating the styryl BODIPY core does not influence the basic photophysical and metal binding properties of the compounds, but has a marked effect on their intracellular retention and thus in their applicability for detection of cellular Mg2+ by fluorescence imaging. In particular, we demonstrate the utility of a triethyleneglycol

  大多数 Mg 2+荧光指示剂对其他二价阳离子（尤其是 Ca 2+ ）的选择性较差，因此不能提供涉及此类金属的过程中细胞 Mg 2+浓度的可靠信息。我们报告了一套新的高选择性荧光指示剂，其基于烷氧基苯乙烯基功能化的 BODIPY 荧光团，并装饰有 4-oxo-4 H -quinolizine-3-carbic Acid 金属结合部分。新型传感器MagQ1和MagQ2在 600 nm 以上显示吸收和发射最大值，在水性缓冲液中配位 Mg 2+后，荧光增强了 29 倍，并具有良好的量子产率 ( Φ > 0.3)。对 Mg 2+的荧光响应不受细胞环境中通常存在的竞争性二价阳离子的影响，并且在生理相关范围内表现出最小的 pH 依赖性。装饰苯乙烯基BODIPY核心的烷氧基的选择不会影响化合物的基本光物理和金属结合特性，但对其细胞内保留具有显着影响，因此对其通过荧光成像检测细胞Mg 2+的适用性具有显着影
• Highly Activatable and Environment-Insensitive Optical Highlighters for Selective Spatiotemporal Imaging of Target Proteins
  作者：Tomonori Kobayashi、Toru Komatsu、Mako Kamiya、Cláudia Campos、Marcos González-Gaitán、Takuya Terai、Kenjiro Hanaoka、Tetsuo Nagano、Yasuteru Urano

  DOI：10.1021/ja212125w

  日期：2012.7.11

  Optical highlighters are photoactivatable fluorescent molecules that exhibit pronounced changes in their spectral properties in response to irradiation with light of a specific wavelength and intensity. Here, we present a novel design strategy for a new class of caged BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) fluorophores, based on the use of photoremovable protecting groups (PRPGs) with

  光学荧光笔是可光活化的荧光分子，在特定波长和强度的光照射下，其光谱特性会发生显着变化。在这里，我们提出了一种新型笼状 BODIPY（4,4-difluoro-4-bora-3a,4a-diaza-s-indacene）荧光团的新设计策略，基于使用光可去除保护基（PRPGs）与高还原电位，通过光诱导电子转移 (PeT) 作为光敏单元和荧光猝灭剂。2,6-二硝基苄基 (DNB) 笼式 BODIPY 被有效地光活化，在水溶液中的活化率超过 600 倍。然后，我们使用成熟的 SNAP 标签技术将此光活化荧光团与 SNAP（O(6)-烷基鸟嘌呤 DNA 烷基转移酶的突变体）配体相结合，以获得用于蛋白质动力学可视化的基于小分子的光学荧光笔。作为概念证明，我们展示了活细胞中具有 SNAP 标签的表皮生长因子受体 (EGFR) 融合蛋白的时空成像。我们还展示了使用组蛋白 2A 的融合蛋白与 SNAP 标签突出显示活斑马鱼胚胎中感兴趣的细胞。
• Long wavelength chemically reactive dipyrrometheneboron difluoride dyes
  申请人：Molecular Probes, Inc.

  公开号：US05274113A1

  公开（公告）日：1993-12-28

  This invention relates to derivatives of dipyrrometheneboron difluoride fluorescent dyes that have an absorption maximum at wavelengths longer than about 525 nm, and are chemically reactive with nucleic acids, proteins, carbohydrates, and other biologically derived or synthetic chemical materials. The dyes generally have the structure: ##STR1## wherein at least one of the substituents R.sub.1 -R.sub.7, is a reactive functional group, and at least one of the substituents R.sub.1 -R.sub.7 contains a bathochromic moiety. The bathochromic moiety is an unsaturated organic group, preferably heteroaryl or alkenyl. The remaining substituents, which may be the same or different, are hydrogen, halogen, alkyl (containing 1-5 carbon atoms), aryl, arylalkyl, or sulfo. The dyes are used to make novel conjugates with members of specific binding pairs that are ligands or receptors.

  这项发明涉及二吡咯甲烷硼二氟化物荧光染料的衍生物，其在波长大约超过525纳米处具有最大吸收，并且在化学上与核酸、蛋白质、碳水化合物和其他生物衍生或合成化学材料发生反应。这些染料通常具有以下结构：##STR1##其中至少一个取代基R.sub.1 -R.sub.7是一个反应性官能团，至少一个取代基R.sub.1 -R.sub.7含有巴托克罗迈基团。巴托克罗迈基团是一个不饱和的有机基团，最好是杂环烷基或烯基。其余的取代基，可以相同也可以不同，是氢、卤素、烷基（含有1-5个碳原子）、芳基、芳基烷基或磺酸基。这些染料用于与特定结合对的成员制备新型共轭物，这些成员是配体或受体。
• Ligand-Directed Approach to Activity-Based Sensing: Developing Palladacycle Fluorescent Probes That Enable Endogenous Carbon Monoxide Detection
  作者：Johannes Morstein、Denis Höfler、Kohei Ueno、Jonah W. Jurss、Ryan R. Walvoord、Kevin J. Bruemmer、Samir P. Rezgui、Thomas F. Brewer、Minoru Saitoe、Brian W. Michel、Christopher J. Chang

  DOI：10.1021/jacs.0c06405

  日期：2020.9.16

  with CO under physiological conditions. These fundamental studies led to the development of an optimized probe, termed Carbon Monoxide Probe-3 Ester Pyridine (COP-3E-Py), which enables imaging of CO release in live cell and brain settings, including monitoring of endogenous CO production that triggers presynaptic dopamine release in fly brains. This work provides a unique tool for studying CO in living

  一氧化碳 (CO) 是一种新兴的气体递质和活性碳物质，具有广泛的抗炎、细胞保护和神经递质功能以及治疗心血管疾病的潜力。与 NO 和 H2S 等其他主要气体传递体相比，生物学和医学中的 CO 化学研究仍然具有挑战性，这在很大程度上是由于可用于直接可视化复杂生命系统中这种瞬态和自由扩散的小分子的可用工具的局限性。在这里，我们报告了一种通过钯介导的羰基化化学检测一氧化碳的配体导向的基于活性的传感 (ABS) 方法。具体而言，设计和合成一系列在钯配体环境中具有系统改变的 ABS 探针（例如 sp3-S、sp3-N、sp2-N) 建立钯环的构效关系，以赋予生理条件下与 CO 的选择性反应性。这些基础研究导致开发了一种优化的探针，称为一氧化碳探针-3 酯吡啶 (COP-3E-Py)，它能够对活细胞和大脑环境中的 CO 释放进行成像，包括监测触发突触前的内源性 CO 产生果蝇大脑中的多巴胺释放。这项工作为研究生命系统中的