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7-propanoylamino-4-methylcoumarin

中文名称
——
中文别名
——
英文名称
7-propanoylamino-4-methylcoumarin
英文别名
N-(4-methyl-2-oxo-2H-chromen-7-yl)propanamid;4-methyl-7-propionamidocoumarin;N-(4-methyl-2-oxo-chromen-7-yl)propanamide;N-(4-methyl-2-oxochromen-7-yl)propanamide
7-propanoylamino-4-methylcoumarin化学式
CAS
——
化学式
C13H13NO3
mdl
——
分子量
231.251
InChiKey
RNZCEHOFHBEXNB-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.9
  • 重原子数:
    17
  • 可旋转键数:
    2
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.23
  • 拓扑面积:
    55.4
  • 氢给体数:
    1
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

点击查看最新优质反应信息

文献信息

  • Cross-Coupling of Amide and Amide Derivatives to Umbelliferone Nonaflates: Synthesis of Coumarin Derivatives and Fluorescent Materials
    作者:Shane M. Hickey、Samuel O. Nitschke、Martin J. Sweetman、Christopher J. Sumby、Douglas A. Brooks、Sally E. Plush、Trent D. Ashton
    DOI:10.1021/acs.joc.0c00813
    日期:2020.6.19
    properties of aqueous-soluble derivatives were determined, and they displayed auxochrome-based variations. Gram-scale synthesis provided an acrylamide analogue, which was used to fabricate a fluorescent poly(2-hydroxylethyl methacrylate) (pHEMA) hydrogel that was resistant to leaching in ultrapure H2O. We envisage that our reported protocol to access 7-amino-4-methylcoumarin derivatives will find use toward
    描述了4-甲基伞形酮衍生的壬二酸酯与酰胺,氨基甲酸酯和磺酰胺之间的布赫瓦尔德-哈特维格交叉偶联反应。以良好至优异的产率制备了多种N-取代的7-香豆素类似物。测定了溶性衍生物的光物理性质,并且它们显示出基于色素的变化。克级合成提供了一种丙烯酰胺类似物,该丙烯酰胺类似物用于制造可抵抗超纯H 2 O浸出的荧光聚(甲基丙烯酸2-羟乙酯)(pHEMA凝胶。我们设想,我们报告的访问7-基-该领域的研究人员将发现4-甲基香豆素生物可用于开发基于荧光香豆素的新型荧光探针。
  • Structure activity studies with xenobiotic substrates using carboxylesterases isolated from Arabidopsis thaliana
    作者:Ian Cummins、Marie Landrum、Patrick G. Steel、Robert Edwards
    DOI:10.1016/j.phytochem.2006.12.014
    日期:2007.3
    cloned, expressed and the purified recombinant proteins assayed for esterase activity with xenobiotic substrates. Two members, AtCXE5 and AtCXE18 were found to be active carboxylesterases, though AtCXE5 proved to be highly unstable as a soluble protein. AtCXE18 and the previously characterised S-formylglutathione hydrolase from Arabidopsis (AtSFGH) were assayed against a series of esters based on methylumbelliferone
    羧酸酯酶 (CXE) 催化异生物质和天然产物解,从根本上改变它们的生物活性。虽然动物 CXE 的底物选择性,如猪肝酯酶 (PLE) 已得到充分研究,但植物中的相应酶尚未确定,其活性尚未确定。使用拟南芥 (At) 作为来源,已经克隆、表达了 α/β 解酶 AtCXE 蛋白质家族的五个代表性成员,并用异生物质底物测定了纯化的重组蛋白酯酶活性。两个成员 AtCXE5 和 AtCXE18 被发现是有活性的羧酸酯酶,尽管 AtCXE5 作为可溶性蛋白质被证明是高度不稳定的。AtCXE18 和先前表征的来自拟南芥 (AtSFGH) 的 S-甲酰谷胱甘肽解酶针对一系列基于甲基伞形酮的酯进行了测定,其中酰基部分的大小和构象各不相同。使用同一系列测定拟南芥植物的粗酯酶制剂,并将结果与​​常用的 PLE 获得的结果进行比较。对于直链酯,AtCXE18 的行为类似于 PLE,但拟南芥解酶证明对支链酰
  • 7‐Amidocoumarins as Multitarget Agents against Neurodegenerative Diseases: Substitution Pattern Modulation
    作者:Fernanda Rodríguez‐Enríquez、Dolores Viña、Eugenio Uriarte、Reyes Laguna、Maria J. Matos
    DOI:10.1002/cmdc.202000454
    日期:2021.1.8
    This study explores the potential of 7‐amidocoumarins as multitarget agents against Parkinson's and Alzheimer's diseases, by modulating the substitution patterns within the scaffold. Sixteen compounds were synthesized via 7‐amino‐4‐methylcoumarin acylation, and in vitro evaluation of the molecules against hMAO‐A, hMAO‐B, hAChE, hBuChE and hBACE1 was performed. Five compounds turned out to be potent
    本研究通过调节支架内的替代模式,探索了 7-香豆素作为抗帕森病和阿尔茨海默病的多靶点药物的潜力。通过7-基-4-甲基香豆素酰化合成了 16 种化合物,并针对h MAO-A、h MAO-B、h AChE、h BuChE 和h BACE1对这些分子进行了体外评估。五种化合物被证明是有效的和选择性ħ在纳摩尔范围内MAO-B抑制剂,六显示的抑制活性ħ MAO-A在低微摩尔范围内,一个显示ħ乙酰胆碱酯酶抑制活性,另一种h BACE1 抑制活性。研究了 7-(4'-氯苯甲酰胺基)-4-甲基香豆素 ( 10 ) 的MAO-B 可逆性,该化合物是一种可逆抑制剂。还研究了对运动皮层神经元的神经毒性和对 H 2 O 2 的神经保护作用,证实了这些分子的安全性。最后,还计算了理论 ADME 特性,表明这些分子是优化先导化合物的良好候选者。结果表明,通过调节支架第 7 位的取代模式,可以实现选择性或多目标分子。
  • Identification of Tissue-Restricted Bioreaction Suitable for in Vivo Targeting by Fluorescent Substrate Library-Based Enzyme Discovery
    作者:Kentaro Yoshioka、Toru Komatsu、Akihiro Nakada、Jun Onagi、Yugo Kuriki、Mitsuyasu Kawaguchi、Takuya Terai、Tasuku Ueno、Kenjiro Hanaoka、Tetsuo Nagano、Yasuteru Urano
    DOI:10.1021/jacs.5b05884
    日期:2015.9.30
    Tissue-restricted bioreactions can be utilized to design chemical-biological tools and prodrugs. We have developed a fluorescent-substrate-library-based enzyme discovery approach to screen tissue extracts for enzymatic activities of interest. Assay-positive candidate proteins were identified by diced electrophoresis gel assay followed by peptide mass fingerprinting. We discovered that pyruvyl anilide is specifically hydrolyzed by carboxylesterase 2 (CES2), which is predominantly localized in the liver and kidney. We show that the pyruvyl targeting group/CES2 enzyme pair can be used to deliver the 7-amino-4-methylcoumarin fluorophore specifically to the liver and kidney in vivo. Our screening approach should be useful to find other masking group/enzyme pairs suitable for development of fluorescent substrates and prodrugs.
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